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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-10-09 21:01:10 UTC

HMDB ID

HMDB0000936

Secondary Accession Numbers

HMDB00936

Metabolite Identification

Common Name

Uroporphyrin I

Description

Uroporphyrin is the porphyrin produced by oxidation of the methylene bridges in uroporphyrinogen. Uroporphyrins have four acetic acid and four propionic acid side chains attached to their pyrrole rings. The enzyme uroporphyrinogen I synthase catalyzes the formation of hydroxymethylbilane from four molecules of porphobilinogen. Uroporphyrinogen III cosynthase then catalyzes the conversion of hydroxymethylbilane into uroporphyrinogen III. Otherwise, hydroxymethylbilane cyclizes nonenzymatically to form uroporphyrinogen I. Uroporphyrinogen I and III yield their respective uroporphyrins via autooxidation or their respective coproporphyrinogens via decarboxylation. Excessive amounts of uroporphyrin I are excreted in congenital erythropoietic porphyria, and both uroporphyrin I and uroporphyrin III are excreted in porphyria cutanea tarda. Uroporphyrin I and III are the most common isomers. Under certain conditions, uroporphyrin I can act as a phototoxin, a neurotoxin, and a metabotoxin. A phototoxin leads to cell damage upon exposure to light. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, porphyria cutanea tarda, and hereditary coproporphyria (HCP). There are several types of porphyrias (most are inherited). Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth). The neurotoxicity of porphyrins may be due to their selective interactions with tubulin, which disrupt microtubule formation and cause neural malformations (PMID: 3441503 ).

Structure

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


  Mrv0541 02231218502D          

 60 64  0  0  0  0            999 V2000
   -1.4888    2.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759    1.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577    1.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4736    2.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7085    0.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9017    1.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076    1.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8940    0.8637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858    3.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -0.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3108    2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1668    4.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7085   -0.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1366    2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8941    2.9206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357    2.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977    0.8448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    4.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    4.5268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0797   -1.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902   -0.8940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456    1.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4320    2.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161    0.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4925   -2.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9017   -1.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577   -1.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8676    1.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440    3.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    0.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -2.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076   -1.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2805    2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403    4.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562    2.8979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970   -0.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198   -3.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1253   -2.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7311   -1.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026    2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494   -1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -0.8637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -4.1442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9282   -2.8903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5230   -2.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5420   -1.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4546   -2.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5117    2.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5117    1.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8751   -1.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2768   -2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881   -3.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063   -2.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8487   -2.9472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3638   -4.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176   -4.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6895   -4.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 13 20  2  0  0  0  0
 14 21  1  0  0  0  0
 14 22  1  0  0  0  0
 17 23  2  0  0  0  0
 17 24  1  0  0  0  0
 18 25  2  0  0  0  0
 21 26  2  0  0  0  0
 21 27  1  0  0  0  0
 22 28  2  0  0  0  0
 23 29  1  0  0  0  0
 24 30  1  0  0  0  0
 25 31  1  0  0  0  0
 26 32  1  0  0  0  0
 27 33  1  0  0  0  0
 28 34  1  0  0  0  0
 29 35  1  0  0  0  0
 30 36  1  0  0  0  0
 30 37  2  0  0  0  0
 31 38  2  0  0  0  0
 32 39  1  0  0  0  0
 33 40  1  0  0  0  0
 34 41  2  0  0  0  0
 35 42  1  0  0  0  0
 38 43  1  0  0  0  0
 38 44  1  0  0  0  0
 39 45  1  0  0  0  0
 39 46  2  0  0  0  0
 40 47  1  0  0  0  0
 40 48  2  0  0  0  0
 41 49  1  0  0  0  0
 42 50  1  0  0  0  0
 42 51  2  0  0  0  0
 43 52  1  0  0  0  0
 49 53  1  0  0  0  0
 52 54  1  0  0  0  0
 53 55  1  0  0  0  0
 54 56  1  0  0  0  0
 54 57  2  0  0  0  0
 55 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  2  0  0  0  0
  5  8  1  0  0  0  0
 23 25  1  0  0  0  0
 26 28  1  0  0  0  0
 41 44  1  0  0  0  0
 43 49  2  0  0  0  0
M  END

