Gallocatechin gallate

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	541f393b-26df-4b58-a8ad-b0e7b2ecf762
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Catechin gallates
IUPAC Name	[(2R,3S)-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+/m0/s1
InChI Key	WMBWREPUVVBILR-GHTZIAJQSA-N
Popularity	93 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₂H₁₈O₁₁
Molecular Weight	458.40 g/mol
Exact Mass	458.08491139 g/mol
Topological Polar Surface Area (TPSA)	197.00 Å²
XlogP	1.20
Atomic LogP (AlogP)	2.23
H-Bond Acceptor	11
H-Bond Donor	8
Rotatable Bonds	3

Synonyms

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(+)-Gallocatechin gallate

5127-64-0

(+)-Gallocatechol gallate

(+)-Gallocatechin-3-o-gallate

UNII-0C056HB16M

gallocatechin-3-gallate

Gallocatechin 3-O-gallate

Gallic acid, ester with gallocatechol

0C056HB16M

Benzoic acid, 3,4,5-trihydroxy-, (2R,3S)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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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

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3596077	Q11130	Alpha-(1,3)-fucosyltransferase 7	700 nM	IC50	via Super-PRED
CHEMBL4860	P10415	Apoptosis regulator Bcl-2	235 nM 335 nM	Ki Ki	via Super-PRED via Super-PRED
CHEMBL4822	P56817	Beta-secretase 1	1800 nM 757 nM	IC50 IC50	PMID: 14592472 via Super-PRED
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	Potency	via Super-PRED
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	330 nM	IC50	via Super-PRED
CHEMBL4302	P08183	P-glycoprotein 1	122.6 nM	IC50	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
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 316.2 nM	Potency Potency	via Super-PRED 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

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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