[(3aS,8aR,9R,9aR)-5-methyl-1,8-dimethylidene-2-oxo-4,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-9-yl] acetate

Details

• Internal ID: 132a39e8-879f-4dca-8c55-aa18f81979da
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aS,8aR,9R,9aR)-5-methyl-1,8-dimethylidene-2-oxo-4,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-9-yl] acetate
• SMILES (Canonical): CC1=C2CCC(=C)C2C(C3C(C1)OC(=O)C3=C)OC(=O)C
• SMILES (Isomeric): CC1=C2CCC(=C)[C@H]2[C@H]([C@H]3[C@H](C1)OC(=O)C3=C)OC(=O)C
• InChI: InChI=1S/C17H20O4/c1-8-5-6-12-9(2)7-13-15(10(3)17(19)21-13)16(14(8)12)20-11(4)18/h13-16H,1,3,5-7H2,2,4H3/t13-,14+,15+,16+/m0/s1
• InChI Key: MAOQLCPOSIMTNI-ZJIFWQFVSA-N
• Popularity: 0 references 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): 52.60 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.70
• 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	+	0.9905	99.05%
Caco-2	+	0.7486	74.86%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6115	61.15%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.9034	90.34%
OATP1B3 inhibitior	+	0.8689	86.89%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8899	88.99%
P-glycoprotein inhibitior	-	0.7451	74.51%
P-glycoprotein substrate	-	0.8779	87.79%
CYP3A4 substrate	+	0.5875	58.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8884	88.84%
CYP3A4 inhibition	-	0.7248	72.48%
CYP2C9 inhibition	-	0.8248	82.48%
CYP2C19 inhibition	-	0.7847	78.47%
CYP2D6 inhibition	-	0.9320	93.20%
CYP1A2 inhibition	+	0.7480	74.80%
CYP2C8 inhibition	-	0.7799	77.99%
CYP inhibitory promiscuity	-	0.8961	89.61%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6584	65.84%
Eye corrosion	-	0.9445	94.45%
Eye irritation	-	0.4781	47.81%
Skin irritation	-	0.5551	55.51%
Skin corrosion	-	0.9127	91.27%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7097	70.97%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.8283	82.83%
skin sensitisation	-	0.7796	77.96%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.8551	85.51%
Acute Oral Toxicity (c)	III	0.4287	42.87%
Estrogen receptor binding	-	0.6311	63.11%
Androgen receptor binding	+	0.5308	53.08%
Thyroid receptor binding	-	0.5602	56.02%
Glucocorticoid receptor binding	+	0.5611	56.11%
Aromatase binding	-	0.8423	84.23%
PPAR gamma	-	0.5704	57.04%
Honey bee toxicity	-	0.7768	77.68%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9960	99.60%

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	94.07%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.01%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.84%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.26%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.71%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	84.88%	97.79%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.64%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.60%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.26%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.79%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.38%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	80.29%	91.19%

Plants that contains it

• Brocchia cinerea

Cross-Links

• PubChem: 162817312
• LOTUS: LTS0210710
• wikiData: Q105160457