HMDB0000936
     RDKit          3D
Uroporphyrin I
 98102  0  0  0  0  0  0  0  0999 V2000
    5.4295    0.5383   -2.5417 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5471    1.7267   -2.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4670    2.6781   -3.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634    2.1714   -0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.0691    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619    0.2885    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -1.0110   -0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -1.9308   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3259   -2.5880   -1.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3015   -2.3381   -2.4357 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -3.4594   -2.2129 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0065   -1.3556    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2754   -2.5498   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865   -2.6543   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1033   -1.8543   -0.5585 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -2.4212   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033   -2.0340   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -0.7275   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2281    0.2382    0.1982 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842    1.4067    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629    2.5546    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7622    2.7265    0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210    1.8750    0.9512 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846    2.4846    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126    2.0380    0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264    0.7861    0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564   -0.2477    0.3704 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366    3.7823    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583    4.8108   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6688    4.3715   -1.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228    3.3188   -2.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6283    5.0743   -2.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2304    3.9506    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    5.1829   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5002    5.9475    0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6287    6.4110    1.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5725    6.2482    2.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    7.1799    2.8928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2939    1.1850    0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3818    2.2125    0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5867    2.7616    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9132    2.2909    2.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4892    3.7723    1.6636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3950   -0.1241   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6644   -0.8026   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1525   -1.8092    0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4321   -2.3674   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4102   -3.2224   -1.1665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6773   -1.9620    0.2162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0096   -3.6256    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656   -4.6257    1.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -5.3996   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056   -6.0320    0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142   -5.4750   -1.2827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3259   -3.7717    0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058   -4.9481    1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031   -5.9316    0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0891   -7.0988    0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -7.9450    1.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4451   -7.2521    0.7066 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6755    2.7349   -3.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644    2.8395   -0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    2.8486   -0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7235    0.4415    0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688    1.5627    1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5102   -1.5035   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4989   -2.7836    0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2724   -3.1628   -2.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239   -3.4030   -0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0208   -0.9131   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -2.7389   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271    3.3623    0.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0991    0.8444    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    2.6921    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7248    5.8053   -0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9851    4.7099    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    5.5623   -3.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    4.8329   -0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899    5.7852   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    5.5011    1.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541    6.9204    0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684    7.2412    3.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623    3.0373   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057    1.7432   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4091    3.5752    2.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4293   -1.3879   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4158   -0.0891   -0.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3597   -1.3275    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4909   -2.6841    0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2575   -1.4644   -0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -5.1836    1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -3.9901    1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -6.3782   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571   -4.5092    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4115   -5.3712    1.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988   -5.5556   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -6.3291   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722   -6.7825    1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 24 28  1  0
 28 29  1  0
 29 30  1  0
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 33 34  1  0
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 57 58  1  0
 58 59  2  0
 58 60  1  0
 26  6  1  0
 27 12  1  0
 55 14  2  0
 44 18  1  0
 33 22  1  0
  3 61  1  0
  4 62  1  0
  4 63  1  0
  5 64  1  0
  5 65  1  0
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 11 68  1  0
 13 69  1  0
 15 70  1  0
 17 71  1  0
 21 72  1  0
 23 73  1  0
 25 74  1  0
 29 75  1  0
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 54 93  1  0
 56 94  1  0
 56 95  1  0
 57 96  1  0
 57 97  1  0
 60 98  1  0
M  END


  Mrv0541 02231218502D          

 60 64  0  0  0  0            999 V2000
   -1.4888    2.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759    1.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577    1.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4736    2.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7085    0.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9017    1.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076    1.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8940    0.8637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858    3.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -0.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3108    2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1668    4.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7085   -0.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1366    2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8941    2.9206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357    2.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977    0.8448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    4.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    4.5268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0797   -1.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902   -0.8940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456    1.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4320    2.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161    0.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4925   -2.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9017   -1.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577   -1.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8676    1.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440    3.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    0.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -2.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076   -1.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2805    2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403    4.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562    2.8979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970   -0.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198   -3.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1253   -2.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7311   -1.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026    2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494   -1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -0.8637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -4.1442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9282   -2.8903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5230   -2.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5420   -1.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4546   -2.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5117    2.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5117    1.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8751   -1.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2768   -2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881   -3.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063   -2.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8487   -2.9472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3638   -4.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176   -4.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6895   -4.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 13 20  2  0  0  0  0
 14 21  1  0  0  0  0
 14 22  1  0  0  0  0
 17 23  2  0  0  0  0
 17 24  1  0  0  0  0
 18 25  2  0  0  0  0
 21 26  2  0  0  0  0
 21 27  1  0  0  0  0
 22 28  2  0  0  0  0
 23 29  1  0  0  0  0
 24 30  1  0  0  0  0
 25 31  1  0  0  0  0
 26 32  1  0  0  0  0
 27 33  1  0  0  0  0
 28 34  1  0  0  0  0
 29 35  1  0  0  0  0
 30 36  1  0  0  0  0
 30 37  2  0  0  0  0
 31 38  2  0  0  0  0
 32 39  1  0  0  0  0
 33 40  1  0  0  0  0
 34 41  2  0  0  0  0
 35 42  1  0  0  0  0
 38 43  1  0  0  0  0
 38 44  1  0  0  0  0
 39 45  1  0  0  0  0
 39 46  2  0  0  0  0
 40 47  1  0  0  0  0
 40 48  2  0  0  0  0
 41 49  1  0  0  0  0
 42 50  1  0  0  0  0
 42 51  2  0  0  0  0
 43 52  1  0  0  0  0
 49 53  1  0  0  0  0
 52 54  1  0  0  0  0
 53 55  1  0  0  0  0
 54 56  1  0  0  0  0
 54 57  2  0  0  0  0
 55 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  2  0  0  0  0
  5  8  1  0  0  0  0
 23 25  1  0  0  0  0
 26 28  1  0  0  0  0
 41 44  1  0  0  0  0
 43 49  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000936

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CC(O)=O)=C3CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-26-19(3-7-35(49)50)23(11-39(57)58)31(43-26)16-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)15-27-18(2-6-34(47)48)22(10-38(55)56)30(42-27)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-

