Isoprunetin

Details

• Internal ID: 64cc4bba-9b00-4d91-8cef-99ec426f7c2a
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflav-2-enes > Isoflavones
• IUPAC Name: 7-hydroxy-3-(4-hydroxyphenyl)-5-methoxychromen-4-one
• InChI: InChI=1S/C16H12O5/c1-20-13-6-11(18)7-14-15(13)16(19)12(8-21-14)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
• InChI Key: YSINCDVRUMTOPK-UHFFFAOYSA-N
• Popularity: 30 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26 g/mol
• Exact Mass: 284.06847348 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.88
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Isoprunetin
• 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-5-methoxy-
• 5--O-Methylgenistein
• 7-Hydroxy-3-(4-hydroxyphenyl)-5-methoxy-4H-1-benzopyran-4-one
• DTXSID00196598
• RefChem:792268
• DTXCID40119089
• 5-O-Methylgenistein
• 7-Hydroxy-3-(4-hydroxyphenyl)-5-methoxy-4H-chromen-4-one
• 7-hydroxy-3-(4-hydroxyphenyl)-5-methoxychromen-4-one
• Q2UG76ML8U
• UNII-Q2UG76ML8U
• 4',7-Dihydroxy-5-methoxyisoflavone
• 5-methoxydaidzein
• MLS000877004
• MEGxp0_000246
• orb1683424
• SCHEMBL2146848
• CHEMBL1479463
• SCHEMBL29929580
• ACon1_000367
• HMS2270K04
• EAA56998
• HY-N9134
• LMPK12050338
• AKOS030553485
• Isoprunetin, >=95% (LC/MS-ELSD)
• NCGC00169144-01
• SMR000440622
• CS-0158830
• NS00097259
• ISOFLAVONE, 4',7-DIHYDROXY-5-METHOXY-
• Q4639636
• BRD-K92298498-001-01-1
• 7-hydroxy-3-(4-hydroxyphenyl)-5-methoxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	+	0.9145	91.45%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8722	87.22%
OATP2B1 inhibitior	+	0.5517	55.17%
OATP1B1 inhibitior	+	0.9492	94.92%
OATP1B3 inhibitior	+	0.9909	99.09%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5334	53.34%
P-glycoprotein inhibitior	-	0.7107	71.07%
P-glycoprotein substrate	-	0.8907	89.07%
CYP3A4 substrate	+	0.5392	53.92%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.6125	61.25%
CYP2C9 inhibition	+	0.9266	92.66%
CYP2C19 inhibition	+	0.9623	96.23%
CYP2D6 inhibition	-	0.7966	79.66%
CYP1A2 inhibition	+	0.9528	95.28%
CYP2C8 inhibition	+	0.7332	73.32%
CYP inhibitory promiscuity	+	0.8179	81.79%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.5611	56.11%
Eye corrosion	-	0.9792	97.92%
Eye irritation	+	0.9018	90.18%
Skin irritation	-	0.5995	59.95%
Skin corrosion	-	0.9716	97.16%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7184	71.84%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9680	96.80%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7472	74.72%
Acute Oral Toxicity (c)	III	0.7059	70.59%
Estrogen receptor binding	+	0.8853	88.53%
Androgen receptor binding	+	0.9410	94.10%
Thyroid receptor binding	+	0.7839	78.39%
Glucocorticoid receptor binding	+	0.8540	85.40%
Aromatase binding	+	0.8399	83.99%
PPAR gamma	+	0.8014	80.14%
Honey bee toxicity	-	0.8616	86.16%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5251	52.51%
Fish aquatic toxicity	+	0.8972	89.72%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.26%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.37%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.29%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.34%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.45%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.24%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	87.01%	98.35%
CHEMBL3194	P02766	Transthyretin	85.71%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.73%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.21%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.05%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.40%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.10%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.62%	99.15%

Plants that contains it

• Amaranthus spinosus
• Cistanche salsa
• Cotoneaster simonsii
• Echinospartum horridum
• Eriosema tuberosum
• Garcinia oblongifolia
• Genista corsica
• Genista ephedroides
• Genista morisii
• Heliotropium hirsutissimum
• Inulanthera calva
• Iris tingitana
• Laburnum anagyroidis
• Lupinus luteus
• Nicotiana raimondii
• Ormosia excelsa
• Ormosia monosperma
• Phaseolus coccineus
• Piper dilatatum
• Piper wightii
• Scolopia chinensis
• Trifolium pratense
• Trifolium resupinatum
• Trollius europaeus
• Ulex europaeus

Cross-Links

• PubChem: 5748551
• NPASS: NPC7013
• ChEMBL: CHEMBL1479463
• LOTUS: LTS0228387
• wikiData: Q4639636