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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-02-26 21:22:44 UTC

HMDB ID

HMDB0000916

Secondary Accession Numbers

HMDB00916

Metabolite Identification

Common Name

Uroporphyrin III

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 III 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


  Mrv1652303031823092D          

 60 64  0  0  0  0            999 V2000
    7.3898   -3.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0135   -2.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5988   -2.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3306   -2.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0415   -2.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7733   -2.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5757   -2.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1114   -2.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7141   -3.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1323   -4.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7141   -5.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1114   -5.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5050   -6.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7733   -6.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0415   -6.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3306   -6.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5988   -6.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0135   -5.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3898   -5.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9716   -4.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2053   -3.6027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8987   -3.6027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8987   -5.3173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2053   -5.3173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5477   -1.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8095   -1.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8585   -0.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1698    0.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5964    0.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2440   -2.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8810   -2.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578   -2.1472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3411   -1.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7403   -1.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5227   -1.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6872   -0.6034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1405   -1.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0093   -2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7947   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5130   -2.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2236   -2.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5208   -3.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6111   -7.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3259   -7.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3027   -8.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0053   -8.9846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5768   -8.9444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9151   -6.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1778   -6.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9864   -7.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6320   -7.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2440   -5.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6184   -7.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9143   -7.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2201   -8.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9344   -8.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6490   -8.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0026   -6.5021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8276   -6.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2400   -7.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0  0  0  0
 16 15  1  0  0  0  0
 13 14  1  0  0  0  0
 23 14  1  0  0  0  0
 24 16  2  0  0  0  0
 17 16  1  0  0  0  0
 11 23  1  0  0  0  0
 12 13  2  0  0  0  0
 11 12  1  0  0  0  0
 10 11  2  0  0  0  0
  9 10  1  0  0  0  0
 22  9  2  0  0  0  0
  8  9  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  2  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  4  5  1  0  0  0  0
 21  4  1  0  0  0  0
  3  4  2  0  0  0  0
  1 21  1  0  0  0  0
  2  1  2  0  0  0  0
 20  1  1  0  0  0  0
  3  2  1  0  0  0  0
 19 20  2  0  0  0  0
 24 19  1  0  0  0  0
 18 19  1  0  0  0  0
 18 17  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 28 27  2  0  0  0  0
 29 27  1  0  0  0  0
 26 27  1  0  0  0  0
  2 30  1  0  0  0  0
 32 31  2  0  0  0  0
 33 31  1  0  0  0  0
 30 31  1  0  0  0  0
  7 34  1  0  0  0  0
 36 35  2  0  0  0  0
 37 35  1  0  0  0  0
 34 35  1  0  0  0  0
  8 38  1  0  0  0  0
 38 39  1  0  0  0  0
 41 40  2  0  0  0  0
 42 40  1  0  0  0  0
 39 40  1  0  0  0  0
 13 43  1  0  0  0  0
 43 44  1  0  0  0  0
 46 45  2  0  0  0  0
 47 45  1  0  0  0  0
 44 45  1  0  0  0  0
 12 48  1  0  0  0  0
 50 49  2  0  0  0  0
 51 49  1  0  0  0  0
 48 49  1  0  0  0  0
 18 52  1  0  0  0  0
 52 59  1  0  0  0  0
 17 53  1  0  0  0  0
 56 54  1  0  0  0  0
 53 54  1  0  0  0  0
 56 55  2  0  0  0  0
 56 57  1  0  0  0  0
 59 58  2  0  0  0  0
 59 60  1  0  0  0  0
M  END

