Fisetinidol-(4alpha,8)-catechin

Details

• Internal ID: 2792f6b2-186f-475e-a56c-ec5ae8ea689c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-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=C3C=CC(=C4)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@H]3[C@@H]([C@H](OC4=C3C=CC(=C4)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• InChI: InChI=1S/C30H26O11/c31-14-3-4-15-24(9-14)40-29(13-2-6-18(33)21(36)8-13)27(39)25(15)26-22(37)11-19(34)16-10-23(38)28(41-30(16)26)12-1-5-17(32)20(35)7-12/h1-9,11,23,25,27-29,31-39H,10H2/t23-,25-,27-,28+,29+/m0/s1
• InChI Key: CVPALQKJIJFGCD-WXMJOIKDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₆O₁₁
• Molecular Weight: 562.50 g/mol
• Exact Mass: 562.14751164 g/mol
• Topological Polar Surface Area (TPSA): 201.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.29
• H-Bond Acceptor: 11
• H-Bond Donor: 9
• Rotatable Bonds: 3

Synonyms

• 57526-59-7
• Fisetinidol-(4alpha-8)-catechin
• CHEMBL5085645
• CHEBI:68334
• DTXSID101310241
• Q27136831
• (2R,2'R,3S,3'S,4S)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5',7,7'-pentol
• (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• [4,8'-Bi-2H-1-benzopyran]-3,3',5',7,7'-pentol,2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-,(2r,2'r,3s,3's,4s)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8698	86.98%
Caco-2	-	0.9080	90.80%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.4793	47.93%
OATP2B1 inhibitior	-	0.5615	56.15%
OATP1B1 inhibitior	+	0.9207	92.07%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8982	89.82%
P-glycoprotein inhibitior	+	0.7225	72.25%
P-glycoprotein substrate	-	0.6632	66.32%
CYP3A4 substrate	+	0.6122	61.22%
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	+	0.7545	75.45%
CYP inhibitory promiscuity	-	0.8625	86.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6139	61.39%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8129	81.29%
Skin irritation	-	0.6044	60.44%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8865	88.65%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7665	76.65%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7182	71.82%
Acute Oral Toxicity (c)	IV	0.5696	56.96%
Estrogen receptor binding	+	0.7496	74.96%
Androgen receptor binding	+	0.7377	73.77%
Thyroid receptor binding	+	0.6767	67.67%
Glucocorticoid receptor binding	+	0.5913	59.13%
Aromatase binding	-	0.5766	57.66%
PPAR gamma	+	0.7637	76.37%
Honey bee toxicity	-	0.7768	77.68%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
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	99.38%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.23%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.42%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.98%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	91.82%	91.49%
CHEMBL236	P41143	Delta opioid receptor	91.33%	99.35%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.70%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.17%	89.00%
CHEMBL2535	P11166	Glucose transporter	89.84%	98.75%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	87.12%	96.42%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.66%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.91%	98.95%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	85.90%	91.79%
CHEMBL3401	O75469	Pregnane X receptor	85.16%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.93%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.93%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.36%	99.23%

Plants that contains it

• Acacia baileyana
• Acacia mearnsii
• Artemisia alba subsp. alba
• Cyperus papyrus
• Dimorphotheca tragus
• Fagus grandifolia
• Ichthyothere latifolia
• Mitragyna inermis
• Neorautanenia ficifolia
• Othonna dentata
• Perriera orientalis
• Pseudofumaria lutea
• Pteris cretica subsp. cretica
• Sabal palmetto
• Scrophularia oblongifolia
• Solanum chenopodioides
• Strychnos erichsonii
• Swertia pseudochinensis

Cross-Links

• PubChem: 11731408
• NPASS: NPC313116
• LOTUS: LTS0043346
• wikiData: Q27136831