IMPPAT Phytochemical information: 
Esculetin

Esculetin
Summary

SMILES: O=c1ccc2c(o1)cc(c(c2)O)O
InChI: InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
InChIKey: ILEDWLMCKZNDJK-UHFFFAOYSA-N
DeepSMILES: O=ccccco6)cccc6)O))O
Scaffold Graph/Node/Bond level: O=c1ccc2ccccc2o1
Scaffold Graph/Node level: OC1CCC2CCCCC2O1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: c=O; cO; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Hydroxycoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
6,7-dihydroxy-coumarin, 6,7-dihydroxycoumarin, 6,7-dihydroxycoumarin (aesculetin), 67-dihydroxycoumarin, aesculetin, esculetin
External chemical identifiers:
CID:5281416; ChEMBL:CHEMBL244743; ChEBI:490095; ZINC:ZINC000000057908; FDASRS:SM2XD6V944; SureChEMBL:SCHEMBL24641; MolPort-000-709-311
Chemical structure download


Esculetin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit


Esculetin
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 1
Ghose filter RDKit Failed
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 0.4694


Esculetin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.52
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Esculetin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000215832MAPK1700
ENSP00000229794MAPK14700
ENSP00000263025MAPK3700
ENSP00000269305TP53700
ENSP00000270202AKT1700
ENSP00000311032CASP3700
ENSP00000330237CASP9700
ENSP00000341045UGT2B15761
ENSP00000353483MAPK8700
ENSP00000354511COMT700
ENSP00000380252NFE2L2700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.