[(4S,4aR,5S)-3,4a,5-trimethyl-9-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-4-yl] acetate

Details

• Internal ID: dea332b7-4628-4ed3-964b-0e1d16749b2d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4S,4aR,5S)-3,4a,5-trimethyl-9-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-4-yl] acetate
• SMILES (Canonical): CC1CCC=C2C1(C(C3=C(C2=O)OC=C3C)OC(=O)C)C
• SMILES (Isomeric): C[C@H]1CCC=C2[C@@]1([C@@H](C3=C(C2=O)OC=C3C)OC(=O)C)C
• InChI: InChI=1S/C17H20O4/c1-9-8-20-15-13(9)16(21-11(3)18)17(4)10(2)6-5-7-12(17)14(15)19/h7-8,10,16H,5-6H2,1-4H3/t10-,16+,17+/m0/s1
• InChI Key: FAZNZOQAEBFDJI-LZVXQISVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₄
• Molecular Weight: 288.34 g/mol
• Exact Mass: 288.13615911 g/mol
• Topological Polar Surface Area (TPSA): 56.50 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.75
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.7853	78.53%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6879	68.79%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.9102	91.02%
OATP1B3 inhibitior	+	0.8615	86.15%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8325	83.25%
P-glycoprotein inhibitior	-	0.7629	76.29%
P-glycoprotein substrate	-	0.8139	81.39%
CYP3A4 substrate	+	0.6222	62.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8906	89.06%
CYP3A4 inhibition	-	0.6217	62.17%
CYP2C9 inhibition	-	0.6105	61.05%
CYP2C19 inhibition	-	0.7052	70.52%
CYP2D6 inhibition	-	0.8633	86.33%
CYP1A2 inhibition	+	0.8637	86.37%
CYP2C8 inhibition	-	0.6228	62.28%
CYP inhibitory promiscuity	+	0.5931	59.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4325	43.25%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9256	92.56%
Skin irritation	-	0.6003	60.03%
Skin corrosion	-	0.8972	89.72%
Ames mutagenesis	-	0.5470	54.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4800	48.00%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5157	51.57%
skin sensitisation	-	0.7487	74.87%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4827	48.27%
Acute Oral Toxicity (c)	III	0.4648	46.48%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.6122	61.22%
Thyroid receptor binding	-	0.5434	54.34%
Glucocorticoid receptor binding	+	0.5666	56.66%
Aromatase binding	+	0.5198	51.98%
PPAR gamma	+	0.6019	60.19%
Honey bee toxicity	-	0.8597	85.97%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9972	99.72%

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	95.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.54%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.12%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.73%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.18%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.19%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.11%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.08%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.96%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	84.93%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.19%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	82.64%	92.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.91%	93.04%

Plants that contains it

• Psacalium radulifolium

Cross-Links

• PubChem: 15558791
• LOTUS: LTS0145351
• wikiData: Q104992512