(7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one

Details

• Internal ID: ce5e8c6c-34e3-41ba-a095-50e853de29a7
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one
• SMILES (Canonical): CC1(CC(CC2(C1=CC(=O)O2)C)O)C
• SMILES (Isomeric): C[C@@]12CC(CC(C1=CC(=O)O2)(C)C)O
• InChI: InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7?,11-/m1/s1
• InChI Key: XEVQXKKKAVVSMW-PLNQYNMKSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.24 g/mol
• Exact Mass: 196.109944368 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.41
• 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	+	0.8458	84.58%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5919	59.19%
OATP2B1 inhibitior	-	0.8471	84.71%
OATP1B1 inhibitior	+	0.8863	88.63%
OATP1B3 inhibitior	+	0.9607	96.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.8774	87.74%
P-glycoprotein inhibitior	-	0.9542	95.42%
P-glycoprotein substrate	-	0.9266	92.66%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.8948	89.48%
CYP2C9 inhibition	-	0.8445	84.45%
CYP2C19 inhibition	-	0.8350	83.50%
CYP2D6 inhibition	-	0.9524	95.24%
CYP1A2 inhibition	-	0.8085	80.85%
CYP2C8 inhibition	-	0.9418	94.18%
CYP inhibitory promiscuity	-	0.9087	90.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8919	89.19%
Carcinogenicity (trinary)	Non-required	0.4317	43.17%
Eye corrosion	-	0.9630	96.30%
Eye irritation	+	0.6442	64.42%
Skin irritation	-	0.5170	51.70%
Skin corrosion	-	0.9124	91.24%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8336	83.36%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5092	50.92%
skin sensitisation	+	0.5289	52.89%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5129	51.29%
Acute Oral Toxicity (c)	III	0.5326	53.26%
Estrogen receptor binding	-	0.8706	87.06%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.7715	77.15%
Glucocorticoid receptor binding	-	0.7617	76.17%
Aromatase binding	-	0.7408	74.08%
PPAR gamma	-	0.7834	78.34%
Honey bee toxicity	-	0.9079	90.79%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8964	89.64%

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	97.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.85%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.76%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.37%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.72%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.98%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.69%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.23%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.43%	99.23%

Plants that contains it

• Calendula officinalis
• Capsicum annuum
• Dendrobium chrysanthum
• Dendrobium chrysotoxum
• Dendrobium fimbriatum
• Dendrobium loddigesii
• Dendrobium moniliforme
• Dendrobium nobile
• Equisetum arvense
• Gentiana pedicellata
• Morus alba
• Morus indica
• Triadica sebifera
• Viburnum dilatatum
• Viola mandshurica
• Viola philippica
• Viscum album
• Viscum coloratum
• Zanthoxylum setulosum

Cross-Links

• PubChem: 12311356
• NPASS: NPC110373
• LOTUS: LTS0273073
• wikiData: Q104254215