Hmdb loader

Showing metabocard for Indolepyruvate (HMDB0060484)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:24:10 UTC
Update Date2023-02-21 17:30:02 UTC
HMDB IDHMDB0060484
Secondary Accession Numbers
  • HMDB60484
Metabolite Identification
Common NameIndolepyruvate
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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060484 (Indolepyruvate)


  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 HMDB0060484 (Indolepyruvate)

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 HMDB0060484 (Indolepyruvate)


  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>
HMDB0060484

> <DATABASE_NAME>
hmdb

> <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 HMDB0060484 (Indolepyruvate)

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 HMDB0060484 (Indolepyruvate)

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 HMDB0060484 (Indolepyruvate)

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 HMDB0060484 (Indolepyruvate)

OC(=O)C(=O)CC1=CNC2=C1C=CC=C2
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INCHI for HMDB0060484 (Indolepyruvate)

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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View in JSmolView Stereo Labels
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
Chemical FormulaC11H9NO3
Average Molecular Weight203.1941
Monoisotopic Molecular Weight203.058243159
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • 3-alkylindole
  • Indole
  • Alpha-keto acid
  • Keto acid
  • Substituted pyrrole
  • Benzenoid
  • Alpha-hydroxy ketone
  • Pyrrole
  • Heteroaromatic compound
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available137.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00002127
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP1.71ALOGPS
logP2ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.16 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.8 m³·mol⁻¹ChemAxon
Polarizability19.72 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.33131661259
DarkChem[M-H]-143.37631661259
DeepCCS[M+H]+140.43330932474
DeepCCS[M-H]-138.03830932474
DeepCCS[M-2H]-172.78830932474
DeepCCS[M+Na]+147.49630932474
AllCCS[M+H]+144.032859911
AllCCS[M+H-H2O]+139.832859911
AllCCS[M+NH4]+147.932859911
AllCCS[M+Na]+149.032859911
AllCCS[M-H]-144.232859911
AllCCS[M+Na-2H]-144.232859911
AllCCS[M+HCOO]-144.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IndolepyruvateOC(=O)C(=O)CC1=CNC2=C1C=CC=C23235.3Standard polar33892256
IndolepyruvateOC(=O)C(=O)CC1=CNC2=C1C=CC=C21625.1Standard non polar33892256
IndolepyruvateOC(=O)C(=O)CC1=CNC2=C1C=CC=C22151.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indolepyruvate,1TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CC1=C[NH]C2=CC=CC=C122156.8Semi standard non polar33892256
Indolepyruvate,1TMS,isomer #2C[Si](C)(C)OC(=CC1=C[NH]C2=CC=CC=C12)C(=O)O2375.4Semi standard non polar33892256
Indolepyruvate,1TMS,isomer #3C[Si](C)(C)N1C=C(CC(=O)C(=O)O)C2=CC=CC=C212245.0Semi standard non polar33892256
Indolepyruvate,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C2388.5Semi standard non polar33892256
Indolepyruvate,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C2135.9Standard non polar33892256
Indolepyruvate,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C2570.8Standard polar33892256
Indolepyruvate,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122192.8Semi standard non polar33892256
Indolepyruvate,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122077.4Standard non polar33892256
Indolepyruvate,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122361.4Standard polar33892256
Indolepyruvate,2TMS,isomer #3C[Si](C)(C)OC(=CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O2472.8Semi standard non polar33892256
Indolepyruvate,2TMS,isomer #3C[Si](C)(C)OC(=CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O2265.1Standard non polar33892256
Indolepyruvate,2TMS,isomer #3C[Si](C)(C)OC(=CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O2553.6Standard polar33892256
Indolepyruvate,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=CN([Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C2439.6Semi standard non polar33892256
Indolepyruvate,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=CN([Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C2229.5Standard non polar33892256
Indolepyruvate,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=CN([Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C2360.9Standard polar33892256
Indolepyruvate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=C[NH]C2=CC=CC=C122445.3Semi standard non polar33892256
Indolepyruvate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CC1=C[NH]C2=CC=CC=C12)C(=O)O2620.1Semi standard non polar33892256
Indolepyruvate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(CC(=O)C(=O)O)C2=CC=CC=C212521.1Semi standard non polar33892256
Indolepyruvate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C2831.2Semi standard non polar33892256
Indolepyruvate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C2519.0Standard non polar33892256
Indolepyruvate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C2767.8Standard polar33892256
Indolepyruvate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122658.5Semi standard non polar33892256
Indolepyruvate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122518.6Standard non polar33892256
Indolepyruvate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122601.9Standard polar33892256
Indolepyruvate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O2894.0Semi standard non polar33892256
Indolepyruvate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O2642.5Standard non polar33892256
Indolepyruvate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O2736.7Standard polar33892256
Indolepyruvate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C3035.6Semi standard non polar33892256
Indolepyruvate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C2750.3Standard non polar33892256
Indolepyruvate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C2668.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Indolepyruvate GC-MS (1 MEOX; 2 TMS)splash10-0fai-7893000000-84ffd1f401950f7c30322014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indolepyruvate GC-MS (1 MEOX; 2 TMS)splash10-0ugi-3794000000-a5d8cc3579802f2ca9612014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indolepyruvate GC-MS (Non-derivatized)splash10-0fai-7893000000-84ffd1f401950f7c30322017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indolepyruvate GC-MS (Non-derivatized)splash10-0ugi-3794000000-a5d8cc3579802f2ca9612017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indolepyruvate GC-EI-TOF (Non-derivatized)splash10-0fai-1931000000-16c0a60dd32e65b8873a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indolepyruvate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-3900000000-a55cf7c697b6ffbaee852016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indolepyruvate GC-MS (1 TMS) - 70eV, Positivesplash10-0fl3-7590000000-c3dd0d149f021914d6e12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indolepyruvate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate LC-ESI-QQ , negative-QTOFsplash10-0udi-0090000000-1ec34b082b3a3f565a122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate LC-ESI-QQ , negative-QTOFsplash10-0udi-0970000000-e68c2677119696ab93462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate LC-ESI-QQ , negative-QTOFsplash10-00kf-0900000000-2b64ec50aa8f1360ff4d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate LC-ESI-QQ , negative-QTOFsplash10-03di-0900000000-ea3949db3c6da8240de82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate LC-ESI-QQ , negative-QTOFsplash10-014i-4900000000-95c91da39b950494114a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate , positive-QTOFsplash10-0a4i-2920000000-9230f7ccfaaaffa719492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate 35V, Negative-QTOFsplash10-0002-9000000000-5abe3dfa1099f9120dc02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate 10V, Negative-QTOFsplash10-0159-0900000000-834e4f99d90f0191c0442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate 40V, Negative-QTOFsplash10-0006-9300000000-41e6877cb3fb43b1168a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate 20V, Negative-QTOFsplash10-000i-3900000000-fb0ea14a3950fc521db62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate 20V, Negative-QTOFsplash10-001i-9600000000-a27b1097894cd1feee712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate 40V, Negative-QTOFsplash10-000t-8900000000-4e6c79f47d063707a8022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indolepyruvate 10V, Negative-QTOFsplash10-0udi-8690000000-da9c2a121361518b150f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 10V, Positive-QTOFsplash10-0f80-0930000000-593d7099407afc68b9692015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 20V, Positive-QTOFsplash10-05o9-0900000000-2ad84f63cbf77a1baa8f2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 40V, Positive-QTOFsplash10-001i-1900000000-6368dc05fa719d5e285a2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 10V, Negative-QTOFsplash10-0udi-1590000000-279e5b29f5fe92cccc072015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 20V, Negative-QTOFsplash10-0a59-1910000000-8f926dbcc372f4b220f72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 40V, Negative-QTOFsplash10-0aou-2900000000-431d30e582a7ac0a48052015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 10V, Positive-QTOFsplash10-001i-0920000000-8595f51ed999e0bf67812021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 20V, Positive-QTOFsplash10-001i-0900000000-2f350b1510e9e56270892021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 40V, Positive-QTOFsplash10-0ugi-2900000000-13dc3bda25eafed55bb32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 10V, Negative-QTOFsplash10-0a4i-0900000000-e09b4e8b59ee5b2050602021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 20V, Negative-QTOFsplash10-0aor-2910000000-93256dde3bb34cbaf5da2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepyruvate 40V, Negative-QTOFsplash10-00or-0900000000-070485cd4db1ed2925cc2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030941
KNApSAcK IDC00007571
Chemspider ID781
KEGG Compound IDC00331
BioCyc IDINDOLE_PYRUVATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound803
PDB ID3IO
ChEBI ID29750
Food Biomarker OntologyNot Available
VMH IDINDPYR
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Schutz A, Golbik R, Konig S, Hubner G, Tittmann K: Intermediates and transition states in thiamin diphosphate-dependent decarboxylases. A kinetic and NMR study on wild-type indolepyruvate decarboxylase and variants using indolepyruvate, benzoylformate, and pyruvate as substrates. Biochemistry. 2005 Apr 26;44(16):6164-79. [PubMed:15835904 ]
  3. Kneen MM, Stan R, Yep A, Tyler RP, Saehuan C, McLeish MJ: Characterization of a thiamin diphosphate-dependent phenylpyruvate decarboxylase from Saccharomyces cerevisiae. FEBS J. 2011 Jun;278(11):1842-53. doi: 10.1111/j.1742-4658.2011.08103.x. Epub 2011 Apr 18. [PubMed:21501384 ]
  4. Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22. [PubMed:29168502 ]
  5. McGettrick AF, Corcoran SE, Barry PJ, McFarland J, Cres C, Curtis AM, Franklin E, Corr SC, Mok KH, Cummins EP, Taylor CT, O'Neill LA, Nolan DP: Trypanosoma brucei metabolite indolepyruvate decreases HIF-1alpha and glycolysis in macrophages as a mechanism of innate immune evasion. Proc Natl Acad Sci U S A. 2016 Nov 29;113(48):E7778-E7787. doi: 10.1073/pnas.1608221113. Epub 2016 Nov 15. [PubMed:27856732 ]

Enzymes

Enzyme Details
1. L-amino-acid oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:
IL4I1
Uniprot ID:
Q96RQ9
Molecular weight:
65327.26
Reactions
L-Tryptophan + Water + Oxygen → Indolepyruvate + Ammonia + Hydrogen peroxidedetails