> <INCHI_KEY>
DAFUFNRZWDWXJP-JRHDEHKPSA-N

> <FORMULA>
C40H38N4O16

> <MOLECULAR_WEIGHT>
830.7469

> <EXACT_MASS>
830.228281188

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
84.92223249243303

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid

> <ALOGPS_LOGP>
0.76

> <JCHEM_LOGP>
3.512340196666666

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-8

> <JCHEM_PKA>
3.5332794019939295

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1649771690291857

> <JCHEM_POLAR_SURFACE_AREA>
355.76

> <JCHEM_REFRACTIVITY>
201.3214000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
uroporphyrin I

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000936
     RDKit          3D
Uroporphyrin I
 98102  0  0  0  0  0  0  0  0999 V2000
    5.4295    0.5383   -2.5417 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5471    1.7267   -2.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4670    2.6781   -3.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634    2.1714   -0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.0691    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619    0.2885    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -1.0110   -0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -1.9308   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3259   -2.5880   -1.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3015   -2.3381   -2.4357 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -3.4594   -2.2129 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0065   -1.3556    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2754   -2.5498   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865   -2.6543   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1033   -1.8543   -0.5585 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -2.4212   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033   -2.0340   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -0.7275   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2281    0.2382    0.1982 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842    1.4067    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629    2.5546    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7622    2.7265    0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210    1.8750    0.9512 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846    2.4846    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126    2.0380    0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264    0.7861    0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564   -0.2477    0.3704 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366    3.7823    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583    4.8108   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6688    4.3715   -1.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228    3.3188   -2.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6283    5.0743   -2.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2304    3.9506    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    5.1829   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5002    5.9475    0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6287    6.4110    1.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5725    6.2482    2.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    7.1799    2.8928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2939    1.1850    0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3818    2.2125    0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5867    2.7616    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9132    2.2909    2.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4892    3.7723    1.6636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3950   -0.1241   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6644   -0.8026   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1525   -1.8092    0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4321   -2.3674   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4102   -3.2224   -1.1665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6773   -1.9620    0.2162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0096   -3.6256    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656   -4.6257    1.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -5.3996   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056   -6.0320    0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142   -5.4750   -1.2827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3259   -3.7717    0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058   -4.9481    1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031   -5.9316    0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0891   -7.0988    0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -7.9450    1.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4451   -7.2521    0.7066 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6755    2.7349   -3.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644    2.8395   -0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    2.8486   -0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7235    0.4415    0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688    1.5627    1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5102   -1.5035   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4989   -2.7836    0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2724   -3.1628   -2.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239   -3.4030   -0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0208   -0.9131   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -2.7389   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271    3.3623    0.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0991    0.8444    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    2.6921    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7248    5.8053   -0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9851    4.7099    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    5.5623   -3.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    4.8329   -0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899    5.7852   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    5.5011    1.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541    6.9204    0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684    7.2412    3.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623    3.0373   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057    1.7432   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4091    3.5752    2.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4293   -1.3879   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4158   -0.0891   -0.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3597   -1.3275    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4909   -2.6841    0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2575   -1.4644   -0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -5.1836    1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -3.9901    1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -6.3782   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571   -4.5092    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4115   -5.3712    1.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988   -5.5556   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -6.3291   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722   -6.7825    1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
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 60 98  1  0
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  C   UNK     0      -2.779   3.847   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.875   2.772   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.414   3.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.751   5.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.189   1.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.417   2.786   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.014   3.656   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.669   1.612   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -4.080   6.173   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.917  -0.035   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.180   4.122   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.351   3.083   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.045   7.707   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.189  -1.435   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -7.722   4.122   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.402   5.452   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.680   3.868   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.676   1.577   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -5.360   8.507   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.694   8.450   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.882  -2.814   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -1.662  -1.669   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       3.818   2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.673   5.409   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.203   1.429   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.786  -3.889   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.417  -2.836   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.414  -3.189   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.353   2.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.002   6.180   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.783   0.007   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.800  -5.424   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.159  -4.186   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.014  -3.705   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.124   4.186   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.995   7.729   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.332   5.409   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.168  -1.414   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.144  -6.187   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -7.701  -4.200   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.365  -3.125   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.658   4.186   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.826  -2.807   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       1.640  -1.612   0.000  0.00  0.00           N+0
HETATM   45  O   UNK     0      -4.151  -7.736   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -5.466  -5.395   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -8.443  -5.551   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -8.478  -2.878   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       2.715  -3.861   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       8.422   5.530   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       8.422   2.857   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       5.367  -2.836   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.864  -5.388   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.117  -4.179   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.271  -6.024   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       7.665  -4.193   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       5.318  -5.501   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       4.412  -7.559   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       5.820  -8.188   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       3.154  -8.436   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    8                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3    5                                                       
CONECT    9    4   13                                                       
CONECT   10    5   14                                                       
CONECT   11    6   15   16                                                  
CONECT   12    7   17   18                                                  
CONECT   13    9   19   20                                                  
CONECT   14   10   21   22                                                  
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17   12   23   24                                                  
CONECT   18   12   25                                                       
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21   14   26   27                                                  
CONECT   22   14   28                                                       
CONECT   23   17   29   25                                                  
CONECT   24   17   30                                                       
CONECT   25   18   31   23                                                  
CONECT   26   21   32   28                                                  
CONECT   27   21   33                                                       
CONECT   28   22   34   26                                                  
CONECT   29   23   35                                                       
CONECT   30   24   36   37                                                  
CONECT   31   25   38                                                       
CONECT   32   26   39                                                       
CONECT   33   27   40                                                       
CONECT   34   28   41                                                       
CONECT   35   29   42                                                       
CONECT   36   30                                                            
CONECT   37   30                                                            
CONECT   38   31   43   44                                                  
CONECT   39   32   45   46                                                  
CONECT   40   33   47   48                                                  
CONECT   41   34   49   44                                                  
CONECT   42   35   50   51                                                  
CONECT   43   38   52   49                                                  
CONECT   44   38   41                                                       
CONECT   45   39                                                            
CONECT   46   39                                                            
CONECT   47   40                                                            
CONECT   48   40                                                            
CONECT   49   41   53   43                                                  
CONECT   50   42                                                            
CONECT   51   42                                                            
CONECT   52   43   54                                                       
CONECT   53   49   55                                                       
CONECT   54   52   56   57                                                  
CONECT   55   53   58                                                       
CONECT   56   54                                                            
CONECT   57   54                                                            
CONECT   58   55   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

