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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (113)transporters (1) Show 114 proteins XML

enzymes (113)transporters (1) Show 114 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 07:55:12 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0003949

Secondary Accession Numbers

HMDB03949

Metabolite Identification

Common Name

(2E)-Octenoyl-CoA

Description

(2E)-Octenoyl-CoA is the main metabolite produced in medium-chain acyl-CoA dehydrogenase (EC 1.3.99.3, MCAD) deficiency; however the product of the enzymatic reaction is not directly detected in several methods for screening of inborn errors of fatty acid oxidation. In order to aid the timely follow-up of screening results that suggest abnormalities in MCAD, rapid and simple confirmatory tests for the enzyme activity and/or gene mutation analysis should be available. Medium-chain fatty acyl-CoA dehydrogenase (MCAD) catalyzes the conversion of different chain length fatty acyl- CoAs into their corresponding trans-enoyl-CoA moieties via two consecutive sequences of steps. The first step involves the concerted abstraction of a proton and a hydride ion from the a- and 8-carbon chains of the fatty acyl-CoA substrates, concomitant with the reduction of the enzyme (E)-bound FAD to FADH2. The reoxidation of EFADH2, to propagate further rounds of catalysis, is accomplished via transfer of electrons to a variety of organic electron acceptors; the natural electron acceptor for this process, under physiological conditions, is the electron-transferring flavoprotein. Of the different chain length fatty acyl-CoA substrates, octanoyl-CoA/octenoyl-CoA have been known as the most efficient (and physiological) substrates for the medium-chain fatty acyl-CoA dehydrogenase (MCAD)-catalyzed reaction. (PMID: 16046200 , 1390638 , 8038175 ).

Structure

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


  Mrv0541 02231219502D          

 57 59  0  0  1  0            999 V2000
   30.2736  -11.9719    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9964  -11.6406    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.5708  -12.6633    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.9921  -12.5165    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.4796  -14.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4433  -12.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3858  -13.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9024  -13.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5495  -11.0284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3842  -11.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2390  -12.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6085  -12.1937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7453  -12.8533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0545  -13.3317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0870  -11.9951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0046  -13.8639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3290  -11.7633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6552  -13.2696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5032  -11.7389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3460  -11.4450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1116  -13.1294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4383  -15.1569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4383  -16.4847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9431  -14.9957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2286  -16.2333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9431  -17.4708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3412  -12.8964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1839  -12.6025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6968  -13.0377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2108  -13.7043    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4810  -13.2941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.6945  -14.3727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.1493  -12.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6576  -15.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9197  -15.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6576  -16.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1666  -12.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9431  -16.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9197  -13.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4135  -12.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5035  -11.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8297  -13.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2286  -15.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5880  -12.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0094  -12.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7625  -12.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4308  -12.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8522  -12.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5378  -11.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8695  -12.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6053  -12.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2909  -11.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1164  -11.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9592  -11.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4481  -12.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6950  -11.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0267  -12.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 51  1  0  0  0  0
  1 57  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 12  2  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  2  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
 29  6  1  6  0  0  0
 30  7  1  6  0  0  0
  8 33  1  0  0  0  0
 13 40  1  0  0  0  0
 16 39  1  0  0  0  0
 19 44  2  0  0  0  0
 20 47  2  0  0  0  0
 21 57  2  0  0  0  0
 32 22  1  1  0  0  0
 22 34  1  0  0  0  0
 22 35  1  0  0  0  0
 23 35  2  0  0  0  0
 23 36  1  0  0  0  0
 24 34  1  0  0  0  0
 24 43  2  0  0  0  0
 25 38  2  0  0  0  0
 25 43  1  0  0  0  0
 26 38  1  0  0  0  0
 27 44  1  0  0  0  0
 27 45  1  0  0  0  0
 28 47  1  0  0  0  0
 28 48  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  1  0  0  0
 34 36  2  0  0  0  0
 36 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 37 41  1  0  0  0  0
 37 42  1  0  0  0  0
 39 44  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 51  1  0  0  0  0
 49 50  1  0  0  0  0
 49 52  1  0  0  0  0
 50 53  1  0  0  0  0
 52 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
M  END

