Showing metabocard for 3-(indol-3-yl)pyruvic acid (MMDBc0032934)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:27:56 UTC
Update Date2024-04-30 19:55:13 UTC
Metabolite IDMMDBc0032934
Metabolite Identification
Common Name3-(indol-3-yl)pyruvic acid
DescriptionThe thiamin diphosphate (ThDP)-dependent enzyme indolepyruvate decarboxylase (IPDC) is involved in the biosynthetic pathway of the phytohormone 3-indoleacetic acid and catalyzes the nonoxidative decarboxylation of 3-indolepyruvate to 3-indoleacetaldehyde and carbon dioxide. (PMID:15835904 )  In addition, the enzyme was compared with the phenylpyruvate decarboxylase from Azospirillum brasilense and the indolepyruvate decarboxylase from Enterobacter cloacae. (PMID:21501384 ) Indole-3-pyruvate is a microbial metabolite, urinary indole-3-pyruvate is produced by Clostridium sporogenes (PMID:29168502 ) and Trypanasoma brucei (PMID:27856732 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9230696b20>


  Mrv1652307222018322D          

 15 16  0  0  0  0            999 V2000
   -1.6433    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.9748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -1.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3271    0.1499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9230696b20>

HMDB0060484
     RDKit          3D
Indolepyruvate
 24 25  0  0  0  0  0  0  0  0999 V2000
    3.5592   -1.7883    0.4523 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4369   -0.5078    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2873    0.1905    1.3137 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056    0.1292   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601    1.4093   -0.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4386   -0.6127   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281   -0.7934   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3614   -1.9830    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -1.7559    0.5514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9085   -0.4479    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276    0.2900    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1438    1.6368    0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0861    2.2205   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612    1.4984   -0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    0.1577   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721    0.2105    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2914   -0.1079   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387   -1.5952   -1.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -2.8894    0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889   -2.4808    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613   -0.2114    1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528    2.1720    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    3.2638   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494    1.9952   -1.0840 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  7  1  0
 15 10  1  0
  3 16  1  0
  6 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
 14 24  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9230696b20>


  Mrv1652307222018322D          

 15 16  0  0  0  0            999 V2000
   -1.6433    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.9748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -1.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3271    0.1499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032934

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C(=O)CC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)

> <INCHI_KEY>
RSTKLPZEZYGQPY-UHFFFAOYSA-N

> <FORMULA>
C11H9NO3

> <MOLECULAR_WEIGHT>
203.1941

> <EXACT_MASS>
203.058243159

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.72292001680295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1H-indol-3-yl)-2-oxopropanoic acid

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.9989757659999996

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.040628284598952

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4941090875988134

> <JCHEM_PKA_STRONGEST_BASIC>
-9.759146672079298

> <JCHEM_POLAR_SURFACE_AREA>
70.16

> <JCHEM_REFRACTIVITY>
53.79810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(indol-3-yl)pyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9230696b20>

HMDB0060484
     RDKit          3D
Indolepyruvate
 24 25  0  0  0  0  0  0  0  0999 V2000
    3.5592   -1.7883    0.4523 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4369   -0.5078    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2873    0.1905    1.3137 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056    0.1292   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601    1.4093   -0.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4386   -0.6127   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281   -0.7934   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3614   -1.9830    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -1.7559    0.5514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9085   -0.4479    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276    0.2900    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1438    1.6368    0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0861    2.2205   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612    1.4984   -0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    0.1577   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721    0.2105    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2914   -0.1079   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387   -1.5952   -1.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -2.8894    0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889   -2.4808    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613   -0.2114    1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528    2.1720    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    3.2638   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494    1.9952   -1.0840 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  7  1  0
 15 10  1  0
  3 16  1  0
  6 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
 14 24  1  0
M  END
Download