COMPND    HMDB0000936
HETATM    1  O1  UNL     1       5.429   0.538  -2.542  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.547   1.727  -2.222  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.467   2.678  -3.242  1.00  0.00           O  
HETATM    4  C2  UNL     1       5.763   2.171  -0.831  1.00  0.00           C  
HETATM    5  C3  UNL     1       5.828   1.069   0.162  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.562   0.288   0.169  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.402  -1.011  -0.097  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.516  -1.931  -0.457  1.00  0.00           C  
HETATM    9  C7  UNL     1       5.326  -2.588  -1.771  1.00  0.00           C  
HETATM   10  O3  UNL     1       4.302  -2.338  -2.436  1.00  0.00           O  
HETATM   11  O4  UNL     1       6.297  -3.459  -2.213  1.00  0.00           O  
HETATM   12  C8  UNL     1       3.006  -1.356   0.028  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.275  -2.550  -0.154  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.886  -2.654  -0.116  1.00  0.00           C  
HETATM   15  N1  UNL     1      -0.103  -1.854  -0.558  1.00  0.00           N  
HETATM   16  C11 UNL     1      -1.269  -2.421  -0.197  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.603  -2.034  -0.340  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.090  -0.727  -0.153  1.00  0.00           C  
HETATM   19  N2  UNL     1      -2.228   0.238   0.198  1.00  0.00           N  
HETATM   20  C14 UNL     1      -2.884   1.407   0.314  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.163   2.555   0.669  1.00  0.00           C  
HETATM   22  C16 UNL     1      -0.762   2.727   0.636  1.00  0.00           C  
HETATM   23  N3  UNL     1       0.221   1.875   0.951  1.00  0.00           N  
HETATM   24  C17 UNL     1       1.385   2.485   0.698  1.00  0.00           C  
HETATM   25  C18 UNL     1       2.713   2.038   0.836  1.00  0.00           C  
HETATM   26  C19 UNL     1       3.226   0.786   0.475  1.00  0.00           C  
HETATM   27  N4  UNL     1       2.356  -0.248   0.370  1.00  0.00           N  
HETATM   28  C20 UNL     1       1.137   3.782   0.202  1.00  0.00           C  
HETATM   29  C21 UNL     1       2.158   4.811  -0.242  1.00  0.00           C  
HETATM   30  C22 UNL     1       2.669   4.371  -1.561  1.00  0.00           C  
HETATM   31  O5  UNL     1       2.223   3.319  -2.068  1.00  0.00           O  
HETATM   32  O6  UNL     1       3.628   5.074  -2.274  1.00  0.00           O  
HETATM   33  C23 UNL     1      -0.230   3.951   0.161  1.00  0.00           C  
HETATM   34  C24 UNL     1      -0.926   5.183  -0.298  1.00  0.00           C  
HETATM   35  C25 UNL     1      -1.500   5.947   0.819  1.00  0.00           C  
HETATM   36  C26 UNL     1      -0.629   6.411   1.895  1.00  0.00           C  
HETATM   37  O7  UNL     1       0.572   6.248   2.082  1.00  0.00           O  
HETATM   38  O8  UNL     1      -1.291   7.180   2.893  1.00  0.00           O  
HETATM   39  C27 UNL     1      -4.294   1.185   0.015  1.00  0.00           C  
HETATM   40  C28 UNL     1      -5.382   2.213   0.019  1.00  0.00           C  
HETATM   41  C29 UNL     1      -5.587   2.762   1.382  1.00  0.00           C  
HETATM   42  O9  UNL     1      -4.913   2.291   2.326  1.00  0.00           O  
HETATM   43  O10 UNL     1      -6.489   3.772   1.664  1.00  0.00           O  
HETATM   44  C30 UNL     1      -4.395  -0.124  -0.268  1.00  0.00           C  
HETATM   45  C31 UNL     1      -5.664  -0.803  -0.655  1.00  0.00           C  
HETATM   46  C32 UNL     1      -6.152  -1.809   0.325  1.00  0.00           C  
HETATM   47  C33 UNL     1      -7.432  -2.367  -0.247  1.00  0.00           C  
HETATM   48  O11 UNL     1      -7.410  -3.222  -1.167  1.00  0.00           O  
HETATM   49  O12 UNL     1      -8.677  -1.962   0.216  1.00  0.00           O  
HETATM   50  C34 UNL     1      -1.010  -3.626   0.493  1.00  0.00           C  
HETATM   51  C35 UNL     1      -1.966  -4.626   1.073  1.00  0.00           C  
HETATM   52  C36 UNL     1      -2.524  -5.400  -0.038  1.00  0.00           C  
HETATM   53  O13 UNL     1      -3.606  -6.032   0.121  1.00  0.00           O  
HETATM   54  O14 UNL     1      -1.914  -5.475  -1.283  1.00  0.00           O  
HETATM   55  C37 UNL     1       0.326  -3.772   0.544  1.00  0.00           C  
HETATM   56  C38 UNL     1       1.006  -4.948   1.183  1.00  0.00           C  
HETATM   57  C39 UNL     1       1.403  -5.932   0.122  1.00  0.00           C  
