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: cC(=O)OC; cO; cOC
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-gallate, (-)-epigallocatechin 3-gallate, (-)-epigallocatechin 3-gallate (egcg), (-)-epigallocatechin 3-o-gallate, (-)-epigallocatechin gallate, (-)-epigallocatechin-3-0-gallate, (-)-epigallocatechin-3-gallate, (-)-epigallocatechin-3-o-gallate, egcg, epigallocatechin gallate, epigallocatechin gallate,(-)-, epigallocatechin-3-gallate, epigallocatechin-3-gallate,, epigallocatechin-3-o-gallate,(-)-
External chemical identifiers:
CID:65064; ChEMBL:CHEMBL297453; 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 properties
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 0.2115
Epigallocatechin gallate
ADMET 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 1.0
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
Epigallocatechin gallate
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000177694TBX21800
ENSP00000200676CETP700
ENSP00000202788700
ENSP00000206249ESR1841
ENSP00000211122GSTA3835
ENSP00000212015SIRT1892
ENSP00000215832MAPK1759
ENSP00000216117HMOX1866
ENSP00000219070MMP2878
ENSP00000221515RETN818
ENSP00000221740CASP14824
ENSP00000222330GSK3A723
ENSP00000222381PON1824
ENSP00000223095SERPINE1839
ENSP00000224237VIM841
ENSP00000225831CCL2949
ENSP00000227163SPI1800
ENSP00000227507CCND1858
ENSP00000228872CDKN1B818
ENSP00000231790MLH1743
ENSP00000233242APOB848
ENSP00000233946IL1R1800
ENSP00000236850APOA1816
ENSP00000237014TTR961
ENSP00000237612ABCG2814
ENSP00000239849TNFSF11816
ENSP00000240652IAPP819
ENSP00000241453FLT3800
ENSP00000242728BHLHE41800
ENSP00000244741CDKN1A782
ENSP00000247970PIN1800
ENSP00000248553HSPB1816
ENSP00000253452COX4I1800
ENSP00000253799AOC2732
ENSP00000254958JAG1824
ENSP00000257497ANXA1800
ENSP00000258743IL6953
ENSP00000260010TLR2822
ENSP00000260302MMP13835
ENSP00000260682CYP2C9800
ENSP00000262186KCNH2800
ENSP00000262209TRPA1800
ENSP00000262320AXIN1800
ENSP00000262887XRCC1824
ENSP00000263025MAPK3818
ENSP00000263339IL1A851
ENSP00000263431PRKCG828
ENSP00000263642IFIH1800
ENSP00000263798TYRO3824
ENSP00000264657STAT3947
ENSP00000264709DNMT3A844
ENSP00000264932SDHA800
ENSP00000265171EGF849
ENSP00000265724ABCB1846
ENSP00000268097HEXA800
ENSP00000269141CDH2800
ENSP00000269305TP53958
ENSP00000269571ERBB2841
ENSP00000270202AKT1964
ENSP00000275493EGFR866
ENSP00000276431TNFRSF10B840
ENSP00000278175ADM700
ENSP00000278616ATM800
ENSP00000283916TMPRSS11D786
ENSP00000284981APP837
ENSP00000286574WIF1800
ENSP00000287820PPARG858
ENSP00000287936HMGCR817
ENSP00000293288BAX756
ENSP00000295256HPGDS837
ENSP00000296545IL15855
ENSP00000297494NOS3958
ENSP00000301645CYP7A1800
ENSP00000302111MGMT723
ENSP00000302564BCL2L1857
ENSP00000302665IGF1864
ENSP00000302846PTGER4800
ENSP00000303394HSPB3817
ENSP00000304592FASN840
ENSP00000304915IL13800
ENSP00000306245FOS946
ENSP00000306512IL8954
ENSP00000311032CASP3967
ENSP00000312029UCP2839
ENSP00000312326AOC3786
ENSP00000312652LEP848
ENSP00000318822BID700
ENSP00000319788NQO1843
ENSP00000320935SLC2A4829
ENSP00000322788MMP1826
ENSP00000324806GSK3B728
ENSP00000327251NOS2805
ENSP00000328547DNMT3B860
ENSP00000329418SOCS1800
ENSP00000330054EEF1A1817
ENSP00000330237CASP9748
ENSP00000332296RARB700
ENSP00000332973SMAD3815
ENSP00000333298LAMP1800
ENSP00000335153HSP90AA1823
ENSP00000335620GSTA1834
ENSP00000336528NR1I2700
ENSP00000337146ENOX2820
ENSP00000337459NOS1822
ENSP00000338018HIF1A700
ENSP00000338345SNCA822
ENSP00000339191CAV1800
ENSP00000340409SMPD1800
ENSP00000342007CYP1A2963
ENSP00000342026PRDX6800
ENSP00000342385PTGES800
ENSP00000343040HMGB1786
ENSP00000344456CTNNB1724
ENSP00000346067RPSA865
ENSP00000347665COL18A1800
ENSP00000351273CASP8741
ENSP00000351885PPP2R4800
ENSP00000352516DNMT1957
ENSP00000353483MAPK8961
ENSP00000354394STAT1847
ENSP00000354612PTGS1838
ENSP00000355206MT-ND3825
ENSP00000355759PARP1746
ENSP00000355890EPRS820
ENSP00000356037C4BPA876
ENSP00000356438PTGS2881
ENSP00000356954CTGF800
ENSP00000358327CASP7844
ENSP00000359998GSTA4833
ENSP00000360266JUN877
ENSP00000361125VEGFA959
ENSP00000361151CEL700
ENSP00000361405MMP9885
ENSP00000362508UGT1A4816
ENSP00000363089TLR4829
ENSP00000363779IKBKAP762
ENSP00000364140COL15A1786
ENSP00000365016IRS2800
ENSP00000365280ID1784
ENSP00000365851BMI1826
ENSP00000367202RECK800
ENSP00000368683EDN1824
ENSP00000369050CYP1A1841
ENSP00000372191SIRT3837
ENSP00000378152AKTIP800
ENSP00000380252NFE2L2857
ENSP00000381932DYRK1A825
ENSP00000387230UPP2800
ENSP00000387356ACAN800
ENSP00000394734CLK1786
ENSP00000394932CDKN2A953
ENSP00000396308DHFR827
ENSP00000396538NFAT5800
ENSP00000398698TNF788
ENSP00000398736CYR61800
ENSP00000408695PRKCA828
ENSP00000411532TOP2A824
ENSP00000419970POR837
ENSP00000420168GSTA2833
ENSP00000435591MUC5AC800
ENSP00000441691ITGAM836
ENSP00000447149NR1H4938
ENSP00000448165APAF1846
ENSP00000457706HSPB2-C11orf52815
ENSP00000466933S1PR2786
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.