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

SMILES: Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
InChIKey: LSHVYAFMTMFKBA-TZIWHRDSSA-N
DeepSMILES: OcccO)ccc6)O[C@@H][C@@H]C6)OC=O)cccO)ccc6)O))O))))))))cccccc6)O))O
Scaffold Graph/Node/Bond level: O=C(OC1Cc2ccccc2OC1c1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC(OC1CC2CCCCC2OC1C1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CC1CC2CCCCC2CC1C1CCCCC1)C1CCCCC1
Functional groups: cO; cOC; cC(=O)OC
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-gallate, (-)-epicatechin-3-o-gallate, Epicatechin gallate,(-)-, l-epicatechin gallate, (-)-epicatechin 3-gallate, (-)-epicatechin gallate, (-)-epicatechin 3-o-gallate, (-)-epicatechin-3-gallate
External chemical identifiers:
CID:CID_107905; ChEMBL:CHEMBL36327; ChEBI:CHEBI:70255; ZINC:ZINC000003978503; FDASRS:92587OVD8Z; SureChEMBL:SCHEMBL39047; MolPort-001-740-964
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(-)-Epicatechin gallate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 442.38
Log P RDKit 2.53
Topological polar surface area (Å2) RDKit 177.14
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.14
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4
(-)-Epicatechin gallate
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.235487
(-)-Epicatechin gallate
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -7.91
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 No
(-)-Epicatechin gallate
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000401ENSG00000163631ALB213ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000290ENSG00000196730DAPK11612BindingDB, NPASS
TAR_EXP_000359ENSG00000196361ELAVL31995ChEMBL, NPASS
TAR_EXP_000331ENSG00000157540DYRK1A1859BindingDB, ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000310ENSG00000228716DHFR1719ChEMBL, NPASS
TAR_EXP_000222ENSG00000112062MAPK141432BindingDB, ChEMBL, NPASS
TAR_EXP_000105ENSG00000154736ADAMTS511096BindingDB, ChEMBL
TAR_EXP_000132ENSG00000137491SLCO2B111309ChEMBL
TAR_EXP_000182ENSG00000023839ABCC21244ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268BindingDB, ChEMBL, NPASS
TAR_EXP_000188ENSG00000188822CNR21269BindingDB, ChEMBL, NPASS
TAR_EXP_000874ENSG00000105976MET4233BindingDB, ChEMBL, NPASS
TAR_EXP_000370ENSG00000116016EPAS12034ChEMBL, NPASS
TAR_EXP_000839ENSG00000143437ARNT405ChEMBL
TAR_EXP_000687ENSG00000100644HIF1A3091ChEMBL, NPASS
TAR_EXP_001838ENSG00000159082SYNJ18867ChEMBL, NPASS
TAR_EXP_001840ENSG00000078269SYNJ28871ChEMBL, NPASS
TAR_EXP_000898ENSG00000103222ABCC14363ChEMBL
TAR_EXP_000891ENSG00000137745MMP134322ChEMBL
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL, NPASS
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL, NPASS
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL, NPASS
TAR_EXP_001073ENSG00000077463SIRT651548ChEMBL
TAR_EXP_001101ENSG00000142657PGD5226BindingDB, ChEMBL, NPASS
TAR_EXP_001359ENSG00000171791BCL2596ChEMBL, NPASS
TAR_EXP_001551ENSG00000145335SNCA6622ChEMBL, NPASS
TAR_EXP_001912ENSG00000158859ADAMTS49507BindingDB, ChEMBL
TAR_EXP_001341ENSG00000002016RAD525893ChEMBL, NPASS
TAR_EXP_001273ENSG00000100804PSMB55693BindingDB, ChEMBL, NPASS