(4aR,5S,8aS)-3,4a,5-trimethyl-6,7,8,8a-tetrahydro-5H-benzo[f][1]benzofuran-4,9-dione

Details

• Internal ID: 884cbf2d-9ee8-4f80-8d68-641798d82622
• 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-6,7,8,8a-tetrahydro-5H-benzo[f][1]benzofuran-4,9-dione
• SMILES (Canonical): CC1CCCC2C1(C(=O)C3=C(C2=O)OC=C3C)C
• SMILES (Isomeric): C[C@H]1CCC[C@H]2[C@@]1(C(=O)C3=C(C2=O)OC=C3C)C
• InChI: InChI=1S/C15H18O3/c1-8-7-18-13-11(8)14(17)15(3)9(2)5-4-6-10(15)12(13)16/h7,9-10H,4-6H2,1-3H3/t9-,10+,15+/m0/s1
• InChI Key: PFHAKEGRVGAZEC-FEUHOPSXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 47.30 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.8305	83.05%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6631	66.31%
OATP2B1 inhibitior	-	0.8522	85.22%
OATP1B1 inhibitior	+	0.8880	88.80%
OATP1B3 inhibitior	+	0.9731	97.31%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8715	87.15%
P-glycoprotein inhibitior	-	0.8799	87.99%
P-glycoprotein substrate	-	0.9399	93.99%
CYP3A4 substrate	+	0.5740	57.40%
CYP2C9 substrate	+	0.6012	60.12%
CYP2D6 substrate	-	0.8275	82.75%
CYP3A4 inhibition	-	0.9288	92.88%
CYP2C9 inhibition	-	0.7113	71.13%
CYP2C19 inhibition	-	0.7559	75.59%
CYP2D6 inhibition	-	0.9416	94.16%
CYP1A2 inhibition	+	0.7197	71.97%
CYP2C8 inhibition	-	0.8383	83.83%
CYP inhibitory promiscuity	-	0.8081	80.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5063	50.63%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.9388	93.88%
Skin irritation	-	0.5905	59.05%
Skin corrosion	-	0.8169	81.69%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6205	62.05%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.6856	68.56%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6160	61.60%
Acute Oral Toxicity (c)	III	0.5041	50.41%
Estrogen receptor binding	+	0.6017	60.17%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5200	52.00%
Glucocorticoid receptor binding	+	0.5619	56.19%
Aromatase binding	-	0.6701	67.01%
PPAR gamma	+	0.6834	68.34%
Honey bee toxicity	-	0.9262	92.62%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9787	97.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.90%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.18%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.14%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.97%	91.11%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.62%	96.21%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	89.23%	86.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.19%	93.04%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.67%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.28%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.34%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.75%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.16%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.67%	99.23%

Plants that contains it

• Senecio lanceus

Cross-Links

• PubChem: 101281702
• LOTUS: LTS0135356
• wikiData: Q105207737