Proanthocyanidin

Details

• Internal ID: b1cd7b87-21cc-4cca-8690-714abbb1706e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): COC1=C(C=C(C=C1O)C2C(CC3=C(O2)C(=C(C=C3O)O)C4C(C(OC5=CC(=CC(=C45)O)O)C6=CC=C(C=C6)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1O)C2[C@@H](CC3=C(O2)C(=C(C=C3O)O)[C@@H]4[C@H]([C@H](OC5=CC(=CC(=C45)O)O)C6=CC=C(C=C6)O)O)O)O
• InChI: InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1
• InChI Key: JPFCOVZKLAXXOE-XBNSMERZSA-N
• Popularity: 727 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₂₈O₁₂
• Molecular Weight: 592.50 g/mol
• Exact Mass: 592.15807632 g/mol
• Topological Polar Surface Area (TPSA): 210.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 12
• H-Bond Donor: 9
• Rotatable Bonds: 4

Synonyms

• Ouratea proanthocyanidin A
• CCRIS 9188
• Proanthocyanidin A
• 18206-61-6
• C31H28O12
• (3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• 274678-42-1
• Zangrado
• (4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2'-(3,5-dihydroxy-4-methoxyphenyl)-3,3',4,4'-tetrahydro-2-(4-hydroxyphenyl)-, (2R-(2alpha,3alpha,4beta(2'R*,3'R*)))-
• C31-H28-O12
• (4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2'-(3,5-dihydroxy-4-methoxyphenyl)-3,3',4,4'-tetrahydro-2-(4-hydroxyphenyl)-, (2R,2'R,3R,3'R,4R)-
• SCHEMBL4747623
• AKOS015967674
• LS-173715
• J-011651
• (2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxychroman-8-yl]-2-(4-hydroxyphenyl)chroman-3,5,7-triol
• 2-(3,5-Dihydroxy-4-methoxyphenyl)-8-[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9361	93.61%
Caco-2	-	0.8759	87.59%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5227	52.27%
OATP2B1 inhibitior	-	0.8459	84.59%
OATP1B1 inhibitior	+	0.7979	79.79%
OATP1B3 inhibitior	+	0.8774	87.74%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8508	85.08%
P-glycoprotein inhibitior	+	0.7303	73.03%
P-glycoprotein substrate	-	0.6408	64.08%
CYP3A4 substrate	+	0.6450	64.50%
CYP2C9 substrate	-	0.5992	59.92%
CYP2D6 substrate	+	0.5931	59.31%
CYP3A4 inhibition	-	0.7295	72.95%
CYP2C9 inhibition	-	0.7296	72.96%
CYP2C19 inhibition	+	0.5513	55.13%
CYP2D6 inhibition	-	0.7383	73.83%
CYP1A2 inhibition	-	0.7050	70.50%
CYP2C8 inhibition	+	0.7505	75.05%
CYP inhibitory promiscuity	-	0.5832	58.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5213	52.13%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.8569	85.69%
Skin irritation	-	0.6955	69.55%
Skin corrosion	-	0.9221	92.21%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9135	91.35%
Micronuclear	+	0.7659	76.59%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8815	88.15%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6458	64.58%
Acute Oral Toxicity (c)	III	0.6109	61.09%
Estrogen receptor binding	+	0.7699	76.99%
Androgen receptor binding	+	0.7205	72.05%
Thyroid receptor binding	+	0.6666	66.66%
Glucocorticoid receptor binding	+	0.6254	62.54%
Aromatase binding	-	0.5739	57.39%
PPAR gamma	+	0.6860	68.60%
Honey bee toxicity	-	0.7922	79.22%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.4902	49.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.54%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.40%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.99%	96.09%
CHEMBL2535	P11166	Glucose transporter	92.80%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.58%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.59%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.38%	94.45%
CHEMBL4208	P20618	Proteasome component C5	87.64%	90.00%
CHEMBL2581	P07339	Cathepsin D	85.74%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.43%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.35%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	84.56%	94.73%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.81%	82.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.99%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.90%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.01%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.13%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.97%	95.89%
CHEMBL236	P41143	Delta opioid receptor	80.47%	99.35%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	80.29%	91.79%

Plants that contains it

• Cinnamomum verum
• Dichrostachys cinerea
• Diospyros kaki
• Ginkgo biloba
• Hamamelis virginiana
• Hippophae rhamnoides
• Humulus lupulus
• Paeonia obovata
• Rubus chingii
• Rubus coreanus
• Vaccinium macrocarpon
• Vantanea peruviana
• Vitis vinifera

Cross-Links

• PubChem: 108065
• NPASS: NPC57338
• LOTUS: LTS0226294
• wikiData: Q82006361