1-[5-Hydroxy-2-(hydroxymethyl)-2-methyl-chromen-6-yl]ethanone

Details

• Internal ID: 485fd22d-5efd-45c2-8c9f-8ec6d3673b19
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans
• IUPAC Name: 1-[5-hydroxy-2-(hydroxymethyl)-2-methylchromen-6-yl]ethanone
• SMILES (Canonical): CC(=O)C1=C(C2=C(C=C1)OC(C=C2)(C)CO)O
• SMILES (Isomeric): CC(=O)C1=C(C2=C(C=C1)OC(C=C2)(C)CO)O
• InChI: InChI=1S/C13H14O4/c1-8(15)9-3-4-11-10(12(9)16)5-6-13(2,7-14)17-11/h3-6,14,16H,7H2,1-2H3
• InChI Key: JKVQMJIPYGVPFF-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.25 g/mol
• Exact Mass: 234.08920892 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.75
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 1-[5-hydroxy-2-(hydroxymethyl)-2-methyl-chromen-6-yl]ethanone
• Ethanone, 1-[5-hydroxy-2-(hydroxymethyl)-2-methyl-2H-1-benzopyran-6-yl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9773	97.73%
Caco-2	+	0.7132	71.32%
Blood Brain Barrier	-	0.6395	63.95%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7126	71.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8605	86.05%
OATP1B3 inhibitior	+	0.9565	95.65%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5700	57.00%
P-glycoprotein inhibitior	-	0.9713	97.13%
P-glycoprotein substrate	-	0.8061	80.61%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.8034	80.34%
CYP2D6 substrate	-	0.8364	83.64%
CYP3A4 inhibition	-	0.5866	58.66%
CYP2C9 inhibition	-	0.6974	69.74%
CYP2C19 inhibition	-	0.5484	54.84%
CYP2D6 inhibition	-	0.8352	83.52%
CYP1A2 inhibition	+	0.7369	73.69%
CYP2C8 inhibition	-	0.7274	72.74%
CYP inhibitory promiscuity	+	0.5329	53.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6320	63.20%
Eye corrosion	-	0.9864	98.64%
Eye irritation	+	0.7707	77.07%
Skin irritation	-	0.7516	75.16%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7364	73.64%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.6069	60.69%
skin sensitisation	-	0.6514	65.14%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6404	64.04%
Acute Oral Toxicity (c)	III	0.5039	50.39%
Estrogen receptor binding	+	0.6889	68.89%
Androgen receptor binding	-	0.5406	54.06%
Thyroid receptor binding	-	0.5203	52.03%
Glucocorticoid receptor binding	+	0.7257	72.57%
Aromatase binding	-	0.4941	49.41%
PPAR gamma	+	0.7332	73.32%
Honey bee toxicity	-	0.9406	94.06%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.8477	84.77%

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	98.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.54%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.60%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.35%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.34%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.69%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	85.80%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.91%	85.14%
CHEMBL4208	P20618	Proteasome component C5	81.40%	90.00%

Plants that contains it

• Heisteria nitida
• Leucoblepharis subsessilis

Cross-Links

• PubChem: 3009663
• LOTUS: LTS0233270
• wikiData: Q105248689