HMDB0003949
     RDKit          3D
(2E)-Octenoyl-CoA
105107  0  0  0  0  0  0  0  0999 V2000
   14.2419    2.0268   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4909    1.0628    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3834   -0.0385    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4475   -0.8277   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7543   -2.1871   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4131   -2.3574   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5262   -1.6031    0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2111   -2.0429    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6602   -3.0037    0.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3881   -0.7948    1.7470 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1617    0.0155    0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0683   -0.8165    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3421   -0.2256   -0.7445 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467    1.0913   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1967    1.9811   -0.0040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625    1.3307   -1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390    1.5371   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    0.5857    0.0100 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -0.4285    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006   -0.5418    2.0002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571   -1.2878    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -1.1819   -1.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -1.0594    0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5178    0.4343    1.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633   -1.9402    2.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930   -1.2165   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -0.9843    0.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562   -1.4306   -1.2326 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.3004   -2.6961   -0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5794   -1.7536   -2.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6324   -0.2891   -1.6849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983    1.2961   -1.3891 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.8966    2.0577   -2.5567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    1.6766   -1.5531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9551    1.9100   -0.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7761    0.8363    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2095    1.1523    0.2611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8061   -0.1025    0.0581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1454    0.1970    0.3831 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.9925   -0.9083    0.1376 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6939   -2.1776    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7651   -2.9690   -0.2094 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8440   -2.1412   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1155   -2.3160   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8425   -3.5578   -0.6352 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0015   -1.2687   -0.5282 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5237   -0.0441   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2113    0.1128   -0.0539 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3365   -0.8464   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9481    0.7357    1.7594 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.0809    1.3189    2.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8415    1.7590    1.4498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5815    2.9069    1.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5979    4.2230    0.7026 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.2883    4.1917    1.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4425    4.2469   -1.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4248    5.6518    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413    2.9958   -0.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2404    2.2744   -0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6029    1.7138   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.4877    0.5015    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5268    1.5300    1.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2894   -0.4386    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4771    0.7369    0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2034   -0.2458   -1.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5409   -1.1586   -0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2665   -2.5307    0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2875   -2.9358   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9521   -3.3546   -0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9320   -0.6510    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258    0.7137    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4508    0.7989    0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3121   -1.1512    1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4388   -1.8420   -0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1693   -0.8234   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6078    0.3630   -2.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8589    2.1748   -2.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    2.5543   -0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878    1.7080   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935    0.9569    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2979   -2.3712    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9971   -0.3144   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3412    0.5945    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5464    1.1101    0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    0.4743    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -1.5258    2.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -2.1107    2.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747   -2.9566    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1384   -2.1258   -0.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347   -0.3743   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -2.7645   -2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    2.6270   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4288   -0.1244   -0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081    0.7331    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4260    1.7536   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3863    1.0544   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6616   -2.5780   -0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4632   -3.8939    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6288   -4.1192   -1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0919    0.8731   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
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 52103  1  1
 56104  1  0
 57105  1  0
M  END


  Mrv0541 02231219502D          

 57 59  0  0  1  0            999 V2000
   30.2736  -11.9719    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9964  -11.6406    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   20.9921  -12.5165    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.4796  -14.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4433  -12.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3858  -13.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9024  -13.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5495  -11.0284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3842  -11.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2390  -12.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   26.0094  -12.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7625  -12.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.5378  -11.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 51  1  0  0  0  0
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  3  8  1  0  0  0  0
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 29  6  1  6  0  0  0
 30  7  1  6  0  0  0
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 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  1  0  0  0
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 36 38  1  0  0  0  0
 37 39  1  0  0  0  0
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 37 41  1  0  0  0  0
 37 42  1  0  0  0  0
 39 44  1  0  0  0  0
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 49 50  1  0  0  0  0
 49 52  1  0  0  0  0
 50 53  1  0  0  0  0
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 53 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003949

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(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/C29H48N7O17P3S/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36/h8-9,16-18,22-24,28,39-40H,4-7,10-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/b9-8+/t18-,22-,23-,24?,28-/m1/s1

> <INCHI_KEY>
CPSDNAXXKWVYIY-DPSCIZRPSA-N

> <FORMULA>
C29H48N7O17P3S

> <MOLECULAR_WEIGHT>
891.714

> <EXACT_MASS>
891.204023371

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
81.25813279649333

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E)-oct-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
-3.820674874966354

