(1,5,8-trimethyl-2-oxo-4,5,5a,6,7,9a-hexahydro-3aH-benzo[e][1]benzofuran-7-yl) acetate

Details

• Internal ID: 666fa6f6-150e-486d-95de-4cdcab9f26da
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (1,5,8-trimethyl-2-oxo-4,5,5a,6,7,9a-hexahydro-3aH-benzo[e][1]benzofuran-7-yl) acetate
• SMILES (Canonical): CC1CC2C(=C(C(=O)O2)C)C3C1CC(C(=C3)C)OC(=O)C
• SMILES (Isomeric): CC1CC2C(=C(C(=O)O2)C)C3C1CC(C(=C3)C)OC(=O)C
• InChI: InChI=1S/C17H22O4/c1-8-6-15-16(10(3)17(19)21-15)13-5-9(2)14(7-12(8)13)20-11(4)18/h5,8,12-15H,6-7H2,1-4H3
• InChI Key: ARFAWNXJYKFWKI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.40 g/mol
• Exact Mass: 290.15180918 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.78
• 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	+	0.9968	99.68%
Caco-2	+	0.8697	86.97%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6439	64.39%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.9180	91.80%
OATP1B3 inhibitior	+	0.9239	92.39%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6825	68.25%
P-glycoprotein inhibitior	-	0.7371	73.71%
P-glycoprotein substrate	-	0.7498	74.98%
CYP3A4 substrate	+	0.5968	59.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9086	90.86%
CYP3A4 inhibition	-	0.5358	53.58%
CYP2C9 inhibition	-	0.8350	83.50%
CYP2C19 inhibition	-	0.8361	83.61%
CYP2D6 inhibition	-	0.9403	94.03%
CYP1A2 inhibition	-	0.5297	52.97%
CYP2C8 inhibition	-	0.7625	76.25%
CYP inhibitory promiscuity	-	0.6085	60.85%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4818	48.18%
Eye corrosion	-	0.9779	97.79%
Eye irritation	-	0.8203	82.03%
Skin irritation	-	0.6038	60.38%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3848	38.48%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.7869	78.69%
skin sensitisation	-	0.7217	72.17%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6203	62.03%
Acute Oral Toxicity (c)	III	0.6654	66.54%
Estrogen receptor binding	+	0.5965	59.65%
Androgen receptor binding	+	0.5525	55.25%
Thyroid receptor binding	-	0.5375	53.75%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6649	66.49%
PPAR gamma	-	0.6192	61.92%
Honey bee toxicity	-	0.8074	80.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9969	99.69%

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	94.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.64%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.58%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.70%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.20%	95.56%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.16%	81.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.56%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.04%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.58%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.51%	85.14%

Plants that contains it

• Ageratina adenophora
• Artemisia annua
• Artemisia capillaris

Cross-Links

• PubChem: 5317292
• NPASS: NPC302208
• LOTUS: LTS0079670
• wikiData: Q104917271