Epicatechin-(4beta->8)-epicatechin-(2beta->7,4beta->8)-catechin

Details

• Internal ID: cd1bc2fe-6c3f-4f0e-b0ee-7378dd7563d9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC3=C2C4C(C(O3)(OC5=C(C(=CC(=C45)O)O)C6C(C(OC7=CC(=CC(=C67)O)O)C8=CC(=C(C=C8)O)O)O)C9=CC(=C(C=C9)O)O)O)O)C1=CC(=C(C=C1)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC3=C2[C@@H]4[C@H]([C@](O3)(OC5=C(C(=CC(=C45)O)O)[C@@H]6[C@H]([C@H](OC7=CC(=CC(=C67)O)O)C8=CC(=C(C=C8)O)O)O)C9=CC(=C(C=C9)O)O)O)O)C1=CC(=C(C=C1)O)O)O
• InChI: InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)60-41(16-2-5-21(48)25(52)8-16)39(58)37(33)34-28(55)13-29(56)35-38-36-32(62-45(44(38)59,63-43(34)35)17-3-6-22(49)26(53)9-17)14-23(50)19-12-30(57)40(61-42(19)36)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38+,39+,40+,41+,44+,45+/m0/s1
• InChI Key: SRWJAXVAWDYXPA-ACNGEOCHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₃₆O₁₈
• Molecular Weight: 864.80 g/mol
• Exact Mass: 864.19016430 g/mol
• Topological Polar Surface Area (TPSA): 320.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 18
• H-Bond Donor: 14
• Rotatable Bonds: 4

Synonyms

• (1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
• Epicatechin-(4b->8)-epicatechin-(2b->7,4b->8)-catechin
• (1R,5R,6S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
• 3,3',3'',4,4',4''-Hexahydro-3alpha,3'alpha,3''beta,5,5',5'',7,7'-octahydroxy-2'beta,7''-epoxy-2alpha,2'alpha,2''alpha-tris(3,4-dihydroxyphenyl)-4beta,8':4'beta,8''-ter[2H-1-benzopyran]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7002	70.02%
Caco-2	-	0.8877	88.77%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5149	51.49%
OATP2B1 inhibitior	-	0.7098	70.98%
OATP1B1 inhibitior	+	0.8996	89.96%
OATP1B3 inhibitior	+	0.8374	83.74%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9000	90.00%
P-glycoprotein inhibitior	+	0.7164	71.64%
P-glycoprotein substrate	-	0.5460	54.60%
CYP3A4 substrate	+	0.6686	66.86%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	+	0.3672	36.72%
CYP3A4 inhibition	-	0.9095	90.95%
CYP2C9 inhibition	-	0.8939	89.39%
CYP2C19 inhibition	-	0.8571	85.71%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.9758	97.58%
CYP2C8 inhibition	+	0.7876	78.76%
CYP inhibitory promiscuity	-	0.9554	95.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6019	60.19%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8848	88.48%
Skin irritation	-	0.6303	63.03%
Skin corrosion	-	0.9314	93.14%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8686	86.86%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8144	81.44%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	IV	0.5178	51.78%
Estrogen receptor binding	+	0.7953	79.53%
Androgen receptor binding	+	0.7816	78.16%
Thyroid receptor binding	+	0.6012	60.12%
Glucocorticoid receptor binding	+	0.5797	57.97%
Aromatase binding	+	0.5712	57.12%
PPAR gamma	+	0.7453	74.53%
Honey bee toxicity	-	0.6388	63.88%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.7943	79.43%

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	99.72%	91.11%
CHEMBL233	P35372	Mu opioid receptor	95.86%	97.93%
CHEMBL236	P41143	Delta opioid receptor	94.80%	99.35%
CHEMBL4040	P28482	MAP kinase ERK2	94.20%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.86%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.75%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.12%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.51%	98.95%
CHEMBL2535	P11166	Glucose transporter	88.74%	98.75%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.23%	96.12%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.59%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	87.44%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.91%	99.15%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.82%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.69%	95.56%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.17%	96.37%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.49%	99.23%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.29%	85.11%

Plants that contains it

• Aizoon africanum
• Alangium premnifolium
• Angelica tarokoensis
• Bombax ceiba
• Diospyros ferrea
• Epimedium davidii
• Erysimum odoratum
• Frullania tamarisci
• Globba variabilis
• Heterotheca inuloides
• Ilex amara
• Isodon japonicus
• Knightia excelsa
• Lasiosiphon lampranthus
• Leonurus glaucescens
• Lepidium draba
• Micromeria pineolens
• Quercus petraea subsp. petraea
• Salacia madagascariensis
• Saussurea lyrata
• Solanum acaule
• Swertia delavayi
• Vaccinium vitis-idaea
• Vepris hiernii
• Vismia jefensis

Cross-Links

• PubChem: 10350652
• NPASS: NPC136771
• LOTUS: LTS0030949
• wikiData: Q76415492