Procyanidin

Details

• Internal ID: 6c904a52-0443-4925-b1e9-d149a106cab9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-2-[[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-3,4-dihydrochromene-3,4,5,7-tetrol
• SMILES (Canonical): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC4(C(C(C5=C(C=C(C=C5O4)O)O)O)O)C6=CC(=C(C=C6)O)O
• SMILES (Isomeric): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC4(C(C(C5=C(C=C(C=C5O4)O)O)O)O)C6=CC(=C(C=C6)O)O
• InChI: InChI=1S/C30H26O13/c31-14-7-19(35)16-11-25(28(41-23(16)9-14)12-1-3-17(33)20(36)5-12)43-30(13-2-4-18(34)21(37)6-13)29(40)27(39)26-22(38)8-15(32)10-24(26)42-30/h1-10,25,27-29,31-40H,11H2
• InChI Key: HGVVOUNEGQIPMS-UHFFFAOYSA-N
• Popularity: 685 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₆O₁₃
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.13734088 g/mol
• Topological Polar Surface Area (TPSA): 230.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.73
• H-Bond Acceptor: 13
• H-Bond Donor: 10
• Rotatable Bonds: 4

Synonyms

• Proanthocyanidins
• 4852-22-6
• 20347-71-1
• Procyanidins
• 2-(3,4-Dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl)oxy)chroman-3,4,5,7-tetraol
• C30H26O13
• BRN 1675863
• 2-(3,4-dihydroxyphenyl)-2-[[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-3,4-dihydrochromene-3,4,5,7-tetrol
• 2-(3,4-Dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl)oxy)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
• 3,3',4,4',5,7-Flavanhexol, 2-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-chromanyl)oxy)-
• 2H-1-Benzopyran-3,4,5,7-tetrol, 2-(3,4-dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl)oxy)-3,4-dihydro-
• epicatechin-4alpha,8-epicatechin
• 2H-1-Benzopyran-3,4,5,7-tetrol, 2-(3,4-dihydroxyphenyl)-2-[[2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl]oxy]-3,4-dihydro-
• Procyanidin, Technical grade
• Procyanidin B-5 3'-O-gallate
• SCHEMBL15091123
• DTXSID90858698
• CHEBI:166895
• BCP25503
• HY-N0794
• MFCD01662851
• s5105
• AKOS025402316
• AC-8032
• CCG-270176
• CCG-270178
• C30-H26-O13
• 2-(3,4-dihydroxyphenyl)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chroman-3-yl]oxy-chromane-3,4,5,7-tetrol
• LS-39919
• CS-0009805
• FT-0688150
• EN300-7388961
• A908663
• 2-(3,4-dihydroxyphenyl)-2-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
• 2-(3,4-dihydroxyphenyl)-2-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-chromen-3-yl]oxy}-3,4,5,7-chromanetetrol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6195	61.95%
Caco-2	-	0.8994	89.94%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6048	60.48%
OATP2B1 inhibitior	-	0.5681	56.81%
OATP1B1 inhibitior	+	0.8702	87.02%
OATP1B3 inhibitior	+	0.7934	79.34%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8246	82.46%
P-glycoprotein inhibitior	+	0.6098	60.98%
P-glycoprotein substrate	-	0.9091	90.91%
CYP3A4 substrate	+	0.6170	61.70%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	+	0.3605	36.05%
CYP3A4 inhibition	-	0.8413	84.13%
CYP2C9 inhibition	-	0.6236	62.36%
CYP2C19 inhibition	+	0.5937	59.37%
CYP2D6 inhibition	-	0.9414	94.14%
CYP1A2 inhibition	-	0.9306	93.06%
CYP2C8 inhibition	+	0.7215	72.15%
CYP inhibitory promiscuity	-	0.8410	84.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5788	57.88%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.7739	77.39%
Skin irritation	-	0.6807	68.07%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8823	88.23%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8483	84.83%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5723	57.23%
Acute Oral Toxicity (c)	IV	0.4169	41.69%
Estrogen receptor binding	+	0.7682	76.82%
Androgen receptor binding	+	0.8008	80.08%
Thyroid receptor binding	+	0.6708	67.08%
Glucocorticoid receptor binding	+	0.7364	73.64%
Aromatase binding	+	0.5624	56.24%
PPAR gamma	+	0.7169	71.69%
Honey bee toxicity	-	0.7251	72.51%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8672	86.72%

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	99.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.91%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.65%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.38%	97.09%
CHEMBL233	P35372	Mu opioid receptor	90.61%	97.93%
CHEMBL2581	P07339	Cathepsin D	88.96%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.14%	93.40%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.61%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.66%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.20%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.80%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.48%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.15%	89.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.55%	96.12%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.53%	96.37%

Plants that contains it

• Annona squamosa
• Cinnamomum aromaticum
• Crataegus pinnatifida
• Eugenia uniflora
• Ginkgo biloba
• Lathyrus pratensis
• Lotus pedunculatus
• Patersonia fragilis
• Pinus brutia
• Pinus halepensis
• Pseudotsuga menziesii
• Sanguisorba officinalis
• Theobroma cacao
• Vitis amurensis

Cross-Links

• PubChem: 107876
• NPASS: NPC75353
• LOTUS: LTS0249995
• wikiData: Q81977791