HETATM   58  C40 UNL     1       2.089  -7.099   0.793  1.00  0.00           C  
HETATM   59  O15 UNL     1       1.418  -7.945   1.440  1.00  0.00           O  
HETATM   60  O16 UNL     1       3.445  -7.252   0.707  1.00  0.00           O  
HETATM   61  H1  UNL     1       4.676   2.735  -3.874  1.00  0.00           H  
HETATM   62  H2  UNL     1       6.664   2.839  -0.793  1.00  0.00           H  
HETATM   63  H3  UNL     1       4.923   2.849  -0.571  1.00  0.00           H  
HETATM   64  H4  UNL     1       6.724   0.441   0.091  1.00  0.00           H  
HETATM   65  H5  UNL     1       5.869   1.563   1.181  1.00  0.00           H  
HETATM   66  H6  UNL     1       6.510  -1.504  -0.380  1.00  0.00           H  
HETATM   67  H7  UNL     1       5.499  -2.784   0.290  1.00  0.00           H  
HETATM   68  H8  UNL     1       7.272  -3.163  -2.173  1.00  0.00           H  
HETATM   69  H9  UNL     1       2.924  -3.403  -0.316  1.00  0.00           H  
HETATM   70  H10 UNL     1       0.021  -0.913  -1.145  1.00  0.00           H  
HETATM   71  H11 UNL     1      -3.387  -2.739  -0.605  1.00  0.00           H  
HETATM   72  H12 UNL     1      -2.827   3.362   0.976  1.00  0.00           H  
HETATM   73  H13 UNL     1       0.099   0.844   1.379  1.00  0.00           H  
HETATM   74  H14 UNL     1       3.500   2.692   1.260  1.00  0.00           H  
HETATM   75  H15 UNL     1       1.725   5.805  -0.278  1.00  0.00           H  
HETATM   76  H16 UNL     1       2.985   4.710   0.491  1.00  0.00           H  
HETATM   77  H17 UNL     1       3.394   5.562  -3.148  1.00  0.00           H  
HETATM   78  H18 UNL     1      -1.753   4.833  -0.974  1.00  0.00           H  
HETATM   79  H19 UNL     1      -0.190   5.785  -0.879  1.00  0.00           H  
HETATM   80  H20 UNL     1      -2.398   5.501   1.322  1.00  0.00           H  
HETATM   81  H21 UNL     1      -1.954   6.920   0.388  1.00  0.00           H  
HETATM   82  H22 UNL     1      -0.968   7.241   3.827  1.00  0.00           H  
HETATM   83  H23 UNL     1      -5.062   3.037  -0.660  1.00  0.00           H  
HETATM   84  H24 UNL     1      -6.306   1.743  -0.311  1.00  0.00           H  
HETATM   85  H25 UNL     1      -7.409   3.575   2.080  1.00  0.00           H  
HETATM   86  H26 UNL     1      -5.429  -1.388  -1.605  1.00  0.00           H  
HETATM   87  H27 UNL     1      -6.416  -0.089  -0.955  1.00  0.00           H  
HETATM   88  H28 UNL     1      -6.360  -1.328   1.304  1.00  0.00           H  
HETATM   89  H29 UNL     1      -5.491  -2.684   0.426  1.00  0.00           H  
HETATM   90  H30 UNL     1      -9.258  -1.464  -0.464  1.00  0.00           H  
HETATM   91  H31 UNL     1      -1.532  -5.184   1.896  1.00  0.00           H  
HETATM   92  H32 UNL     1      -2.784  -3.990   1.516  1.00  0.00           H  
HETATM   93  H33 UNL     1      -1.815  -6.378  -1.716  1.00  0.00           H  
HETATM   94  H34 UNL     1       1.957  -4.509   1.617  1.00  0.00           H  
HETATM   95  H35 UNL     1       0.412  -5.371   1.981  1.00  0.00           H  
HETATM   96  H36 UNL     1       2.099  -5.556  -0.636  1.00  0.00           H  
HETATM   97  H37 UNL     1       0.525  -6.329  -0.436  1.00  0.00           H  
HETATM   98  H38 UNL     1       4.072  -6.783   1.339  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   61
CONECT    4    5   62   63
CONECT    5    6   64   65
CONECT    6    7    7   26
CONECT    7    8   12
CONECT    8    9   66   67
CONECT    9   10   10   11
CONECT   11   68
CONECT   12   13   13   27
CONECT   13   14   69
CONECT   14   15   55   55
CONECT   15   16   70
CONECT   16   17   50   50
CONECT   17   18   18   71
CONECT   18   19   44
CONECT   19   20   20
CONECT   20   21   39
CONECT   21   22   22   72
CONECT   22   23   33
CONECT   23   24   73
CONECT   24   25   25   28
CONECT   25   26   74
CONECT   26   27   27
CONECT   28   29   33   33
CONECT   29   30   75   76
CONECT   30   31   31   32
CONECT   32   77
CONECT   33   34
CONECT   34   35   78   79
CONECT   35   36   80   81
CONECT   36   37   37   38
CONECT   38   82
CONECT   39   40   44   44
CONECT   40   41   83   84
CONECT   41   42   42   43
CONECT   43   85
CONECT   44   45
CONECT   45   46   86   87
CONECT   46   47   88   89
CONECT   47   48   48   49
CONECT   49   90
CONECT   50   51   55
CONECT   51   52   91   92
CONECT   52   53   53   54
CONECT   54   93
CONECT   55   56
CONECT   56   57   94   95
CONECT   57   58   96   97
CONECT   58   59   59   60
CONECT   60   98
END

