NP-MRD: Showing NP-Card for Hydroxymethylbilane (NP0054938)

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Record Information

Version

2.0

Created at

2022-04-28 01:08:16 UTC

Updated at

2022-04-28 01:08:16 UTC

NP-MRD ID

NP0054938

Secondary Accession Numbers

None

Natural Product 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. Hydroxymethylbilane is found in Arabidopsis thaliana and Escherichia coli. In the absence of the enzyme, the compound undergoes spontaneous cyclization and becomes uroporphyrinogen I.

Structure

MOL 3D MOL SDF 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
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    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
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   -2.5609    1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3407   -2.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    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
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    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

     RDKit          3D

107110  0  0  0  0  0  0  0  0999 V2000
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   10.9479    1.4625   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1837    1.0885    0.1903 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7395    1.0999    0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2459    1.3160    0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5085    2.2025    1.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3394   -0.6219    1.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2294   -0.7620    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0425   -2.3516   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652307212017092D          

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M  END
> <DATABASE_ID>
NP0054938

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

854.8098 Da

Monoisotopic Mass

854.28580 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	Plant	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Escherichia coli	Bacteria	KNApSAcK
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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