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.67877117985815

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252479627216065

> <JCHEM_PKA_STRONGEST_BASIC>
4.946047024039826

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999999

> <JCHEM_REFRACTIVITY>
200.93320000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E)-oct-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003949
     RDKit          3D
(2E)-Octenoyl-CoA
105107  0  0  0  0  0  0  0  0999 V2000
   14.2419    2.0268   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4909    1.0628    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3834   -0.0385    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4475   -0.8277   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7543   -2.1871   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4131   -2.3574   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5262   -1.6031    0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2111   -2.0429    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6602   -3.0037    0.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3881   -0.7948    1.7470 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1617    0.0155    0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0683   -0.8165    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3421   -0.2256   -0.7445 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467    1.0913   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1967    1.9811   -0.0040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625    1.3307   -1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390    1.5371   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    0.5857    0.0100 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -0.4285    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006   -0.5418    2.0002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571   -1.2878    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -1.1819   -1.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -1.0594    0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5178    0.4343    1.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633   -1.9402    2.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.1454    0.1970    0.3831 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.9925   -0.9083    0.1376 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6939   -2.1776    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7651   -2.9690   -0.2094 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8440   -2.1412   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1155   -2.3160   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -14.0015   -1.2687   -0.5282 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5237   -0.0441   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2113    0.1128   -0.0539 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3365   -0.8464   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9481    0.7357    1.7594 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.0809    1.3189    2.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8415    1.7590    1.4498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5815    2.9069    1.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5979    4.2230    0.7026 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.2883    4.1917    1.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4248    5.6518    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.2404    2.2744   -0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6029    1.7138   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.4877    0.5015    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2547    5.6605    0.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      56.511 -22.348   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0      31.727 -21.729   0.000  0.00  0.00           P+0
HETATM    3  P   UNK     0      36.532 -23.638   0.000  0.00  0.00           P+0
HETATM    4  P   UNK     0      39.185 -23.364   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      32.629 -26.356   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      30.694 -22.872   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      28.720 -25.579   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      35.284 -24.541   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      32.759 -20.586   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      30.584 -20.696   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      37.779 -22.735   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      32.869 -22.762   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      40.591 -23.993   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      37.435 -24.886   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      35.629 -22.391   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      44.809 -25.879   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      39.814 -21.958   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      38.556 -24.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      45.739 -21.913   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      51.046 -21.364   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      58.075 -24.508   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      30.685 -28.293   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      30.685 -30.771   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      27.894 -27.992   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      26.560 -30.302   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      27.894 -32.612   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      47.304 -24.073   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      52.610 -23.525   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      31.167 -24.337   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.260 -25.581   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      32.631 -24.816   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      31.163 -26.829   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      33.879 -23.913   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      29.228 -28.762   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      31.583 -29.532   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      29.228 -30.302   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      43.244 -23.719   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      27.894 -31.072   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      44.650 -24.347   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      41.839 -23.090   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      43.873 -22.313   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      42.615 -25.125   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      26.560 -28.762   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      45.898 -23.445   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      48.551 -23.170   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      49.957 -23.799   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      51.204 -22.896   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      53.857 -22.622   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      64.471 -21.525   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      63.223 -22.428   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      55.263 -23.251   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      65.876 -22.154   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      61.817 -21.799   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      67.124 -21.251   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      60.570 -22.702   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      59.164 -22.073   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      57.917 -22.976   0.000  0.00  0.00           C+0
CONECT    1   51   57                                                       
CONECT    2    6    9   10   12                                             
CONECT    3    8   11   14   15                                             
CONECT    4   11   13   17   18                                             
CONECT    5   31   32                                                       
CONECT    6    2   29                                                       
CONECT    7   30                                                            
CONECT    8    3   33                                                       
CONECT    9    2                                                            
CONECT   10    2                                                            
CONECT   11    3    4                                                       
CONECT   12    2                                                            
CONECT   13    4   40                                                       
CONECT   14    3                                                            
CONECT   15    3                                                            
CONECT   16   39                                                            
CONECT   17    4                                                            
CONECT   18    4                                                            
CONECT   19   44                                                            
CONECT   20   47                                                            
CONECT   21   57                                                            
CONECT   22   32   34   35                                                  
CONECT   23   35   36                                                       
CONECT   24   34   43                                                       
CONECT   25   38   43                                                       
CONECT   26   38                                                            
CONECT   27   44   45                                                       
CONECT   28   47   48                                                       
CONECT   29    6   30   31                                                  
CONECT   30    7   29   32                                                  
CONECT   31    5   29   33                                                  
CONECT   32    5   22   30                                                  
CONECT   33    8   31                                                       
CONECT   34   22   24   36                                                  
CONECT   35   22   23                                                       
CONECT   36   23   34   38                                                  
CONECT   37   39   40   41   42                                             
CONECT   38   25   26   36                                                  
CONECT   39   16   37   44                                                  
CONECT   40   13   37                                                       
CONECT   41   37                                                            
CONECT   42   37                                                            
CONECT   43   24   25                                                       
CONECT   44   19   27   39                                                  
CONECT   45   27   46                                                       
CONECT   46   45   47                                                       
CONECT   47   20   28   46                                                  
CONECT   48   28   51                                                       
CONECT   49   50   52                                                       
CONECT   50   49   53                                                       
CONECT   51    1   48                                                       
CONECT   52   49   54                                                       
CONECT   53   50   55                                                       
CONECT   54   52                                                            
CONECT   55   53   56                                                       
CONECT   56   55   57                                                       
CONECT   57    1   21   56                                                  
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