HMDB0000936
     RDKit          3D
Uroporphyrin I
 98102  0  0  0  0  0  0  0  0999 V2000
    5.4295    0.5383   -2.5417 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5471    1.7267   -2.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4670    2.6781   -3.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634    2.1714   -0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.0691    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619    0.2885    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -1.0110   -0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -1.9308   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3259   -2.5880   -1.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3015   -2.3381   -2.4357 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -3.4594   -2.2129 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0065   -1.3556    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2754   -2.5498   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865   -2.6543   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1033   -1.8543   -0.5585 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -2.4212   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033   -2.0340   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -0.7275   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2281    0.2382    0.1982 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842    1.4067    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629    2.5546    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7622    2.7265    0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210    1.8750    0.9512 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846    2.4846    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126    2.0380    0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264    0.7861    0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564   -0.2477    0.3704 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366    3.7823    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583    4.8108   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6688    4.3715   -1.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228    3.3188   -2.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6283    5.0743   -2.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2304    3.9506    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    5.1829   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5002    5.9475    0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6287    6.4110    1.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5725    6.2482    2.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    7.1799    2.8928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2939    1.1850    0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3818    2.2125    0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5867    2.7616    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9132    2.2909    2.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4892    3.7723    1.6636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3950   -0.1241   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6644   -0.8026   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1525   -1.8092    0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4321   -2.3674   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4102   -3.2224   -1.1665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6773   -1.9620    0.2162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0096   -3.6256    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656   -4.6257    1.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -5.3996   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056   -6.0320    0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142   -5.4750   -1.2827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3259   -3.7717    0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058   -4.9481    1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031   -5.9316    0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0891   -7.0988    0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -7.9450    1.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4451   -7.2521    0.7066 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6755    2.7349   -3.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644    2.8395   -0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    2.8486   -0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7235    0.4415    0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688    1.5627    1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5102   -1.5035   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4989   -2.7836    0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2724   -3.1628   -2.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239   -3.4030   -0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0208   -0.9131   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -2.7389   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271    3.3623    0.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0991    0.8444    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    2.6921    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7248    5.8053   -0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9851    4.7099    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    5.5623   -3.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    4.8329   -0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899    5.7852   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    5.5011    1.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541    6.9204    0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684    7.2412    3.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623    3.0373   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057    1.7432   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4091    3.5752    2.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4293   -1.3879   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4158   -0.0891   -0.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3597   -1.3275    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4909   -2.6841    0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2575   -1.4644   -0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -5.1836    1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -3.9901    1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -6.3782   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571   -4.5092    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4115   -5.3712    1.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988   -5.5556   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -6.3291   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722   -6.7825    1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 24 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 28 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 20 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  2  0
 41 43  1  0
 39 44  2  0
 44 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  2  0
 47 49  1  0
 16 50  2  0
 50 51  1  0
 51 52  1  0
 52 53  2  0
 52 54  1  0
 50 55  1  0
 55 56  1  0
 56 57  1  0
 57 58  1  0
 58 59  2  0
 58 60  1  0
 26  6  1  0
 27 12  1  0
 55 14  2  0
 44 18  1  0
 33 22  1  0
  3 61  1  0
  4 62  1  0
  4 63  1  0
  5 64  1  0
  5 65  1  0
  8 66  1  0
  8 67  1  0
 11 68  1  0
 13 69  1  0
 15 70  1  0
 17 71  1  0
 21 72  1  0
 23 73  1  0
 25 74  1  0
 29 75  1  0
 29 76  1  0
 32 77  1  0
 34 78  1  0
 34 79  1  0
 35 80  1  0
 35 81  1  0
 38 82  1  0
 40 83  1  0
 40 84  1  0
 43 85  1  0
 45 86  1  0
 45 87  1  0
 46 88  1  0
 46 89  1  0
 49 90  1  0
 51 91  1  0
 51 92  1  0
 54 93  1  0
 56 94  1  0
 56 95  1  0
 57 96  1  0
 57 97  1  0
 60 98  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,7,12,17-Porphinetetrapropionic acid	ChEBI
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropionic acid	ChEBI
2,7,12,17-Porphinetetrapropionate	Generator
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropionate	Generator
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-21H,23H-porphine-2,7,12,17-tetrayl)-tetrakis-propionate	HMDB
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-21H,23H-porphine-2,7,12,17-tetrayl)-tetrakis-propionic acid	HMDB
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-porphyrin-2,7,12,17-tetrayl)-tetra-propionate	HMDB
3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-porphyrin-2,7,12,17-tetrayl)-tetra-propionic acid	HMDB
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropanoate	HMDB
3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropanoic acid	HMDB
3-[7,12,17-Tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionate	HMDB
3-[7,12,17-Tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionic acid	HMDB