HMDB0000916
     RDKit          3D
Uroporphyrin III
 98102  0  0  0  0  0  0  0  0999 V2000
   -3.8935    7.0690   -1.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934    6.2984   -2.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699    6.7688   -3.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1535    4.8831   -2.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3583    4.6236   -0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0217    3.2051   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8379    2.2871    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2881    2.4271    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6638    2.2331    1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8022    2.0216    2.8144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9907    2.2856    2.3083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612    1.0841    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272   -0.2181    1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4876   -1.3341    0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1656   -1.4688    1.1358 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510   -2.7444    0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865   -3.4152    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175   -2.9911    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -1.7053    0.1148 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0039   -1.4331   -0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2692   -0.1180   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4164    0.9906   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    1.1292   -0.7854 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7899    2.4019   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    3.0847   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899    2.6207   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798    1.3611    0.2335 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349    3.1147   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338    4.5604    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    5.4821   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9383    5.0965   -1.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0052    6.8546   -0.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573    2.2175   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765    2.5575    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7273    2.1620    1.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1486    2.5421    1.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9643    2.3057    0.9459 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6030    3.1431    3.0261 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7233   -2.6884   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1505   -2.8672   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3355   -3.0771   -2.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691   -2.0180   -2.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -1.9362   -3.2854 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7595   -1.0530   -3.3402 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -3.6038    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2187   -5.0398    0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3677   -5.9433   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434   -5.5306   -1.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5037   -7.3140   -0.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9925   -3.4567    0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1206   -4.8974   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6018   -4.9551   -1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691   -4.0171   -2.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116   -6.2398   -1.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0273   -2.5567    0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481   -2.9615    0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1544   -3.4586    1.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3212   -2.5929    2.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995   -2.1516    2.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401   -2.1469    3.4348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235    7.7559   -3.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515    4.6476   -2.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345    4.2050   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3852    4.8370   -0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6721    5.3113    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6059    3.4496    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8819    1.7674   -0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3482    1.7549    3.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3453   -0.2631    1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4730   -0.6843    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -4.4495    1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.0076   -1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4119    0.3422   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571    4.1450   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703    4.6887    1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390    4.6144    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905    7.4161   -0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145    2.0528   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5507    3.6505    0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    2.7106    2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6238    1.0616    1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5570    4.1626    3.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7400   -1.9502   -0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5466   -3.7578   -0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4073   -3.2600   -2.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8038   -4.0317   -2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035   -0.0988   -3.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -5.2560    0.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095   -5.2327    1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384   -7.7968    0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251   -5.2720    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4283   -5.4839    0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4230   -3.7676   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9707   -2.1125   -0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1699   -3.8075    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3600   -1.1410    3.6562 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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 54 93  1  0
 56 94  1  0
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 57 96  1  0
 57 97  1  0
 60 98  1  0
M  END


  Mrv1652303031823092D          

 60 64  0  0  0  0            999 V2000
    7.3898   -3.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0135   -2.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5988   -2.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3306   -2.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0415   -2.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7733   -2.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5757   -2.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1114   -2.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7141   -3.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1323   -4.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7141   -5.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1114   -5.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5050   -6.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7733   -6.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9716   -4.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2053   -3.6027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8987   -3.6027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8987   -5.3173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2053   -5.3173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5477   -1.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8095   -1.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8585   -0.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1698    0.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5964    0.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2440   -2.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8810   -2.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578   -2.1472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3411   -1.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7403   -1.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5227   -1.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6872   -0.6034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1405   -1.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0093   -2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7947   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5130   -2.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2236   -2.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5208   -3.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6111   -7.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3259   -7.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3027   -8.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0053   -8.9846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5768   -8.9444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9151   -6.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1778   -6.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9864   -7.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6320   -7.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2440   -5.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6184   -7.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9143   -7.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2201   -8.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9344   -8.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6490   -8.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0026   -6.5021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8276   -6.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2400   -7.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0  0  0  0
 16 15  1  0  0  0  0
 13 14  1  0  0  0  0
 23 14  1  0  0  0  0
 24 16  2  0  0  0  0
 17 16  1  0  0  0  0
 11 23  1  0  0  0  0
 12 13  2  0  0  0  0
 11 12  1  0  0  0  0
 10 11  2  0  0  0  0
  9 10  1  0  0  0  0
 22  9  2  0  0  0  0
  8  9  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  2  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  4  5  1  0  0  0  0
 21  4  1  0  0  0  0
  3  4  2  0  0  0  0
  1 21  1  0  0  0  0
  2  1  2  0  0  0  0
 20  1  1  0  0  0  0
  3  2  1  0  0  0  0
 19 20  2  0  0  0  0
 24 19  1  0  0  0  0
 18 19  1  0  0  0  0
 18 17  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 28 27  2  0  0  0  0
 29 27  1  0  0  0  0
 26 27  1  0  0  0  0
  2 30  1  0  0  0  0
 32 31  2  0  0  0  0
 33 31  1  0  0  0  0
 30 31  1  0  0  0  0
  7 34  1  0  0  0  0
 36 35  2  0  0  0  0
 37 35  1  0  0  0  0
 34 35  1  0  0  0  0
  8 38  1  0  0  0  0
 38 39  1  0  0  0  0
 41 40  2  0  0  0  0
 42 40  1  0  0  0  0
 39 40  1  0  0  0  0
 13 43  1  0  0  0  0
 43 44  1  0  0  0  0
 46 45  2  0  0  0  0
 47 45  1  0  0  0  0
 44 45  1  0  0  0  0
 12 48  1  0  0  0  0
 50 49  2  0  0  0  0
 51 49  1  0  0  0  0
 48 49  1  0  0  0  0
 18 52  1  0  0  0  0
 52 59  1  0  0  0  0
 17 53  1  0  0  0  0
 56 54  1  0  0  0  0
 53 54  1  0  0  0  0
 56 55  2  0  0  0  0
 56 57  1  0  0  0  0
 59 58  2  0  0  0  0
 59 60  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000916