COMPND    HMDB0003949
HETATM    1  C1  UNL     1      14.242   2.027  -0.505  1.00  0.00           C  
HETATM    2  C2  UNL     1      14.491   1.063   0.594  1.00  0.00           C  
HETATM    3  C3  UNL     1      13.383  -0.039   0.565  1.00  0.00           C  
HETATM    4  C4  UNL     1      13.447  -0.828  -0.670  1.00  0.00           C  
HETATM    5  C5  UNL     1      12.754  -2.187  -0.640  1.00  0.00           C  
HETATM    6  C6  UNL     1      11.413  -2.357  -0.273  1.00  0.00           C  
HETATM    7  C7  UNL     1      10.526  -1.603   0.371  1.00  0.00           C  
HETATM    8  C8  UNL     1       9.211  -2.043   0.600  1.00  0.00           C  
HETATM    9  O1  UNL     1       8.660  -3.004   0.188  1.00  0.00           O  
HETATM   10  S1  UNL     1       8.388  -0.795   1.747  1.00  0.00           S  
HETATM   11  C9  UNL     1       7.162   0.015   0.776  1.00  0.00           C  
HETATM   12  C10 UNL     1       6.068  -0.816   0.256  1.00  0.00           C  
HETATM   13  N1  UNL     1       5.342  -0.226  -0.744  1.00  0.00           N  
HETATM   14  C11 UNL     1       4.847   1.091  -0.779  1.00  0.00           C  
HETATM   15  O2  UNL     1       5.197   1.981  -0.004  1.00  0.00           O  
HETATM   16  C12 UNL     1       3.762   1.331  -1.804  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.539   1.537  -0.818  1.00  0.00           C  
HETATM   18  N2  UNL     1       2.276   0.586   0.010  1.00  0.00           N  
HETATM   19  C14 UNL     1       2.132  -0.429   1.037  1.00  0.00           C  
HETATM   20  O3  UNL     1       2.701  -0.542   2.000  1.00  0.00           O  
HETATM   21  C15 UNL     1       0.957  -1.288   0.350  1.00  0.00           C  
HETATM   22  O4  UNL     1       1.036  -1.182  -1.028  1.00  0.00           O  
HETATM   23  C16 UNL     1      -0.318  -1.059   0.955  1.00  0.00           C  
HETATM   24  C17 UNL     1      -0.518   0.434   1.232  1.00  0.00           C  
HETATM   25  C18 UNL     1      -0.663  -1.940   2.010  1.00  0.00           C  
HETATM   26  C19 UNL     1      -1.293  -1.216  -0.292  1.00  0.00           C  
HETATM   27  O5  UNL     1      -2.583  -0.984   0.093  1.00  0.00           O  
HETATM   28  P1  UNL     1      -3.556  -1.431  -1.233  1.00  0.00           P  
HETATM   29  O6  UNL     1      -4.300  -2.696  -0.818  1.00  0.00           O  
HETATM   30  O7  UNL     1      -2.579  -1.754  -2.612  1.00  0.00           O  
HETATM   31  O8  UNL     1      -4.632  -0.289  -1.685  1.00  0.00           O  
HETATM   32  P2  UNL     1      -4.098   1.296  -1.389  1.00  0.00           P  
HETATM   33  O9  UNL     1      -4.897   2.058  -2.557  1.00  0.00           O  
HETATM   34  O10 UNL     1      -2.560   1.677  -1.553  1.00  0.00           O  
HETATM   35  O11 UNL     1      -4.955   1.910  -0.016  1.00  0.00           O  
HETATM   36  C20 UNL     1      -5.776   0.836   0.300  1.00  0.00           C  
HETATM   37  C21 UNL     1      -7.209   1.152   0.261  1.00  0.00           C  
HETATM   38  O12 UNL     1      -7.806  -0.103   0.058  1.00  0.00           O  
HETATM   39  C22 UNL     1      -9.145   0.197   0.383  1.00  0.00           C  
HETATM   40  N3  UNL     1      -9.992  -0.908   0.138  1.00  0.00           N  
HETATM   41  C23 UNL     1      -9.694  -2.178   0.003  1.00  0.00           C  
HETATM   42  N4  UNL     1     -10.765  -2.969  -0.209  1.00  0.00           N  
HETATM   43  C24 UNL     1     -11.844  -2.141  -0.236  1.00  0.00           C  
HETATM   44  C25 UNL     1     -13.115  -2.316  -0.465  1.00  0.00           C  
HETATM   45  N5  UNL     1     -13.843  -3.558  -0.635  1.00  0.00           N  
HETATM   46  N6  UNL     1     -14.002  -1.269  -0.528  1.00  0.00           N  
HETATM   47  C26 UNL     1     -13.524  -0.044  -0.313  1.00  0.00           C  
HETATM   48  N7  UNL     1     -12.211   0.113  -0.054  1.00  0.00           N  
HETATM   49  C27 UNL     1     -11.337  -0.846  -0.012  1.00  0.00           C  
HETATM   50  C28 UNL     1      -8.948   0.736   1.759  1.00  0.00           C  
HETATM   51  O13 UNL     1     -10.081   1.319   2.205  1.00  0.00           O  
HETATM   52  C29 UNL     1      -7.841   1.759   1.450  1.00  0.00           C  
HETATM   53  O14 UNL     1      -8.581   2.907   1.049  1.00  0.00           O  
HETATM   54  P3  UNL     1      -7.598   4.223   0.703  1.00  0.00           P  
HETATM   55  O15 UNL     1      -6.288   4.192   1.410  1.00  0.00           O  
HETATM   56  O16 UNL     1      -7.443   4.247  -1.010  1.00  0.00           O  
HETATM   57  O17 UNL     1      -8.425   5.652   1.085  1.00  0.00           O  
HETATM   58  H1  UNL     1      13.841   2.996  -0.084  1.00  0.00           H  
HETATM   59  H2  UNL     1      15.240   2.274  -0.966  1.00  0.00           H  
HETATM   60  H3  UNL     1      13.603   1.714  -1.327  1.00  0.00           H  
