MiMeDB: Showing metabocard for Indolepyruvate (MMDBc0031706)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:45:09 UTC

Update Date

2022-08-31 18:23:39 UTC

Metabolite ID

MMDBc0031706

Metabolite Identification

Common Name

Indolepyruvate

Description

Indolepyruvate is a member of the chemical class known as Indolyl Carboxylic Acids and Derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Indolepyruvate is invovled in Tryptophan metabolism. (KEGG)

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303082008132D          

 15 16  0  0  0  0            999 V2000
   -2.2673    1.8818    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083    2.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
M  CHG  1   1  -1
M  END
> <DATABASE_ID>
MMDBc0031706

> <DATABASE_NAME>
MIME

> <SMILES>
[O-]C(=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)/p-1

> <INCHI_KEY>
RSTKLPZEZYGQPY-UHFFFAOYSA-M

> <FORMULA>
C11H8NO3

> <MOLECULAR_WEIGHT>
202.1861

> <EXACT_MASS>
202.050418127

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
19.310834903143476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.9989757659999996

> <ALOGPS_LOGS>
-2.55

> <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>
72.99

> <JCHEM_REFRACTIVITY>
64.63520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(indol-3-yl)pyruvate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  O   UNK     0      -4.232   3.513   0.000  0.00  0.00           O-1
HETATM    2  C   UNK     0      -2.726   3.193   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.695   4.337   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.281   0.584   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

Synonyms

Value	Source
Indole-3-pyruvic acid	Generator
Indole-3-pyruvate	ChEBI
3-(indol-3-yl)Pyruvic acid	Generator

Molecular Formula

C₁₁H₈NO₃

Average Mass

202.1861

Monoisotopic Mass

202.050418127

IUPAC Name

3-(1H-indol-3-yl)-2-oxopropanoate

Traditional Name

3-(indol-3-yl)pyruvate

CAS Registry Number

35656-49-6

SMILES

[O-]C(=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)/p-1

InChI Key

RSTKLPZEZYGQPY-UHFFFAOYSA-M

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Indole
Alpha-keto acid
Keto acid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indol-3-yl carboxylic acid anion (CHEBI:17640 )
a small molecule (INDOLE_PYRUVATE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	1.66	ALOGPS
logP	2	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	-9.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.64 m³·mol⁻¹	ChemAxon
Polarizability	19.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0190000000-099eea97686fe22227e0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udj-0940000000-dd34dff35249f0fa72f6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f8m-0900000000-64e2789d5d176547210b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-4dba5e53cc4fc565891b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0290000000-26b99d3c3a5e9bda3434	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-4900000000-7ba4288fe633538d4168	2015-09-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012658	Oxoglutaric acid	L-Glutamic acid	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	126	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	82	Human feces; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	215	Human ; Human feces; Human pleural fluid plaque; Pig ; Cattle	Metabolic reconstruction
Bacteria	Bacteroidetes	81	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	1	Human ; Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	4

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5460337

PDB ID

Not Available

ChEBI ID

17640

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Indolepyruvate (MMDBc0031706)

MOL for #<Metabolite:0x00005634c28a8638>

3D MOL for #<Metabolite:0x00005634c28a8638>

3D SDF for #<Metabolite:0x00005634c28a8638>

3D-SDF for #<Metabolite:0x00005634c28a8638>

PDB for #<Metabolite:0x00005634c28a8638>

3D PDB for #<Metabolite:0x00005634c28a8638>

SMILES for #<Metabolite:0x00005634c28a8638>

INCHI for #<Metabolite:0x00005634c28a8638>

Structure for #<Metabolite:0x00005634c28a8638>

3D Structure for #<Metabolite:0x00005634c28a8638>