> <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(CCC(O)=O)=C4CC(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)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)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-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

> <INCHI_KEY>
VZVFNUAIRVUCEW-UJJXFSCMSA-N

> <FORMULA>
C40H38N4O16

> <MOLECULAR_WEIGHT>
830.7469

> <EXACT_MASS>
830.228281188

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
85.11525153387961

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
3.512340196666666

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-8

> <JCHEM_PKA>
3.4816110444902053

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.108325482263556

> <JCHEM_POLAR_SURFACE_AREA>
355.76

> <JCHEM_REFRACTIVITY>
201.32140000000018

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000916
     RDKit          3D
Uroporphyrin III
 98102  0  0  0  0  0  0  0  0999 V2000
   -3.8935    7.0690   -1.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934    6.2984   -2.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699    6.7688   -3.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1535    4.8831   -2.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3583    4.6236   -0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0217    3.2051   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8379    2.2871    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2881    2.4271    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6638    2.2331    1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8022    2.0216    2.8144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9907    2.2856    2.3083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612    1.0841    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272   -0.2181    1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4876   -1.3341    0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1656   -1.4688    1.1358 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510   -2.7444    0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865   -3.4152    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175   -2.9911    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -1.7053    0.1148 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0039   -1.4331   -0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2692   -0.1180   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4164    0.9906   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    1.1292   -0.7854 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7899    2.4019   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    3.0847   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899    2.6207   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798    1.3611    0.2335 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349    3.1147   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338    4.5604    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    5.4821   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9383    5.0965   -1.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0052    6.8546   -0.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573    2.2175   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765    2.5575    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7273    2.1620    1.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1486    2.5421    1.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9643    2.3057    0.9459 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6030    3.1431    3.0261 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7233   -2.6884   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1505   -2.8672   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3355   -3.0771   -2.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691   -2.0180   -2.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -1.9362   -3.2854 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7595   -1.0530   -3.3402 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -3.6038    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2187   -5.0398    0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3677   -5.9433   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434   -5.5306   -1.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5037   -7.3140   -0.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9925   -3.4567    0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1206   -4.8974   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6018   -4.9551   -1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691   -4.0171   -2.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116   -6.2398   -1.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0273   -2.5567    0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481   -2.9615    0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1544   -3.4586    1.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3212   -2.5929    2.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995   -2.1516    2.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401   -2.1469    3.4348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235    7.7559   -3.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515    4.6476   -2.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345    4.2050   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3852    4.8370   -0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6721    5.3113    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6059    3.4496    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8819    1.7674   -0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3482    1.7549    3.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3453   -0.2631    1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4730   -0.6843    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -4.4495    1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.0076   -1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4119    0.3422   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571    4.1450   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703    4.6887    1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390    4.6144    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905    7.4161   -0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145    2.0528   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5507    3.6505    0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    2.7106    2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6238    1.0616    1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5570    4.1626    3.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7400   -1.9502   -0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5466   -3.7578   -0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4073   -3.2600   -2.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8038   -4.0317   -2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035   -0.0988   -3.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -5.2560    0.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095   -5.2327    1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384   -7.7968    0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251   -5.2720    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4283   -5.4839    0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7769   -6.6346   -2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4230   -3.7676   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9707   -2.1125   -0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1699   -3.8075    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994   -4.4427    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600   -1.1410    3.6562 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
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 46 47  1  0
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 16 50  2  0
 50 51  1  0
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 26  6  1  0
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 57 96  1  0
 57 97  1  0
 60 98  1  0
M  END