HETATM   61  H4  UNL     1      15.488   0.502   0.407  1.00  0.00           H  
HETATM   62  H5  UNL     1      14.527   1.530   1.545  1.00  0.00           H  
HETATM   63  H6  UNL     1      13.289  -0.439   1.517  1.00  0.00           H  
HETATM   64  H7  UNL     1      12.477   0.737   0.484  1.00  0.00           H  
HETATM   65  H8  UNL     1      13.203  -0.246  -1.605  1.00  0.00           H  
HETATM   66  H9  UNL     1      14.541  -1.159  -0.828  1.00  0.00           H  
HETATM   67  H10 UNL     1      13.267  -2.531   0.475  1.00  0.00           H  
HETATM   68  H11 UNL     1      13.288  -2.936  -1.235  1.00  0.00           H  
HETATM   69  H12 UNL     1      10.952  -3.355  -0.615  1.00  0.00           H  
HETATM   70  H13 UNL     1      10.932  -0.651   0.654  1.00  0.00           H  
HETATM   71  H14 UNL     1       6.626   0.714   1.625  1.00  0.00           H  
HETATM   72  H15 UNL     1       7.451   0.799   0.069  1.00  0.00           H  
HETATM   73  H16 UNL     1       5.312  -1.151   1.079  1.00  0.00           H  
HETATM   74  H17 UNL     1       6.439  -1.842  -0.048  1.00  0.00           H  
HETATM   75  H18 UNL     1       5.169  -0.823  -1.630  1.00  0.00           H  
HETATM   76  H19 UNL     1       3.608   0.363  -2.348  1.00  0.00           H  
HETATM   77  H20 UNL     1       3.859   2.175  -2.365  1.00  0.00           H  
HETATM   78  H21 UNL     1       2.749   2.554  -0.458  1.00  0.00           H  
HETATM   79  H22 UNL     1       1.688   1.708  -1.637  1.00  0.00           H  
HETATM   80  H23 UNL     1       3.493   0.957   0.811  1.00  0.00           H  
HETATM   81  H24 UNL     1       1.298  -2.371   0.554  1.00  0.00           H  
HETATM   82  H25 UNL     1       0.997  -0.314  -1.436  1.00  0.00           H  
HETATM   83  H26 UNL     1       0.341   0.595   1.990  1.00  0.00           H  
HETATM   84  H27 UNL     1      -0.546   1.110   0.411  1.00  0.00           H  
HETATM   85  H28 UNL     1      -1.405   0.474   1.879  1.00  0.00           H  
HETATM   86  H29 UNL     1      -1.298  -1.526   2.800  1.00  0.00           H  
HETATM   87  H30 UNL     1       0.346  -2.111   2.563  1.00  0.00           H  
HETATM   88  H31 UNL     1      -0.975  -2.957   1.641  1.00  0.00           H  
HETATM   89  H32 UNL     1      -1.138  -2.126  -0.804  1.00  0.00           H  
HETATM   90  H33 UNL     1      -0.935  -0.374  -1.021  1.00  0.00           H  
HETATM   91  H34 UNL     1      -2.479  -2.764  -2.716  1.00  0.00           H  
HETATM   92  H35 UNL     1      -2.439   2.627  -1.723  1.00  0.00           H  
HETATM   93  H36 UNL     1      -5.429  -0.124  -0.061  1.00  0.00           H  
HETATM   94  H37 UNL     1      -5.508   0.733   1.502  1.00  0.00           H  
HETATM   95  H38 UNL     1      -7.426   1.754  -0.680  1.00  0.00           H  
HETATM   96  H39 UNL     1      -9.386   1.054  -0.307  1.00  0.00           H  
HETATM   97  H40 UNL     1      -8.662  -2.578  -0.014  1.00  0.00           H  
HETATM   98  H41 UNL     1     -14.463  -3.894   0.083  1.00  0.00           H  
HETATM   99  H42 UNL     1     -13.629  -4.119  -1.491  1.00  0.00           H  
HETATM  100  H43 UNL     1     -14.092   0.873  -0.302  1.00  0.00           H  
HETATM  101  H44 UNL     1      -8.547  -0.051   2.447  1.00  0.00           H  
HETATM  102  H45 UNL     1     -10.720   0.573   2.451  1.00  0.00           H  
HETATM  103  H46 UNL     1      -7.185   2.003   2.248  1.00  0.00           H  
HETATM  104  H47 UNL     1      -6.618   4.663  -1.290  1.00  0.00           H  
HETATM  105  H48 UNL     1      -9.255   5.660   0.493  1.00  0.00           H  
CONECT    1    2   58   59   60
CONECT    2    3   61   62
CONECT    3    4   63   64
CONECT    4    5   65   66
CONECT    5    6   67   68
CONECT    6    7    7   69
CONECT    7    8   70
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   71   72
CONECT   12   13   73   74
CONECT   13   14   75
CONECT   14   15   15   16
CONECT   16   17   76   77
CONECT   17   18   78   79
CONECT   18   19   80
CONECT   19   20   20   21
CONECT   21   22   23   81
CONECT   22   82
CONECT   23   24   25   26
CONECT   24   83   84   85
CONECT   25   86   87   88
CONECT   26   27   89   90
CONECT   27   28
CONECT   28   29   29   30   31
CONECT   30   91
CONECT   31   32
CONECT   32   33   33   34   35
CONECT   34   92
CONECT   35   36
CONECT   36   37   93   94
CONECT   37   38   52   95
CONECT   38   39
CONECT   39   40   50   96
CONECT   40   41   49
CONECT   41   42   42   97
CONECT   42   43
CONECT   43   44   44   49
CONECT   44   45   46
CONECT   45   98   99
CONECT   46   47   47
CONECT   47   48  100
CONECT   48   49   49
CONECT   50   51   52  101
CONECT   51  102
CONECT   52   53  103
CONECT   53   54
CONECT   54   55   55   56   57
CONECT   56  104
CONECT   57  105
END

