3,4-Dihydroxy-6-methoxy-7-(3-methylbut-2-enoxy)chromen-2-one

Details

• Internal ID: ecacfe63-403d-4e55-bff1-ca260b98a1cf
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 4-hydroxycoumarins
• IUPAC Name: 3,4-dihydroxy-6-methoxy-7-(3-methylbut-2-enoxy)chromen-2-one
• SMILES (Canonical): CC(=CCOC1=C(C=C2C(=C1)OC(=O)C(=C2O)O)OC)C
• SMILES (Isomeric): CC(=CCOC1=C(C=C2C(=C1)OC(=O)C(=C2O)O)OC)C
• InChI: InChI=1S/C15H16O6/c1-8(2)4-5-20-12-7-10-9(6-11(12)19-3)13(16)14(17)15(18)21-10/h4,6-7,16-17H,5H2,1-3H3
• InChI Key: CIYCRWXVDIOYTL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₆
• Molecular Weight: 292.28 g/mol
• Exact Mass: 292.09468823 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9599	95.99%
Caco-2	+	0.5921	59.21%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7461	74.61%
OATP2B1 inhibitior	-	0.5742	57.42%
OATP1B1 inhibitior	+	0.9075	90.75%
OATP1B3 inhibitior	+	0.8566	85.66%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7022	70.22%
P-glycoprotein substrate	-	0.6766	67.66%
CYP3A4 substrate	+	0.5216	52.16%
CYP2C9 substrate	-	0.5736	57.36%
CYP2D6 substrate	-	0.8725	87.25%
CYP3A4 inhibition	-	0.8903	89.03%
CYP2C9 inhibition	+	0.5224	52.24%
CYP2C19 inhibition	+	0.8138	81.38%
CYP2D6 inhibition	-	0.6164	61.64%
CYP1A2 inhibition	+	0.8610	86.10%
CYP2C8 inhibition	-	0.7023	70.23%
CYP inhibitory promiscuity	+	0.6305	63.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7409	74.09%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.5678	56.78%
Skin irritation	-	0.7847	78.47%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6547	65.47%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8007	80.07%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8273	82.73%
Acute Oral Toxicity (c)	III	0.7295	72.95%
Estrogen receptor binding	+	0.9101	91.01%
Androgen receptor binding	+	0.5960	59.60%
Thyroid receptor binding	+	0.5665	56.65%
Glucocorticoid receptor binding	+	0.8294	82.94%
Aromatase binding	+	0.8314	83.14%
PPAR gamma	+	0.8995	89.95%
Honey bee toxicity	-	0.8722	87.22%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9913	99.13%

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	98.73%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.26%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.84%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.30%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.98%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.45%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.66%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.32%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	87.97%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.43%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.19%	95.56%
CHEMBL2535	P11166	Glucose transporter	81.95%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.51%	92.94%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.24%	92.38%

Plants that contains it

• Nepenthes rafflesiana
• Pterocaulon polystachyum

Cross-Links

• PubChem: 162868576
• LOTUS: LTS0173358
• wikiData: Q105195578