HEADER    PROTEIN                                 03-MAR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAR-18         0                                  
HETATM    1  C   UNK     0      13.794  -6.998   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.092  -5.593   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.184  -4.501   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.550  -5.203   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.877  -4.423   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.243  -5.203   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.741  -4.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.741  -5.593   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.000  -6.998   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.780  -8.325   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.000  -9.652   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.741 -11.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.609 -12.150   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.243 -11.448   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.877 -12.228   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.550 -11.448   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.184 -12.150   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.092 -11.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.794  -9.652   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.014  -8.325   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      15.316  -6.725   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      18.478  -6.725   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      18.478  -9.926   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      15.316  -9.926   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      14.089  -2.871   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.711  -1.962   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.803  -0.425   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.517   0.423   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      14.180   0.265   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.655  -5.496   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.978  -4.113   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.441  -4.008   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      11.837  -2.834   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      20.049  -3.124   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.509  -2.635   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      21.816  -1.126   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      22.662  -3.656   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      22.417  -5.393   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.883  -4.528   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      25.224  -5.285   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      26.551  -4.503   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      25.239  -6.825   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      19.807 -13.604   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      21.142 -14.425   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      21.098 -15.964   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      22.410 -16.771   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      19.743 -16.696   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      22.241 -11.360   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      22.732 -12.820   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      24.241 -13.125   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      21.713 -13.975   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      11.655 -11.038   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      14.221 -13.648   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      12.907 -14.450   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      11.611 -16.759   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      12.944 -15.989   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      14.278 -16.759   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       9.338 -12.137   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      10.878 -12.137   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      11.648 -13.471   0.000  0.00  0.00           O+0
CONECT    1   21    2   20                                                  
CONECT    2    1    3   30                                                  
CONECT    3    4    2   25                                                  
CONECT    4    5   21    3                                                  
CONECT    5    6    4                                                       
CONECT    6   22    7    5                                                  
CONECT    7    8    6   34                                                  
CONECT    8    9    7   38                                                  
CONECT    9   10   22    8                                                  
CONECT   10   11    9                                                       
CONECT   11   23   12   10                                                  
CONECT   12   13   11   48                                                  
CONECT   13   14   12   43                                                  
CONECT   14   15   13   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   24   17                                                  
CONECT   17   16   18   53                                                  
CONECT   18   19   17   52                                                  
CONECT   19   20   24   18                                                  
CONECT   20    1   19                                                       
CONECT   21    4    1                                                       
CONECT   22    9    6                                                       
CONECT   23   14   11                                                       
CONECT   24   16   19                                                       
CONECT   25    3   26                                                       
CONECT   26   25   27                                                       
CONECT   27   28   29   26                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    2   31                                                       
CONECT   31   32   33   30                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    7   35                                                       
CONECT   35   36   37   34                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    8   39                                                       
CONECT   39   38   40                                                       
CONECT   40   41   42   39                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   13   44                                                       
CONECT   44   43   45                                                       
CONECT   45   46   47   44                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   12   49                                                       
CONECT   49   50   51   48                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   18   59                                                       
CONECT   53   17   54                                                       
CONECT   54   56   53                                                       
CONECT   55   56                                                            
CONECT   56   54   55   57                                                  
CONECT   57   56                                                            
CONECT   58   59                                                            
CONECT   59   52   58   60                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