HMDB0003949
     RDKit          3D
(2E)-Octenoyl-CoA
105107  0  0  0  0  0  0  0  0999 V2000
   14.2419    2.0268   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4909    1.0628    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3834   -0.0385    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4475   -0.8277   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7543   -2.1871   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4131   -2.3574   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5262   -1.6031    0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2111   -2.0429    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6602   -3.0037    0.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3881   -0.7948    1.7470 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1617    0.0155    0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0683   -0.8165    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3421   -0.2256   -0.7445 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467    1.0913   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1967    1.9811   -0.0040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625    1.3307   -1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390    1.5371   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    0.5857    0.0100 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -0.4285    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006   -0.5418    2.0002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571   -1.2878    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -1.1819   -1.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -1.0594    0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5178    0.4343    1.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633   -1.9402    2.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930   -1.2165   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -0.9843    0.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562   -1.4306   -1.2326 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.3004   -2.6961   -0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5794   -1.7536   -2.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6324   -0.2891   -1.6849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983    1.2961   -1.3891 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.8966    2.0577   -2.5567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    1.6766   -1.5531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9551    1.9100   -0.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7761    0.8363    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2095    1.1523    0.2611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8061   -0.1025    0.0581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1454    0.1970    0.3831 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.9925   -0.9083    0.1376 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6939   -2.1776    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7651   -2.9690   -0.2094 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8440   -2.1412   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1155   -2.3160   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8425   -3.5578   -0.6352 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0015   -1.2687   -0.5282 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5237   -0.0441   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2113    0.1128   -0.0539 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3365   -0.8464   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9481    0.7357    1.7594 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.0809    1.3189    2.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8415    1.7590    1.4498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5815    2.9069    1.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5979    4.2230    0.7026 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.2883    4.1917    1.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4425    4.2469   -1.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4248    5.6518    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413    2.9958   -0.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2404    2.2744   -0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6029    1.7138   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.4877    0.5015    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5268    1.5300    1.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2894   -0.4386    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4771    0.7369    0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2034   -0.2458   -1.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5409   -1.1586   -0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2665   -2.5307    0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2875   -2.9358   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9521   -3.3546   -0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9320   -0.6510    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258    0.7137    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4508    0.7989    0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3121   -1.1512    1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4388   -1.8420   -0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1693   -0.8234   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6078    0.3630   -2.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8589    2.1748   -2.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    2.5543   -0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878    1.7080   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935    0.9569    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2979   -2.3712    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9971   -0.3144   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3412    0.5945    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5464    1.1101    0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    0.4743    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -1.5258    2.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -2.1107    2.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747   -2.9566    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1384   -2.1258   -0.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347   -0.3743   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -2.7645   -2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    2.6270   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4288   -0.1244   -0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081    0.7331    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4260    1.7536   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3863    1.0544   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6616   -2.5780   -0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4632   -3.8939    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6288   -4.1192   -1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0919    0.8731   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5471   -0.0509    2.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7196    0.5733    2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1849    2.0027    2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6180    4.6633   -1.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2547    5.6605    0.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 44 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 39 50  1  0
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 11 71  1  0
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 24 83  1  0
 24 84  1  0
 24 85  1  0
 25 86  1  0
 25 87  1  0
 25 88  1  0
 26 89  1  0
 26 90  1  0
 30 91  1  0
 34 92  1  0
 36 93  1  0
 36 94  1  0
 37 95  1  6
 39 96  1  6
 41 97  1  0
 45 98  1  0
 45 99  1  0
 47100  1  0
 50101  1  1
 51102  1  0
 52103  1  1
 56104  1  0
 57105  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(e)-S-2-Octenoate	HMDB
(e)-S-2-Octenoate CoA	HMDB
(e)-S-2-Octenoate coenzyme A	HMDB
(e)-S-2-Octenoic acid	HMDB
2,3-trans-Octenoyl coenzyme A	HMDB
Oct-2-trans-enoyl-CoA	HMDB
Oct-2-trans-enoyl-coenzyme A	HMDB
Oct-trans-2-enoyl coenzyme A	HMDB
S-(2E)-2-Octenoate	HMDB
S-(2E)-2-Octenoate CoA	HMDB
S-(2E)-2-Octenoate coenzyme A	HMDB
S-(2E)-2-Octenoic acid	HMDB
trans-D2,3-Octenoyl-CoA	HMDB
trans-D2,3-Octenoyl-coenzyme A	HMDB
trans-Oct-2-enoyl-CoA	HMDB
trans-Oct-2-enoyl-coenzyme A	HMDB

