Epigallocatechin Gallate

Details

• Internal ID: d4ba337e-33aa-4d45-bd27-8e2ecc19de46
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Catechin gallates
• IUPAC Name: [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)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
• InChI Key: WMBWREPUVVBILR-WIYYLYMNSA-N
• Popularity: 11,513 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₈O₁₁
• Molecular Weight: 458.40 g/mol
• Exact Mass: 458.08491139 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.23
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 3

Synonyms

• EGCG
• 989-51-5
• Epigallocatechin gallate
• Epigallocatechin 3-gallate
• Tea catechin
• Epigallocatechin-3-gallate
• Teavigo
• Epigallocatechin-3-monogallate
• (-)-Epigallocatechin-3-o-gallate
• (-)-epigallocatechin 3-gallate
• EGCG cpd
• PF-EGCg 90
• (-)-Epigallocatechol gallate
• NVP-XAA 723
• CCRIS 3729
• (2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate
• epigallo-catechin gallate
• Catechin deriv.
• UNII-BQM438CTEL
• BQM438CTEL
• epigallocatechin-3-O-gallate
• CHEBI:4806
• Epigallocatechingallate
• Epigallocatechin-gallate
• Epigallocatechol, 3-gallate, (-)-
• C22H18O11
• L-Epigallocatechin gallate
• (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
• EPIGALOCATECHIN GALLATE
• CHEMBL297453
• [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• DTXSID1029889
• (-)-epigallocatechin 3-O-gallate
• [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate
• Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester
• (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• Gallic acid, 3-ester with epigallocatechol, (-)-
• DTXCID80567
• (-)-Epigallocatechin gallate (85% (-)-epigallocatechin gallate, 10% (-)-epigallocatechin, 5% (-)- epicatechin gallate)
• Benzoic acid, 3,4,5-trihydroxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester, (2R-cis)-
• CAS-989-51-5
• SMR000449288
• SR-01000759328
• (-)-EPIGALLOCATECHIN-3-O-GALLATE (USP-RS)
• (-)-EPIGALLOCATECHIN-3-O-GALLATE [USP-RS]
• Epigallocate
• Sunphenon
• (-)-EGCG
• Epigallocic acid
• Teatannin II
• GTPs,Anagen
• 2kdh
• 3oob
• 4awm
• (-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate
• C22-H18-O11
• EGCG, Anagen
• KDH
• Epigallocatcchin Gallate
• Epigallocatechol Gallate
• Spectrum_000316
• SpecPlus_000277
• Spectrum2_000168
• Spectrum3_000244
• Spectrum4_001541
• Spectrum5_000102
• Galloyl-L-epigallocatechol
• EGCG [WHO-DD]
• D0E9DB
• D0U2BH
• EGCG [MI]
• 3-O-Galloylepigallocatechin
• (-)-Epigallocatechin gallat
• (-)-Epigallocatehin gallate
• SCHEMBL35258
• BSPBio_001628
• epigallocatechin-gallate-(-)
• KBioGR_002002
• KBioSS_000796
• SPECTRUM210239
• cid_65064
• MLS000758300
• MLS001424000
• DivK1c_006373
• SPBio_000035
• Epigallocatechin monogallate, B
• GTPL7002
• MEGxp0_001166
• Epigallocatechin gallate, Anagen
• (-)-Epigallocatechin-3-gallate
• ACon1_001054
• KBio1_001317
• KBio2_000796
• KBio2_003364
• KBio2_005932
• KBio3_001128
• (-)-cis-3,3',4',5,5',7-Hexahydroxy-flavane-3-gallate
• HMS2051K21
• HMS3649E08
• 3-O-Galloyl-(-)-epigallocatechin
• EPIGALLOCATECHIN 3-O-GALLATE
• Tox21_201468
• Tox21_303457
• BDBM50070942
• CCG-38378
• FR-109
• LMPK12030005
• s2250
• AKOS015918182
• CS-1258
• CS-O-01489
• DB12116
• DS-9030
• EPIGALLOCATECHIN GALLATE [INCI]
• LS-2197
• NC00078
• SDCCGMLS-0066550.P001
• (-)-Epigallocatechin gallate, >=95%
• (-)-Epigallocatechin-3-gallate; EGCG
• NCGC00164319-01
• NCGC00164319-02
• NCGC00164319-03
• NCGC00164319-04
• NCGC00164319-06
• NCGC00257243-01
• NCGC00259019-01
• AC-34075
• BP-30205
• HY-13653
• E0694
• SW197458-3
• C09731
• M01719
• (-)-Epigallocatechin gallate, >=97.0% (HPLC)
• (-)-Epigallocatechin gallate, analytical standard
• A845931
• Q393339
• SR-01000946601
• Q-100914
• SR-01000759328-5
• SR-01000759328-6
• SR-01000946601-1
• ANTIOXIDANT MODEL (TRAMP) -EPIGALLOCATECHIN GALLATE
• Epigallocatechin-3-gallate 1000 microg/mL in Acetonitrile
• (-)-Epigallocatechin gallate, >=80% (HPLC), from green tea
• Epigallocatechin gallate, primary pharmaceutical reference standard
• ((2R,3R)-2-(3,4,5-trihydroxyphenyl)-5,7-dihydroxy-chroman-3-yl) 3,4,5-trihydroxybenzoate
• (-)-Epigallocatechin-3-O-gallate, United States Pharmacopeia (USP) Reference Standard
• (2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl3,4,5-trihydroxybenzoate
• [5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 2,3,4-trihydroxybenzoate
• Epigallocatechin gallate, Pharmaceutical Secondary Standard; Certified Reference Material
• (-)-cis-3,4-Dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1(2H)-benzopyran-3-yl Gallate
• (-)-EPIGALLOCATECHIN GALLATE (85% (-)-EPIGALLOCATECHIN GALLATE, 10% (-)-EPIGALLOCATECHIN, 5% (-)-EPICATECHIN GALLATE)
• (-)-EPIGALLOCATECHIN-3-O-GALLATE (EGCG) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT)
• (2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl-3,4,5-trihydroxybenzoate
• (2R-cis)-3,4-Dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl 3,4,5-Trihydroxybenzoate
• [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl]3,4,5-trihydroxybenzoate
• 3,4,5-Trihydroxybenzoic acid (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester
• 3,4-Dihydro-5,7-dihydroxy-2R-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3R-yl-3,4,5-trihydroxybenzoate
• Benzoic acid, 3,4,5-trihydroxy-,(2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8422	84.22%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6166	61.66%
OATP2B1 inhibitior	+	0.7036	70.36%
OATP1B1 inhibitior	-	0.4147	41.47%
OATP1B3 inhibitior	-	0.5697	56.97%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4915	49.15%
P-glycoprotein inhibitior	-	0.5518	55.18%
P-glycoprotein substrate	-	0.8848	88.48%
CYP3A4 substrate	+	0.5673	56.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7217	72.17%
CYP3A4 inhibition	-	0.7662	76.62%
CYP2C9 inhibition	-	0.8369	83.69%
CYP2C19 inhibition	-	0.8089	80.89%
CYP2D6 inhibition	-	0.9553	95.53%
CYP1A2 inhibition	-	0.8058	80.58%
CYP2C8 inhibition	+	0.6551	65.51%
CYP inhibitory promiscuity	-	0.8067	80.67%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6339	63.39%
Eye corrosion	-	0.9906	99.06%
Eye irritation	+	0.5642	56.42%
Skin irritation	-	0.6348	63.48%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8916	89.16%
Micronuclear	+	0.8859	88.59%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	-	0.8369	83.69%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6893	68.93%
Acute Oral Toxicity (c)	IV	0.3764	37.64%
Estrogen receptor binding	+	0.7801	78.01%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5973	59.73%
Glucocorticoid receptor binding	+	0.6468	64.68%
Aromatase binding	-	0.8515	85.15%
PPAR gamma	+	0.6545	65.45%
Honey bee toxicity	-	0.8534	85.34%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5550	55.50%
Fish aquatic toxicity	+	0.9197	91.97%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3404	P52209	6-phosphogluconate dehydrogenase	720 nM	IC50	PMID: 18313308
CHEMBL3596077	Q11130	Alpha-(1,3)-fucosyltransferase 7	700 nM	IC50	via Super-PRED
CHEMBL4860	P10415	Apoptosis regulator Bcl-2	234.42 nM; 335 nM; 235 nM; 335 nM	Ki; Ki; Ki; Ki	PMID: 18040043; DOI: 10.1007/s00044-009-9233-5; via Super-PRED; via Super-PRED
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	3162.3 nM	Potency	via CMAUP
CHEMBL2487	P05067	Beta amyloid A4 protein	500 nM; 3000 nM; 4600 nM	IC50; IC50; IC50	PMID: 25978520; PMID: 24878198; PMID: 24878198
CHEMBL4822	P56817	Beta-secretase 1	757 nM; 757 nM; 1600 nM	IC50; IC50; IC50	PMID: 22225636; via Super-PRED; PMID: 22225636
CHEMBL5747	Q92793	CREB-binding protein	50000 nM	IC50	PMID: 26701186
CHEMBL1993	P26358	DNA (cytosine-5)-methyltransferase 1	500 nM; 500 nM	IC50; IC50	via Super-PRED; PMID: 25406944
CHEMBL2392	P06746	DNA polymerase beta	446.7 nM; 446.7 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	277 nM	IC50	via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.1 nM	Potency	via Super-PRED
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	13440 nM; 330 nM; 330 nM	IC50; IC50; IC50	PMID: 22154664; PMID: 24188002; via Super-PRED
CHEMBL3717	P08581	Hepatocyte growth factor receptor	10000 nM	IC50	PMID: 19839593
CHEMBL3784	Q09472	Histone acetyltransferase p300	30000 nM	IC50	PMID: 26701186
CHEMBL248	P08246	Leukocyte elastase	12800 nM	IC50	PMID: 20004577
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	8912.5 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	3981.1 nM	Potency	via CMAUP
CHEMBL260	Q16539	MAP kinase p38 alpha	2210 nM	IC50	PMID: 21080642
CHEMBL3869	P50281	Matrix metalloproteinase 14	6800 nM	IC50	PMID: 19524436
CHEMBL333	P08253	Matrix metalloproteinase-2	9600 nM	IC50	PMID: 19524436
CHEMBL1293224	P10636	Microtubule-associated protein tau	1800 nM	IC50	PMID: 23484434
CHEMBL4302	P08183	P-glycoprotein 1	122.6 nM; 124.1 nM; 122.6 nM	IC50; IC50; IC50	PMID: 25985195; PMID: 25985195; via Super-PRED
CHEMBL3334418	P18669	Phosphoglycerate mutase 1	490 nM	IC50	via Super-PRED
CHEMBL4662	P28074	Proteasome Macropain subunit MB1	187 nM; 86 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	3981.1 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL6101	P42224	Signal transducer and activator of transcription 1-alpha/beta	700 nM	Kd	via Super-PRED
CHEMBL2916	O14746	Telomerase reverse transcriptase	1000 nM; 1000 nM; 1080 nM	IC50; IC50; IC50	DOI: 10.1039/C0MD00241K; PMID: 22413845; PMID: 22413845
CHEMBL3194	P02766	Transthyretin	400 nM	Kd	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	223.9 nM; 316.2 nM; 316.2 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	93.85%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.05%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.21%	86.33%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	89.01%	83.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	88.84%	96.37%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.11%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.34%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.68%	99.17%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	85.77%	97.53%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.70%	89.00%
CHEMBL2535	P11166	Glucose transporter	85.10%	98.75%
CHEMBL2581	P07339	Cathepsin D	83.41%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.50%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.74%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.24%	94.00%

Plants that contains it

• Acanthophyllum elatius
• Aconitum heterophylloides
• Aframomum limbatum
• Aldama oblongifolia
• Alhagi sparsifolia
• Alnus sieboldiana
• Alyxia reinwardtii
• Andrographis paniculata
• Angelica lucida
• Archidendron jiringa
• Aristolochia zollingeriana
• Artemisia schimperi
• Astragalus cibarius
• Averrhoa carambola
• Balanophora involucrata
• Bartramia pomiformis
• Beilschmiedia anacardioides
• Boronia coerulescens
• Brocchia cinerea
• Cajanus trinervius
• Camellia crassicolumna
• Camellia sinensis
• Camellia taliensis
• Castanea sativa
• Cedrus libani
• Centaurea linifolia
• Cephalaria kotschyi
• Cerinthe minor
• Chrysophyllum marginatum
• Cistus × incanus
• Cneoridium dumosum
• Coccoloba mollis
• Craspidospermum verticillatum
• Cratoxylum formosum subsp. pruniflorum
• Cucurbita pepo
• Daphniphyllum paxianum
• Dasiphora fruticosa
• Dioscorea japonica
• Diospyros kaki
• Ehretia dicksonii
• Elephantopus mollis
• Eschweilera coriacea
• Eugenia myrcianthes
• Eugenia selloi
• Euphorbia hirta
• Euryops algoensis
• Fagopyrum megacarpum
• Gardenia jasminoides
• Ginkgo biloba
• Gomortega keule
• Hibiscus cannabinus
• Hylotelephium telephium
• Hymenoxys insignis
• Hypericum ascyron
• Ilex chinensis
• Iris ensata
• Iryanthera coriacea
• Ixeris stolonifera
• Jacobaea renardii
• Khaya ivorensis
• Khaya senegalensis
• Larix gmelinii var. gmelinii
• Lespedeza bicolor
• Leuzea centauroides
• Limonium gmelinii
• Limonium sinense
• Litsea pungens
• Lotus japonicus
• Lupinus verbasciformis
• Machilus glaucescens
• Mallotus japonicus
• Melaleuca rhaphiophylla
• Melochia tomentosa
• Microtropis fokienensis
• Mimusops caffra
• Morus alba
• Myrica rubra
• Myrtus communis
• Neonauclea sessilifolia
• Nerine bowdenii
• Nuphar lutea
• Ornithogalum nutans
• Parapiptadenia rigida
• Parkia biglobosa
• Petasites hybridus
• Phoenix loureiroi
• Phyllanthus emblica
• Phyllanthus niruri
• Picea mariana
• Pistacia vera
• Platycarya strobilacea
• Pteroxygonum giraldii
• Quercus robur
• Rhodiola chrysanthemifolia subsp. sacra
• Rhodiola crenulata
• Rhodiola heterodonta
• Rhodiola kirilowii
• Rhodiola semenovii
• Rosa rugosa
• Rubia oncotricha
• Salvia parryi
• Sclerocarya birrea
• Sedum crassularia
• Sempervivum tectorum
• Senegalia catechu
• Senegalia polyacantha
• Senna siamea
• Sesbania bispinosa
• Sextonia rubra
• Sideroxylon inerme
• Solanum nigrum
• Solidago serotina
• Sorbaria sorbifolia
• Staphylea ternata
• Strophanthus kombe
• Stryphnodendron adstringens
• Syzygium samarangense
• Terminalia catappa
• Thalictrum longistylum
• Theobroma cacao
• Thymus vulgaris
• Triaenophora rupestris
• Uncaria tomentosa
• Vasconcellea cauliflora
• Veratrum dahuricum
• Veronica arvensis
• Viburnum urceolatum
• Virola multinervia
• Vitellaria paradoxa
• Vitis vinifera
• Xyris pterygoblephara
• Ziziphus jujuba

Cross-Links

• PubChem: 65064
• NPASS: NPC250436
• ChEMBL: CHEMBL297453
• LOTUS: LTS0173211
• wikiData: Q393339