Epigallocatechin 3-O-(3-O-methyl)gallate

Details

• Internal ID: 3f5c2563-599c-4280-ba67-3e9c905e9d7b
• 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-dihydroxy-5-methoxybenzoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C(=O)OC2CC3=C(C=C(C=C3OC2C4=CC(=C(C(=C4)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)C(=O)O[C@@H]2CC3=C(C=C(C=C3O[C@@H]2C4=CC(=C(C(=C4)O)O)O)O)O
• InChI: InChI=1S/C23H20O11/c1-32-18-5-10(4-16(28)21(18)30)23(31)34-19-8-12-13(25)6-11(24)7-17(12)33-22(19)9-2-14(26)20(29)15(27)3-9/h2-7,19,22,24-30H,8H2,1H3/t19-,22-/m1/s1
• InChI Key: WVRDOLPMKOCJRJ-DENIHFKCSA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₀O₁₁
• Molecular Weight: 472.40 g/mol
• Exact Mass: 472.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• (-)-EGCG-3''-O-Me
• Epigallocatechin 3-O-(3-O-methyl)gallate
• Egcg3''me
• (-)-Epigallocatechin-3-(3''-O-methyl) gallate
• UNII-O97U9TPY8V
• O97U9TPY8V
• Epigallocatechin 3-O-(3-O-methylgallate)
• CHEMBL562716
• (-)-Epigallocatechin 3-O-(3-O-methylgallate)
• (-)-Epigallocatechin-3-O-(3'-O-methyl)-gallate
• [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4-dihydroxy-5-methoxybenzoate
• (-)-Epigallocatechin 3-(3-methyl-gallate)
• Benzoic acid, 3,4-dihydroxy-5-methoxy-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester
• Benzoic acid, 3,4-dihydroxy-5-methoxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester, (2R-cis)-
• Epigallocatechin 3-O-(3-O-Methyl)-Gallate
• SCHEMBL14143057
• CHEBI:169839
• DTXSID501273994
• HY-N2228
• BDBM50296234
• LMPK12020121
• AKOS040760379
• Epigallocatechin 3-(3-methyl-gallate)
• 3-O-(3-O-Methylgalloyl)epigallocatechin
• Epigallocatechin 3-(3-O-methyl-gallate)
• CS-0019551
• (-)-epigallocatechin-3-(3''''-O-methyl)gallate
• Q27285508
• (2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4-dihydroxy-5-methoxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8590	85.90%
Caco-2	-	0.8814	88.14%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6248	62.48%
OATP2B1 inhibitior	+	0.5662	56.62%
OATP1B1 inhibitior	-	0.3358	33.58%
OATP1B3 inhibitior	+	0.8811	88.11%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6628	66.28%
P-glycoprotein inhibitior	-	0.4391	43.91%
P-glycoprotein substrate	-	0.7154	71.54%
CYP3A4 substrate	+	0.6227	62.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7217	72.17%
CYP3A4 inhibition	-	0.7667	76.67%
CYP2C9 inhibition	-	0.9044	90.44%
CYP2C19 inhibition	-	0.7861	78.61%
CYP2D6 inhibition	-	0.9298	92.98%
CYP1A2 inhibition	-	0.6081	60.81%
CYP2C8 inhibition	+	0.7614	76.14%
CYP inhibitory promiscuity	-	0.7709	77.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6029	60.29%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.5951	59.51%
Skin irritation	-	0.6906	69.06%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8201	82.01%
Micronuclear	+	0.8759	87.59%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.9163	91.63%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7068	70.68%
Acute Oral Toxicity (c)	III	0.5372	53.72%
Estrogen receptor binding	+	0.8328	83.28%
Androgen receptor binding	+	0.7939	79.39%
Thyroid receptor binding	+	0.5762	57.62%
Glucocorticoid receptor binding	+	0.6815	68.15%
Aromatase binding	-	0.7955	79.55%
PPAR gamma	+	0.6232	62.32%
Honey bee toxicity	-	0.8474	84.74%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5151	51.51%
Fish aquatic toxicity	+	0.8540	85.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3869	P50281	Matrix metalloproteinase 14	1700 nM	IC50	PMID: 19524436
CHEMBL333	P08253	Matrix metalloproteinase-2	8700 nM	IC50	PMID: 19524436

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.41%	96.09%
CHEMBL3194	P02766	Transthyretin	94.84%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.83%	86.33%
CHEMBL4302	P08183	P-glycoprotein 1	92.89%	92.98%
CHEMBL2535	P11166	Glucose transporter	92.31%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.24%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.64%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.64%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.35%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.07%	89.00%
CHEMBL1993	P26358	DNA (cytosine-5)-methyltransferase 1	85.54%	95.44%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.70%	92.62%
CHEMBL2581	P07339	Cathepsin D	84.06%	98.95%
CHEMBL4208	P20618	Proteasome component C5	83.68%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.20%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.01%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.53%	97.09%

Plants that contains it

• Angelica lucida
• Brocchia cinerea
• Castanea sativa
• Daphniphyllum paxianum
• Hymenoxys insignis
• Lespedeza bicolor
• Limonium sinense
• Mimusops caffra
• Neonauclea sessilifolia
• Nerine bowdenii
• Sesbania bispinosa
• Solidago serotina
• Sorbaria sorbifolia
• Strophanthus kombe
• Veronica arvensis

Cross-Links

• PubChem: 9804842
• NPASS: NPC87317
• ChEMBL: CHEMBL562716
• LOTUS: LTS0022663
• wikiData: Q27285508