Chemical Formula

C₂₉H₄₈N₇O₁₇P₃S

Average Molecular Weight

891.714

Monoisotopic Molecular Weight

891.204023371

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E)-oct-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E)-oct-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

10018-94-7

SMILES

CCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(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/C29H48N7O17P3S/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36/h8-9,16-18,22-24,28,39-40H,4-7,10-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/b9-8+/t18-,22-,23-,24?,28-/m1/s1

InChI Key

CPSDNAXXKWVYIY-DPSCIZRPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Medium-chain 2-enoyl 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
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Fatty acyl CoAs (C05276 )

Ontology

Not Available

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	-1.281	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.13 g/L	ALOGPS
logP	0.55	ALOGPS
logP	-3.8	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	200.93 m³·mol⁻¹	ChemAxon
Polarizability	81.26 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]+	218.66	30932474
DeepCCS	[M-H]-	217.007	30932474
DeepCCS	[M-2H]-	251.04	30932474
DeepCCS	[M+Na]+	225.735	30932474
AllCCS	[M+H]+	267.8	32859911
AllCCS	[M+H-H2O]+	268.3	32859911
AllCCS	[M+NH4]+	267.3	32859911
AllCCS	[M+Na]+	267.1	32859911
AllCCS	[M-H]-	265.1	32859911
AllCCS	[M+Na-2H]-	270.0	32859911
AllCCS	[M+HCOO]-	275.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2E)-Octenoyl-CoA	CCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(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	6415.5	Standard polar	33892256
(2E)-Octenoyl-CoA	CCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(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	4828.0	Standard non polar	33892256
(2E)-Octenoyl-CoA	CCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(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	6799.5	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 10V, Positive-QTOF	splash10-000i-1912000120-6a4c400b3152685ddc42	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 20V, Positive-QTOF	splash10-000i-0933000000-6bfba9e629e0c41c1c83	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 40V, Positive-QTOF	splash10-000i-1911000000-7bd78cc2705414ac12aa	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 10V, Negative-QTOF	splash10-00gl-3911030340-0a6b8d53ed19f026db3f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 20V, Negative-QTOF	splash10-00ai-3910010010-8cc155429b1ae945edc0	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 40V, Negative-QTOF	splash10-057i-6900000000-8852cd72aadbe50cd70b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 10V, Positive-QTOF	splash10-0006-0000000190-ffcd2eab73ff60157945	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 20V, Positive-QTOF	splash10-000i-1910101580-d4dfe3fd333b1bef04a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 40V, Positive-QTOF	splash10-000i-0029000000-94de84f8ae35a8bb2b05	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 10V, Negative-QTOF	splash10-0006-0000000090-15ef43bffda7c547e777	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 20V, Negative-QTOF	splash10-009f-5300303790-609e6396a205775b94b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-Octenoyl-CoA 40V, Negative-QTOF	splash10-014r-4103402920-b4cc1e40b5e853471683	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fatty acid Metabolism
Fatty Acid Elongation In Mitochondria
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids		Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids		Not Available
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)		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

FDB023268

KNApSAcK ID

Not Available

Chemspider ID

4444335

KEGG Compound ID

C05276

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280769

PDB ID

Not Available

ChEBI ID

27537

Food Biomarker Ontology

Not Available

VMH ID

HC01415

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Reiser, S. E.; Gruys, K. J.; Mitsky, T. A. Characterization and cloning of an (R)-specific trans-2,3-enoylacyl-CoA hydratase from Rhodospirillum rubrum and use of this enzyme for PHA production in Escherichia coli. Applied Microbiology and Biotechnology (2000), 53(2), 209-218.