PDB for #<Metabolite:0x00007f9230696b20>

HEADER    PROTEIN                                 22-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-20         0                                  
HETATM    1  C   UNK     0      -3.067   0.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.543  -0.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.513  -2.131   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.007  -1.811   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.791   2.131   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.561   0.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.531  -0.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.876   0.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.715   1.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.210  -0.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.543   0.280   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.543   1.820   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.877  -0.490   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.877  -2.030   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.211   0.280   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   14   15   11                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END
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3D PDB for #<Metabolite:0x00007f9230696b20>

COMPND    HMDB0060484
HETATM    1  O1  UNL     1       3.559  -1.788   0.452  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.437  -0.508   0.497  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.287   0.190   1.314  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.406   0.129  -0.311  1.00  0.00           C  
HETATM    5  O3  UNL     1       2.360   1.409  -0.284  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.439  -0.613  -1.128  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.128  -0.793  -0.481  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.361  -1.983   0.053  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.576  -1.756   0.551  1.00  0.00           N  
HETATM   10  C6  UNL     1      -1.908  -0.448   0.363  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.028   0.290   0.695  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.144   1.637   0.406  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.086   2.220  -0.233  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.961   1.498  -0.571  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.836   0.158  -0.287  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.272   0.210   1.114  1.00  0.00           H  
HETATM   17  H2  UNL     1       1.291  -0.108  -2.135  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.839  -1.595  -1.388  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.233  -2.889   0.015  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.189  -2.481   1.025  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.861  -0.211   1.208  1.00  0.00           H  
HETATM   22  H7  UNL     1      -4.053   2.172   0.693  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.097   3.264  -0.484  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.149   1.995  -1.084  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5    5    6
CONECT    6    7   17   18
CONECT    7    8    8   15
CONECT    8    9   19
CONECT    9   10   20
CONECT   10   11   11   15
CONECT   11   12   21
CONECT   12   13   13   22
CONECT   13   14   23
CONECT   14   15   15   24
END
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SMILES for #<Metabolite:0x00007f9230696b20>

OC(=O)C(=O)CC1=CNC2=C1C=CC=C2
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INCHI for #<Metabolite:0x00007f9230696b20>

InChI=1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)
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Synonyms
ValueSource
Indole-3-pyruvic acidChEBI
Indolepyruvic acidChEBI
(indol-3-yl)PyruvateKegg
Indole-3-pyruvateKegg
3-(indol-3-yl)PyruvateKegg
(indol-3-yl)Pyruvic acidGenerator
3-(indol-3-yl)Pyruvic acidGenerator
Indol-3-yl pyruvic acidMeSH
1H-Indole-3-pyruvic acidHMDB
3-(1H-Indol-3-yl)-2-oxopropanoic acidHMDB
3-(1H-Indol-3-yl)-2-oxopropionic acidHMDB
3-(3-Indolyl)-2-oxopropanoic acidHMDB
3-(3-Indolyl)-2-oxopropionic acidHMDB
3-(3-Indolyl)pyruvic acidHMDB
3-Indole-2-oxopropanoateHMDB
3-Indole-2-oxopropionateHMDB
3-Indolylpyroracemic acidHMDB
3-Indolylpyruvic acidHMDB
IPAHMDB
IndolepyruvateHMDB
Indolyl-3-pyruvateHMDB
alpha-Oxo-1H-indole-3-propanoic acidHMDB
alpha-Oxo-1H-indole-3-propionic acidHMDB
beta-Indolepyruvic acidHMDB
beta-Indolylpyruvic acidHMDB
α-Oxo-1H-indole-3-propanoic acidHMDB
α-Oxo-1H-indole-3-propionic acidHMDB
β-Indolepyruvic acidHMDB
β-Indolylpyruvic acidHMDB
Molecular FormulaC11H9NO3
Average Mass203.1941
Monoisotopic Mass203.058243159
IUPAC Name3-(1H-indol-3-yl)-2-oxopropanoic acid
Traditional Name3-(indol-3-yl)pyruvic acid
CAS Registry Number392-12-1
SMILES
OC(=O)C(=O)CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)
InChI KeyRSTKLPZEZYGQPY-UHFFFAOYSA-N