COMPND    HMDB0000916
HETATM    1  O1  UNL     1      -3.894   7.069  -1.426  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.493   6.298  -2.326  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.370   6.769  -3.611  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.154   4.883  -2.003  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.358   4.624  -0.535  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.022   3.205  -0.143  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.838   2.287   0.308  1.00  0.00           C  
HETATM    8  C6  UNL     1      -5.288   2.427   0.537  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.664   2.233   1.949  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.802   2.022   2.814  1.00  0.00           O  
HETATM   11  O4  UNL     1      -6.991   2.286   2.308  1.00  0.00           O  
HETATM   12  C8  UNL     1      -3.061   1.084   0.556  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.327  -0.218   1.008  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.488  -1.334   0.918  1.00  0.00           C  
HETATM   15  N1  UNL     1      -1.166  -1.469   1.136  1.00  0.00           N  
HETATM   16  C11 UNL     1      -0.851  -2.744   0.839  1.00  0.00           C  
HETATM   17  C12 UNL     1       0.387  -3.415   0.892  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.617  -2.991   0.458  1.00  0.00           C  
HETATM   19  N2  UNL     1       1.727  -1.705   0.115  1.00  0.00           N  
HETATM   20  C14 UNL     1       3.004  -1.433  -0.311  1.00  0.00           C  
HETATM   21  C15 UNL     1       3.269  -0.118  -0.664  1.00  0.00           C  
HETATM   22  C16 UNL     1       2.416   0.991  -0.554  1.00  0.00           C  
HETATM   23  N3  UNL     1       1.105   1.129  -0.785  1.00  0.00           N  
HETATM   24  C17 UNL     1       0.790   2.402  -0.498  1.00  0.00           C  
HETATM   25  C18 UNL     1      -0.435   3.085  -0.555  1.00  0.00           C  
HETATM   26  C19 UNL     1      -1.690   2.621  -0.194  1.00  0.00           C  
HETATM   27  N4  UNL     1      -1.780   1.361   0.233  1.00  0.00           N  
HETATM   28  C20 UNL     1       1.935   3.115  -0.070  1.00  0.00           C  
HETATM   29  C21 UNL     1       2.034   4.560   0.360  1.00  0.00           C  
HETATM   30  C22 UNL     1       1.990   5.482  -0.755  1.00  0.00           C  
HETATM   31  O5  UNL     1       1.938   5.096  -1.936  1.00  0.00           O  
HETATM   32  O6  UNL     1       2.005   6.855  -0.511  1.00  0.00           O  
HETATM   33  C23 UNL     1       2.957   2.218  -0.109  1.00  0.00           C  
HETATM   34  C24 UNL     1       4.376   2.557   0.269  1.00  0.00           C  
HETATM   35  C25 UNL     1       4.727   2.162   1.667  1.00  0.00           C  
HETATM   36  C26 UNL     1       6.149   2.542   1.872  1.00  0.00           C  
HETATM   37  O7  UNL     1       6.964   2.306   0.946  1.00  0.00           O  
HETATM   38  O8  UNL     1       6.603   3.143   3.026  1.00  0.00           O  
HETATM   39  C27 UNL     1       3.723  -2.688  -0.212  1.00  0.00           C  
HETATM   40  C28 UNL     1       5.150  -2.867  -0.530  1.00  0.00           C  
HETATM   41  C29 UNL     1       5.335  -3.077  -2.011  1.00  0.00           C  
HETATM   42  C30 UNL     1       4.869  -2.018  -2.896  1.00  0.00           C  
HETATM   43  O9  UNL     1       3.680  -1.936  -3.285  1.00  0.00           O  
HETATM   44  O10 UNL     1       5.759  -1.053  -3.340  1.00  0.00           O  
HETATM   45  C31 UNL     1       2.917  -3.604   0.242  1.00  0.00           C  
HETATM   46  C32 UNL     1       3.219  -5.040   0.516  1.00  0.00           C  
HETATM   47  C33 UNL     1       2.368  -5.943  -0.274  1.00  0.00           C  
HETATM   48  O11 UNL     1       1.543  -5.531  -1.113  1.00  0.00           O  
HETATM   49  O12 UNL     1       2.504  -7.314  -0.063  1.00  0.00           O  
HETATM   50  C34 UNL     1      -1.992  -3.457   0.423  1.00  0.00           C  
HETATM   51  C35 UNL     1      -2.121  -4.897  -0.008  1.00  0.00           C  
HETATM   52  C36 UNL     1      -1.602  -4.955  -1.383  1.00  0.00           C  
HETATM   53  O13 UNL     1      -1.169  -4.017  -2.053  1.00  0.00           O  
HETATM   54  O14 UNL     1      -1.612  -6.240  -1.977  1.00  0.00           O  
HETATM   55  C37 UNL     1      -3.027  -2.557   0.479  1.00  0.00           C  
HETATM   56  C38 UNL     1      -4.448  -2.962   0.206  1.00  0.00           C  
HETATM   57  C39 UNL     1      -5.154  -3.459   1.417  1.00  0.00           C  
HETATM   58  C40 UNL     1      -5.321  -2.593   2.550  1.00  0.00           C  
HETATM   59  O15 UNL     1      -6.499  -2.152   2.817  1.00  0.00           O  
HETATM   60  O16 UNL     1      -4.340  -2.147   3.435  1.00  0.00           O  
HETATM   61  H1  UNL     1      -3.523   7.756  -3.828  1.00  0.00           H  
HETATM   62  H2  UNL     1      -2.151   4.648  -2.340  1.00  0.00           H  
HETATM   63  H3  UNL     1      -3.835   4.205  -2.572  1.00  0.00           H  
HETATM   64  H4  UNL     1      -4.385   4.837  -0.293  1.00  0.00           H  
HETATM   65  H5  UNL     1      -2.672   5.311   0.014  1.00  0.00           H  
HETATM   66  H6  UNL     1      -5.606   3.450   0.273  1.00  0.00           H  
HETATM   67  H7  UNL     1      -5.882   1.767  -0.147  1.00  0.00           H  
HETATM   68  H8  UNL     1      -7.348   1.755   3.114  1.00  0.00           H  
HETATM   69  H9  UNL     1      -4.345  -0.263   1.437  1.00  0.00           H  
HETATM   70  H10 UNL     1      -0.473  -0.684   1.511  1.00  0.00           H  
HETATM   71  H11 UNL     1       0.419  -4.449   1.322  1.00  0.00           H  
HETATM   72  H12 UNL     1       4.309  -0.008  -1.038  1.00  0.00           H  
HETATM   73  H13 UNL     1       0.412   0.342  -1.172  1.00  0.00           H  
HETATM   74  H14 UNL     1      -0.457   4.145  -0.907  1.00  0.00           H  
HETATM   75  H15 UNL     1       1.170   4.689   1.072  1.00  0.00           H  
HETATM   76  H16 UNL     1       2.939   4.614   1.011  1.00  0.00           H  
HETATM   77  H17 UNL     1       1.290   7.416  -0.986  1.00  0.00           H  
HETATM   78  H18 UNL     1       5.015   2.053  -0.473  1.00  0.00           H  
HETATM   79  H19 UNL     1       4.551   3.651   0.113  1.00  0.00           H  
HETATM   80  H20 UNL     1       4.111   2.711   2.399  1.00  0.00           H  
HETATM   81  H21 UNL     1       4.624   1.062   1.811  1.00  0.00           H  
HETATM   82  H22 UNL     1       6.557   4.163   3.182  1.00  0.00           H  
HETATM   83  H23 UNL     1       5.740  -1.950  -0.253  1.00  0.00           H  
HETATM   84  H24 UNL     1       5.547  -3.758  -0.022  1.00  0.00           H  
HETATM   85  H25 UNL     1       6.407  -3.260  -2.250  1.00  0.00           H  
HETATM   86  H26 UNL     1       4.804  -4.032  -2.333  1.00  0.00           H  
HETATM   87  H27 UNL     1       5.604  -0.099  -3.066  1.00  0.00           H  
HETATM   88  H28 UNL     1       4.281  -5.256   0.299  1.00  0.00           H  
HETATM   89  H29 UNL     1       3.110  -5.233   1.616  1.00  0.00           H  
HETATM   90  H30 UNL     1       1.638  -7.797   0.238  1.00  0.00           H  
HETATM   91  H31 UNL     1      -3.125  -5.272   0.138  1.00  0.00           H  
HETATM   92  H32 UNL     1      -1.428  -5.484   0.628  1.00  0.00           H  
HETATM   93  H33 UNL     1      -0.777  -6.635  -2.372  1.00  0.00           H  
HETATM   94  H34 UNL     1      -4.423  -3.768  -0.550  1.00  0.00           H  
HETATM   95  H35 UNL     1      -4.971  -2.113  -0.236  1.00  0.00           H  
HETATM   96  H36 UNL     1      -6.170  -3.807   1.066  1.00  0.00           H  
HETATM   97  H37 UNL     1      -4.699  -4.443   1.774  1.00  0.00           H  
HETATM   98  H38 UNL     1      -4.360  -1.141   3.656  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   45
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   45   45
CONECT   40   41   83   84
CONECT   41   42   85   86
CONECT   42   43   43   44
CONECT   44   87
CONECT   45   46
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

