procyanidin B3 3'-O-gallate

Details

• Internal ID: 0aa6db60-82f4-4a78-afb2-f70528f8b891
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: [(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@H]3[C@@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
• InChI: InChI=1S/C37H30O16/c38-16-9-23(44)29-27(10-16)51-35(14-2-4-19(40)22(43)6-14)33(49)31(29)30-24(45)12-20(41)17-11-28(52-37(50)15-7-25(46)32(48)26(47)8-15)34(53-36(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,28,31,33-35,38-49H,11H2/t28-,31-,33-,34+,35+/m0/s1
• InChI Key: VLFKNLZNDSEVBZ-LBSACNJESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₃₀O₁₆
• Molecular Weight: 730.60 g/mol
• Exact Mass: 730.15338487 g/mol
• Topological Polar Surface Area (TPSA): 288.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.98
• H-Bond Acceptor: 16
• H-Bond Donor: 12
• Rotatable Bonds: 5

Synonyms

• CHEBI:75662
• CHEMBL2414344
• Q27145456
• (+)-catechin-(4alpha->8)-(+)-catechin-3'-O-gallate
• (2R,2'R,3S,3'S,4S)-2,2'-bis(3,4-dihydroxyphenyl)-3,5,5',7,7'-pentahydroxy-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromen-3'-yl 3,4,5-trihydroxybenzoate
• [(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8063	80.63%
Caco-2	-	0.9139	91.39%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6485	64.85%
OATP2B1 inhibitior	-	0.7031	70.31%
OATP1B1 inhibitior	+	0.8435	84.35%
OATP1B3 inhibitior	-	0.4057	40.57%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8904	89.04%
P-glycoprotein inhibitior	+	0.7154	71.54%
P-glycoprotein substrate	-	0.6836	68.36%
CYP3A4 substrate	+	0.6715	67.15%
CYP2C9 substrate	-	0.7962	79.62%
CYP2D6 substrate	-	0.7126	71.26%
CYP3A4 inhibition	-	0.7658	76.58%
CYP2C9 inhibition	-	0.8173	81.73%
CYP2C19 inhibition	-	0.7636	76.36%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.8594	85.94%
CYP2C8 inhibition	+	0.8119	81.19%
CYP inhibitory promiscuity	-	0.8411	84.11%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6439	64.39%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.8808	88.08%
Skin irritation	-	0.6484	64.84%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8693	86.93%
Micronuclear	+	0.8659	86.59%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8408	84.08%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7275	72.75%
Acute Oral Toxicity (c)	IV	0.3703	37.03%
Estrogen receptor binding	+	0.7884	78.84%
Androgen receptor binding	+	0.7974	79.74%
Thyroid receptor binding	+	0.5713	57.13%
Glucocorticoid receptor binding	+	0.5720	57.20%
Aromatase binding	-	0.5870	58.70%
PPAR gamma	+	0.6822	68.22%
Honey bee toxicity	-	0.7493	74.93%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9003	90.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.63%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.81%	91.49%
CHEMBL3194	P02766	Transthyretin	96.21%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.64%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.67%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	92.65%	83.82%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	92.53%	83.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	91.32%	96.12%
CHEMBL2535	P11166	Glucose transporter	91.28%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.19%	89.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.27%	95.17%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	89.63%	96.37%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.09%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.77%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.90%	99.23%
CHEMBL4208	P20618	Proteasome component C5	86.43%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.57%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.31%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.03%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.80%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.45%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.32%	94.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.31%	97.53%

Plants that contains it

• Rodgersia sambucifolia

Cross-Links

• PubChem: 11686333
• LOTUS: LTS0258068
• wikiData: Q27145456