Chemical Formula

C₄₀H₃₈N₄O₁₆

Average Molecular Weight

830.7469

Monoisotopic Molecular Weight

830.228281188

IUPAC Name

3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid

Traditional Name

uroporphyrin I

CAS Registry Number

607-14-7

SMILES

OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CC(O)=O)=C3CCC(O)=O

InChI Identifier

InChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-26-19(3-7-35(49)50)23(11-39(57)58)31(43-26)16-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)15-27-18(2-6-34(47)48)22(10-38(55)56)30(42-27)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-

InChI Key

DAFUFNRZWDWXJP-JRHDEHKPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Porphyrins

Direct Parent

Porphyrins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

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	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	267.787	30932474
[M+H]+	MetCCS_train_pos	285.099	30932474
[M-H]-	Not Available	267.787	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000334
[M+H]+	Not Available	286.237	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000334

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.037 g/L	ALOGPS
logP	0.76	ALOGPS
logP	3.51	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
Physiological Charge	-8	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	355.76 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	201.32 m³·mol⁻¹	ChemAxon
Polarizability	84.92 Å³	ChemAxon
Number of Rings	5	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
AllCCS	[M+H]+	277.44	32859911
AllCCS	[M-H]-	273.248	32859911
DeepCCS	[M+H]+	272.448	30932474
DeepCCS	[M-H]-	270.423	30932474
DeepCCS	[M-2H]-	303.972	30932474
DeepCCS	[M+Na]+	278.36	30932474
AllCCS	[M+H]+	277.4	32859911
AllCCS	[M+H-H2O]+	277.4	32859911
AllCCS	[M+NH4]+	277.5	32859911
AllCCS	[M+Na]+	277.5	32859911
AllCCS	[M-H]-	273.2	32859911
AllCCS	[M+Na-2H]-	277.9	32859911
AllCCS	[M+HCOO]-	283.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Uroporphyrin I	OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CC(O)=O)=C3CCC(O)=O	7825.8	Standard polar	33892256
Uroporphyrin I	OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CC(O)=O)=C3CCC(O)=O	4929.5	Standard non polar	33892256
Uroporphyrin I	OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CC(O)=O)=C3CCC(O)=O	8113.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 10V, Positive-QTOF	splash10-03xs-0000000940-dfb6a1c5995e614eac9a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 20V, Positive-QTOF	splash10-0gbi-0000000910-609babbc27a206d09ad4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 40V, Positive-QTOF	splash10-0f9i-0000000900-ffd2454f165fe2594021	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 10V, Negative-QTOF	splash10-004i-0000000790-377067e19f6ade3d5860	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 20V, Negative-QTOF	splash10-02vi-1000000940-9415a48c2a747a58ce1d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 40V, Negative-QTOF	splash10-066r-5000000900-22e5a1d377afd75f3366	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 10V, Positive-QTOF	splash10-03xr-0000000980-fa8ef8e410767e523954	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 20V, Positive-QTOF	splash10-00p0-0000000900-d455288feb5e6056af12	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 40V, Positive-QTOF	splash10-0170-0000000900-e223edb8a02cb6503ce4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 10V, Negative-QTOF	splash10-00ku-0000000900-b16843991f1b653b1397	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 20V, Negative-QTOF	splash10-00ku-0000000900-5880fbaaad32a34fdb0f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin I 40V, Negative-QTOF	splash10-00kr-0000000900-dddaee25a158e99d04c4	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Urine