HMDB0000916
     RDKit          3D
Uroporphyrin III
 98102  0  0  0  0  0  0  0  0999 V2000
   -3.8935    7.0690   -1.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934    6.2984   -2.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699    6.7688   -3.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1535    4.8831   -2.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3583    4.6236   -0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0217    3.2051   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8379    2.2871    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2881    2.4271    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6638    2.2331    1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8022    2.0216    2.8144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9907    2.2856    2.3083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612    1.0841    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272   -0.2181    1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4876   -1.3341    0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1656   -1.4688    1.1358 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510   -2.7444    0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865   -3.4152    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175   -2.9911    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -1.7053    0.1148 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0039   -1.4331   -0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2692   -0.1180   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4164    0.9906   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    1.1292   -0.7854 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7899    2.4019   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    3.0847   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899    2.6207   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798    1.3611    0.2335 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349    3.1147   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338    4.5604    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    5.4821   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9383    5.0965   -1.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0052    6.8546   -0.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573    2.2175   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765    2.5575    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7273    2.1620    1.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1486    2.5421    1.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9643    2.3057    0.9459 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6030    3.1431    3.0261 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7233   -2.6884   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1505   -2.8672   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3355   -3.0771   -2.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691   -2.0180   -2.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -1.9362   -3.2854 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7595   -1.0530   -3.3402 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -3.6038    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2187   -5.0398    0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3677   -5.9433   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434   -5.5306   -1.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5037   -7.3140   -0.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9925   -3.4567    0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1206   -4.8974   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6018   -4.9551   -1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691   -4.0171   -2.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116   -6.2398   -1.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0273   -2.5567    0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481   -2.9615    0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1544   -3.4586    1.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3212   -2.5929    2.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995   -2.1516    2.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401   -2.1469    3.4348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235    7.7559   -3.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515    4.6476   -2.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345    4.2050   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3852    4.8370   -0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6721    5.3113    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6059    3.4496    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8819    1.7674   -0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3482    1.7549    3.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3453   -0.2631    1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4730   -0.6843    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -4.4495    1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.0076   -1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4119    0.3422   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571    4.1450   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703    4.6887    1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390    4.6144    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905    7.4161   -0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145    2.0528   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5507    3.6505    0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    2.7106    2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6238    1.0616    1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5570    4.1626    3.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7400   -1.9502   -0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5466   -3.7578   -0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4073   -3.2600   -2.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8038   -4.0317   -2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035   -0.0988   -3.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -5.2560    0.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095   -5.2327    1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384   -7.7968    0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251   -5.2720    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4283   -5.4839    0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7769   -6.6346   -2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4230   -3.7676   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9707   -2.1125   -0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1699   -3.8075    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994   -4.4427    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600   -1.1410    3.6562 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  1  0
 42 43  2  0
 42 44  1  0
 39 45  2  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
 45 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
 41 85  1  0
 41 86  1  0
 44 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
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropionic acid	ChEBI
Uroporphyrin 3	ChEBI
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropionate	Generator
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoate	HMDB
3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoic acid	HMDB
3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionate	HMDB
3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionic acid	HMDB
Coproporphyrin III	HMDB

