(4aR,5S,8aS)-3,4a,5-trimethyl-4,5,6,7,8a,9-hexahydrobenzo[f][1]benzofuran-8-one

Details

• Internal ID: 1c2830b6-4a36-4c0f-9542-4b1c88963c00
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4aR,5S,8aS)-3,4a,5-trimethyl-4,5,6,7,8a,9-hexahydrobenzo[f][1]benzofuran-8-one
• SMILES (Canonical): CC1CCC(=O)C2C1(CC3=C(C2)OC=C3C)C
• SMILES (Isomeric): C[C@H]1CCC(=O)[C@@H]2[C@@]1(CC3=C(C2)OC=C3C)C
• InChI: InChI=1S/C15H20O2/c1-9-8-17-14-6-12-13(16)5-4-10(2)15(12,3)7-11(9)14/h8,10,12H,4-7H2,1-3H3/t10-,12+,15+/m0/s1
• InChI Key: MHEQQQWHNMVBFL-JVLSTEMRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 30.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• DTXSID401131678
• NSC-317298
• 52061-43-5
• (4aR,5S,8aS)-4a,5,6,7,8a,9-Hexahydro-3,4a,5-trimethylnaphtho[2,3-b]furan-8(4H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8387	83.87%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5782	57.82%
OATP2B1 inhibitior	-	0.8482	84.82%
OATP1B1 inhibitior	+	0.9275	92.75%
OATP1B3 inhibitior	+	0.9770	97.70%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.8076	80.76%
P-glycoprotein inhibitior	-	0.9271	92.71%
P-glycoprotein substrate	-	0.8968	89.68%
CYP3A4 substrate	+	0.5591	55.91%
CYP2C9 substrate	-	0.5652	56.52%
CYP2D6 substrate	-	0.7276	72.76%
CYP3A4 inhibition	-	0.7649	76.49%
CYP2C9 inhibition	-	0.8047	80.47%
CYP2C19 inhibition	+	0.5313	53.13%
CYP2D6 inhibition	-	0.9406	94.06%
CYP1A2 inhibition	+	0.5080	50.80%
CYP2C8 inhibition	-	0.8990	89.90%
CYP inhibitory promiscuity	-	0.8292	82.92%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5069	50.69%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.8197	81.97%
Skin irritation	-	0.5631	56.31%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.6530	65.30%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6643	66.43%
Acute Oral Toxicity (c)	III	0.6728	67.28%
Estrogen receptor binding	-	0.7401	74.01%
Androgen receptor binding	+	0.5921	59.21%
Thyroid receptor binding	-	0.6382	63.82%
Glucocorticoid receptor binding	-	0.6577	65.77%
Aromatase binding	-	0.6499	64.99%
PPAR gamma	+	0.6479	64.79%
Honey bee toxicity	-	0.8065	80.65%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9754	97.54%

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	93.15%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.25%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.40%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.34%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.28%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.87%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.71%	93.04%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.17%	86.00%
CHEMBL1902	P62942	FK506-binding protein 1A	82.97%	97.05%
CHEMBL1871	P10275	Androgen Receptor	81.76%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.19%	99.23%

Plants that contains it

• Smyrnium olusatrum

Cross-Links

• PubChem: 330229
• LOTUS: LTS0006070
• wikiData: Q105163764