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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:09 UTC

HMDB ID

HMDB0001375

Secondary Accession Numbers

HMDB01375

Metabolite Identification

Common Name

3-Hydroxy-3-methylglutaryl-CoA

Description

3-Hydroxy-3-methylglutaryl-CoA (HMG-CoA) (CAS: 1553-55-5) is formed when acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes (PMID: 14689582 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309042000222D          

 58 60  0  0  1  0            999 V2000
   27.2588   -1.4900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.5913   -1.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0039   -2.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.9239   -1.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1788   -2.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.4888   -2.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5131   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2559   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7986   -5.9435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0842   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3697   -5.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -4.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0842   -4.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -3.4685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3981   -3.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1125   -3.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5415   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4145   -1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -1.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2395   -1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1125   -2.2309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3980   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2559   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9059   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5559   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -2.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -2.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -1.8184    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -1.8184    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.1393   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -2.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8689   -3.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5189   -3.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -3.7671    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -4.5921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0434   -1.2351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6566   -1.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3790   -0.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3710   -1.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6566   -2.6121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1995   -0.5676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0855   -1.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3711   -3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0855   -2.6120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7999   -1.3745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9704   -5.5310    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.6849   -6.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6849   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3994   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8283   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5428   -6.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5428   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2573   -5.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5263   -6.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1138   -5.9435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.7013   -6.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 57  1  0  0  0  0
 57 52  1  0  0  0  0
 52 54  1  0  0  0  0
 54 53  2  0  0  0  0
 54 55  1  0  0  0  0
 57 56  1  1  0  0  0
 57 58  1  6  0  0  0
M  END

HMDB0001375
     RDKit          3D
3-Hydroxy-3-methylglutaryl-CoA
102104  0  0  0  0  0  0  0  0999 V2000
    1.7352   -2.2865    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2426   -1.1340   -0.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -1.3074   -1.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2730   -1.1692   -0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9212   -1.0791    0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888   -1.1242    0.2868 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.2897   -1.8889    1.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424   -1.8451   -1.2327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2139    0.4652    0.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5124    0.6058    1.2163 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.9675    1.1526    2.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2055   -0.8987    1.5688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6646    1.7101    0.6916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5005    1.1643   -0.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5398    2.1708   -0.7400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3157    1.5644   -1.6918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5543    1.2776   -1.1937 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.1062    0.0408   -1.6321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5702   -0.7862   -2.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3835   -1.8462   -2.6788 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4512   -1.7183   -1.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5822   -2.4670   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7600   -3.6993   -2.2767 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4953   -2.0460   -0.6982 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3007   -0.8677   -0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2051   -0.1359   -0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2544   -0.5023   -1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4461    1.3466    0.3331 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.6556    1.6871    0.9047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4152    2.4477    0.4603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.0997    3.6593    0.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8329    4.6253    1.7315 P   0  0  0  0  0  5  0  0  0  0  0  0
   -8.4289    6.0346    1.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2918    4.7268    2.5829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6939    3.9227    2.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273    0.2065    0.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0500    0.3085    1.3392 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1284    0.3509    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506    0.1884    1.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.6468   -0.9064 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3156    0.8385   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3009   -0.2239   -0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5673   -0.5797    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3108    0.2083    1.4819 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1424   -1.8736    0.8608 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3920   -2.1932    2.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3801   -1.3485    2.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0456   -1.4418    2.3987 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4472   -0.7870    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5878   -0.3197    0.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8700   -0.8294    0.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0373   -0.1785   -0.9437 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5185   -0.2584   -1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2707   -0.8438   -1.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6714    1.2816   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4921    2.0568    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2909    2.0258    1.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5270    2.8537   -0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -2.1260    1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8096   -2.4220    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241   -3.2001   -0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -0.4214   -2.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -2.2420   -2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8797   -1.4777   -1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216   -2.1518   -1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5946   -0.3596   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3499   -2.6879   -1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4853   -1.3785    0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9796    0.2262    0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8827    0.9234   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9971    3.0503   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2258    2.1366   -1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6496   -0.6883   -3.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7263   -3.8005   -3.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9359   -4.5610   -1.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0063   -0.4831    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0177    0.4087    0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6184    1.4997    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8386    2.3688    1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0078    4.9168    1.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1196    4.6012    3.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686    0.9930   -0.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6799   -0.1501    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698    0.7943   -1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689    1.7654   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5078    1.1730   -2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2875    0.1509   -1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0529   -1.1656   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3389   -2.5025    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7864   -3.2625    2.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4297   -2.1929    2.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3577   -1.7090    4.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0176   -0.2706    2.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2498   -1.8767    0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4501   -0.2898    1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0496    0.6255   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9654   -1.2192   -1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4779   -0.1542   -2.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7556   -1.6892   -2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8564    1.6921   -1.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6053    1.4608   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5925    3.8071   -0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 17 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
  2 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  2  0
 43 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  2  0
 49 51  1  0
 51 52  1  0
 52 53  1  0
 52 54  1  6
 52 55  1  0
 55 56  1  0
 56 57  2  0
 56 58  1  0
 30 15  1  0
 27 18  1  0
 27 21  1  0
  1 59  1  0
  1 60  1  0
  1 61  1  0
  3 62  1  0
  3 63  1  0
  3 64  1  0
  4 65  1  0
  4 66  1  0
  8 67  1  0
 12 68  1  0
 14 69  1  0
 14 70  1  0
 15 71  1  6
 17 72  1  6
 19 73  1  0
 23 74  1  0
 23 75  1  0
 25 76  1  0
 28 77  1  1
 29 78  1  0
 30 79  1  1
 34 80  1  0
 35 81  1  0
 36 82  1  6
 37 83  1  0
 40 84  1  0
 41 85  1  0
 41 86  1  0
 42 87  1  0
 42 88  1  0
 45 89  1  0
 46 90  1  0
 46 91  1  0
 47 92  1  0
 47 93  1  0
 51 94  1  0
 51 95  1  0
 53 96  1  0
 53 97  1  0
 53 98  1  0
 54 99  1  0
 55100  1  0
 55101  1  0
 58102  1  0
M  END


