5-Hydroxy-8-(hydroxymethyl)-2-methyl-6,9-dihydropyrano[3,2-h][1]benzoxepin-4-one

Details

• Internal ID: f66e9a7a-6c6d-4242-8822-2e1749249cff
• Taxonomy: Organoheterocyclic compounds > Benzoxepines
• IUPAC Name: 5-hydroxy-8-(hydroxymethyl)-2-methyl-6,9-dihydropyrano[3,2-h][1]benzoxepin-4-one
• SMILES (Canonical): CC1=CC(=O)C2=C(C3=C(C=C2O1)OCC(=CC3)CO)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C3=C(C=C2O1)OCC(=CC3)CO)O
• InChI: InChI=1S/C15H14O5/c1-8-4-11(17)14-13(20-8)5-12-10(15(14)18)3-2-9(6-16)7-19-12/h2,4-5,16,18H,3,6-7H2,1H3
• InChI Key: MTYPSGQGXPXUOS-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27 g/mol
• Exact Mass: 274.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.66
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 5-hydroxy-8-(hydroxymethyl)-2-methyl-6,9-dihydropyrano[3,2-h][1]benzoxepin-4-one
• 6,9-Dihydro-5-hydroxy-8-hydroxymethyl-2-methyl-4H-pyrano[3,2-h][1]benzoxepin-4-one
• CHEMBL4745291

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9702	97.02%
Caco-2	+	0.6884	68.84%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8292	82.92%
OATP2B1 inhibitior	-	0.7116	71.16%
OATP1B1 inhibitior	+	0.9262	92.62%
OATP1B3 inhibitior	+	0.9692	96.92%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.6319	63.19%
P-glycoprotein inhibitior	-	0.8767	87.67%
P-glycoprotein substrate	-	0.7561	75.61%
CYP3A4 substrate	+	0.5362	53.62%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.8189	81.89%
CYP3A4 inhibition	-	0.5673	56.73%
CYP2C9 inhibition	-	0.6459	64.59%
CYP2C19 inhibition	+	0.6761	67.61%
CYP2D6 inhibition	-	0.7120	71.20%
CYP1A2 inhibition	+	0.5269	52.69%
CYP2C8 inhibition	-	0.7651	76.51%
CYP inhibitory promiscuity	+	0.6093	60.93%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.7034	70.34%
Eye corrosion	-	0.9874	98.74%
Eye irritation	+	0.6512	65.12%
Skin irritation	-	0.7790	77.90%
Skin corrosion	-	0.9565	95.65%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5143	51.43%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.7931	79.31%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7060	70.60%
Acute Oral Toxicity (c)	III	0.3719	37.19%
Estrogen receptor binding	+	0.7704	77.04%
Androgen receptor binding	+	0.7279	72.79%
Thyroid receptor binding	-	0.6603	66.03%
Glucocorticoid receptor binding	+	0.7374	73.74%
Aromatase binding	+	0.7582	75.82%
PPAR gamma	+	0.9109	91.09%
Honey bee toxicity	-	0.9006	90.06%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9800	98.00%

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	98.65%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	96.46%	94.73%
CHEMBL2581	P07339	Cathepsin D	96.15%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.15%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.16%	89.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.39%	89.34%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.94%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.73%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.50%	90.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.39%	93.99%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.79%	93.65%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.16%	99.23%

Plants that contains it

• Cedrelopsis grevei

Cross-Links

• PubChem: 12314734
• LOTUS: LTS0260377
• wikiData: Q104399994