IMPPAT Phytochemical information: 
1H-Indole-3-acetic acid, 2,3-dihydro-3-hydroxy-2-oxo-

1H-Indole-3-acetic acid, 2,3-dihydro-3-hydroxy-2-oxo-
Summary

SMILES: OC(=O)CC1(O)C(=O)Nc2c1cccc2
InChI: InChI=1S/C10H9NO4/c12-8(13)5-10(15)6-3-1-2-4-7(6)11-9(10)14/h1-4,15H,5H2,(H,11,14)(H,12,13)
InChIKey: MHLHEINWUCSPTL-UHFFFAOYSA-N
DeepSMILES: OC=O)CCO)C=O)Ncc5cccc6
Scaffold Graph/Node/Bond level: O=C1Cc2ccccc2N1
Scaffold Graph/Node level: OC1CC2CCCCC2N1
Scaffold Graph level: CC1CC2CCCCC2C1
Functional groups: CC(=O)O; CO; cNC(=O)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 oxindole alkaloids
Synonymous chemical names:
dioxindole-3-acetic acid
External chemical identifiers:
CID:CID_10488522; SureChEMBL:SCHEMBL1460831
Chemical structure download


1H-Indole-3-acetic acid, 2,3-dihydro-3-hydroxy-2-oxo-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 207.19
Log P RDKit 0.3
Topological polar surface area (Å2) RDKit 86.63
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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


1H-Indole-3-acetic acid, 2,3-dihydro-3-hydroxy-2-oxo-
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.650573


1H-Indole-3-acetic acid, 2,3-dihydro-3-hydroxy-2-oxo-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.50
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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