  Mrv1652309042000222D          

 58 60  0  0  1  0            999 V2000
   27.2588   -1.4900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.5913   -1.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0039   -2.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.9239   -1.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1788   -2.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.4888   -2.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5131   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2559   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7986   -5.9435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0842   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3697   -5.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -4.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0842   -4.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -3.4685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3981   -3.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1125   -3.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5415   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4145   -1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8270   -1.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2395   -1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1125   -2.2309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3980   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2559   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9059   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5559   -1.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -2.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -2.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0809   -1.8184    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.7308   -1.8184    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.1393   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -2.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8689   -3.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5189   -3.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -3.7671    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.6939   -4.5921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0434   -1.2351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6566   -1.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3790   -0.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3710   -1.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6566   -2.6121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1995   -0.5676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0855   -1.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3711   -3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0855   -2.6120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7999   -1.3745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9704   -5.5310    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.6849   -6.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6849   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3994   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8283   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5428   -6.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5428   -5.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2573   -5.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5263   -6.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1138   -5.9435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.7013   -6.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 57  1  0  0  0  0
 57 52  1  0  0  0  0
 52 54  1  0  0  0  0
 54 53  2  0  0  0  0
 54 55  1  0  0  0  0
 57 56  1  1  0  0  0
 57 58  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001375

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1

> <INCHI_KEY>
CABVTRNMFUVUDM-VRHQGPGLSA-N

> <FORMULA>
C27H44N7O20P3S

> <MOLECULAR_WEIGHT>
911.659

> <EXACT_MASS>
911.157467109

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
82.3702140669648

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-6.406678756765139

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.8977913368307053

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8207666712061181

> <JCHEM_PKA_STRONGEST_BASIC>
3.810786962925538

> <JCHEM_POLAR_SURFACE_AREA>
421.1599999999999

> <JCHEM_REFRACTIVITY>
193.70200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
HMG-CoA

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001375
     RDKit          3D
3-Hydroxy-3-methylglutaryl-CoA
102104  0  0  0  0  0  0  0  0999 V2000
    1.7352   -2.2865    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2426   -1.1340   -0.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -1.3074   -1.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2730   -1.1692   -0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9212   -1.0791    0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888   -1.1242    0.2868 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.2897   -1.8889    1.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424   -1.8451   -1.2327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2139    0.4652    0.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5124    0.6058    1.2163 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.9675    1.1526    2.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2055   -0.8987    1.5688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6646    1.7101    0.6916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5005    1.1643   -0.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5398    2.1708   -0.7400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3157    1.5644   -1.6918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5543    1.2776   -1.1937 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.1062    0.0408   -1.6321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5702   -0.7862   -2.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3835   -1.8462   -2.6788 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4512   -1.7183   -1.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5822   -2.4670   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7600   -3.6993   -2.2767 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4953   -2.0460   -0.6982 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3007   -0.8677   -0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2051   -0.1359   -0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2544   -0.5023   -1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4461    1.3466    0.3331 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.6556    1.6871    0.9047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4152    2.4477    0.4603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.0997    3.6593    0.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8329    4.6253    1.7315 P   0  0  0  0  0  5  0  0  0  0  0  0
   -8.4289    6.0346    1.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2918    4.7268    2.5829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6939    3.9227    2.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273    0.2065    0.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0500    0.3085    1.3392 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1284    0.3509    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506    0.1884    1.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.6468   -0.9064 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3156    0.8385   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3009   -0.2239   -0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5673   -0.5797    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3108    0.2083    1.4819 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1424   -1.8736    0.8608 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3920   -2.1932    2.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3801   -1.3485    2.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0456   -1.4418    2.3987 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4472   -0.7870    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5878   -0.3197    0.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8700   -0.8294    0.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0373   -0.1785   -0.9437 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5185   -0.2584   -1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2707   -0.8438   -1.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6714    1.2816   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4921    2.0568    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2909    2.0258    1.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5270    2.8537   -0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -2.1260    1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8096   -2.4220    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241   -3.2001   -0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -0.4214   -2.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5925    3.8071   -0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
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 58102  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      50.883  -2.781   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      49.637  -1.876   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      50.407  -4.246   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      48.391  -2.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      48.867  -4.246   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      51.312  -5.492   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      38.291 -10.325   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.678 -11.095   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      36.957 -11.095   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      35.624 -10.325   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      34.290 -11.095   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      37.010  -8.015   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.624  -8.785   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      37.010  -6.475   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      34.343  -6.475   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      35.677  -5.704   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.344  -4.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.240  -2.061   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.010  -3.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.780  -2.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.677  -4.164   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      34.343  -3.394   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      39.678  -3.394   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      42.758  -3.394   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      45.838  -3.394   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      41.218  -1.854   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      41.218  -4.934   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      44.297  -1.854   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      44.297  -4.934   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      41.218  -3.394   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      44.297  -3.394   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      46.927  -2.306   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      47.962  -5.492   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      46.422  -7.032   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      49.502  -7.032   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      47.962  -7.032   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      47.962  -8.572   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      52.348  -2.306   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      53.492  -3.336   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      52.974  -0.899   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      54.826  -2.566   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      53.492  -4.876   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      54.506  -1.060   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      56.160  -3.336   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      54.826  -5.646   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      56.160  -4.876   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      57.493  -2.566   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      41.011 -10.325   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      42.345 -12.635   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      42.345 -11.095   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      43.679 -10.325   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      46.346 -10.325   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      47.680 -12.635   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      47.680 -11.095   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      49.014 -10.325   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      45.782 -12.428   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      45.012 -11.095   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      44.242 -12.428   0.000  0.00  0.00           O+0
CONECT    1   38    2    3                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2   32    5                                                  
CONECT    5    3    4   33                                                  
CONECT    6    3                                                            
CONECT    7    9    8                                                       
CONECT    8    7   48                                                       
CONECT    9    7   10                                                       
CONECT   10    9   13   11                                                  
CONECT   11   10                                                            
CONECT   12   14   13                                                       
CONECT   13   10   12                                                       
CONECT   14   12   16                                                       
CONECT   15   16                                                            
CONECT   16   14   15   21                                                  
CONECT   17   19   23                                                       
CONECT   18   19                                                            
CONECT   19   17   18   21   20                                             
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21                                                            
CONECT   23   17   30                                                       
CONECT   24   30   31                                                       
CONECT   25   31   32                                                       
CONECT   26   30                                                            
CONECT   27   30                                                            
CONECT   28   31                                                            
CONECT   29   31                                                            
CONECT   30   23   24   26   27                                             
CONECT   31   24   25   28   29                                             
CONECT   32    4   25                                                       
CONECT   33    5   36                                                       
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   33   34   35   37                                             
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38   41   42                                                  
CONECT   40   38   43                                                       
CONECT   41   39   44   43                                                  
CONECT   42   39   45                                                       
CONECT   43   40   41                                                       
CONECT   44   41   46   47                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47   44                                                            
CONECT   48    8   50                                                       
CONECT   49   50                                                            
CONECT   50   48   49   51                                                  
CONECT   51   50   57                                                       
CONECT   52   57   54                                                       
CONECT   53   54                                                            
CONECT   54   52   53   55                                                  
CONECT   55   54                                                            
CONECT   56   57                                                            
CONECT   57   51   52   56   58                                             
CONECT   58   57                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

