Showing metabocard for 5,6-Dihydroxyindole-2-carboxylic acid (MMDBc0047923)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:15:42 UTC
Update Date2024-04-30 20:32:39 UTC
Metabolite IDMMDBc0047923
Metabolite Identification
Common Name5,6-Dihydroxyindole-2-carboxylic acid
Description5,6-Dihydroxyindole-2-carboxylic acid is an intermediate in the metabolism of Tyrosine. It is a substrate for Dopachrome tautomerase.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9238121c50>


  Mrv1652309152017122D          

 14 15  0  0  0  0            999 V2000
   -2.4807    1.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4844   -0.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3524    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0669    1.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815    0.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -0.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670   -0.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -0.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -0.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172    0.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4322    1.0730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    0.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1547   -0.3090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1548    1.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  9 10  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 14  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9238121c50>

HMDB0001253
     RDKit          3D
5,6-Dihydroxyindole-2-carboxylic acid
 21 22  0  0  0  0  0  0  0  0999 V2000
    4.3279   -0.8115    0.0547 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145    0.1809   -0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1977    1.3953   -0.4429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622    0.0874   -0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569    1.1319   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0220    0.6560   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2641    1.2377   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199    0.4746   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6540    1.0853   -0.2098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295   -0.8651    0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5030   -1.6098    0.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -1.4329    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0866   -0.6830    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3930   -0.9836    0.1545 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1070    2.1834    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5874    2.1363   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3107    2.2830   -0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4843    0.5407   -0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4660   -2.5915    0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996   -2.4773    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8013   -1.9380    0.3624 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14  4  1  0
 13  6  1  0
  3 15  1  0
  5 16  1  0
  7 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
 14 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9238121c50>


  Mrv1652309152017122D          

 14 15  0  0  0  0            999 V2000
   -2.4807    1.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4844   -0.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3524    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0669    1.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815    0.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -0.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670   -0.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -0.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -0.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172    0.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4322    1.0730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    0.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1547   -0.3090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1548    1.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  9 10  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 14  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047923

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=CC2=CC(O)=C(O)C=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)

> <INCHI_KEY>
YFTGOBNOJKXZJC-UHFFFAOYSA-N

> <FORMULA>
C9H7NO4

> <MOLECULAR_WEIGHT>
193.1562

> <EXACT_MASS>
193.037507717

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
18.17230678832179

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-1H-indole-2-carboxylic acid

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
1.042461197333333

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.725907037742457

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.112577263473689

> <JCHEM_PKA_STRONGEST_BASIC>
-6.3311678836379786

> <JCHEM_POLAR_SURFACE_AREA>
93.55000000000001

> <JCHEM_REFRACTIVITY>
48.24

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dhica

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9238121c50>

HMDB0001253
     RDKit          3D
5,6-Dihydroxyindole-2-carboxylic acid
 21 22  0  0  0  0  0  0  0  0999 V2000
    4.3279   -0.8115    0.0547 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145    0.1809   -0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1977    1.3953   -0.4429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622    0.0874   -0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569    1.1319   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0220    0.6560   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2641    1.2377   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199    0.4746   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6540    1.0853   -0.2098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295   -0.8651    0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5030   -1.6098    0.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -1.4329    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0866   -0.6830    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3930   -0.9836    0.1545 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1070    2.1834    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5874    2.1363   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3107    2.2830   -0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4843    0.5407   -0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4660   -2.5915    0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996   -2.4773    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8013   -1.9380    0.3624 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14  4  1  0
 13  6  1  0
  3 15  1  0
  5 16  1  0
  7 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
 14 21  1  0
M  END
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PDB for #<Metabolite:0x00007f9238121c50>

HEADER    PROTEIN                                 15-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-20         0                                  
HETATM    1  O   UNK     0      -4.631   2.293   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -4.638  -0.760   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.658   1.527   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.992   2.297   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.326   1.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.326  -0.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.992  -0.783   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.658  -0.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.807  -0.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.712   0.757   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.807   2.003   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.252   0.757   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.022  -0.577   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.022   2.091   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    4    8   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    1                                                  
CONECT    6    5    7    2                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9   10    8                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    3                                                       
CONECT   12   10   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for #<Metabolite:0x00007f9238121c50>

COMPND    HMDB0001253
HETATM    1  O1  UNL     1       4.328  -0.811   0.055  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.614   0.181  -0.156  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.198   1.395  -0.443  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.162   0.087  -0.104  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.257   1.132  -0.322  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.022   0.656  -0.188  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.264   1.238  -0.294  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.420   0.475  -0.097  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.654   1.085  -0.210  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.329  -0.865   0.205  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.503  -1.610   0.398  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.081  -1.433   0.308  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.087  -0.683   0.113  1.00  0.00           C  
HETATM   14  N1  UNL     1       1.393  -0.984   0.155  1.00  0.00           N  
HETATM   15  H1  UNL     1       4.107   2.183   0.211  1.00  0.00           H  
HETATM   16  H2  UNL     1       1.587   2.136  -0.557  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.311   2.283  -0.530  1.00  0.00           H  
HETATM   18  H4  UNL     1      -4.484   0.541  -0.069  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.466  -2.591   0.620  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.000  -2.477   0.543  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.801  -1.938   0.362  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5    5   14
CONECT    5    6   16
CONECT    6    7    7   13
CONECT    7    8   17
CONECT    8    9   10   10
CONECT    9   18
CONECT   10   11   12
CONECT   11   19
CONECT   12   13   13   20
CONECT   13   14
CONECT   14   21
END
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SMILES for #<Metabolite:0x00007f9238121c50>

OC(=O)C1=CC2=CC(O)=C(O)C=C2N1
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INCHI for #<Metabolite:0x00007f9238121c50>

InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)
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Synonyms
ValueSource
5,6-DHICAChEBI
5,6-Dihydroxy-2-indolecarboxylic acidChEBI
5,6-Dihydroxy-2-indolylcarboxylic acidChEBI
5,6-Dihydroxyindole-2-carboxylateChEBI
DHI2cChEBI
DHICAChEBI
5,6-Dihydroxy-2-indolecarboxylateGenerator
5,6-Dihydroxy-2-indolylcarboxylateGenerator
5,6-Dihydroxy-1H-indole-2-carboxylateHMDB
5,6-Dihydroxy-1H-indole-2-carboxylic acidHMDB
2-Carboxy-5,6-dihydroxyindoleHMDB
5,6-Dihydroxy-2-carboxyindoleHMDB
5,6-Dihydroxyindole-2-carboxylic acidHMDB
Molecular FormulaC9H7NO4
Average Mass193.1562
Monoisotopic Mass193.037507717
IUPAC Name5,6-dihydroxy-1H-indole-2-carboxylic acid
Traditional Namedhica
CAS Registry Number4790-08-3
SMILES
OC(=O)C1=CC2=CC(O)=C(O)C=C2N1
InChI Identifier
InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)
InChI KeyYFTGOBNOJKXZJC-UHFFFAOYSA-N