IMPPAT Phytochemical information: 
Epigallocatechin gallate
Epigallocatechin gallate
Summary

SMILES: Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1cc(O)c(c(c1)O)O
InChI: InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
InChIKey: WMBWREPUVVBILR-WIYYLYMNSA-N
DeepSMILES: OcccO)ccc6)O[C@@H][C@@H]C6)OC=O)cccO)ccc6)O))O))))))))cccO)ccc6)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:
epigallocatechin-3-gallate, (+)-epigallocatechin-gallate, Epigallocatechin gallate,(-)-, Epigallocatechin-3-gallate,, egcg, (-)-epigallocatechin-3-0-gallate, (-)-epigallocatechin-3-gallate, (-)-epigallocatechin 3-gallate, (-)-epigallocatechin-3-o-gallate, Epigallocatechin-3-O-gallate,(-)-, epigallocatechin gallate, (-)-epigallocatechin gallate, (-)-epigallocatechin 3-o-gallate, (-)-epigallocatechin 3-gallate (egcg)
External chemical identifiers:
CID:CID_65064; ChEMBL:CHEMBL297453; ChEBI:CHEBI:4806; ZINC:ZINC000003870412; FDASRS:BQM438CTEL; SureChEMBL:SCHEMBL35258; MolPort-001-741-358
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Epigallocatechin gallate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 458.38
Log P RDKit 2.23
Topological polar surface area (Å2) RDKit 197.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 11
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
Epigallocatechin gallate
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
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 0.211503
Epigallocatechin gallate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -8.27
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
Epigallocatechin 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_001636ENSG00000118271TTR7276ChEMBL, NPASS
TAR_EXP_001632ENSG00000116918TSNAX7257ChEMBL, NPASS
TAR_EXP_001633ENSG00000128311TST7263ChEMBL, NPASS
TAR_EXP_000401ENSG00000163631ALB213ChEMBL, NPASS
TAR_EXP_000424ENSG00000169710FASN2194ChEMBL, NPASS
TAR_EXP_000491ENSG00000186318BACE123621BindingDB, ChEMBL, NPASS
TAR_EXP_000611ENSG00000174876AMY1B277BindingDB
TAR_EXP_000519ENSG00000171298GAA2548NPASS
TAR_EXP_000515ENSG00000010810FYN2534BindingDB, ChEMBL
TAR_EXP_000505ENSG00000198793MTOR2475BindingDB, ChEMBL
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_001772ENSG00000143479DYRK38444BindingDB, ChEMBL
TAR_EXP_000357ENSG00000277571ELANE1991BindingDB, ChEMBL, NPASS
TAR_EXP_001833ENSG00000114166KAT2B8850BindingDB, ChEMBL, NPASS
TAR_EXP_001834ENSG00000176749CDK5R18851ChEMBL
TAR_EXP_001875ENSG00000105204DYRK1B9149BindingDB, ChEMBL
TAR_EXP_001912ENSG00000158859ADAMTS49507BindingDB, ChEMBL
TAR_EXP_001914ENSG00000148344PTGES9536BindingDB, ChEMBL, NPASS
TAR_EXP_000007ENSG00000137875BCL2L1010017ChEMBL
TAR_EXP_001823ENSG00000010219DYRK48798BindingDB, ChEMBL
TAR_EXP_000032ENSG00000164885CDK51020ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000132ENSG00000137491SLCO2B111309ChEMBL
TAR_EXP_000138ENSG00000162438CTRC11330ChEMBL, NPASS
TAR_EXP_000167ENSG00000013441CLK11195BindingDB, ChEMBL
TAR_EXP_000168ENSG00000176444CLK21196BindingDB, ChEMBL
TAR_EXP_000057ENSG00000172977KAT510524BindingDB, ChEMBL, NPASS
TAR_EXP_001817ENSG00000074266EED8726ChEMBL
TAR_EXP_001808ENSG00000276582ABCB118647ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000331ENSG00000157540DYRK1A1859BindingDB, ChEMBL, NPASS
TAR_EXP_000322ENSG00000197635DPP41803BindingDB, ChEMBL, NPASS
TAR_EXP_000319ENSG00000130816DNMT11786ChEMBL, NPASS
TAR_EXP_000310ENSG00000228716DHFR1719ChEMBL, NPASS
TAR_EXP_000295ENSG00000159640ACE1636ChEMBL, NPASS
TAR_EXP_000246ENSG00000141086CTRL1506ChEMBL, NPASS
TAR_EXP_000245ENSG00000285346CTRB11504ChEMBL, NPASS
TAR_EXP_001775ENSG00000127334DYRK28445BindingDB, ChEMBL
TAR_EXP_000228ENSG00000213923CSNK1E1454ChEMBL
TAR_EXP_000222ENSG00000112062MAPK141432BindingDB, ChEMBL, NPASS
TAR_EXP_000209ENSG00000005339CREBBP1387BindingDB, ChEMBL, NPASS
TAR_EXP_000190ENSG00000108821COL1A11277ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268BindingDB, ChEMBL, NPASS
TAR_EXP_000169ENSG00000179335CLK31198ChEMBL
TAR_EXP_001796ENSG00000089022MAPKAPK58550BindingDB, ChEMBL, NPASS
TAR_EXP_000369ENSG00000100393EP3002033BindingDB, ChEMBL, NPASS
TAR_EXP_000105ENSG00000154736ADAMTS511096BindingDB, ChEMBL
TAR_EXP_000188ENSG00000188822CNR21269BindingDB, ChEMBL, NPASS
TAR_EXP_001117ENSG00000121879PIK3CA5290BindingDB, ChEMBL
TAR_EXP_001364ENSG00000171552BCL2L1598ChEMBL
TAR_EXP_001361ENSG00000140379BCL2A1597ChEMBL
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001125ENSG00000127445PIN15300BindingDB, ChEMBL, NPASS
TAR_EXP_001295ENSG00000113240CLK457396BindingDB, ChEMBL
TAR_EXP_001288ENSG00000002330BAD572ChEMBL
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL
TAR_EXP_001359ENSG00000171791BCL2596ChEMBL, NPASS
TAR_EXP_001341ENSG00000002016RAD525893ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL, NPASS
TAR_EXP_001273ENSG00000100804PSMB55693BindingDB, ChEMBL, NPASS
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001599ENSG00000164362TERT7015BindingDB, ChEMBL, NPASS
TAR_EXP_001567ENSG00000115415STAT16772BindingDB, ChEMBL, NPASS
TAR_EXP_001551ENSG00000145335SNCA6622ChEMBL, NPASS
TAR_EXP_000707ENSG00000117594HSD11B13290BindingDB, ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932BindingDB, ChEMBL
TAR_EXP_001511ENSG00000008130NADK65220BindingDB, ChEMBL
TAR_EXP_000674ENSG00000123636BAZ2B29994ChEMBL, NPASS
TAR_EXP_001128ENSG00000067225PKM5315ChEMBL, NPASS
TAR_EXP_001148ENSG00000172115CYCS54205ChEMBL, NPASS
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL, NPASS
TAR_EXP_001171ENSG00000132170PPARG5468NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001467ENSG00000188130MAPK126300ChEMBL
TAR_EXP_001477ENSG00000015475BID637ChEMBL
TAR_EXP_001236ENSG00000185386MAPK115600ChEMBL
TAR_EXP_001239ENSG00000156711MAPK135603ChEMBL
TAR_EXP_000708ENSG00000176387HSD11B23291BindingDB, ChEMBL
TAR_EXP_000715ENSG00000044574HSPA53309ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL, NPASS
TAR_EXP_000886ENSG00000137673MMP74316BindingDB, ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000824ENSG00000134333LDHA3939ChEMBL, NPASS
TAR_EXP_000821ENSG00000168028RPSA3921ChEMBL, NPASS
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL, NPASS
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000752ENSG00000142192APP351BindingDB, ChEMBL, NPASS
TAR_EXP_000884ENSG00000087245MMP24313ChEMBL, NPASS
TAR_EXP_000745ENSG00000184584STING1340061ChEMBL
TAR_EXP_000742ENSG00000090339ICAM13383ChEMBL, NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_000725ENSG00000115541HSPE13336ChEMBL, NPASS
TAR_EXP_000724ENSG00000144381HSPD13329ChEMBL, NPASS
TAR_EXP_001365ENSG00000129473BCL2L2599ChEMBL
TAR_EXP_000723ENSG00000096384HSP90AB13326BindingDB, NPASS
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_000891ENSG00000137745MMP134322ChEMBL
TAR_EXP_000892ENSG00000157227MMP144323ChEMBL, NPASS
TAR_EXP_000899ENSG00000284810CTRB2440387ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000968ENSG00000109320NFKB14790ChEMBL, NPASS
TAR_EXP_001020ENSG00000106366SERPINE15054BindingDB
TAR_EXP_001073ENSG00000077463SIRT651548ChEMBL
TAR_EXP_001100ENSG00000171314PGAM15223ChEMBL, NPASS
TAR_EXP_001101ENSG00000142657PGD5226BindingDB, ChEMBL, NPASS
TAR_EXP_000864ENSG00000143384MCL14170ChEMBL
TAR_EXP_000874ENSG00000105976MET4233BindingDB, ChEMBL, NPASS