(4aR,8aR)-9a-hydroxy-6,9,9-trimethyl-4a,7,8,8a-tetrahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: e28532ee-b337-451c-84e6-601e2b722e16
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (4aR,8aR)-9a-hydroxy-6,9,9-trimethyl-4a,7,8,8a-tetrahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=CC2CC3=CC(=O)OC3(C(C2CC1)(C)C)O
• SMILES (Isomeric): CC1=C[C@H]2CC3=CC(=O)OC3(C([C@@H]2CC1)(C)C)O
• InChI: InChI=1S/C15H20O3/c1-9-4-5-12-10(6-9)7-11-8-13(16)18-15(11,17)14(12,2)3/h6,8,10,12,17H,4-5,7H2,1-3H3/t10-,12+,15?/m0/s1
• InChI Key: DKCBQKUYOUNXGH-QFZKOWMDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.6948	69.48%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7403	74.03%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.8982	89.82%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.8619	86.19%
P-glycoprotein inhibitior	-	0.9472	94.72%
P-glycoprotein substrate	-	0.8437	84.37%
CYP3A4 substrate	+	0.6064	60.64%
CYP2C9 substrate	-	0.8226	82.26%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.7163	71.63%
CYP2C9 inhibition	-	0.6748	67.48%
CYP2C19 inhibition	-	0.6211	62.11%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	+	0.5852	58.52%
CYP2C8 inhibition	-	0.7406	74.06%
CYP inhibitory promiscuity	-	0.7396	73.96%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5028	50.28%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9707	97.07%
Skin irritation	+	0.5485	54.85%
Skin corrosion	-	0.9302	93.02%
Ames mutagenesis	-	0.5834	58.34%
Human Ether-a-go-go-Related Gene inhibition	-	0.4828	48.28%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6283	62.83%
skin sensitisation	-	0.6121	61.21%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5122	51.22%
Estrogen receptor binding	+	0.6868	68.68%
Androgen receptor binding	+	0.6996	69.96%
Thyroid receptor binding	-	0.6604	66.04%
Glucocorticoid receptor binding	+	0.5927	59.27%
Aromatase binding	-	0.5703	57.03%
PPAR gamma	+	0.6396	63.96%
Honey bee toxicity	-	0.8850	88.50%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	96.02%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.72%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.88%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.18%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.11%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.09%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.78%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.01%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.18%	97.09%
CHEMBL1871	P10275	Androgen Receptor	82.35%	96.43%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.95%	86.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.57%	95.89%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163186302
• LOTUS: LTS0222582
• wikiData: Q104983009