6-(1-Hydroxy-3-oxobutyl)-7-methoxycoumarin

Details

• Internal ID: 287ca68a-d2a6-45d3-8c67-f2d64f730f71
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 6-(1-hydroxy-3-oxobutyl)-7-methoxychromen-2-one
• SMILES (Canonical): CC(=O)CC(C1=C(C=C2C(=C1)C=CC(=O)O2)OC)O
• SMILES (Isomeric): CC(=O)CC(C1=C(C=C2C(=C1)C=CC(=O)O2)OC)O
• InChI: InChI=1S/C14H14O5/c1-8(15)5-11(16)10-6-9-3-4-14(17)19-12(9)7-13(10)18-2/h3-4,6-7,11,16H,5H2,1-2H3
• InChI Key: IKTQFLXJWYKGDA-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.26 g/mol
• Exact Mass: 262.08412354 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.81
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 6-(1-hydroxy-3-oxobutyl)-7-methoxycoumarin
• 6-(1-hydroxy-3-oxobutyl)-7-methoxychromen-2-one
• 6-(1-hydroxy-3-oxobutyl)-7-methoxy-2H-chromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9670	96.70%
Caco-2	+	0.5711	57.11%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6490	64.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9267	92.67%
OATP1B3 inhibitior	+	0.9596	95.96%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5626	56.26%
P-glycoprotein inhibitior	-	0.8566	85.66%
P-glycoprotein substrate	-	0.6679	66.79%
CYP3A4 substrate	-	0.5580	55.80%
CYP2C9 substrate	-	0.7938	79.38%
CYP2D6 substrate	-	0.8002	80.02%
CYP3A4 inhibition	-	0.8782	87.82%
CYP2C9 inhibition	-	0.8307	83.07%
CYP2C19 inhibition	-	0.9173	91.73%
CYP2D6 inhibition	-	0.8605	86.05%
CYP1A2 inhibition	+	0.5118	51.18%
CYP2C8 inhibition	-	0.8390	83.90%
CYP inhibitory promiscuity	-	0.8804	88.04%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6520	65.20%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.7725	77.25%
Skin irritation	-	0.8142	81.42%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7423	74.23%
Micronuclear	+	0.7259	72.59%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9315	93.15%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.3922	39.22%
Estrogen receptor binding	+	0.6438	64.38%
Androgen receptor binding	-	0.4933	49.33%
Thyroid receptor binding	-	0.7340	73.40%
Glucocorticoid receptor binding	+	0.5765	57.65%
Aromatase binding	-	0.5586	55.86%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9205	92.05%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9370	93.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.43%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.94%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.33%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.14%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.11%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.10%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.90%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.43%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.22%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	83.50%	90.20%

Plants that contains it

• Citrus maxima

Cross-Links

• PubChem: 101664569
• LOTUS: LTS0026112
• wikiData: Q105114931