Licoisoflavone A

Details

• Internal ID: c5cf7c81-25f8-4cf7-b2c9-7469650b1139
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflav-2-enes > Isoflavones
• IUPAC Name: 3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxychromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1O)C2=COC3=CC(=CC(=C3C2=O)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1O)C2=COC3=CC(=CC(=C3C2=O)O)O)O)C
• InChI: InChI=1S/C20H18O6/c1-10(2)3-4-13-15(22)6-5-12(19(13)24)14-9-26-17-8-11(21)7-16(23)18(17)20(14)25/h3,5-9,21-24H,4H2,1-2H3
• InChI Key: KCUZCRLRQVRBBV-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.11033829 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 66056-19-7
• phaseoluteone
• UNII-6O34S2M9VL
• 3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxychromen-4-one
• 6O34S2M9VL
• 2',4',5,7-Tetrahydroxy-3'-(3,3-dimethylallyl)isoflavone
• CHEBI:28620
• DTXSID10216256
• LicoisoflavoneA
• 4H-1-BENZOPYRAN-4-ONE, 3-(2,4-DIHYDROXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-5,7-DIHYDROXY-
• Licoisoflavone
• 3-(2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)-5,7-dihydroxy-4H-chromen-4-one
• 3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one
• Flavone base + 4O, 1Prenyl
• SCHEMBL5614024
• CHEMBL4061300
• DTXCID10138747
• GLXC-14667
• HY-N3389
• LMPK12050286
• AKOS032962743
• 3-[2,4-Dihydroxy-3-(3-methyl-but-2-enyl)-phenyl]-5,7-dihydroxy-1-benzopyran-4-one
• MS-25517
• CS-0024074
• FT-0775782
• 3'-Isopentenyl-2',4',5,7-tetrahydroxyisoflavone
• Q27103795
• B0005-477606
• [2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one, 9CI
• 3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-chromen-4-one
• 4H-1-Benzopyran-4-one, 3-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	+	0.5802	58.02%
Blood Brain Barrier	-	0.5379	53.79%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7620	76.20%
OATP2B1 inhibitior	+	0.5807	58.07%
OATP1B1 inhibitior	+	0.8641	86.41%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5832	58.32%
P-glycoprotein inhibitior	-	0.6275	62.75%
P-glycoprotein substrate	-	0.7809	78.09%
CYP3A4 substrate	+	0.5634	56.34%
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	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.9498	94.98%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7012	70.12%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.6938	69.38%
Skin irritation	-	0.7159	71.59%
Skin corrosion	-	0.9161	91.61%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5549	55.49%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.7133	71.33%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.4754	47.54%
Acute Oral Toxicity (c)	III	0.6307	63.07%
Estrogen receptor binding	+	0.9372	93.72%
Androgen receptor binding	+	0.8618	86.18%
Thyroid receptor binding	+	0.6499	64.99%
Glucocorticoid receptor binding	+	0.9239	92.39%
Aromatase binding	+	0.6941	69.41%
PPAR gamma	+	0.9062	90.62%
Honey bee toxicity	-	0.8566	85.66%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.59%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.11%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	96.07%	91.49%
CHEMBL1929	P47989	Xanthine dehydrogenase	94.71%	96.12%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.11%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.93%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.77%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.39%	95.56%
CHEMBL4208	P20618	Proteasome component C5	87.11%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.68%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.74%	99.15%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.69%	91.38%
CHEMBL3194	P02766	Transthyretin	82.03%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.03%	90.71%

Plants that contains it

• Glycyrrhiza
• Glycyrrhiza aspera
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Lupinus albus
• Lupinus angustifolius
• Mitracarpus hirtus
• Phaseolus coccineus
• Phaseolus vulgaris
• Sophora koreensis
• Sophora moorcroftiana

Cross-Links

• PubChem: 5281789
• NPASS: NPC232947
• LOTUS: LTS0263391
• wikiData: Q27103795