Chemical Formula

C₄₀H₃₈N₄O₁₆

Average Molecular Weight

830.7469

Monoisotopic Molecular Weight

830.228281188

IUPAC Name

3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid

Traditional Name

CAS Registry Number

18273-06-8

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(CCC(O)=O)=C4CC(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)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)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-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

InChI Key

VZVFNUAIRVUCEW-UJJXFSCMSA-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

Physiological effect

Health effect

Porphyria (HMDB: HMDB0000916)
Hereditary coproporphyria (HMDB: HMDB0000916)

Disposition

Biological location

Liver (HMDB: HMDB0000916)

Cellular substructure

Organelle

Mitochondria

Mitochondria (HMDB: HMDB0000916)

Biofluid or Excreta

Urine (HMDB: HMDB0000916)

Organ

Liver (HMDB: HMDB0000916)

Excreta

Biofluid or Excreta

Urine (PMID: 11836151)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000916)

Source

Endogenous

Endogenous (HMDB: HMDB0000916)

Plant

Glycine max (HMDB: HMDB0000916)

Exogenous

Food

Food (HMDB: HMDB0000916)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Soy

Soy bean (FooDB: FOOD00085)

Process

Naturally occurring process

Biological process

Biochemical pathway

Acute intermittent porphyria (HMDB: HMDB0000916)

Metabolic pathway

Porphyrin Metabolism (PathBank: SMP0000024)
Porphyrin Metabolism (PathBank: SMP0002363)

Disease pathway

Acute Intermittent Porphyria (PathBank: SMP0000344)
Porphyria Variegata (PV) (PathBank: SMP0000346)
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease (PathBank: SMP0000345)
Hereditary Coproporphyria (HCP) (PathBank: SMP0000342)

Role

Indirect biological role

Phototoxin (HMDB: HMDB0000916)

Metabotoxin

Metabotoxin (HMDB: HMDB0000916)

