4-Hydroxy-5-(1-hydroxyethyl)-3-(3-methylbut-2-enyl)chromen-2-one

Details

• Internal ID: 836749aa-1e6d-4952-9814-aba946256faa
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 4-hydroxycoumarins
• IUPAC Name: 4-hydroxy-5-(1-hydroxyethyl)-3-(3-methylbut-2-enyl)chromen-2-one
• SMILES (Canonical): CC(C1=C2C(=CC=C1)OC(=O)C(=C2O)CC=C(C)C)O
• SMILES (Isomeric): CC(C1=C2C(=CC=C1)OC(=O)C(=C2O)CC=C(C)C)O
• InChI: InChI=1S/C16H18O4/c1-9(2)7-8-12-15(18)14-11(10(3)17)5-4-6-13(14)20-16(12)19/h4-7,10,17-18H,8H2,1-3H3
• InChI Key: RWUSHQFMUNEPEY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.31 g/mol
• Exact Mass: 274.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.06
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	+	0.7563	75.63%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7686	76.86%
OATP2B1 inhibitior	-	0.7122	71.22%
OATP1B1 inhibitior	+	0.8460	84.60%
OATP1B3 inhibitior	+	0.9040	90.40%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5705	57.05%
P-glycoprotein inhibitior	-	0.7555	75.55%
P-glycoprotein substrate	-	0.8165	81.65%
CYP3A4 substrate	-	0.5129	51.29%
CYP2C9 substrate	+	0.6673	66.73%
CYP2D6 substrate	-	0.8532	85.32%
CYP3A4 inhibition	-	0.9006	90.06%
CYP2C9 inhibition	+	0.8109	81.09%
CYP2C19 inhibition	+	0.7861	78.61%
CYP2D6 inhibition	-	0.7723	77.23%
CYP1A2 inhibition	+	0.7138	71.38%
CYP2C8 inhibition	-	0.9233	92.33%
CYP inhibitory promiscuity	+	0.7363	73.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6396	63.96%
Eye corrosion	-	0.9918	99.18%
Eye irritation	+	0.5296	52.96%
Skin irritation	-	0.6909	69.09%
Skin corrosion	-	0.9580	95.80%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8267	82.67%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5300	53.00%
skin sensitisation	-	0.7017	70.17%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8205	82.05%
Acute Oral Toxicity (c)	III	0.6387	63.87%
Estrogen receptor binding	+	0.7101	71.01%
Androgen receptor binding	-	0.5194	51.94%
Thyroid receptor binding	-	0.5297	52.97%
Glucocorticoid receptor binding	+	0.8603	86.03%
Aromatase binding	+	0.6087	60.87%
PPAR gamma	+	0.8969	89.69%
Honey bee toxicity	-	0.8886	88.86%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.60%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.46%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	97.85%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.20%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.58%	89.34%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.21%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.58%	89.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	87.95%	83.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.63%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.19%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.67%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.61%	99.23%

Plants that contains it

• Bothriocline longipes

Cross-Links

• PubChem: 163019636
• LOTUS: LTS0177147
• wikiData: Q105246768