(6S,6aS,9aR,9bR)-3,6,9a-trimethyl-5,6,6a,7,8,9b-hexahydro-4H-azuleno[8,7-b]furan-2,9-dione

Details

• Internal ID: 50971a69-5dd3-465c-bad6-6c1036a714e5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (6S,6aS,9aR,9bR)-3,6,9a-trimethyl-5,6,6a,7,8,9b-hexahydro-4H-azuleno[8,7-b]furan-2,9-dione
• SMILES (Canonical): CC1CCC2=C(C(=O)OC2C3(C1CCC3=O)C)C
• SMILES (Isomeric): C[C@H]1CCC2=C(C(=O)O[C@H]2[C@]3([C@H]1CCC3=O)C)C
• InChI: InChI=1S/C15H20O3/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(15)16/h8,11,13H,4-7H2,1-3H3/t8-,11-,13+,15-/m0/s1
• InChI Key: NEHXPIGRYFZMOE-BUWBAVOPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.64
• 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	+	0.9946	99.46%
Caco-2	+	0.8582	85.82%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6337	63.37%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.8966	89.66%
OATP1B3 inhibitior	+	0.9649	96.49%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	-	0.8765	87.65%
P-glycoprotein inhibitior	-	0.8216	82.16%
P-glycoprotein substrate	-	0.9246	92.46%
CYP3A4 substrate	+	0.5913	59.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.8616	86.16%
CYP2C9 inhibition	-	0.8558	85.58%
CYP2C19 inhibition	-	0.8193	81.93%
CYP2D6 inhibition	-	0.9619	96.19%
CYP1A2 inhibition	+	0.7798	77.98%
CYP2C8 inhibition	-	0.8801	88.01%
CYP inhibitory promiscuity	-	0.9458	94.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5276	52.76%
Eye corrosion	-	0.9705	97.05%
Eye irritation	-	0.7711	77.11%
Skin irritation	+	0.5893	58.93%
Skin corrosion	-	0.8537	85.37%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5274	52.74%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.7002	70.02%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.4551	45.51%
Acute Oral Toxicity (c)	III	0.4536	45.36%
Estrogen receptor binding	-	0.6677	66.77%
Androgen receptor binding	+	0.6052	60.52%
Thyroid receptor binding	-	0.6353	63.53%
Glucocorticoid receptor binding	-	0.5315	53.15%
Aromatase binding	-	0.7461	74.61%
PPAR gamma	-	0.5285	52.85%
Honey bee toxicity	-	0.9075	90.75%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9860	98.60%

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	92.08%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.03%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.82%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.38%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.76%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.68%	97.25%
CHEMBL1871	P10275	Androgen Receptor	84.58%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.96%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.09%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.96%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.34%	93.04%
CHEMBL1937	Q92769	Histone deacetylase 2	81.30%	94.75%
CHEMBL2581	P07339	Cathepsin D	80.35%	98.95%

Plants that contains it

• Ambrosia artemisiifolia

Cross-Links

• PubChem: 12310890
• LOTUS: LTS0243597
• wikiData: Q105177936