Isoangustone A

Details

• Internal ID: ea0a9835-5a2e-4921-aefd-3a00f64fa718
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 3-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)C2=COC3=C(C2=O)C(=C(C(=C3)O)CC=C(C)C)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)C2=COC3=C(C2=O)C(=C(C(=C3)O)CC=C(C)C)O)O)O)C
• InChI: InChI=1S/C25H26O6/c1-13(2)5-7-15-9-16(10-20(27)23(15)28)18-12-31-21-11-19(26)17(8-6-14(3)4)24(29)22(21)25(18)30/h5-6,9-12,26-29H,7-8H2,1-4H3
• InChI Key: QNLGNISMYMFVHP-UHFFFAOYSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₆
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.17293854 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.30
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 129280-34-8
• 3-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
• CHEMBL3809403
• 58NM254N9T
• 5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone
• IsoangustoneA
• 3-(3,4-Dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 3-(3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-
• 4H-1-Benzopyran-4-one, 3-(3,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-
• UNII-58NM254N9T
• Flavone base + 4O, 2Prenyl
• SCHEMBL24075572
• CHEBI:175387
• DTXSID401317327
• HY-N4006
• BDBM50172093
• LMPK12050243
• AKOS032962703
• CS-0024416
• 3-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9577	95.77%
Caco-2	-	0.7178	71.78%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5980	59.80%
OATP2B1 inhibitior	+	0.5785	57.85%
OATP1B1 inhibitior	+	0.9336	93.36%
OATP1B3 inhibitior	+	0.9716	97.16%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8769	87.69%
P-glycoprotein inhibitior	+	0.5953	59.53%
P-glycoprotein substrate	-	0.8210	82.10%
CYP3A4 substrate	+	0.5482	54.82%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.8389	83.89%
CYP3A4 inhibition	-	0.7803	78.03%
CYP2C9 inhibition	+	0.8538	85.38%
CYP2C19 inhibition	+	0.7835	78.35%
CYP2D6 inhibition	-	0.6554	65.54%
CYP1A2 inhibition	+	0.7729	77.29%
CYP2C8 inhibition	+	0.5306	53.06%
CYP inhibitory promiscuity	+	0.8414	84.14%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6930	69.30%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.5411	54.11%
Skin irritation	-	0.7231	72.31%
Skin corrosion	-	0.9189	91.89%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4044	40.44%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.5927	59.27%
skin sensitisation	-	0.7690	76.90%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6239	62.39%
Acute Oral Toxicity (c)	III	0.5414	54.14%
Estrogen receptor binding	+	0.9369	93.69%
Androgen receptor binding	+	0.7570	75.70%
Thyroid receptor binding	+	0.6051	60.51%
Glucocorticoid receptor binding	+	0.8231	82.31%
Aromatase binding	+	0.6317	63.17%
PPAR gamma	+	0.8927	89.27%
Honey bee toxicity	-	0.8406	84.06%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9940	99.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	3000 nM	IC50	PMID: 26841168

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.17%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.65%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.25%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.48%	85.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.44%	89.34%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.48%	86.33%
CHEMBL3038469	P24941	CDK2/Cyclin A	87.87%	91.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.77%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.44%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.89%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.27%	99.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.09%	97.28%
CHEMBL3194	P02766	Transthyretin	81.75%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.24%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.23%	95.64%
CHEMBL4208	P20618	Proteasome component C5	80.52%	90.00%

Plants that contains it

• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 21591148
• NPASS: NPC203077
• ChEMBL: CHEMBL3809403
• LOTUS: LTS0076706
• wikiData: Q105224531