IMPPAT Phytochemical information: 
Esculin
Esculin
View 3D structure using JSmol
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc3ccc(=O)oc3cc2O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1
InChIKey: XHCADAYNFIFUHF-TVKJYDDYSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc=O)oc6cc%10O))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1ccc2cc(OC3CCCCO3)ccc2o1
Scaffold Graph/Node level: OC1CCC2CC(OC3CCCCO3)CCC2O1
Scaffold Graph level: CC1CCC2CC(CC3CCCCC3)CCC2C1
Functional groups: CO; c=O; cO; cO[C@@H](C)OC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Coumarin glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
aesculin, esculin
External chemical identifiers:
CID:5281417; ChEMBL:CHEMBL482581; ChEBI:4853; ZINC:ZINC000003860441; FDASRS:1Y1L18LQAF; SureChEMBL:SCHEMBL2893; MolPort-001-683-942
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Esculin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 340.28
Log P RDKit -1.32
Topological polar surface area (Å2) RDKit 149.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 3
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 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Esculin
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 Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4285
Esculin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.81
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
Esculin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000241052CAT701
ENSP00000361405MMP9800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.
800