Material Safety Data Sheet (MSDS)

Not Available

General References

Tajima G, Sakura N, Yofune H, Nishimura Y, Ono H, Hasegawa Y, Hata I, Kimura M, Yamaguchi S, Shigematsu Y, Kobayashi M: Enzymatic diagnosis of medium-chain acyl-CoA dehydrogenase deficiency by detecting 2-octenoyl-CoA production using high-performance liquid chromatography: a practical confirmatory test for tandem mass spectrometry newborn screening in Japan. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 5;823(2):122-30. [PubMed:16046200 ]
Cummings JG, Lau SM, Powell PJ, Thorpe C: Reductive half-reaction in medium-chain acyl-CoA dehydrogenase: modulation of internal equilibrium by carboxymethylation of a specific methionine residue. Biochemistry. 1992 Sep 15;31(36):8523-9. [PubMed:1390638 ]
Kumar NR, Srivastava DK: Reductive half-reaction of medium-chain fatty acyl-CoA dehydrogenase utilizing octanoyl-CoA/octenoyl-CoA as a physiological substrate/product pair: similarity in the microscopic pathways of octanoyl-CoA oxidation and octenoyl-CoA binding. Biochemistry. 1994 Jul 26;33(29):8833-41. [PubMed:8038175 ]

Only showing the first 10 proteins. There are 114 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 3-ketoacyl-CoA thiolase, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:: ACAA2
Uniprot ID:: P42765
Molecular weight:: 41923.82

Enzyme Details

2. 3-ketoacyl-CoA thiolase, peroxisomal

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: ACAA1
Uniprot ID:: P09110
Molecular weight:: 34664.46

Enzyme Details

3. Trifunctional enzyme subunit beta, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: HADHB
Uniprot ID:: P55084
Molecular weight:: 51293.955

Enzyme Details

4. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:: ALDH6A1
Uniprot ID:: Q02252
Molecular weight:: 57839.31

Enzyme Details

5. Long-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADL
Uniprot ID:: P28330
Molecular weight:: 47655.275

Reactions

Octanoyl-CoA + FAD → (2E)-Octenoyl-CoA + FADH	details

Enzyme Details

6. Short-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADS
Uniprot ID:: P16219
Molecular weight:: 44296.705

Enzyme Details

7. Medium-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:: ACADM
Uniprot ID:: P11310
Molecular weight:: 46587.98

Reactions

Octanoyl-CoA + FAD → (2E)-Octenoyl-CoA + FADH	details

Enzyme Details

8. Peroxisomal acyl-coenzyme A oxidase 1

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:: ACOX1
Uniprot ID:: Q15067
Molecular weight:: 70135.205

Reactions

Octanoyl-CoA + FAD → (2E)-Octenoyl-CoA + FADH	details

Enzyme Details

9. Peroxisomal acyl-coenzyme A oxidase 2

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:: ACOX2
Uniprot ID:: Q99424
Molecular weight:: 76826.14

Enzyme Details

10. Isovaleryl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: IVD
Uniprot ID:: P26440
Molecular weight:: 43055.325

Transporters

Enzyme Details

1. Long-chain fatty acid transport protein 1

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:: SLC27A1
Uniprot ID:: Q6PCB7
Molecular weight:: 71107.5

Only showing the first 10 proteins. There are 114 proteins in total.

Show all enzymes and transporters

Showing metabocard for (2E)-Octenoyl-CoA (HMDB0003949)

MOL for HMDB0003949 ((2E)-Octenoyl-CoA)

3D MOL for HMDB0003949 ((2E)-Octenoyl-CoA)

3D SDF for HMDB0003949 ((2E)-Octenoyl-CoA)

3D-SDF for HMDB0003949 ((2E)-Octenoyl-CoA)

PDB for HMDB0003949 ((2E)-Octenoyl-CoA)

3D PDB for HMDB0003949 ((2E)-Octenoyl-CoA)

SMILES for HMDB0003949 ((2E)-Octenoyl-CoA)

INCHI for HMDB0003949 ((2E)-Octenoyl-CoA)

Structure for HMDB0003949 ((2E)-Octenoyl-CoA)

3D Structure for HMDB0003949 ((2E)-Octenoyl-CoA)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Transporters