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 178.14
Log P RDKit 1.2
Topological polar surface area (Å2) RDKit 70.67
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
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 9
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 0
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


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.