6,8-Diprenylgenistein

Details

• Internal ID: e49a92da-9e94-4ccb-9536-d1cbd6e9b1ae
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 5,7-dihydroxy-3-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C(=CO2)C3=CC=C(C=C3)O)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C(=CO2)C3=CC=C(C=C3)O)CC=C(C)C)O)C
• InChI: InChI=1S/C25H26O5/c1-14(2)5-11-18-22(27)19(12-6-15(3)4)25-21(23(18)28)24(29)20(13-30-25)16-7-9-17(26)10-8-16/h5-10,13,26-28H,11-12H2,1-4H3
• InChI Key: UCHYSPNEUSDFQR-UHFFFAOYSA-N
• Popularity: 35 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₅
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.17802393 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 5.59
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 51225-28-6
• 5,7,4'-trihydroxy-6,8-diprenylisoflavone
• 8-Prenylwighteone
• 5,7-dihydroxy-3-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-enyl)chromen-4-one
• RLK2TR6W3N
• CHEMBL494252
• CHEBI:66263
• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6,8-bis(3-methyl-2-buten-1-yl)-
• 5,7-dihydroxy-3-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-4h-chromen-4-one
• UNII-RLK2TR6W3N
• MLS000863648
• SCHEMBL958215
• MEGxp0_000423
• ACon1_000023
• DTXSID201314991
• HMS2271K10
• 8-gamma,gamma-Dimethylallylwighteone
• BDBM50442403
• LMPK12050191
• AKOS015896250
• 8-(gamma,gamma-dimethylallyl)-wighteone
• NCGC00168867-01
• SMR000440770
• XD180731
• Q27134806
• 4',5,7-Trihydroxy-6,8-diprenylisoflavone, >=85% (LC/MS-UV)
• 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-8-(-3-methyl-but-2-enyl)-6-(3-methyl-but-2-enyl)-1-benzopyran-4-one
• NCGC00168867-02!5,7-dihydroxy-3-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-enyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.5799	57.99%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7672	76.72%
OATP2B1 inhibitior	+	0.5706	57.06%
OATP1B1 inhibitior	+	0.8820	88.20%
OATP1B3 inhibitior	+	0.9021	90.21%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7882	78.82%
P-glycoprotein inhibitior	+	0.6912	69.12%
P-glycoprotein substrate	-	0.8618	86.18%
CYP3A4 substrate	+	0.5370	53.70%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	-	0.6880	68.80%
CYP2C9 inhibition	+	0.8752	87.52%
CYP2C19 inhibition	+	0.9083	90.83%
CYP2D6 inhibition	-	0.7874	78.74%
CYP1A2 inhibition	+	0.8424	84.24%
CYP2C8 inhibition	+	0.5558	55.58%
CYP inhibitory promiscuity	+	0.9224	92.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7280	72.80%
Eye corrosion	-	0.9903	99.03%
Eye irritation	+	0.6467	64.67%
Skin irritation	-	0.7427	74.27%
Skin corrosion	-	0.9406	94.06%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7273	72.73%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5304	53.04%
skin sensitisation	-	0.7530	75.30%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5768	57.68%
Acute Oral Toxicity (c)	III	0.6102	61.02%
Estrogen receptor binding	+	0.9311	93.11%
Androgen receptor binding	+	0.8535	85.35%
Thyroid receptor binding	+	0.6846	68.46%
Glucocorticoid receptor binding	+	0.8018	80.18%
Aromatase binding	+	0.6886	68.86%
PPAR gamma	+	0.9103	91.03%
Honey bee toxicity	-	0.8743	87.43%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9970	99.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4040	P28482	MAP kinase ERK2	19952.6 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	9300 nM	IC50	PMID: 26704263

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.48%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.95%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.31%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.47%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.36%	91.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.27%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.78%	93.10%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.78%	94.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.62%	97.28%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.49%	86.92%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.16%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.37%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.49%	89.34%
CHEMBL1937	Q92769	Histone deacetylase 2	80.28%	94.75%

Plants that contains it

• Anthotroche myoporoides
• Astragalus flexus
• Brachypterum scandens
• Deguelia scandens
• Erythrina senegalensis
• Erythrina sigmoidea
• Erythrina variegata
• Erythrina vogelii
• Euchresta horsfieldii
• Euchresta japonica
• Flemingia macrophylla
• Flemingia prostrata
• Glycyrrhiza
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Helenium virginicum
• Heliotropium digynum
• Hypericum caprifoliatum
• Lupinus pilosus
• Maclura tricuspidata
• Millettia pachycarpa
• Mitracarpus hirtus
• Nannoglottis ravida

Cross-Links

• PubChem: 480783
• NPASS: NPC204985
• ChEMBL: CHEMBL494252
• LOTUS: LTS0014786
• wikiData: Q27134806