COMPND    HMDB0001375
HETATM    1  C1  UNL     1       1.735  -2.287   0.348  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.243  -1.134  -0.503  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.787  -1.307  -1.893  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.273  -1.169  -0.635  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.921  -1.079   0.571  1.00  0.00           O  
HETATM    6  P1  UNL     1      -2.589  -1.124   0.287  1.00  0.00           P  
HETATM    7  O2  UNL     1      -3.290  -1.889   1.375  1.00  0.00           O  
HETATM    8  O3  UNL     1      -2.842  -1.845  -1.233  1.00  0.00           O  
HETATM    9  O4  UNL     1      -3.214   0.465   0.167  1.00  0.00           O  
HETATM   10  P2  UNL     1      -4.512   0.606   1.216  1.00  0.00           P  
HETATM   11  O5  UNL     1      -3.968   1.153   2.539  1.00  0.00           O  
HETATM   12  O6  UNL     1      -5.206  -0.899   1.569  1.00  0.00           O  
HETATM   13  O7  UNL     1      -5.665   1.710   0.692  1.00  0.00           O  
HETATM   14  C5  UNL     1      -6.500   1.164  -0.284  1.00  0.00           C  
HETATM   15  C6  UNL     1      -7.540   2.171  -0.740  1.00  0.00           C  
HETATM   16  O8  UNL     1      -8.316   1.564  -1.692  1.00  0.00           O  
HETATM   17  C7  UNL     1      -9.554   1.278  -1.194  1.00  0.00           C  
HETATM   18  N1  UNL     1     -10.106   0.041  -1.632  1.00  0.00           N  
HETATM   19  C8  UNL     1      -9.570  -0.786  -2.537  1.00  0.00           C  
HETATM   20  N2  UNL     1     -10.384  -1.846  -2.679  1.00  0.00           N  
HETATM   21  C9  UNL     1     -11.451  -1.718  -1.871  1.00  0.00           C  
HETATM   22  C10 UNL     1     -12.582  -2.467  -1.593  1.00  0.00           C  
HETATM   23  N3  UNL     1     -12.760  -3.699  -2.277  1.00  0.00           N  
HETATM   24  N4  UNL     1     -13.495  -2.046  -0.698  1.00  0.00           N  
HETATM   25  C11 UNL     1     -13.301  -0.868  -0.060  1.00  0.00           C  
HETATM   26  N5  UNL     1     -12.205  -0.136  -0.324  1.00  0.00           N  
HETATM   27  C12 UNL     1     -11.254  -0.502  -1.209  1.00  0.00           C  
HETATM   28  C13 UNL     1      -9.446   1.347   0.333  1.00  0.00           C  
HETATM   29  O9  UNL     1     -10.656   1.687   0.905  1.00  0.00           O  
HETATM   30  C14 UNL     1      -8.415   2.448   0.460  1.00  0.00           C  
HETATM   31  O10 UNL     1      -9.100   3.659   0.372  1.00  0.00           O  
HETATM   32  P3  UNL     1      -8.833   4.625   1.732  1.00  0.00           P  
HETATM   33  O11 UNL     1      -8.429   6.035   1.361  1.00  0.00           O  
HETATM   34  O12 UNL     1     -10.292   4.727   2.583  1.00  0.00           O  
HETATM   35  O13 UNL     1      -7.694   3.923   2.769  1.00  0.00           O  
HETATM   36  C15 UNL     1       1.627   0.206   0.048  1.00  0.00           C  
HETATM   37  O14 UNL     1       1.050   0.309   1.339  1.00  0.00           O  
HETATM   38  C16 UNL     1       3.128   0.351   0.186  1.00  0.00           C  
HETATM   39  O15 UNL     1       3.551   0.188   1.336  1.00  0.00           O  
HETATM   40  N6  UNL     1       3.938   0.647  -0.906  1.00  0.00           N  
HETATM   41  C17 UNL     1       5.316   0.838  -1.118  1.00  0.00           C  
HETATM   42  C18 UNL     1       6.301  -0.224  -0.842  1.00  0.00           C  
HETATM   43  C19 UNL     1       6.567  -0.580   0.547  1.00  0.00           C  
HETATM   44  O16 UNL     1       6.311   0.208   1.482  1.00  0.00           O  
HETATM   45  N7  UNL     1       7.142  -1.874   0.861  1.00  0.00           N  
HETATM   46  C20 UNL     1       7.392  -2.193   2.230  1.00  0.00           C  
HETATM   47  C21 UNL     1       8.380  -1.348   2.956  1.00  0.00           C  
HETATM   48  S1  UNL     1      10.046  -1.442   2.399  1.00  0.00           S  
HETATM   49  C22 UNL     1      10.447  -0.787   0.813  1.00  0.00           C  
HETATM   50  O17 UNL     1       9.588  -0.320   0.107  1.00  0.00           O  
HETATM   51  C23 UNL     1      11.870  -0.829   0.379  1.00  0.00           C  
HETATM   52  C24 UNL     1      12.037  -0.179  -0.944  1.00  0.00           C  
HETATM   53  C25 UNL     1      13.519  -0.258  -1.393  1.00  0.00           C  
HETATM   54  O18 UNL     1      11.271  -0.844  -1.891  1.00  0.00           O  
HETATM   55  C26 UNL     1      11.671   1.282  -0.886  1.00  0.00           C  
HETATM   56  C27 UNL     1      12.492   2.057   0.076  1.00  0.00           C  
HETATM   57  O19 UNL     1      12.291   2.026   1.317  1.00  0.00           O  
HETATM   58  O20 UNL     1      13.527   2.854  -0.391  1.00  0.00           O  
