procyanidin B2 3-O-gallate

Details

• Internal ID: 07112185-c23e-41c1-9dc9-8c0e66c28ef4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: [(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-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)OC(=O)C6=CC(=C(C(=C6)O)O)O)O)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)OC(=O)C6=CC(=C(C(=C6)O)O)O)O)O)C7=CC(=C(C=C7)O)O)O
• InChI: InChI=1S/C37H30O16/c38-16-9-23(44)29-28(10-16)51-34(14-2-4-19(40)22(43)6-14)36(53-37(50)15-7-25(46)32(49)26(47)8-15)31(29)30-24(45)12-20(41)17-11-27(48)33(52-35(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,27,31,33-34,36,38-49H,11H2/t27-,31-,33-,34-,36-/m1/s1
• InChI Key: BXWABJPTCUDBMM-QOCBQNCISA-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:75652
• Procyanidin B2 3-gallate
• CHEMBL2414341
• Q27145448
• (-)-epicatechin-(4beta->8)-(-)-epicatechin-3-O-gallate
• (2R,2'R,3R,3'R,4R)-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8367	83.67%
Caco-2	-	0.9165	91.65%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5726	57.26%
OATP2B1 inhibitior	-	0.5644	56.44%
OATP1B1 inhibitior	+	0.8243	82.43%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8824	88.24%
P-glycoprotein inhibitior	+	0.7287	72.87%
P-glycoprotein substrate	-	0.6684	66.84%
CYP3A4 substrate	+	0.6605	66.05%
CYP2C9 substrate	-	0.7962	79.62%
CYP2D6 substrate	-	0.7126	71.26%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9429	94.29%
CYP2C19 inhibition	-	0.9118	91.18%
CYP2D6 inhibition	-	0.9417	94.17%
CYP1A2 inhibition	-	0.9403	94.03%
CYP2C8 inhibition	+	0.8138	81.38%
CYP inhibitory promiscuity	-	0.9256	92.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6306	63.06%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.8708	87.08%
Skin irritation	-	0.6568	65.68%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	+	0.5946	59.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.8414	84.14%
Micronuclear	+	0.8759	87.59%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8377	83.77%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8010	80.10%
Acute Oral Toxicity (c)	IV	0.4212	42.12%
Estrogen receptor binding	+	0.8068	80.68%
Androgen receptor binding	+	0.8052	80.52%
Thyroid receptor binding	+	0.6040	60.40%
Glucocorticoid receptor binding	+	0.5778	57.78%
Aromatase binding	-	0.6176	61.76%
PPAR gamma	+	0.7247	72.47%
Honey bee toxicity	-	0.7601	76.01%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.8606	86.06%

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	99.67%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.67%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.21%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.96%	83.82%
CHEMBL3194	P02766	Transthyretin	94.37%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.93%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.82%	89.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.31%	83.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.39%	86.33%
CHEMBL4208	P20618	Proteasome component C5	89.01%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.51%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.02%	99.17%
CHEMBL236	P41143	Delta opioid receptor	87.93%	99.35%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.46%	99.23%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.34%	96.12%
CHEMBL2581	P07339	Cathepsin D	85.28%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.93%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	83.14%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.74%	95.89%
CHEMBL233	P35372	Mu opioid receptor	82.07%	97.93%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.36%	96.37%
CHEMBL2535	P11166	Glucose transporter	80.40%	98.75%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.36%	94.42%

Plants that contains it

• Acacia adunca
• Adiantum philippense
• Aldama incana
• Annona cornifolia
• Artemisia pedemontana subsp. assoana
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Chaenomeles sinensis
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hibiscus cannabinus
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Marrubium anisodon
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scutellaria amoena
• Solanum laxum
• Swertia franchetiana
• Vaccinium oxycoccos
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 46181828
• NPASS: NPC61990
• LOTUS: LTS0219611
• wikiData: Q27145448