4-Methoxy-9-[[(Z)-3-(hydroxymethyl)-2-butenyl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one

Details

• Internal ID: 8ee48dfb-cbf8-4299-b624-6cde4e823ffc
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens > 5-methoxypsoralens
• IUPAC Name: 9-[(Z)-4-hydroxy-3-methylbut-2-enoxy]-4-methoxyfuro[3,2-g]chromen-7-one
• SMILES (Canonical): CC(=CCOC1=C2C(=C(C3=C1OC(=O)C=C3)OC)C=CO2)CO
• SMILES (Isomeric): C/C(=C/COC1=C2C(=C(C3=C1OC(=O)C=C3)OC)C=CO2)/CO
• InChI: InChI=1S/C17H16O6/c1-10(9-18)5-7-22-17-15-12(6-8-21-15)14(20-2)11-3-4-13(19)23-16(11)17/h3-6,8,18H,7,9H2,1-2H3/b10-5-
• InChI Key: KMKUKYQGOPARRG-YHYXMXQVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₆
• Molecular Weight: 316.30 g/mol
• Exact Mass: 316.09468823 g/mol
• Topological Polar Surface Area (TPSA): 78.10 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9630	96.30%
Caco-2	+	0.6277	62.77%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6710	67.10%
OATP2B1 inhibitior	-	0.7247	72.47%
OATP1B1 inhibitior	+	0.9258	92.58%
OATP1B3 inhibitior	+	0.9075	90.75%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6666	66.66%
P-glycoprotein inhibitior	-	0.4610	46.10%
P-glycoprotein substrate	-	0.7738	77.38%
CYP3A4 substrate	+	0.5277	52.77%
CYP2C9 substrate	-	0.6755	67.55%
CYP2D6 substrate	-	0.8357	83.57%
CYP3A4 inhibition	+	0.6152	61.52%
CYP2C9 inhibition	-	0.6886	68.86%
CYP2C19 inhibition	+	0.6234	62.34%
CYP2D6 inhibition	-	0.6056	60.56%
CYP1A2 inhibition	-	0.6629	66.29%
CYP2C8 inhibition	+	0.4667	46.67%
CYP inhibitory promiscuity	+	0.7244	72.44%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5394	53.94%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.7629	76.29%
Skin irritation	-	0.7557	75.57%
Skin corrosion	-	0.9566	95.66%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7767	77.67%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.7671	76.71%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8012	80.12%
Acute Oral Toxicity (c)	III	0.4306	43.06%
Estrogen receptor binding	+	0.8064	80.64%
Androgen receptor binding	+	0.6986	69.86%
Thyroid receptor binding	-	0.5071	50.71%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.7274	72.74%
PPAR gamma	+	0.8432	84.32%
Honey bee toxicity	-	0.8801	88.01%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9863	98.63%

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	96.98%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.85%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.64%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.66%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.89%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.39%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.04%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.28%	89.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.25%	94.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.16%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.55%	93.99%
CHEMBL1951	P21397	Monoamine oxidase A	80.29%	91.49%

Plants that contains it

• Casimiroa tetrameria
• Kopsia profunda
• Tropaeolum majus

Cross-Links

• PubChem: 102465417
• NPASS: NPC105984
• LOTUS: LTS0183125
• wikiData: Q105143011