Tissue Locations

Liver

Pathways

Name	SMPDB/PathBank	KEGG
Porphyrin Metabolism
Acute Intermittent Porphyria		Not Available
Porphyria Variegata (PV)		Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease		Not Available
Hereditary Coproporphyria (HCP)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0006 (0.0000-0.0012) uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.012 (0.000-0.024) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.00092 +/- 0.00032 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0 uM	Adult (>18 years old)	Male	Protoporphyria, Erythropoietic	13765301	details
Urine	Detected and Quantified	0 umol/mmol creatinine	Adult (>18 years old)	Male	Protoporphyria, Erythropoietic	13765301	details

Associated Disorders and Diseases

Disease References

Protoporphyria, Erythropoietic
MAGNUS IA, JARRETT A, PRANKERD TA, RIMINGTON C: Erythropoietic protoporphyria. A new porphyria syndrome with solar urticaria due to protoporphyrinaemia. Lancet. 1961 Aug 26;2(7200):448-51. [PubMed:13765301 ]

Associated OMIM IDs

177000 (Protoporphyria, Erythropoietic)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022326

KNApSAcK ID

Not Available

Chemspider ID

16736725

KEGG Compound ID

C05767

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5885

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

27484

Food Biomarker Ontology

Not Available

VMH ID

C05767

MarkerDB ID

MDB00000285

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Ding Y, Lin B, Huie CW: Binding studies of porphyrins to human serum albumin using affinity capillary electrophoresis. Electrophoresis. 2001 Jul;22(11):2210-6. [PubMed:11504054 ]
Sunyer J, Herrero C, Ozalla D, Sala M, Ribas-Fito N, Grimalt J, Basagana X: Serum organochlorines and urinary porphyrin pattern in a population highly exposed to hexachlorobenzene. Environ Health. 2002 Jul 19;1(1):1. [PubMed:12495451 ]
Ged C, Moreau-Gaudry F, Taine L, Hombrados I, Calvas P, Colombies P, De Verneuil H: Prenatal diagnosis in congenital erythropoietic porphyria by metabolic measurement and DNA mutation analysis. Prenat Diagn. 1996 Jan;16(1):83-6. [PubMed:8821859 ]
Geronimi F, Richard E, Lamrissi-Garcia I, Lalanne M, Ged C, Redonnet-Vernhet I, Moreau-Gaudry F, de Verneuil H: Lentivirus-mediated gene transfer of uroporphyrinogen III synthase fully corrects the porphyric phenotype in human cells. J Mol Med (Berl). 2003 May;81(5):310-20. Epub 2003 Apr 30. [PubMed:12721665 ]
Bu W, Myers N, McCarty JD, O'Neill T, Hollar S, Stetson PL, Sved DW: Simultaneous determination of six urinary porphyrins using liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jan 15;783(2):411-23. [PubMed:12482484 ]
Fritsch C, Bolsen K, Ruzicka T, Goerz G: Congenital erythropoietic porphyria. J Am Acad Dermatol. 1997 Apr;36(4):594-610. [PubMed:9092747 ]
Zhang W, Zhang L, Ping G, Zhang Y, Kettrup A: Study on the multiple sites binding of human serum albumin and porphyrin by affinity capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):211-4. [PubMed:11939554 ]
Oguz F, Sidal M, Bayram C, Sansoy N, Hekim N: Ocular involvement in two symptomatic congenital erythropoietic porphyria. Eur J Pediatr. 1993 Aug;152(8):671-3. [PubMed:8404971 ]
Akhtar MK, Kaderbhai NN, Hopper DJ, Kelly SL, Kaderbhai MA: Export of a heterologous cytochrome P450 (CYP105D1) in Escherichia coli is associated with periplasmic accumulation of uroporphyrin. J Biol Chem. 2003 Nov 14;278(46):45555-62. Epub 2003 Aug 20. [PubMed:12930844 ]
Gorchein A, Guo R, Lim CK, Raimundo A, Pullon HW, Bellingham AJ: Porphyrins in urine, plasma, erythrocytes, bile and faeces in a case of congenital erythropoietic porphyria (Gunther's disease) treated with blood transfusion and iron chelation: lack of benefit from oral charcoal. Biomed Chromatogr. 1998 Nov-Dec;12(6):350-6. [PubMed:9861496 ]
Doss MO: Porphyrinurias and occupational disease. Ann N Y Acad Sci. 1987;514:204-18. [PubMed:3327428 ]
Winkelman JW, Collins GH: Neurotoxicity of tetraphenylporphinesulfonate TPPS4 and its relation to photodynamic therapy. Photochem Photobiol. 1987 Nov;46(5):801-7. [PubMed:3441503 ]

Showing metabocard for Uroporphyrin I (HMDB0000936)

MOL for HMDB0000936 (Uroporphyrin I)

3D MOL for HMDB0000936 (Uroporphyrin I)

3D SDF for HMDB0000936 (Uroporphyrin I)

3D-SDF for HMDB0000936 (Uroporphyrin I)

PDB for HMDB0000936 (Uroporphyrin I)

3D PDB for HMDB0000936 (Uroporphyrin I)

SMILES for HMDB0000936 (Uroporphyrin I)

INCHI for HMDB0000936 (Uroporphyrin I)

Structure for HMDB0000936 (Uroporphyrin I)

3D Structure for HMDB0000936 (Uroporphyrin I)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra