(+)-Catechin 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	eb89944d-23c3-41a0-8fdb-85a4671223b2
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Catechin gallates
IUPAC Name	[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-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)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)OC(=O)C4=CC(=C(C(=C4)O)O)O
InChI	InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21+/m0/s1
InChI Key	LSHVYAFMTMFKBA-PZJWPPBQSA-N
Popularity	143 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₂H₁₈O₁₀
Molecular Weight	442.40 g/mol
Exact Mass	442.08999677 g/mol
Topological Polar Surface Area (TPSA)	177.00 Å²
XlogP	1.50
Atomic LogP (AlogP)	2.53
H-Bond Acceptor	10
H-Bond Donor	7
Rotatable Bonds	3

Synonyms

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(+)-Catechin gallate

catechin gallate

Catechin gallate, (+)-

Catechin-3-Gallate

25615-05-8

Catechin 3-O-gallate

CHEBI:76132

UNII-78OW2GLG8Q

78OW2GLG8Q

Benzoic acid, 3,4,5-trihydroxy-, (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-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	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6166	61.66%
OATP2B1 inhibitior	+	0.7032	70.32%
OATP1B1 inhibitior	+	0.7038	70.38%
OATP1B3 inhibitior	-	0.5697	56.97%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4828	48.28%
P-glycoprotein inhibitior	-	0.5530	55.30%
P-glycoprotein substrate	-	0.8973	89.73%
CYP3A4 substrate	+	0.5954	59.54%
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	+	0.7473	74.73%
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	+	0.6035	60.35%
Skin irritation	-	0.6348	63.48%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8554	85.54%
Micronuclear	+	0.8859	88.59%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8369	83.69%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7481	74.81%
Acute Oral Toxicity (c)	IV	0.3764	37.64%
Estrogen receptor binding	+	0.7558	75.58%
Androgen receptor binding	+	0.8604	86.04%
Thyroid receptor binding	+	0.6077	60.77%
Glucocorticoid receptor binding	+	0.6545	65.45%
Aromatase binding	-	0.8091	80.91%
PPAR gamma	+	0.6090	60.90%
Honey bee toxicity	-	0.8279	82.79%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5750	57.50%
Fish aquatic toxicity	+	0.9197	91.97%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4860	P10415	Apoptosis regulator Bcl-2	400 nM 230 nM 230 nM	Ki Ki Ki	via Super-PRED via Super-PRED DOI: 10.1007/s00044-009-9233-5
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	707.9 nM	Potency	via Super-PRED
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	255 nM	IC50	via Super-PRED
CHEMBL4105924	Q14576	ELAV-like protein 3	200 nM	IC50	via Super-PRED
CHEMBL4662	P28074	Proteasome Macropain subunit MB1	124 nM 194 nM	IC50 IC50	via Super-PRED via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	281.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.49%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.32%	91.49%
CHEMBL3194	P02766	Transthyretin	96.50%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.67%	96.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	92.47%	83.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.88%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.49%	86.33%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	88.53%	96.37%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.40%	99.23%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	87.25%	97.53%
CHEMBL2535	P11166	Glucose transporter	86.71%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.67%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.66%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.58%	95.56%
CHEMBL4208	P20618	Proteasome component C5	82.85%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.82%	99.15%
CHEMBL2581	P07339	Cathepsin D	82.77%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	80.58%	91.19%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Andrographis paniculata

Annona impressivenia

Arbutus unedo

Aristolochia zollingeriana

Artemisia schimperi

Balanophora involucrata

Bartramia pomiformis