Bilobetin

Details

• Internal ID: bcb31062-aa9d-4786-96ec-9e3b260afb3a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O)C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O)C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)O
• InChI: InChI=1S/C31H20O10/c1-39-24-7-4-15(26-12-22(37)29-19(34)9-17(33)10-27(29)40-26)8-18(24)28-20(35)11-21(36)30-23(38)13-25(41-31(28)30)14-2-5-16(32)6-3-14/h2-13,32-36H,1H3
• InChI Key: IWEIJEPIYMAGTH-UHFFFAOYSA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₂₀O₁₀
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.10564683 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.44
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 521-32-4
• 4'-Monomethylamentoflavone
• AJ4UE8X6JZ
• 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• 3''',8-Biflavone, 4',5,5'',7,7''-pentahydroxy-4'''-methoxy-
• 8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 8-(5-(5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-2-YL)-2-METHOXYPHENYL)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• 8-(5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• 8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• C31H20O10
• UNII-AJ4UE8X6JZ
• SCHEMBL13485655
• DTXSID70200095
• CHEBI:192880
• BDBM513134
• acs.jmedchem.1c00409_ST.731
• HY-N2118
• MFCD00597036
• AKOS032948310
• 5,7-Dihydroxy-8-[2-methoxy-5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenyl]-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• AC-34039
• MS-30093
• CS-0018638
• FT-0708565
• A871059
• Biflavonoid-flavone base + 3O and flavone base + 2O + 1MeO
• 4',5,5'',7,7''-Pentahydroxy-4'''-methoxy-3''',8-Biflavone
• 4H-1-BENZOPYRAN-4-ONE, 8-(5-(5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-2-YL)-2-METHOXYPHENYL)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-
• 8-(5-(5,7-BIS(OXIDANYL)-4-OXIDANYLIDENE-CHROMEN-2-YL)-2-METHOXY-PHENYL)-2-(4-HYDROXYPHENYL)-5,7-BIS(OXIDANYL)CHROMEN-4-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9430	94.30%
Caco-2	-	0.8062	80.62%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8174	81.74%
OATP2B1 inhibitior	-	0.5611	56.11%
OATP1B1 inhibitior	-	0.6487	64.87%
OATP1B3 inhibitior	+	0.9706	97.06%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8239	82.39%
P-glycoprotein inhibitior	+	0.7612	76.12%
P-glycoprotein substrate	-	0.5304	53.04%
CYP3A4 substrate	+	0.6390	63.90%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.5760	57.60%
CYP2C9 inhibition	+	0.7647	76.47%
CYP2C19 inhibition	+	0.7471	74.71%
CYP2D6 inhibition	-	0.7766	77.66%
CYP1A2 inhibition	+	0.8002	80.02%
CYP2C8 inhibition	+	0.9129	91.29%
CYP inhibitory promiscuity	+	0.6806	68.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5868	58.68%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.8192	81.92%
Skin irritation	-	0.6647	66.47%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6569	65.69%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9499	94.99%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.4888	48.88%
Acute Oral Toxicity (c)	III	0.6544	65.44%
Estrogen receptor binding	+	0.9041	90.41%
Androgen receptor binding	+	0.9442	94.42%
Thyroid receptor binding	+	0.6342	63.42%
Glucocorticoid receptor binding	+	0.8355	83.55%
Aromatase binding	+	0.5652	56.52%
PPAR gamma	+	0.7569	75.69%
Honey bee toxicity	-	0.7221	72.21%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5849	58.49%
Fish aquatic toxicity	+	0.8837	88.37%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4822	P56817	Beta-secretase 1	2020 nM	IC50	PMID: 20598535

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL242	Q92731	Estrogen receptor beta	97.72%	98.35%
CHEMBL3194	P02766	Transthyretin	97.27%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.91%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.47%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.25%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.99%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.51%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.55%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.18%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.79%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.40%	95.78%
CHEMBL1951	P21397	Monoamine oxidase A	88.08%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.82%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.49%	86.92%
CHEMBL308	P06493	Cyclin-dependent kinase 1	83.35%	91.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.05%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.74%	90.00%
CHEMBL1255126	O15151	Protein Mdm4	82.62%	90.20%
CHEMBL3401	O75469	Pregnane X receptor	82.29%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.07%	99.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.92%	97.28%
CHEMBL2535	P11166	Glucose transporter	81.86%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.88%	94.45%
CHEMBL1921	P47901	Vasopressin V1b receptor	80.37%	92.50%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.35%	85.00%

Plants that contains it

• Cephalotaxus nana
• Chamaecyparis thyoides
• Dysoxylum lenticellare
• Ginkgo biloba
• Piranhea mexicana
• Selaginella pulvinata
• Selaginella tamariscina
• Selaginella willdenowii
• Taxus baccata
• Taxus wallichiana var. chinensis
• Tetraclinis articulata
• Torreya nucifera

Cross-Links

• PubChem: 5315459
• NPASS: NPC71061
• ChEMBL: CHEMBL378188
• LOTUS: LTS0013591
• wikiData: Q72443484