IMPPAT Phytochemical information: 
Indole-3-pyruvic acid

Indole-3-pyruvic acid
Summary

SMILES: OC(=O)C(=O)Cc1c[nH]c2c1cccc2
InChI: 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)
InChIKey: RSTKLPZEZYGQPY-UHFFFAOYSA-N
DeepSMILES: OC=O)C=O)Ccc[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CC(=O)C(=O)O; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indolyl carboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
indole-3-pyruvic acid
External chemical identifiers:
CID:803; ChEMBL:CHEMBL485012; ChEBI:29750; ZINC:ZINC000001532617; FDASRS:4QM0LT13A8; SureChEMBL:SCHEMBL125249; MolPort-001-763-717
Chemical structure download


Indole-3-pyruvic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 203.2
Log P RDKit 1.36
Topological polar surface area (Å2) RDKit 70.16
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.09
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Indole-3-pyruvic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7398


Indole-3-pyruvic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.62
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Indole-3-pyruvic acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000302227CCBL1915
ENSP00000340684MAOA900
ENSP00000342557IL4I1900
ENSP00000354193AOC1900
ENSP00000367309MAOB900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.