Isofraxetin

Details

• Internal ID: 02e5d988-476c-4305-8c8d-f1b73b48b5e6
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins
• IUPAC Name: 5,6-dihydroxy-7-methoxychromen-2-one
• SMILES (Canonical): COC1=C(C(=C2C=CC(=O)OC2=C1)O)O
• SMILES (Isomeric): COC1=C(C(=C2C=CC(=O)OC2=C1)O)O
• InChI: InChI=1S/C10H8O5/c1-14-7-4-6-5(9(12)10(7)13)2-3-8(11)15-6/h2-4,12-13H,1H3
• InChI Key: ICFLIFNKWPXOAM-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₈O₅
• Molecular Weight: 208.17 g/mol
• Exact Mass: 208.03717335 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.21
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 50656-75-2
• AC41B525YC
• 5,6-Dihydroxy-7-methoxy-2H-chromen-2-one
• 2H-1-Benzopyran-2-one, 5,6-dihydroxy-7-methoxy-
• UNII-AC41B525YC
• CHEMBL3894520
• 5,6-dihydroxy-7-methoxycoumarin
• Q27273858

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9099	90.99%
Caco-2	+	0.5289	52.89%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7038	70.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8850	88.50%
OATP1B3 inhibitior	+	0.9900	99.00%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8339	83.39%
P-glycoprotein inhibitior	-	0.9052	90.52%
P-glycoprotein substrate	-	0.7881	78.81%
CYP3A4 substrate	-	0.5782	57.82%
CYP2C9 substrate	-	0.8321	83.21%
CYP2D6 substrate	-	0.8219	82.19%
CYP3A4 inhibition	-	0.8829	88.29%
CYP2C9 inhibition	-	0.9518	95.18%
CYP2C19 inhibition	-	0.8196	81.96%
CYP2D6 inhibition	-	0.9321	93.21%
CYP1A2 inhibition	+	0.9101	91.01%
CYP2C8 inhibition	-	0.6998	69.98%
CYP inhibitory promiscuity	-	0.7452	74.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5729	57.29%
Eye corrosion	-	0.9656	96.56%
Eye irritation	+	0.9397	93.97%
Skin irritation	-	0.5679	56.79%
Skin corrosion	-	0.9552	95.52%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8610	86.10%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9199	91.99%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8202	82.02%
Acute Oral Toxicity (c)	III	0.6874	68.74%
Estrogen receptor binding	+	0.8205	82.05%
Androgen receptor binding	+	0.7837	78.37%
Thyroid receptor binding	-	0.7264	72.64%
Glucocorticoid receptor binding	+	0.7700	77.00%
Aromatase binding	+	0.7060	70.60%
PPAR gamma	+	0.5944	59.44%
Honey bee toxicity	-	0.9342	93.42%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	+	0.9129	91.29%

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	98.72%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.79%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.80%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.02%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.85%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.45%	89.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.48%	94.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.65%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.91%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.01%	90.71%
CHEMBL2535	P11166	Glucose transporter	80.81%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.46%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.27%	99.17%

Plants that contains it

• Haplophyllum obtusifolium
• Rhamnus disperma

Cross-Links

• PubChem: 10104491
• LOTUS: LTS0069346
• wikiData: Q27273858