IMPPAT Phytochemical information: 
(-)-Epicatechin
(-)-Epicatechin
Summary

SMILES: Oc1cc2O[C@H](c3ccc(c(c3)O)O)[C@@H](Cc2c(c1)O)O
InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N
DeepSMILES: OcccO[C@H]cccccc6)O))O)))))[C@@H]Cc6cc%10)O))))O
Scaffold Graph/Node/Bond level: c1ccc(C2CCc3ccccc3O2)cc1
Scaffold Graph/Node level: C1CCC(C2CCC3CCCCC3O2)CC1
Scaffold Graph level: C1CCC(C2CCC3CCCCC3C2)CC1
Functional groups: cO; cOC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavan-3-ols
Synonymous chemical names:
(-)-epicatechin, epicatechin, l-epicatechin, catechin,epi,(-), epicatechin,(-)-, catechin,epi (-), (-) epicatechin, (-)-epicatechol, (-)epicatechin, catechin, epi, (-), catechin,epi(-), epi-catechin (-), catechin, epi (-), catechol,epi,(-)
External chemical identifiers:
CID:CID_72276; ChEMBL:CHEMBL583912; ChEBI:CHEBI:90; ZINC:ZINC000000119988; FDASRS:34PHS7TU43; SureChEMBL:SCHEMBL19412; MolPort-001-740-232
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(-)-Epicatechin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 290.27
Log P RDKit 1.55
Topological polar surface area (Å2) RDKit 110.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 3
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 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3
(-)-Epicatechin
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 0.509593
(-)-Epicatechin
ADME 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 -7.82
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
(-)-Epicatechin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000216117HMOX1838
ENSP00000258743IL6800
ENSP00000297494NOS3818
ENSP00000327251NOS2794
ENSP00000337459NOS1813
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.