Isowighteone

Details

• Internal ID: 83357f30-3c8e-45ca-a2a8-05c44e8d3140
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflav-2-enes > Isoflavones
• IUPAC Name: 5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1)C2=COC3=CC(=CC(=C3C2=O)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1)C2=COC3=CC(=CC(=C3C2=O)O)O)O)C
• InChI: InChI=1S/C20H18O5/c1-11(2)3-4-13-7-12(5-6-16(13)22)15-10-25-18-9-14(21)8-17(23)19(18)20(15)24/h3,5-10,21-23H,4H2,1-2H3
• InChI Key: SWDSVBNAMCDHTF-UHFFFAOYSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.11542367 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.09
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]chromen-4-one
• 3'-(gamma,gamma-dimethylallyl)genistein
• CHEBI:69749
• 3'-(g,g-Dimethylallyl)genistein
• 5,7-Dihydroxy-3-(4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl)-4H-chromen-4-one
• 5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-4H-chromen-4-one
• 5,7-Dihydroxy-3-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one, 9CI
• 5,7-dihydroxy-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)chromen-4-one
• 5,7-Dihydroxy-3-(4-hydroxy-3-(3-methyl-2-butenyl)phenyl)-4H-1-benzopyran-4-one, 9ci
• RefChem:150143
• 68436-47-5
• Isowightenon
• Isowigtheone
• 3'-Prenylgenistein
• 5,7,4'-Trihydroxy-3'-prenylisoflavone
• CHEMBL1812593
• 3'-prenyl-5,7,4'-trihydroxyisoflavone
• 3'-isoprenylgenistein
• 3'Dimethylallylgenistein
• 3'-Dimethylallylgenistein
• CHEMBL464460
• orb1681284
• P89WCN5Q95
• SCHEMBL27013640
• DTXSID801317874
• HY-N3448
• BDBM50349975
• LMPK12050192
• AKOS032962333
• FS-8957
• DA-64581
• FI138625
• CS-0024260
• Q27138091
• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-
• 5,7-Dihydroxy-3-[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-4H-1-benzopyran-4-one
• 5,7-Dihydroxy-3-[4-hydroxy-3-(3-methyl-but-2-enyl)-phenyl]-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	+	0.7066	70.66%
Blood Brain Barrier	-	0.5379	53.79%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7620	76.20%
OATP2B1 inhibitior	+	0.5728	57.28%
OATP1B1 inhibitior	+	0.9448	94.48%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7573	75.73%
P-glycoprotein inhibitior	-	0.5893	58.93%
P-glycoprotein substrate	-	0.8157	81.57%
CYP3A4 substrate	+	0.5432	54.32%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	+	0.5630	56.30%
CYP2C9 inhibition	+	0.9394	93.94%
CYP2C19 inhibition	+	0.9320	93.20%
CYP2D6 inhibition	-	0.7264	72.64%
CYP1A2 inhibition	+	0.9115	91.15%
CYP2C8 inhibition	+	0.6142	61.42%
CYP inhibitory promiscuity	+	0.9498	94.98%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7012	70.12%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.6641	66.41%
Skin irritation	-	0.7159	71.59%
Skin corrosion	-	0.9161	91.61%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5462	54.62%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.7133	71.33%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6937	69.37%
Acute Oral Toxicity (c)	III	0.6307	63.07%
Estrogen receptor binding	+	0.9390	93.90%
Androgen receptor binding	+	0.8540	85.40%
Thyroid receptor binding	+	0.6938	69.38%
Glucocorticoid receptor binding	+	0.9302	93.02%
Aromatase binding	+	0.7783	77.83%
PPAR gamma	+	0.9244	92.44%
Honey bee toxicity	-	0.8344	83.44%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9944	99.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1929	P47989	Xanthine dehydrogenase	98.96%	96.12%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.93%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.67%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.64%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.43%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.45%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.53%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.44%	97.28%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.83%	91.38%
CHEMBL3194	P02766	Transthyretin	86.24%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.57%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.23%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.10%	94.00%

Plants that contains it

• Cajanus cajan
• Cullen corylifolium
• Erythrina poeppigiana
• Erythrina vogelii
• Ficus mucuso
• Glycyrrhiza aspera
• Glycyrrhiza uralensis
• Lupinus albus
• Piscidia piscipula
• Sophora tomentosa
• Ulex europaeus subsp. europaeus

Cross-Links

• PubChem: 5494866
• NPASS: NPC213659
• LOTUS: LTS0080015
• wikiData: Q27138091