Biological role

human metabolite (HMDB: HMDB0000916)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.037 g/L	ALOGPS
logP	0.79	ALOGPS
logP	3.51	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.11	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	85.12 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]+	276.04	32859911
AllCCS	[M-H]-	273.919	32859911
DeepCCS	[M+H]+	274.454	30932474
DeepCCS	[M-H]-	272.438	30932474
DeepCCS	[M-2H]-	306.167	30932474
DeepCCS	[M+Na]+	280.444	30932474
AllCCS	[M+H]+	276.0	32859911
AllCCS	[M+H-H2O]+	276.0	32859911
AllCCS	[M+NH4]+	276.1	32859911
AllCCS	[M+Na]+	276.1	32859911
AllCCS	[M-H]-	273.9	32859911
AllCCS	[M+Na-2H]-	278.6	32859911
AllCCS	[M+HCOO]-	283.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Uroporphyrin III	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(CCC(O)=O)=C4CC(O)=O)/C(CC(O)=O)=C3CCC(O)=O	7825.8	Standard polar	33892256
Uroporphyrin III	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(CCC(O)=O)=C4CC(O)=O)/C(CC(O)=O)=C3CCC(O)=O	4929.6	Standard non polar	33892256
Uroporphyrin III	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(CCC(O)=O)=C4CC(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 III 10V, Positive-QTOF	splash10-0hft-0000000920-cc03b9bed8ec1e3756f2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 20V, Positive-QTOF	splash10-0gbi-0000000900-b9c5416788c41a1b932d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 40V, Positive-QTOF	splash10-0ftr-0000000900-ddf789a09baa29543062	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 10V, Negative-QTOF	splash10-02t9-0000000940-171f6daf64defe53ba6e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 20V, Negative-QTOF	splash10-014i-0000000910-e893ced4f4069e732360	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 40V, Negative-QTOF	splash10-014i-2000000900-e8e4a229f7baf3810285	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 10V, Negative-QTOF	splash10-014r-0000000900-1ba54d2ecd921bbf981c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 20V, Negative-QTOF	splash10-014u-0000000900-8dfb85a7347e408fafae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 40V, Negative-QTOF	splash10-00ku-0000000900-cc696857ebd0630cc06a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 10V, Positive-QTOF	splash10-02t9-0000000930-9dd5499b3b084b8cef39	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 20V, Positive-QTOF	splash10-00or-0000000900-e6018a2ba33c9cad4454	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Uroporphyrin III 40V, Positive-QTOF	splash10-0173-0000000900-24c512158030a2f09176	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

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

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.00005 (0.00005-0.0007) umol/mmol creatinine	Newborn (0-30 days old)	Both	Hexachlorobenzene exposure	11836151	details

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

FDB005664

KNApSAcK ID

Not Available

Chemspider ID

16736727

KEGG Compound ID

C02469

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5870

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15436

Food Biomarker Ontology

Not Available

VMH ID

C02469

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kajiwara, Masahiro; Mizutani, Minoru; Kojima, Ichiro. Manufacture of uroporphyrin III with Arthrobacter. Jpn. Kokai Tokkyo Koho (1993), 7 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Schonning C, Leeming R, Stenstrom TA: Faecal contamination of source-separated human urine based on the content of faecal sterols. Water Res. 2002 Apr;36(8):1965-72. [PubMed:12092571 ]
Luo J, Lim CK: Isolation and characterization of new porphyrin metabolites in human porphyria cutanea tarda and in rats treated with hexachlorobenzene by HPTLC, HPLC and liquid secondary ion mass spectrometry. Biomed Chromatogr. 1995 May-Jun;9(3):113-22. [PubMed:7655298 ]
Salen G, Berginer V, Shore V, Horak I, Horak E, Tint GS, Shefer S: Increased concentrations of cholestanol and apolipoprotein B in the cerebrospinal fluid of patients with cerebrotendinous xanthomatosis. Effect of chenodeoxycholic acid. N Engl J Med. 1987 May 14;316(20):1233-8. [PubMed:3106810 ]
Tsai SF, Bishop DF, Desnick RJ: Purification and properties of uroporphyrinogen III synthase from human erythrocytes. J Biol Chem. 1987 Jan 25;262(3):1268-73. [PubMed:3805019 ]
Bozek P, Hutta M, Hrivnakova B: Rapid analysis of porphyrins at low ng/l and microg/l levels in human urine by a gradient liquid chromatography method using octadecylsilica monolithic columns. J Chromatogr A. 2005 Aug 19;1084(1-2):24-32. [PubMed:16114232 ]
Hernandez-Zavala A, Del Razo LM, Garcia-Vargas GG, Aguilar C, Borja VH, Albores A, Cebrian ME: Altered activity of heme biosynthesis pathway enzymes in individuals chronically exposed to arsenic in Mexico. Arch Toxicol. 1999 Mar;73(2):90-5. [PubMed:10350189 ]
To-Figueras J, Ozalla D, Mateu CH: Long-standing changes in the urinary profile of porphyrin isomers after clinical remission of porphyria cutanea tarda. Ann Clin Lab Sci. 2003 Summer;33(3):251-6. [PubMed:12956438 ]
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 III (HMDB0000916)

MOL for HMDB0000916 (Uroporphyrin III)

3D MOL for HMDB0000916 (Uroporphyrin III)

3D SDF for HMDB0000916 (Uroporphyrin III)

3D-SDF for HMDB0000916 (Uroporphyrin III)

PDB for HMDB0000916 (Uroporphyrin III)

3D PDB for HMDB0000916 (Uroporphyrin III)

SMILES for HMDB0000916 (Uroporphyrin III)

INCHI for HMDB0000916 (Uroporphyrin III)

Structure for HMDB0000916 (Uroporphyrin III)

3D Structure for HMDB0000916 (Uroporphyrin III)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra