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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-07-21 15:10:08 UTC

HMDB ID

HMDB0001137

Secondary Accession Numbers

HMDB01137

Metabolite Identification

Common Name

Hydroxymethylbilane

Description

Hydroxymethylbilane, also known as preuroporphyrinogen, belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next. The compound is generated from four molecules of porphobilinogen by the enzyme porphobilinogen deaminase:The enzyme uroporphyrinogen III synthase closes the chain to form a porphyrinogen a class of compounds with the hexahydroporphine macrocycle; specifically, uroporphyrinogen III. The chain starts with a hydroxymethyl group −CH2−OH and ends with an hydrogen, in place of the respective methylene bridges. Hydroxymethylbilane is a weakly acidic compound (based on its pKa). Hydroxymethylbilane exists in all living species, ranging from bacteria to humans. In humans, hydroxymethylbilane is involved in the metabolic disorder called congenital erythropoietic porphyria (cep) or gunther disease pathway. Outside of the human body, Hydroxymethylbilane has been detected, but not quantified in, several different foods, such as garden tomato, chinese cabbages, persian limes, rosemaries, and sacred lotus. This could make hydroxymethylbilane a potential biomarker for the consumption of these foods. The name is often abbreviated as HMB.The compound is a substituted bilane, a chain of four pyrrole rings interconnected by methylene bridges −CH2−. The other two carbon atoms of each pyrrole cycle are connected to an acetic acid group −CH2−COOH and a propionic acid group −CH2−CH2−COOH, in that order. In the absence of the enzyme, the compound undergoes spontaneous cyclization and becomes uroporphyrinogen I.

Structure

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


  Mrv1652307212017092D          

 61 64  0  0  0  0            999 V2000
   -1.3840    0.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4491    1.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2585    1.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9909    1.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343    0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550   -0.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9406   -1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058   -2.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777   -1.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981   -0.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    0.1999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.5115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5630   -1.5191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7499   -2.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1812    1.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276    0.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1630   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3728   -3.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688   -3.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -2.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9552   -3.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747   -4.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787   -4.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -5.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707    0.1922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5609    1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7630    0.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7780    1.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7929    2.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759    2.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1566    1.4221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7197    1.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407   -2.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1384   -2.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7192   -1.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0978   -1.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5170   -1.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342   -2.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1235    1.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094    0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5054    0.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995   -0.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7530   -3.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3337   -3.1183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -4.5003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -2.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -0.9681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1319   -1.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278   -1.9830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983    2.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0347    3.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8175    2.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0196    2.5511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9297    2.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7256    2.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7315    3.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9355    3.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496    3.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772   -2.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772   -3.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 26  1  0  0  0  0
 28  1  2  0  0  0  0
 11  1  1  0  0  0  0
  2  3  1  0  0  0  0
 26  2  1  0  0  0  0
 16  2  2  0  0  0  0
  3  4  1  0  0  0  0
  4 12  1  0  0  0  0
 33  4  2  0  0  0  0
  5  6  1  0  0  0  0
 12  5  1  0  0  0  0
 17  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7 13  1  0  0  0  0
  7 34  2  0  0  0  0
  8 60  1  0  0  0  0
 21  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 18  9  2  0  0  0  0
 10 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  2  0  0  0  0
 16 28  1  0  0  0  0
 33 17  1  0  0  0  0
 34 21  1  0  0  0  0
 15 18  1  0  0  0  0
 15 47  1  0  0  0  0
 16 51  1  0  0  0  0
 17 40  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 44  1  0  0  0  0
 44 46  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  2  0  0  0  0
 27 29  1  0  0  0  0
 28 27  1  0  0  0  0
 29 31  1  0  0  0  0
 31 30  1  0  0  0  0
 31 32  2  0  0  0  0
 33 55  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 38  1  0  0  0  0
 38 37  1  0  0  0  0
 38 39  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 44 45  2  0  0  0  0
 47 49  1  0  0  0  0
 49 48  2  0  0  0  0
 49 50  1  0  0  0  0
 51 53  1  0  0  0  0
 53 52  2  0  0  0  0
 53 54  1  0  0  0  0
 55 56  1  0  0  0  0
 56 58  1  0  0  0  0
 58 57  1  0  0  0  0
 58 59  2  0  0  0  0
 60 61  1  0  0  0  0
M  END

HMDB0001137
     RDKit          3D
Hydroxymethylbilane
107110  0  0  0  0  0  0  0  0999 V2000
   12.1263    0.3884   -0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9633    0.2721   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2778    1.1291   -1.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1802   -0.7798    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8945   -1.1443   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8533   -1.2970    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3213   -2.4935    0.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2703   -2.1191    1.4695 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7189   -1.0359    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6603   -0.4373    2.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3987   -0.3896    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3916    0.4699    1.7358 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3306    0.4739    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564    1.3547    0.9397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290    1.0218    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621    0.0759    0.9770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.1347    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0942   -0.9596    0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4268   -0.2646    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8536    0.7794   -0.0892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1114    0.9874   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0397    1.8504   -0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0060    1.1309   -2.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6823   -0.0167    0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0933   -0.1087    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4886    1.0017    2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6632    1.3048    2.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5166    1.6408    2.6995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5639   -0.8062    1.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7449   -2.0369    1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8513   -3.2441    1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0097   -3.2105    0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1295   -3.3267    0.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7326   -3.0412   -1.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7495    0.6379   -1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464    0.6168   -2.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9960    1.8443   -2.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391    2.0295   -4.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    2.8784   -1.9644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    1.3722   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1906    2.4773   -1.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    3.8180   -1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025    3.9529    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    4.9184    0.9631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0279    3.2021    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -0.5060   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8775   -0.9353   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0491    0.0305   -2.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -0.2428   -3.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096    1.1807   -2.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727   -1.0537    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870   -2.2368   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5318   -2.0276   -1.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5263   -3.1519   -1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7174   -2.8204   -1.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1904   -4.4531   -1.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7784   -0.2616    0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8423    1.0091    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8390    1.6366    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9009    1.0002    2.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5206    2.7262    1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4283    2.1495   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8453   -1.7070    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0079   -0.4235    1.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6765   -0.4012   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1224   -2.1152   -1.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9299   -3.4456    0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413   -2.9573    2.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705    0.6254    2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3795   -0.9199    3.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    1.0177    2.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959    2.2778    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0348    1.7366    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -0.5113    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2118   -1.7438   -0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0173   -1.6015    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1524    1.5644   -0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9609    1.9936   -0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4481    2.7808   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0718    0.1217   -1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6735   -0.0633    0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3001   -1.0324    1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7246    2.0729    2.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7303   -2.1344    2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5117   -1.9119    2.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9063   -3.4474    0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0387   -4.1116    1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3210   -2.6447   -1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089    0.1306   -3.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723   -0.1943   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5750    2.7138   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6356    2.4088   -2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    2.2662   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
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 61107  1  0
M  END


  Mrv1652307212017092D          

 61 64  0  0  0  0            999 V2000
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 60 61  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001137

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=C(CC(O)=O)C(CCC(O)=O)=C(CC2=C(CC(O)=O)C(CCC(O)=O)=C(CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=CN4)N3)N2)N1

> <INCHI_IDENTIFIER>
InChI=1S/C40H46N4O17/c45-17-32-25(12-40(60)61)21(4-8-36(52)53)29(44-32)15-31-24(11-39(58)59)20(3-7-35(50)51)28(43-31)14-30-23(10-38(56)57)19(2-6-34(48)49)27(42-30)13-26-22(9-37(54)55)18(16-41-26)1-5-33(46)47/h16,41-45H,1-15,17H2,(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)

> <INCHI_KEY>
WDFJYRZCZIUBPR-UHFFFAOYSA-N

> <FORMULA>
C40H46N4O17

> <MOLECULAR_WEIGHT>
854.8098

> <EXACT_MASS>
854.285796066

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
107

> <JCHEM_AVERAGE_POLARIZABILITY>
85.68481619191945

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(5-{[3-(2-carboxyethyl)-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-2-yl]methyl}-2-{[4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-4-(carboxymethyl)-1H-pyrrol-3-yl)propanoic acid

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.9672566426666659

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-8

> <JCHEM_PKA>
3.626386055193484

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.253943717832704

> <JCHEM_POLAR_SURFACE_AREA>
381.78999999999996

> <JCHEM_REFRACTIVITY>
209.9212000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(5-{[3-(2-carboxyethyl)-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-2-yl]methyl}-2-{[4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-4-(carboxymethyl)-1H-pyrrol-3-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001137
     RDKit          3D
Hydroxymethylbilane
107110  0  0  0  0  0  0  0  0999 V2000
   12.1263    0.3884   -0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9633    0.2721   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2778    1.1291   -1.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1802   -0.7798    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8945   -1.1443   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8533   -1.2970    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3213   -2.4935    0.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2703   -2.1191    1.4695 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7189   -1.0359    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6603   -0.4373    2.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3987   -0.3896    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3916    0.4699    1.7358 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3306    0.4739    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564    1.3547    0.9397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290    1.0218    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621    0.0759    0.9770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.1347    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0942   -0.9596    0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4268   -0.2646    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8536    0.7794   -0.0892 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0397    1.8504   -0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0060    1.1309   -2.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.0933   -0.1087    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4886    1.0017    2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6632    1.3048    2.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5166    1.6408    2.6995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5639   -0.8062    1.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7449   -2.0369    1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8513   -3.2441    1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0097   -3.2105    0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1295   -3.3267    0.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7326   -3.0412   -1.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7495    0.6379   -1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464    0.6168   -2.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9960    1.8443   -2.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391    2.0295   -4.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    2.8784   -1.9644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    1.3722   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1906    2.4773   -1.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    3.8180   -1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025    3.9529    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    4.9184    0.9631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0279    3.2021    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -0.5060   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9009    1.0002    2.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5206    2.7262    1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.8453   -1.7070    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3311    1.0177    2.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959    2.2778    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0348    1.7366    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -0.5113    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2118   -1.7438   -0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0173   -1.6015    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.6735   -0.0633    0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3001   -1.0324    1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7246    2.0729    2.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7303   -2.1344    2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5117   -1.9119    2.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9063   -3.4474    0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0387   -4.1116    1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3210   -2.6447   -1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089    0.1306   -3.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723   -0.1943   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5750    2.7138   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6356    2.4088   -2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    2.2662   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1995    4.2799   -0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2454   -1.9048   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029   -1.0665   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5954    1.9831   -1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9695   -2.8609    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -2.9220   -0.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8883   -1.0404   -1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3856    1.2247   -0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8825    3.2736    1.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 21-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUL-20         0                                  
HETATM    1  C   UNK     0      -2.583   0.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.838   1.879   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.483   2.664   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.850   1.891   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.611   0.107   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.396  -1.214   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.623  -2.542   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.878  -4.342   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.810  -4.354   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.572  -2.570   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.356  -1.248   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.090   0.373   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       2.105  -2.821   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      -1.051  -2.836   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -3.266  -3.975   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.205   2.575   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.345   1.513   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.171  -5.061   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.563  -6.551   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.048  -6.956   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.244  -5.037   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.650  -6.523   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.926  -8.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.440  -8.445   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.347  -9.529   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0      -1.065   0.359   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -4.780   1.871   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.291   1.479   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.186   3.356   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.080   5.234   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.675   3.748   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.759   2.655   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.210   2.599   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.369  -3.941   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.858  -4.333   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.943  -3.239   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.516  -2.537   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.432  -3.631   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.837  -5.117   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.830   1.918   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.924   0.834   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       8.410   1.240   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       6.532  -0.655   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       5.139  -6.915   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       6.223  -5.821   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       5.544  -8.401   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -4.752  -4.380   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -5.454  -1.807   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -5.846  -3.296   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -7.332  -3.702   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -2.610   4.060   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -1.931   6.640   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -1.526   5.154   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -0.037   4.762   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       3.602   4.088   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       5.088   4.493   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       6.966   6.388   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       5.480   5.983   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       4.386   7.067   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       0.518  -5.127   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       0.518  -6.667   0.000  0.00  0.00           O+0
CONECT    1   26   28   11                                                  
CONECT    2    3   26   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3   12   33                                                  
CONECT    5    6   12   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6   13   34                                                  
CONECT    8   60   21   13                                                  
CONECT    9   14   18                                                       
CONECT   10   11   14   15                                                  
CONECT   11    1   10                                                       
CONECT   12    4    5                                                       
CONECT   13    7    8                                                       
CONECT   14    9   10                                                       
CONECT   15   10   18   47                                                  
CONECT   16    2   28   51                                                  
CONECT   17    5   33   40                                                  
CONECT   18    9   15   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   24                                                       
CONECT   21    8   34   22                                                  
CONECT   22   21   44                                                       
CONECT   23   24                                                            
CONECT   24   20   23   25                                                  
CONECT   25   24                                                            
CONECT   26    1    2                                                       
CONECT   27   29   28                                                       
CONECT   28    1   16   27                                                  
CONECT   29   27   31                                                       
CONECT   30   31                                                            
CONECT   31   29   30   32                                                  
CONECT   32   31                                                            
CONECT   33    4   17   55                                                  
CONECT   34    7   21   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   38                                                       
CONECT   37   38                                                            
CONECT   38   36   37   39                                                  
CONECT   39   38                                                            
CONECT   40   17   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   22   46   45                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   15   49                                                       
CONECT   48   49                                                            
CONECT   49   47   48   50                                                  
CONECT   50   49                                                            
CONECT   51   16   53                                                       
CONECT   52   53                                                            
CONECT   53   51   52   54                                                  
CONECT   54   53                                                            
CONECT   55   33   56                                                       
CONECT   56   55   58                                                       
CONECT   57   58                                                            
CONECT   58   56   57   59                                                  
CONECT   59   58                                                            
CONECT   60    8   61                                                       
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

COMPND    HMDB0001137
HETATM    1  O1  UNL     1      12.126   0.388  -0.386  1.00  0.00           O  
HETATM    2  C1  UNL     1      10.963   0.272  -0.544  1.00  0.00           C  
HETATM    3  O2  UNL     1      10.278   1.129  -1.388  1.00  0.00           O  
HETATM    4  C2  UNL     1      10.180  -0.780   0.126  1.00  0.00           C  
HETATM    5  C3  UNL     1       8.894  -1.144  -0.525  1.00  0.00           C  
HETATM    6  C4  UNL     1       7.853  -1.297   0.357  1.00  0.00           C  
HETATM    7  C5  UNL     1       7.321  -2.494   0.962  1.00  0.00           C  
HETATM    8  N1  UNL     1       6.270  -2.119   1.470  1.00  0.00           N  
HETATM    9  C6  UNL     1       5.719  -1.036   1.557  1.00  0.00           C  
HETATM   10  C7  UNL     1       4.660  -0.437   2.074  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.399  -0.390   1.404  1.00  0.00           C  
HETATM   12  N2  UNL     1       2.392   0.470   1.736  1.00  0.00           N  
HETATM   13  C9  UNL     1       1.331   0.474   0.855  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.256   1.355   0.940  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.029   1.022   0.418  1.00  0.00           C  
HETATM   16  N3  UNL     1      -1.862   0.076   0.977  1.00  0.00           N  
HETATM   17  C12 UNL     1      -3.000  -0.135   0.116  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.094  -0.960   0.393  1.00  0.00           C  
HETATM   19  C14 UNL     1      -5.427  -0.265   0.589  1.00  0.00           C  
HETATM   20  N4  UNL     1      -5.854   0.779  -0.089  1.00  0.00           N  
HETATM   21  C15 UNL     1      -7.111   0.987  -0.056  1.00  0.00           C  
HETATM   22  C16 UNL     1      -8.040   1.850  -0.856  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.006   1.131  -2.194  1.00  0.00           O  
HETATM   24  C17 UNL     1      -7.682  -0.017   0.750  1.00  0.00           C  
HETATM   25  C18 UNL     1      -9.093  -0.109   1.076  1.00  0.00           C  
HETATM   26  C19 UNL     1      -9.489   1.002   2.008  1.00  0.00           C  
HETATM   27  O4  UNL     1     -10.663   1.305   2.098  1.00  0.00           O  
HETATM   28  O5  UNL     1      -8.517   1.641   2.700  1.00  0.00           O  
HETATM   29  C20 UNL     1      -6.564  -0.806   1.133  1.00  0.00           C  
HETATM   30  C21 UNL     1      -6.745  -2.037   1.926  1.00  0.00           C  
HETATM   31  C22 UNL     1      -6.851  -3.244   1.064  1.00  0.00           C  
HETATM   32  C23 UNL     1      -8.010  -3.211   0.133  1.00  0.00           C  
HETATM   33  O6  UNL     1      -9.129  -3.327   0.550  1.00  0.00           O  
HETATM   34  O7  UNL     1      -7.733  -3.041  -1.188  1.00  0.00           O  
HETATM   35  C24 UNL     1      -2.749   0.638  -1.060  1.00  0.00           C  
HETATM   36  C25 UNL     1      -3.546   0.617  -2.261  1.00  0.00           C  
HETATM   37  C26 UNL     1      -3.996   1.844  -2.829  1.00  0.00           C  
HETATM   38  O8  UNL     1      -4.139   2.030  -4.072  1.00  0.00           O  
HETATM   39  O9  UNL     1      -4.280   2.878  -1.964  1.00  0.00           O  
HETATM   40  C27 UNL     1      -1.586   1.372  -0.759  1.00  0.00           C  
HETATM   41  C28 UNL     1      -1.191   2.477  -1.697  1.00  0.00           C  
HETATM   42  C29 UNL     1      -1.194   3.818  -1.015  1.00  0.00           C  
HETATM   43  C30 UNL     1      -2.002   3.953   0.165  1.00  0.00           C  
HETATM   44  O10 UNL     1      -1.716   4.918   0.963  1.00  0.00           O  
HETATM   45  O11 UNL     1      -3.028   3.202   0.558  1.00  0.00           O  
HETATM   46  C31 UNL     1       1.678  -0.506  -0.124  1.00  0.00           C  
HETATM   47  C32 UNL     1       0.877  -0.935  -1.251  1.00  0.00           C  
HETATM   48  C33 UNL     1       1.049   0.030  -2.383  1.00  0.00           C  
HETATM   49  O12 UNL     1       0.463  -0.243  -3.441  1.00  0.00           O  
HETATM   50  O13 UNL     1       1.810   1.181  -2.292  1.00  0.00           O  
HETATM   51  C34 UNL     1       2.873  -1.054   0.276  1.00  0.00           C  
HETATM   52  C35 UNL     1       3.587  -2.237  -0.267  1.00  0.00           C  
HETATM   53  C36 UNL     1       4.532  -2.028  -1.348  1.00  0.00           C  
HETATM   54  C37 UNL     1       5.526  -3.152  -1.451  1.00  0.00           C  
HETATM   55  O14 UNL     1       6.717  -2.820  -1.511  1.00  0.00           O  
HETATM   56  O15 UNL     1       5.190  -4.453  -1.475  1.00  0.00           O  
HETATM   57  C38 UNL     1       6.778  -0.262   0.734  1.00  0.00           C  
HETATM   58  C39 UNL     1       6.842   1.009   0.293  1.00  0.00           C  
HETATM   59  C40 UNL     1       7.839   1.637   1.364  1.00  0.00           C  
HETATM   60  O16 UNL     1       7.901   1.000   2.419  1.00  0.00           O  
HETATM   61  O17 UNL     1       8.521   2.726   1.178  1.00  0.00           O  
HETATM   62  H1  UNL     1      10.428   2.149  -1.146  1.00  0.00           H  
HETATM   63  H2  UNL     1      10.845  -1.707   0.248  1.00  0.00           H  
HETATM   64  H3  UNL     1      10.008  -0.424   1.158  1.00  0.00           H  
HETATM   65  H4  UNL     1       8.676  -0.401  -1.355  1.00  0.00           H  
HETATM   66  H5  UNL     1       9.122  -2.115  -1.139  1.00  0.00           H  
HETATM   67  H6  UNL     1       7.930  -3.446   0.953  1.00  0.00           H  
HETATM   68  H7  UNL     1       5.841  -2.957   2.297  1.00  0.00           H  
HETATM   69  H8  UNL     1       4.970   0.625   2.374  1.00  0.00           H  
HETATM   70  H9  UNL     1       4.380  -0.920   3.057  1.00  0.00           H  
HETATM   71  H10 UNL     1       2.331   1.018   2.686  1.00  0.00           H  
HETATM   72  H11 UNL     1       0.596   2.278   0.358  1.00  0.00           H  
HETATM   73  H12 UNL     1       0.035   1.737   1.928  1.00  0.00           H  
HETATM   74  H13 UNL     1      -1.724  -0.511   1.761  1.00  0.00           H  
HETATM   75  H14 UNL     1      -4.212  -1.744  -0.486  1.00  0.00           H  
HETATM   76  H15 UNL     1      -4.017  -1.602   1.291  1.00  0.00           H  
HETATM   77  H16 UNL     1      -5.152   1.564  -0.277  1.00  0.00           H  
HETATM   78  H17 UNL     1      -8.961   1.994  -0.580  1.00  0.00           H  
HETATM   79  H18 UNL     1      -7.448   2.781  -1.198  1.00  0.00           H  
HETATM   80  H19 UNL     1      -8.072   0.122  -1.998  1.00  0.00           H  
HETATM   81  H20 UNL     1      -9.674  -0.063   0.168  1.00  0.00           H  
HETATM   82  H21 UNL     1      -9.300  -1.032   1.696  1.00  0.00           H  
HETATM   83  H22 UNL     1      -7.725   2.073   2.295  1.00  0.00           H  
HETATM   84  H23 UNL     1      -5.730  -2.134   2.487  1.00  0.00           H  
HETATM   85  H24 UNL     1      -7.512  -1.912   2.691  1.00  0.00           H  
HETATM   86  H25 UNL     1      -5.906  -3.447   0.572  1.00  0.00           H  
HETATM   87  H26 UNL     1      -7.039  -4.112   1.799  1.00  0.00           H  
HETATM   88  H27 UNL     1      -8.321  -2.645  -1.899  1.00  0.00           H  
HETATM   89  H28 UNL     1      -2.809   0.131  -3.045  1.00  0.00           H  
HETATM   90  H29 UNL     1      -4.272  -0.194  -2.159  1.00  0.00           H  
HETATM   91  H30 UNL     1      -4.575   2.714  -1.056  1.00  0.00           H  
HETATM   92  H31 UNL     1      -1.636   2.409  -2.615  1.00  0.00           H  
HETATM   93  H32 UNL     1      -0.155   2.266  -1.791  1.00  0.00           H  
HETATM   94  H33 UNL     1      -1.675   4.550  -1.833  1.00  0.00           H  
HETATM   95  H34 UNL     1      -0.200   4.280  -0.894  1.00  0.00           H  
HETATM   96  H35 UNL     1      -3.188   2.692   1.379  1.00  0.00           H  
HETATM   97  H36 UNL     1       1.245  -1.905  -1.608  1.00  0.00           H  
HETATM   98  H37 UNL     1      -0.203  -1.066  -1.031  1.00  0.00           H  
HETATM   99  H38 UNL     1       1.595   1.983  -1.709  1.00  0.00           H  
HETATM  100  H39 UNL     1       3.970  -2.861   0.587  1.00  0.00           H  
HETATM  101  H40 UNL     1       2.717  -2.922  -0.621  1.00  0.00           H  
HETATM  102  H41 UNL     1       3.955  -2.238  -2.375  1.00  0.00           H  
HETATM  103  H42 UNL     1       4.888  -1.040  -1.455  1.00  0.00           H  
HETATM  104  H43 UNL     1       4.311  -4.738  -1.068  1.00  0.00           H  
HETATM  105  H44 UNL     1       5.891   1.597   0.251  1.00  0.00           H  
HETATM  106  H45 UNL     1       7.386   1.225  -0.638  1.00  0.00           H  
HETATM  107  H46 UNL     1       8.883   3.274   1.947  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   62
CONECT    4    5   63   64
CONECT    5    6   65   66
CONECT    6    7    7   57
CONECT    7    8   67
CONECT    8    9   68
CONECT    9   10   57   57
CONECT   10   11   69   70
CONECT   11   12   51   51
CONECT   12   13   71
CONECT   13   14   46   46
CONECT   14   15   72   73
CONECT   15   16   40   40
CONECT   16   17   74
CONECT   17   18   35   35
CONECT   18   19   75   76
CONECT   19   20   29   29
CONECT   20   21   77
CONECT   21   22   24   24
CONECT   22   23   78   79
CONECT   23   80
CONECT   24   25   29
CONECT   25   26   81   82
CONECT   26   27   27   28
CONECT   28   83
CONECT   29   30
CONECT   30   31   84   85
CONECT   31   32   86   87
CONECT   32   33   33   34
CONECT   34   88
CONECT   35   36   40
CONECT   36   37   89   90
CONECT   37   38   38   39
CONECT   39   91
CONECT   40   41
CONECT   41   42   92   93
CONECT   42   43   94   95
CONECT   43   44   44   45
CONECT   45   96
CONECT   46   47   51
CONECT   47   48   97   98
CONECT   48   49   49   50
CONECT   50   99
CONECT   51   52
CONECT   52   53  100  101
CONECT   53   54  102  103
CONECT   54   55   55   56
CONECT   56  104
CONECT   57   58
CONECT   58   59  105  106
CONECT   59   60   60   61
CONECT   61  107
END

HMDB0001137
     RDKit          3D
Hydroxymethylbilane
107110  0  0  0  0  0  0  0  0999 V2000
   12.1263    0.3884   -0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9633    0.2721   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2778    1.1291   -1.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1802   -0.7798    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8945   -1.1443   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8533   -1.2970    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3213   -2.4935    0.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2703   -2.1191    1.4695 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7189   -1.0359    1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6603   -0.4373    2.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3987   -0.3896    1.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3916    0.4699    1.7358 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3306    0.4739    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564    1.3547    0.9397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290    1.0218    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621    0.0759    0.9770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.1347    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0942   -0.9596    0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4268   -0.2646    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8536    0.7794   -0.0892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1114    0.9874   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0397    1.8504   -0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0060    1.1309   -2.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6823   -0.0167    0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0933   -0.1087    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4886    1.0017    2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6632    1.3048    2.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5166    1.6408    2.6995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5639   -0.8062    1.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7449   -2.0369    1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8513   -3.2441    1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0097   -3.2105    0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1295   -3.3267    0.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7326   -3.0412   -1.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7495    0.6379   -1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464    0.6168   -2.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9960    1.8443   -2.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391    2.0295   -4.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    2.8784   -1.9644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    1.3722   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1906    2.4773   -1.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    3.8180   -1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025    3.9529    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    4.9184    0.9631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0279    3.2021    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -0.5060   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8775   -0.9353   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0491    0.0305   -2.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -0.2428   -3.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096    1.1807   -2.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727   -1.0537    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870   -2.2368   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5318   -2.0276   -1.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5263   -3.1519   -1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7174   -2.8204   -1.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1904   -4.4531   -1.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7784   -0.2616    0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8423    1.0091    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8390    1.6366    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9009    1.0002    2.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5206    2.7262    1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4283    2.1495   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8453   -1.7070    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0079   -0.4235    1.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6765   -0.4012   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1224   -2.1152   -1.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9299   -3.4456    0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413   -2.9573    2.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705    0.6254    2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3795   -0.9199    3.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    1.0177    2.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959    2.2778    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0348    1.7366    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -0.5113    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2118   -1.7438   -0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0173   -1.6015    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1524    1.5644   -0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9609    1.9936   -0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4481    2.7808   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0718    0.1217   -1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6735   -0.0633    0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3001   -1.0324    1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7246    2.0729    2.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7303   -2.1344    2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5117   -1.9119    2.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9063   -3.4474    0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0387   -4.1116    1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3210   -2.6447   -1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089    0.1306   -3.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723   -0.1943   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5750    2.7138   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6356    2.4088   -2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    2.2662   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754    4.5504   -1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995    4.2799   -0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1882    2.6915    1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2454   -1.9048   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029   -1.0665   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5954    1.9831   -1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9695   -2.8609    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -2.9220   -0.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -2.2382   -2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883   -1.0404   -1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111   -4.7378   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8912    1.5971    0.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3856    1.2247   -0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8825    3.2736    1.9466 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 24 29  1  0
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 31 32  1  0
 32 33  2  0
 32 34  1  0
 17 35  2  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 37 39  1  0
 35 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  2  0
 43 45  1  0
 13 46  2  0
 46 47  1  0
 47 48  1  0
 48 49  2  0
 48 50  1  0
 46 51  1  0
 51 52  1  0
 52 53  1  0
 53 54  1  0
 54 55  2  0
 54 56  1  0
  9 57  2  0
 57 58  1  0
 58 59  1  0
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 51 11  2  0
 40 15  2  0
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  3 62  1  0
  4 63  1  0
  4 64  1  0
  5 65  1  0
  5 66  1  0
  7 67  1  0
  8 68  1  0
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 50 99  1  0
 52100  1  0
 52101  1  0
 53102  1  0
 53103  1  0
 56104  1  0
 58105  1  0
 58106  1  0
 61107  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Hydroxymethyl)bilane	ChEBI
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,22,23,24-hexahydro-19-(hydroxymethyl)-21H-biline-2,7,12,17-tetrapropanoic acid	ChEBI
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,22,23,24-hexahydro-19-(hydroxymethyl)-21H-biline-2,7,12,17-tetrapropanoate	Generator
3,8,13,18-Tetrakis(carboxymethyl)-19-(hydroxymethyl)bilane-2,7,12,17-tetrapropanoate	HMDB
3,8,13,18-Tetrakis(carboxymethyl)-19-(hydroxymethyl)bilane-2,7,12,17-tetrapropanoic acid	HMDB
3-[2-[[4-(2-Carboxyethyl)-5-[[4-(2-carboxyethyl)-5-[[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-3-yl]propanoate	HMDB
3-[2-[[4-(2-Carboxyethyl)-5-[[4-(2-carboxyethyl)-5-[[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-3-yl]propanoic acid	HMDB
Preuroporphyrinogen	HMDB
3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,22,23,24-hexahydro-19-(hydroxymethyl)-21H-biline-2,7,12,17-tetrapropionic acid	HMDB
Hydroxymethylbilane	HMDB

Chemical Formula

C₄₀H₄₆N₄O₁₇

Average Molecular Weight

854.8098

Monoisotopic Molecular Weight

854.285796066

IUPAC Name

3-(5-{[3-(2-carboxyethyl)-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-2-yl]methyl}-2-{[4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-4-(carboxymethyl)-1H-pyrrol-3-yl)propanoic acid

Traditional Name

CAS Registry Number

71861-60-4

SMILES

OCC1=C(CC(O)=O)C(CCC(O)=O)=C(CC2=C(CC(O)=O)C(CCC(O)=O)=C(CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=CN4)N3)N2)N1

InChI Identifier

InChI=1S/C40H46N4O17/c45-17-32-25(12-40(60)61)21(4-8-36(52)53)29(44-32)15-31-24(11-39(58)59)20(3-7-35(50)51)28(43-31)14-30-23(10-38(56)57)19(2-6-34(48)49)27(42-30)13-26-22(9-37(54)55)18(16-41-26)1-5-33(46)47/h16,41-45H,1-15,17H2,(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)

InChI Key

WDFJYRZCZIUBPR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Not Available

Direct Parent

Tetrapyrroles and derivatives

Alternative Parents

Substituents

Tetrapyrrole skeleton
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Azacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Aromatic alcohol
Organic oxygen compound
Organic nitrogen compound
Alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

bilanes (CHEBI:16645 )

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	0.53	ALOGPS
logP	0.97	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.25	ChemAxon
Physiological Charge	-8	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	381.79 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	209.92 m³·mol⁻¹	ChemAxon
Polarizability	85.68 Å³	ChemAxon
Number of Rings	4	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]+	284.23	32859911
AllCCS	[M-H]-	285.648	32859911
DeepCCS	[M+H]+	271.182	30932474
DeepCCS	[M-H]-	269.286	30932474
DeepCCS	[M-2H]-	303.043	30932474
DeepCCS	[M+Na]+	276.972	30932474
AllCCS	[M+H]+	284.2	32859911
AllCCS	[M+H-H2O]+	284.1	32859911
AllCCS	[M+NH4]+	284.3	32859911
AllCCS	[M+Na]+	284.3	32859911
AllCCS	[M-H]-	285.6	32859911
AllCCS	[M+Na-2H]-	291.5	32859911
AllCCS	[M+HCOO]-	297.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.77 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1898 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.21 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	335.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1451.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	160.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	117.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	139.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	375.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	387.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	605.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	857.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	598.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1763.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	275.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	481.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	306.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	757.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxymethylbilane	OCC1=C(CC(O)=O)C(CCC(O)=O)=C(CC2=C(CC(O)=O)C(CCC(O)=O)=C(CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=CN4)N3)N2)N1	7356.3	Standard polar	33892256
Hydroxymethylbilane	OCC1=C(CC(O)=O)C(CCC(O)=O)=C(CC2=C(CC(O)=O)C(CCC(O)=O)=C(CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=CN4)N3)N2)N1	5103.0	Standard non polar	33892256
Hydroxymethylbilane	OCC1=C(CC(O)=O)C(CCC(O)=O)=C(CC2=C(CC(O)=O)C(CCC(O)=O)=C(CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=CN4)N3)N2)N1	7680.1	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16645

Food Biomarker Ontology

Not Available

VMH ID

HMBIL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

Enzyme Details

1. Uroporphyrinogen-III synthase

General function:: Involved in uroporphyrinogen-III synthase activity
Specific function:: Catalyzes cyclization of the linear tetrapyrrole, hydroxymethylbilane, to the macrocyclic uroporphyrinogen III, the branch point for the various sub-pathways leading to the wide diversity of porphyrins. Porphyrins act as cofactors for a multitude of enzymes that perform a variety of processes within the cell such as methionine synthesis (vitamin B12) or oxygen transport (heme).
Gene Name:: UROS
Uniprot ID:: P10746
Molecular weight:: 28627.37

Reactions

Hydroxymethylbilane → Uroporphyrinogen III + Water	details

Enzyme Details

2. Porphobilinogen deaminase

General function:: Involved in hydroxymethylbilane synthase activity
Specific function:: Tetrapolymerization of the monopyrrole PBG into the hydroxymethylbilane pre-uroporphyrinogen in several discrete steps.
Gene Name:: HMBS
Uniprot ID:: P08397
Molecular weight:: 39329.74

Reactions

Porphobilinogen + Water → Hydroxymethylbilane + Ammonia	details

Showing metabocard for Hydroxymethylbilane (HMDB0001137)

MOL for HMDB0001137 (Hydroxymethylbilane)

3D MOL for HMDB0001137 (Hydroxymethylbilane)

3D SDF for HMDB0001137 (Hydroxymethylbilane)

3D-SDF for HMDB0001137 (Hydroxymethylbilane)

PDB for HMDB0001137 (Hydroxymethylbilane)

3D PDB for HMDB0001137 (Hydroxymethylbilane)

SMILES for HMDB0001137 (Hydroxymethylbilane)

INCHI for HMDB0001137 (Hydroxymethylbilane)

Structure for HMDB0001137 (Hydroxymethylbilane)

3D Structure for HMDB0001137 (Hydroxymethylbilane)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Enzymes

Reactions

Reactions