HETATM   59  H1  UNL     1       1.609  -2.126   1.421  1.00  0.00           H  
HETATM   60  H2  UNL     1       2.810  -2.422   0.139  1.00  0.00           H  
HETATM   61  H3  UNL     1       1.224  -3.200  -0.029  1.00  0.00           H  
HETATM   62  H4  UNL     1       1.484  -0.421  -2.490  1.00  0.00           H  
HETATM   63  H5  UNL     1       1.317  -2.242  -2.361  1.00  0.00           H  
HETATM   64  H6  UNL     1       2.880  -1.478  -1.850  1.00  0.00           H  
HETATM   65  H7  UNL     1      -0.522  -2.152  -1.086  1.00  0.00           H  
HETATM   66  H8  UNL     1      -0.595  -0.360  -1.299  1.00  0.00           H  
HETATM   67  H9  UNL     1      -3.350  -2.688  -1.156  1.00  0.00           H  
HETATM   68  H10 UNL     1      -5.485  -1.378   0.751  1.00  0.00           H  
HETATM   69  H11 UNL     1      -6.980   0.226   0.055  1.00  0.00           H  
HETATM   70  H12 UNL     1      -5.883   0.923  -1.184  1.00  0.00           H  
HETATM   71  H13 UNL     1      -6.997   3.050  -1.107  1.00  0.00           H  
HETATM   72  H14 UNL     1     -10.226   2.137  -1.487  1.00  0.00           H  
HETATM   73  H15 UNL     1      -8.650  -0.688  -3.098  1.00  0.00           H  
HETATM   74  H16 UNL     1     -12.726  -3.800  -3.313  1.00  0.00           H  
HETATM   75  H17 UNL     1     -12.936  -4.561  -1.718  1.00  0.00           H  
HETATM   76  H18 UNL     1     -14.006  -0.483   0.670  1.00  0.00           H  
HETATM   77  H19 UNL     1      -9.018   0.409   0.736  1.00  0.00           H  
HETATM   78  H20 UNL     1     -10.618   1.500   1.875  1.00  0.00           H  
HETATM   79  H21 UNL     1      -7.839   2.369   1.407  1.00  0.00           H  
HETATM   80  H22 UNL     1     -11.008   4.917   1.896  1.00  0.00           H  
HETATM   81  H23 UNL     1      -7.120   4.601   3.207  1.00  0.00           H  
HETATM   82  H24 UNL     1       1.269   0.993  -0.620  1.00  0.00           H  
HETATM   83  H25 UNL     1       1.680  -0.150   1.947  1.00  0.00           H  
HETATM   84  H26 UNL     1       3.370   0.794  -1.868  1.00  0.00           H  
HETATM   85  H27 UNL     1       5.669   1.765  -0.542  1.00  0.00           H  
HETATM   86  H28 UNL     1       5.508   1.173  -2.196  1.00  0.00           H  
HETATM   87  H29 UNL     1       7.288   0.151  -1.294  1.00  0.00           H  
HETATM   88  H30 UNL     1       6.053  -1.166  -1.446  1.00  0.00           H  
HETATM   89  H31 UNL     1       7.339  -2.502   0.067  1.00  0.00           H  
HETATM   90  H32 UNL     1       7.786  -3.263   2.314  1.00  0.00           H  
HETATM   91  H33 UNL     1       6.430  -2.193   2.834  1.00  0.00           H  
HETATM   92  H34 UNL     1       8.358  -1.709   4.043  1.00  0.00           H  
HETATM   93  H35 UNL     1       8.018  -0.271   2.963  1.00  0.00           H  
HETATM   94  H36 UNL     1      12.250  -1.877   0.410  1.00  0.00           H  
HETATM   95  H37 UNL     1      12.450  -0.290   1.177  1.00  0.00           H  
HETATM   96  H38 UNL     1      14.050   0.625  -1.004  1.00  0.00           H  
HETATM   97  H39 UNL     1      13.965  -1.219  -1.112  1.00  0.00           H  
HETATM   98  H40 UNL     1      13.478  -0.154  -2.508  1.00  0.00           H  
HETATM   99  H41 UNL     1      11.756  -1.689  -2.156  1.00  0.00           H  
HETATM  100  H42 UNL     1      11.856   1.692  -1.928  1.00  0.00           H  
HETATM  101  H43 UNL     1      10.605   1.461  -0.712  1.00  0.00           H  
HETATM  102  H44 UNL     1      13.592   3.807  -0.001  1.00  0.00           H  
CONECT    1    2   59   60   61
CONECT    2    3    4   36
CONECT    3   62   63   64
CONECT    4    5   65   66
CONECT    5    6
CONECT    6    7    7    8    9
CONECT    8   67
CONECT    9   10
CONECT   10   11   11   12   13
CONECT   12   68
CONECT   13   14
CONECT   14   15   69   70
CONECT   15   16   30   71
CONECT   16   17
CONECT   17   18   28   72
CONECT   18   19   27
CONECT   19   20   20   73
CONECT   20   21
CONECT   21   22   22   27
CONECT   22   23   24
CONECT   23   74   75
CONECT   24   25   25
CONECT   25   26   76
CONECT   26   27   27
CONECT   28   29   30   77
CONECT   29   78
CONECT   30   31   79
CONECT   31   32
CONECT   32   33   33   34   35
CONECT   34   80
CONECT   35   81
CONECT   36   37   38   82
CONECT   37   83
CONECT   38   39   39   40
CONECT   40   41   84
CONECT   41   42   85   86
CONECT   42   43   87   88
CONECT   43   44   44   45
CONECT   45   46   89
CONECT   46   47   90   91
CONECT   47   48   92   93
CONECT   48   49
CONECT   49   50   50   51
CONECT   51   52   94   95
CONECT   52   53   54   55
CONECT   53   96   97   98
CONECT   54   99
CONECT   55   56  100  101
CONECT   56   57   57   58
CONECT   58  102
END

