Procyanidin C2

Details

• Internal ID: d9ecc277-6a45-4dde-b5bf-39f13305ccd2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=C(C(=CC(=C34)O)O)C5C(C(OC6=CC(=CC(=C56)O)O)C7=CC(=C(C=C7)O)O)O)C8=CC(=C(C=C8)O)O)O)O)O)C9=CC(=C(C=C9)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@H]3[C@@H]([C@H](OC4=C(C(=CC(=C34)O)O)[C@H]5[C@@H]([C@H](OC6=CC(=CC(=C56)O)O)C7=CC(=C(C=C7)O)O)O)C8=CC(=C(C=C8)O)O)O)O)O)C9=CC(=C(C=C9)O)O)O
• InChI: InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41+,42+,43+/m0/s1
• InChI Key: MOJZMWJRUKIQGL-WNCKYJNFSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₃₈O₁₈
• Molecular Weight: 866.80 g/mol
• Exact Mass: 866.20581436 g/mol
• Topological Polar Surface Area (TPSA): 331.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 4.44
• H-Bond Acceptor: 18
• H-Bond Donor: 15
• Rotatable Bonds: 5

Synonyms

• Procyanidin trimer C2
• catechin-(4alpha->8)-catechin-(4alpha->8)-catechin
• (2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• SCHEMBL18732034
• CHEBI:75644
• GTPL12426
• DTXSID001028796
• 37064-31-6
• C-(4,8)-C-(4,8)-C
• Q15426987
• (2R,2'R,2''R,3S,3'S,3''S,4S,4'R)-2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-2H,2'H,2''H-4,8':4',8''-terchromene-3,3',3'',5,5',5'',7,7',7''-nonol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8698	86.98%
Caco-2	-	0.8992	89.92%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4793	47.93%
OATP2B1 inhibitior	-	0.7086	70.86%
OATP1B1 inhibitior	+	0.9422	94.22%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8302	83.02%
P-glycoprotein inhibitior	+	0.6925	69.25%
P-glycoprotein substrate	-	0.7908	79.08%
CYP3A4 substrate	+	0.5813	58.13%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	+	0.5264	52.64%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9155	91.55%
CYP2C8 inhibition	+	0.6873	68.73%
CYP inhibitory promiscuity	-	0.8625	86.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6139	61.39%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8858	88.58%
Skin irritation	-	0.6044	60.44%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8766	87.66%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.7665	76.65%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.5806	58.06%
Acute Oral Toxicity (c)	IV	0.5696	56.96%
Estrogen receptor binding	+	0.7764	77.64%
Androgen receptor binding	+	0.7454	74.54%
Thyroid receptor binding	+	0.6035	60.35%
Glucocorticoid receptor binding	-	0.4898	48.98%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7277	72.77%
Honey bee toxicity	-	0.7708	77.08%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.6855	68.55%

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	99.52%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	99.15%	83.82%
CHEMBL1951	P21397	Monoamine oxidase A	96.88%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.80%	96.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.59%	96.12%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.66%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.86%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.73%	99.15%
CHEMBL2535	P11166	Glucose transporter	86.62%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.17%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	84.40%	94.73%
CHEMBL3194	P02766	Transthyretin	83.39%	90.71%
CHEMBL236	P41143	Delta opioid receptor	82.54%	99.35%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.46%	94.45%

Plants that contains it

• Actiniopteris radiata
• Aglaia laxiflora
• Artemisia carvifolia
• Callicarpa maingayi
• Cephalaria uralensis
• Crotalaria aegyptiaca
• Dicoma capensis
• Digitalis isabelliana
• Ericameria parryi
• Euphorbia turczaninowii
• Geranium sylvaticum
• Haplophyllum ferganicum
• Potentilla longifolia
• Scopolia carniolica
• Sonchus ortunoi
• Styrax ferrugineus
• Vincetoxicum hirundinaria
• Vitis vinifera

Cross-Links

• PubChem: 11182062
• NPASS: NPC109245
• LOTUS: LTS0099537
• wikiData: Q15426987