5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate

Details

• Internal ID: fe0796d8-61cb-4925-941f-504fa4af9233
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Catechin gallates
• IUPAC Name: [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): 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
• 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
• InChI Key: WMBWREPUVVBILR-UHFFFAOYSA-N
• Popularity: 5,311 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

• 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
• Tea, ext.
• [5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• 107965-88-8
• CHEMBL311663
• 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• 5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate
• (-)-Gallocatechin 3-O-gallate
• epigallocatechol-3-gallate
• (+)-epigallocatechin gallate
• SCHEMBL161547
• ChEMBL_134784
• DTXSID00859570
• CHEBI:182308
• HMS3393K21
• HMS3426I15
• HMS3651I16
• HMS3868K03
• BCP28205
• BBL033816
• BDBM50093882
• STL372995
• AKOS025248011
• CCG-269314
• NCGC00095722-01
• VS-12292
• FT-0604392
• FT-0686614
• E80553
• (?)-cis-3,3',4',5,5',7-Hexahydroxy-flavane-3-gallate
• B0005-465433
• (?)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate
• [5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate
• 2-(3,4,5-Trihydroxyphenyl)-3-[(3,4,5-trihydroxybenzoyl)oxy]-3,4-dihydro-2H-1-benzopyran-5,7-diol
• 3,4,5-Trihydroxy-benzoic acid 5,7-dihydroxy-2-(3,4,5-trihydroxy-phenyl)-chroman-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
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	19952.6 nM	Potency	via CMAUP
CHEMBL3596077	Q11130	Alpha-(1,3)-fucosyltransferase 7	700 nM	IC50	via Super-PRED
CHEMBL4860	P10415	Apoptosis regulator Bcl-2	335 nM; 235 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	1995.3 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	1584.9 nM	Potency	via CMAUP
CHEMBL4822	P56817	Beta-secretase 1	757 nM	IC50	via Super-PRED
CHEMBL1293237	P54132	Bloom syndrome protein	25118.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1993	P26358	DNA (cytosine-5)-methyltransferase 1	500 nM	IC50	via Super-PRED
CHEMBL2392	P06746	DNA polymerase beta	446.7 nM	Potency	via Super-PRED
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	277 nM	IC50	via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.1 nM; 89.1 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	330 nM	IC50	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	7943.3 nM	Potency	via CMAUP
CHEMBL1293257	P51570	Galactokinase	9431.4 nM	Potency	via CMAUP
CHEMBL240	Q12809	HERG	6025.6 nM	IC50	PMID: 21185626
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	2511.9 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	6309.6 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	122.6 nM	IC50	via Super-PRED
CHEMBL4662	P28074	Proteasome Macropain subunit MB1	187 nM; 86 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL6101	P42224	Signal transducer and activator of transcription 1-alpha/beta	700 nM	Kd	via Super-PRED
CHEMBL3194	P02766	Transthyretin	400 nM	Kd	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	223.9 nM; 223.9 nM; 316.2 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via Super-PRED
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	25118.9 nM	Potency	via CMAUP

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

• Alhagi sparsifolia
• Ampelopsis japonica
• Archidendron jiringa
• Ardisia japonica
• Camellia crassicolumna
• Camellia sinensis
• Chrysophyllum marginatum
• Cistus × incanus
• Coccoloba mollis
• Diospyros kaki
• Eriobotrya japonica
• Eugenia selloi
• Fagopyrum megacarpum
• Hibiscus cannabinus
• Limonium gmelinii
• Limonium sinense
• Mallotus japonicus
• Morus alba
• Parapiptadenia rigida
• Phedimus stoloniferus
• Phyllanthus emblica
• Phyllanthus niruri
• Platycarya strobilacea
• Portulaca oleracea
• Potentilla erecta
• Pteroxygonum giraldii
• Quercus robur
• Rhodiola chrysanthemifolia subsp. sacra
• Rhodiola heterodonta
• Rhodiola kirilowii
• Rhodiola rosea
• Rhodiola semenovii
• Rosa rugosa
• Sclerocarya birrea
• Scurrula atropurpurea
• Solanum nigrum
• Syzygium samarangense
• Terminalia catappa
• Ziziphus jujuba

Cross-Links

• PubChem: 1287
• NPASS: NPC88803
• ChEMBL: CHEMBL311663
• LOTUS: LTS0127856
• wikiData: Q104200389