HMDB0001375
     RDKit          3D
3-Hydroxy-3-methylglutaryl-CoA
102104  0  0  0  0  0  0  0  0999 V2000
    1.7352   -2.2865    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2426   -1.1340   -0.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -1.3074   -1.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2730   -1.1692   -0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9212   -1.0791    0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888   -1.1242    0.2868 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.2897   -1.8889    1.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424   -1.8451   -1.2327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2139    0.4652    0.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5124    0.6058    1.2163 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.9675    1.1526    2.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2055   -0.8987    1.5688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6646    1.7101    0.6916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5005    1.1643   -0.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5398    2.1708   -0.7400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3157    1.5644   -1.6918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5543    1.2776   -1.1937 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.1062    0.0408   -1.6321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5702   -0.7862   -2.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3835   -1.8462   -2.6788 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4512   -1.7183   -1.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5822   -2.4670   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7600   -3.6993   -2.2767 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4953   -2.0460   -0.6982 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3007   -0.8677   -0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2051   -0.1359   -0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2544   -0.5023   -1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4461    1.3466    0.3331 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.6556    1.6871    0.9047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4152    2.4477    0.4603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.0997    3.6593    0.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8329    4.6253    1.7315 P   0  0  0  0  0  5  0  0  0  0  0  0
   -8.4289    6.0346    1.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2918    4.7268    2.5829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6939    3.9227    2.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273    0.2065    0.0478 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0500    0.3085    1.3392 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1284    0.3509    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506    0.1884    1.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.6468   -0.9064 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3156    0.8385   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3009   -0.2239   -0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5673   -0.5797    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3108    0.2083    1.4819 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1424   -1.8736    0.8608 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3920   -2.1932    2.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3801   -1.3485    2.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0456   -1.4418    2.3987 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4472   -0.7870    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5878   -0.3197    0.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8700   -0.8294    0.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0373   -0.1785   -0.9437 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5185   -0.2584   -1.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2707   -0.8438   -1.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6714    1.2816   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4921    2.0568    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2909    2.0258    1.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5270    2.8537   -0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -2.1260    1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8096   -2.4220    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241   -3.2001   -0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -0.4214   -2.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -2.2420   -2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8797   -1.4777   -1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216   -2.1518   -1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5946   -0.3596   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3499   -2.6879   -1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4853   -1.3785    0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9796    0.2262    0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8827    0.9234   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9971    3.0503   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2258    2.1366   -1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6496   -0.6883   -3.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7263   -3.8005   -3.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9359   -4.5610   -1.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0063   -0.4831    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0177    0.4087    0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6184    1.4997    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8386    2.3688    1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0078    4.9168    1.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1196    4.6012    3.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686    0.9930   -0.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6799   -0.1501    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698    0.7943   -1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689    1.7654   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5078    1.1730   -2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2875    0.1509   -1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0529   -1.1656   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3389   -2.5025    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7864   -3.2625    2.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4297   -2.1929    2.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3577   -1.7090    4.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0176   -0.2706    2.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2498   -1.8767    0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4501   -0.2898    1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0496    0.6255   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9654   -1.2192   -1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4779   -0.1542   -2.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7556   -1.6892   -2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8564    1.6921   -1.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6053    1.4608   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5925    3.8071   -0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 17 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
  2 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  2  0
 43 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  2  0
 49 51  1  0
 51 52  1  0
 52 53  1  0
 52 54  1  6
 52 55  1  0
 55 56  1  0
 56 57  2  0
 56 58  1  0
 30 15  1  0
 27 18  1  0
 27 21  1  0
  1 59  1  0
  1 60  1  0
  1 61  1  0
  3 62  1  0
  3 63  1  0
  3 64  1  0
  4 65  1  0
  4 66  1  0
  8 67  1  0
 12 68  1  0
 14 69  1  0
 14 70  1  0
 15 71  1  6
 17 72  1  6
 19 73  1  0
 23 74  1  0
 23 75  1  0
 25 76  1  0
 28 77  1  1
 29 78  1  0
 30 79  1  1
 34 80  1  0
 35 81  1  0
 36 82  1  6
 37 83  1  0
 40 84  1  0
 41 85  1  0
 41 86  1  0
 42 87  1  0
 42 88  1  0
 45 89  1  0
 46 90  1  0
 46 91  1  0
 47 92  1  0
 47 93  1  0
 51 94  1  0
 51 95  1  0
 53 96  1  0
 53 97  1  0
 53 98  1  0
 54 99  1  0
 55100  1  0
 55101  1  0
 58102  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3S)-3-Hydroxy-3-methylglutaryl-coenzyme A	ChEBI
(S)-3-Hydroxy-3-methylglutaryl-CoA	ChEBI
(S)-3-Hydroxy-3-methylglutaryl-coenzyme A	ChEBI
HMG-CoA	ChEBI
HMG-coenzyme A	ChEBI
Hydroxymethylglutaroyl coenzyme A	ChEBI
Hydroxymethylglutaryl-CoA	ChEBI
(3S)-3-Hydroxy-3-methylglutaryl-CoA	HMDB
(S)-3-Hydroxy-3-methylglutaryl coenzyme A	HMDB
3-Hydroxy-3-methylglutaryl CoA	HMDB
3-Hydroxy-3-methylglutaryl coenzyme A	HMDB
Hydroxymethylglutaryl CoA	HMDB
Hydroxymethylglutaryl coenzyme A	HMDB
beta-Hydroxy-beta-methylglutaryl CoA	HMDB
beta-Hydroxy-beta-methylglutaryl-CoA	HMDB
beta-Hydroxy-beta-methylglutaryl-coenzyme A	HMDB
Β-hydroxy-β-methylglutaryl CoA	HMDB
Β-hydroxy-β-methylglutaryl-CoA	HMDB
Β-hydroxy-β-methylglutaryl-coenzyme A	HMDB
3-Hydroxy-3-methylglutaryl-CoA	ChEBI, KEGG

Chemical Formula

C₂₇H₄₄N₇O₂₀P₃S

Average Molecular Weight

911.659

Monoisotopic Molecular Weight

911.157467109

IUPAC Name

(3S)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid

Traditional Name

HMG-CoA

CAS Registry Number

26926-09-0

SMILES

C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1

InChI Key

CABVTRNMFUVUDM-VRHQGPGLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (s)-3-hydroxy-3-alkylglutaryl coas. These are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

(S)-3-hydroxy-3-alkylglutaryl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Alkyl phosphate
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Fatty amide
Pyrimidine
Phosphoric acid ester
Tetrahydrofuran
Tertiary alcohol
Imidazole
Heteroaromatic compound
Azole
Secondary alcohol
Thiocarboxylic acid ester
Amino acid
Carboxamide group
Amino acid or derivatives
Carbothioic s-ester
Secondary carboxylic acid amide
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Azacycle
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organosulfur compound
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3-hydroxy fatty acyl-CoA (CHEBI:15467 )
3-hydroxy-3-methylglutaryl-CoA (CHEBI:15467 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0001375)
Intestine (HMDB: HMDB0001375)

Cellular substructure

Organelle

Mitochondria

Mitochondria (HMDB: HMDB0001375)

Endoplasmic reticulum (HMDB: HMDB0001375)

Biofluid or Excreta

Blood (HMDB: HMDB0001375)
Urine (HMDB: HMDB0001375)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0001375)

Fibroblasts (HMDB: HMDB0001375)

Organ

Gland

Endocrine gland

Adrenal gland (HMDB: HMDB0001375)
Adrenal gland (HMDB: HMDB0001375)

Intestine (HMDB: HMDB0001375)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001375)

Source

Endogenous

Endogenous (HMDB: HMDB0001375)

Animal

Animal (HMDB: HMDB0001375)

Exogenous

Food

Food (HMDB: HMDB0001375)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Butyrate Metabolism (HMDB: HMDB0001375)
Ketone Body Metabolism (HMDB: HMDB0001375)
Steroid Biosynthesis (HMDB: HMDB0001375)
Valine, Leucine, and Isoleucine Degradation (HMDB: HMDB0001375)
Steroid Biosynthesis (PathBank: SMP0002381)
Ketone Body Metabolism (PathBank: SMP0002383)
Terpenoid Backbone Biosynthesis (PathBank: SMP0002384)
Leucine Degradation (PathBank: SMP0002433)
Cholesterol Biosynthesis and Metabolism CE(14:0) (PathBank: SMP0002435)
Cholesterol Biosynthesis and Metabolism CE(10:0) (PathBank: SMP0002436)
Cholesterol Biosynthesis and Metabolism CE(12:0) (PathBank: SMP0002438)
Cholesterol Biosynthesis and Metabolism CE(16:0) (PathBank: SMP0002440)
Cholesterol Biosynthesis and Metabolism CE(18:0) (PathBank: SMP0002441)
Butanoate Metabolism (PathBank: SMP0012467)
Cholesterol Biosynthesis and Metabolism (PathBank: SMP0070041)
Mevalonate Pathway (PathBank: SMP0121055)

Alendronate Action Pathway (HMDB: HMDB0001375)

Disease pathway

beta-Ketothiolase Deficiency (PathBank: SMP0000173)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0000137)
Propionic Acidemia (PathBank: SMP0000236)
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency (PathBank: SMP0000138)
Maple Syrup Urine Disease (PathBank: SMP0000199)
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I (PathBank: SMP0000237)
3-Methylglutaconic Aciduria Type I (PathBank: SMP0000139)
3-Methylglutaconic Aciduria Type III (PathBank: SMP0000140)
Methylmalonate Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0000384)
Methylmalonic Aciduria (PathBank: SMP0000200)
Isovaleric Aciduria (PathBank: SMP0000238)
Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0000389)
CHILD Syndrome (PathBank: SMP0000387)
Desmosterolosis (PathBank: SMP0000386)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (PathBank: SMP0000388)
Lysosomal Acid Lipase Deficiency (Wolman Disease) (PathBank: SMP0000319)
3-Methylglutaconic Aciduria Type IV (PathBank: SMP0000141)
Hypercholesterolemia (PathBank: SMP0000209)
Cholesteryl Ester Storage Disease (PathBank: SMP0000508)
Hyper-IgD Syndrome (PathBank: SMP0000509)
Mevalonic Aciduria (PathBank: SMP0000510)
Wolman Disease (PathBank: SMP0000511)
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency (PathBank: SMP0000521)
3-Hydroxyisobutyric Aciduria (PathBank: SMP0000522)
Isobutyryl-CoA Dehydrogenase Deficiency (PathBank: SMP0000523)
Isovaleric Acidemia (PathBank: SMP0000524)
Succinyl CoA: 3-Ketoacid CoA Transferase Deficiency (PathBank: SMP0000569)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120439)

Drug action pathway

Ibandronate Action Pathway (PathBank: SMP0000079)
Simvastatin Action Pathway (PathBank: SMP0000082)
Pravastatin Action Pathway (PathBank: SMP0000089)
Rosuvastatin Action Pathway (PathBank: SMP0000092)
Alendronate Action Pathway (PathBank: SMP0000095)
Lovastatin Action Pathway (PathBank: SMP0000099)
Zoledronate Action Pathway (PathBank: SMP0000107)
Cerivastatin Action Pathway (PathBank: SMP0000111)
Risedronate Action Pathway (PathBank: SMP0000112)
Pamidronate Action Pathway (PathBank: SMP0000117)
Fluvastatin Action Pathway (PathBank: SMP0000119)
Atorvastatin Action Pathway (PathBank: SMP0000131)

Chemical reaction

Lipid peroxidation (HMDB: HMDB0001375)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0001375)

Cellular process

Cell signaling (HMDB: HMDB0001375)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0001375)
human metabolite (HMDB: HMDB0001375)

Nutrient

Nutrient (HMDB: HMDB0001375)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001375)

Emulsifier (HMDB: HMDB0001375)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.1 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	-6.4	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	3.81	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	421.16 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	193.7 m³·mol⁻¹	ChemAxon
Polarizability	82.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	193.115	30932474
DeepCCS	[M-H]-	191.29	30932474
DeepCCS	[M-2H]-	225.558	30932474
DeepCCS	[M+Na]+	200.189	30932474
AllCCS	[M+H]+	263.5	32859911
AllCCS	[M+H-H2O]+	264.1	32859911
AllCCS	[M+NH4]+	262.8	32859911
AllCCS	[M+Na]+	262.7	32859911
AllCCS	[M-H]-	265.9	32859911
AllCCS	[M+Na-2H]-	270.4	32859911
AllCCS	[M+HCOO]-	275.4	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 10V, Positive-QTOF	splash10-000l-0891000250-052d51ef28faa9ab5b73	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 20V, Positive-QTOF	splash10-000i-0971100000-dc16942c0a4531c8cb60	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 40V, Positive-QTOF	splash10-000i-1950000000-12dcb50a3caaf20a9aa5	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 10V, Negative-QTOF	splash10-00o4-4901031462-49fbf273ff8df18347bb	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 20V, Negative-QTOF	splash10-001i-3900110010-0be1f0212b5d814ea24c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 40V, Negative-QTOF	splash10-057i-6900100000-fffa063c59d4fcd54e7a	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 10V, Negative-QTOF	splash10-03dm-0000000094-b818de142848216a6af3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 20V, Negative-QTOF	splash10-0a4u-9500001521-8d0d8c41c4c284cc696f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 40V, Negative-QTOF	splash10-004m-9202503430-001456d7b42e54584702	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 10V, Positive-QTOF	splash10-03di-0000000169-47d0ed82d5acca38b9e0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 20V, Positive-QTOF	splash10-002r-1500000391-9d63a322b718612b8587	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-3-methylglutaryl-CoA 40V, Positive-QTOF	splash10-0a4i-0011900000-766a56d8ca4793434590	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria
Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Not Available

Tissue Locations

Adrenal Gland
Fibroblasts
Intestine

Pathways

Name	SMPDB/PathBank	KEGG
Butyrate Metabolism
Valine, leucine and isoleucine degradation	Not Available
Steroid Biosynthesis
Ketone Body Metabolism
Succinyl CoA: 3-ketoacid CoA transferase deficiency		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

3-HYDROXY-3-METHYL-GLUTARYL-COA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

