(4-acetyloxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-8-yl) acetate

Details

• Internal ID: c38382f5-9c08-41e9-8606-8d7f39cf4974
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (4-acetyloxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-8-yl) acetate
• SMILES (Canonical): CC1C2C(CC(=C)C3CC(C(=C)C3C2OC1=O)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC1C2C(CC(=C)C3CC(C(=C)C3C2OC1=O)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C19H24O6/c1-8-6-15(24-12(5)21)17-10(3)19(22)25-18(17)16-9(2)14(7-13(8)16)23-11(4)20/h10,13-18H,1-2,6-7H2,3-5H3
• InChI Key: YQAAKILPZPSNKX-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.18
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	+	0.5741	57.41%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5672	56.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8797	87.97%
OATP1B3 inhibitior	+	0.9171	91.71%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5164	51.64%
P-glycoprotein inhibitior	-	0.5778	57.78%
P-glycoprotein substrate	-	0.5928	59.28%
CYP3A4 substrate	+	0.6080	60.80%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8605	86.05%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.7653	76.53%
CYP2D6 inhibition	-	0.9612	96.12%
CYP1A2 inhibition	-	0.6245	62.45%
CYP2C8 inhibition	-	0.8732	87.32%
CYP inhibitory promiscuity	-	0.7827	78.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9168	91.68%
Carcinogenicity (trinary)	Non-required	0.5472	54.72%
Eye corrosion	-	0.9050	90.50%
Eye irritation	-	0.5972	59.72%
Skin irritation	-	0.6820	68.20%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5918	59.18%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.7211	72.11%
skin sensitisation	-	0.6651	66.51%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6763	67.63%
Acute Oral Toxicity (c)	II	0.4351	43.51%
Estrogen receptor binding	+	0.7117	71.17%
Androgen receptor binding	+	0.5428	54.28%
Thyroid receptor binding	+	0.5460	54.60%
Glucocorticoid receptor binding	+	0.6740	67.40%
Aromatase binding	-	0.6030	60.30%
PPAR gamma	-	0.6338	63.38%
Honey bee toxicity	-	0.6156	61.56%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9786	97.86%

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	90.10%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	89.71%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.13%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.39%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.41%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.75%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.71%	97.25%
CHEMBL2581	P07339	Cathepsin D	81.01%	98.95%
CHEMBL1902	P62942	FK506-binding protein 1A	80.74%	97.05%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.16%	99.23%

Plants that contains it

• Cyclolepis genistoides

Cross-Links

• PubChem: 162949307
• LOTUS: LTS0077312
• wikiData: Q105352101