445127

PDB ID

Not Available

ChEBI ID

15467

Food Biomarker Ontology

Not Available

VMH ID

HMGCOA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Williamson I P; Rodwell V W Isolation and purification of 3-hydroxy-3-methylglutaryl-coenzyme A by ion-exchange chromatography. Journal of lipid research (1981), 22(1), 184-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sato T, Oouchi M, Nagakubo H, Chiba T, Ogawa S, Sato C, Sugimura K, Fukuda M: Effect of pravastatin on plasma ketone bodies in diabetics with hypercholesterolemia. Tohoku J Exp Med. 1998 May;185(1):25-9. [PubMed:9710942 ]
Wysocki SJ, Wilkinson SP, Hahnel R, Wong CY, Panegyres PK: 3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria. Clin Chim Acta. 1976 Aug 2;70(3):399-406. [PubMed:947633 ]
Lange Y, Ye J, Steck TL: Activation of membrane cholesterol by displacement from phospholipids. J Biol Chem. 2005 Oct 28;280(43):36126-31. Epub 2005 Aug 29. [PubMed:16129675 ]
Li X, Liu L, Tupper JC, Bannerman DD, Winn RK, Sebti SM, Hamilton AD, Harlan JM: Inhibition of protein geranylgeranylation and RhoA/RhoA kinase pathway induces apoptosis in human endothelial cells. J Biol Chem. 2002 May 3;277(18):15309-16. Epub 2002 Feb 11. [PubMed:11839765 ]
Mital BK, Garg SK: Anticarcinogenic, hypocholesterolemic, and antagonistic activities of Lactobacillus acidophilus. Crit Rev Microbiol. 1995;21(3):175-214. [PubMed:8845062 ]
Nozaki S, Nakagawa T, Nakata A, Yamashita S, Kameda-Takemura K, Nakamura T, Keno Y, Tokunaga K, Matsuzawa Y: Effects of pravastatin on plasma and urinary mevalonate concentrations in subjects with familial hypercholesterolaemia: a comparison of morning and evening administration. Eur J Clin Pharmacol. 1996;49(5):361-4. [PubMed:8866629 ]
Ubels FL, Muntinga JH, van Doormaal JJ, Reitsma WD, Smit AJ: Effects of initial and long-term lipid-lowering therapy on vascular wall characteristics. Atherosclerosis. 2001 Jan;154(1):155-61. [PubMed:11137095 ]
Huang L, Wang Y, Grimm S: ATP-dependent transport of rosuvastatin in membrane vesicles expressing breast cancer resistance protein. Drug Metab Dispos. 2006 May;34(5):738-42. Epub 2006 Jan 13. [PubMed:16415124 ]
Son BK, Kozaki K, Iijima K, Eto M, Kojima T, Ota H, Senda Y, Maemura K, Nakano T, Akishita M, Ouchi Y: Statins protect human aortic smooth muscle cells from inorganic phosphate-induced calcification by restoring Gas6-Axl survival pathway. Circ Res. 2006 Apr 28;98(8):1024-31. Epub 2006 Mar 23. [PubMed:16556867 ]
Gianni L, Di Padova F, Zuin M, Podda M: Bile acid-induced inhibition of the lymphoproliferative response to phytohemagglutinin and pokeweed mitogen: an in vitro study. Gastroenterology. 1980 Feb;78(2):231-5. [PubMed:7350045 ]
Jenke HS, Lowel M, Berndt J: Effect of alterations in vitro and in vivo of the cholesterol content in rat liver microsomes on the activity of 3-hydroxy-3-methylglutaryl-CoA reductase. Hoppe Seylers Z Physiol Chem. 1983 Feb;364(2):135-40. [PubMed:6840702 ]
Naseem SM, Heald FP: Sex mediated lipid metabolism in human aortic smooth muscle cells. Biochem Biophys Res Commun. 1987 Apr 14;144(1):284-91. [PubMed:3579907 ]
Knight BL, Patel DD, Soutar AK: The regulation of 3-hydroxy-3-methylglutaryl-CoA reductase activity, cholesterol esterification and the expression of low-density lipoprotein receptors in cultured monocyte-derived macrophages. Biochem J. 1983 Feb 15;210(2):523-32. [PubMed:6305342 ]
Martin J, Denver R, Bailey M, Krum H: In vitro inhibitory effects of atorvastatin on cardiac fibroblasts: implications for ventricular remodelling. Clin Exp Pharmacol Physiol. 2005 Sep;32(9):697-701. [PubMed:16173924 ]
Plotkin D, Miller S, Nakajima S, Peskin E, Burkman R, Richardson D, Mitchel Y, Waldstreicher J, Liu M, Shapiro D, Santoro N: Lowering low density lipoprotein cholesterol with simvastatin, a hydroxy-3-methylglutaryl-coenzyme a reductase inhibitor, does not affect luteal function in premenopausal women. J Clin Endocrinol Metab. 2002 Jul;87(7):3155-61. [PubMed:12107216 ]
Gil G, Smith JR, Goldstein JL, Brown MS: Optional exon in the 5'-untranslated region of 3-hydroxy-3-methylglutaryl coenzyme A synthase gene: conserved sequence and splicing pattern in humans and hamsters. Proc Natl Acad Sci U S A. 1987 Apr;84(7):1863-6. [PubMed:3470763 ]
Freeman MR, Solomon KR: Cholesterol and prostate cancer. J Cell Biochem. 2004 Jan 1;91(1):54-69. [PubMed:14689582 ]

Enzymes

Enzyme Details

1. Hydroxymethylglutaryl-CoA lyase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Key enzyme in ketogenesis (ketone body formation). Terminal step in leucine catabolism.
Gene Name:: HMGCL
Uniprot ID:: P35914
Molecular weight:: 34359.84

Reactions

3-Hydroxy-3-methylglutaryl-CoA → Acetyl-CoA + Acetoacetic acid	details

Enzyme Details

2. Hydroxymethylglutaryl-CoA synthase, mitochondrial

General function:: Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:: This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:: HMGCS2
Uniprot ID:: P54868
Molecular weight:: 52481.065

Reactions

Acetyl-CoA + Water + Acetoacetyl-CoA → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A	details
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A → Acetyl-CoA + Water + Acetoacetyl-CoA	details

Enzyme Details

3. Hydroxymethylglutaryl-CoA synthase, cytoplasmic

General function:: Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:: This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:: HMGCS1
Uniprot ID:: Q01581
Molecular weight:: 57293.105

Reactions

Acetyl-CoA + Water + Acetoacetyl-CoA → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A	details
3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A → Acetyl-CoA + Water + Acetoacetyl-CoA	details

Enzyme Details

4. 3-hydroxy-3-methylglutaryl-coenzyme A reductase

General function:: Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:: Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:: HMGCR
Uniprot ID:: P04035
Molecular weight:: 97475.155

Reactions

Mevalonic acid + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPH	details
Mevalonic acid + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPH + Hydrogen Ion	details

Enzyme Details

5. Methylglutaconyl-CoA hydratase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of 3-methylglutaconyl-CoA to 3-hydroxy-3-methylglutaryl-CoA. Has very low enoyl-CoA hydratase activity. Was originally identified as RNA-binding protein that binds in vitro to clustered 5'-AUUUA-3' motifs.
Gene Name:: AUH
Uniprot ID:: Q13825
Molecular weight:: 35608.18

Reactions

3-Hydroxy-3-methylglutaryl-CoA → 3-Methylglutaconyl-CoA + Water	details
3-Hydroxy-3-methylglutaryl-CoA → 3-Methylglutaconyl-CoA + Water	details

Enzyme Details

6. 3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic

General function:: Involved in catalytic activity
Specific function:: Non-mitochondrial 3-hydroxymethyl-3-methylglutaryl-CoA lyase that catalyzes a cation-dependent cleavage of (S)-3-hydroxy-3-methylglutaryl-CoA into acetyl-CoA and acetoacetate, a key step in ketogenesis, the products of which support energy production in nonhepatic animal tissues.
Gene Name:: HMGCLL1
Uniprot ID:: Q8TB92
Molecular weight:: 36327.465

Reactions

3-Hydroxy-3-methylglutaryl-CoA → Acetyl-CoA + Acetoacetic acid	details

Showing metabocard for 3-Hydroxy-3-methylglutaryl-CoA (HMDB0001375)

MOL for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

3D MOL for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

3D SDF for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

3D-SDF for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

PDB for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

3D PDB for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

SMILES for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

INCHI for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

Structure for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

3D Structure for HMDB0001375 (3-Hydroxy-3-methylglutaryl-CoA)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra

NMR Spectra

Enzymes

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