(3aS,9aR,9bR)-6,9a-dimethyl-3-methylidene-3a,4,5,9b-tetrahydroazuleno[8,7-b]furan-2,9-dione

Details

• Internal ID: 483a6bdb-6092-4207-be85-62c4dff2b34c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3aS,9aR,9bR)-6,9a-dimethyl-3-methylidene-3a,4,5,9b-tetrahydroazuleno[8,7-b]furan-2,9-dione
• SMILES (Canonical): CC1=C2C=CC(=O)C2(C3C(CC1)C(=C)C(=O)O3)C
• SMILES (Isomeric): CC1=C2C=CC(=O)[C@]2([C@H]3[C@@H](CC1)C(=C)C(=O)O3)C
• InChI: InChI=1S/C15H16O3/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(15)16/h6-7,10,13H,2,4-5H2,1,3H3/t10-,13+,15-/m0/s1
• InChI Key: XSWAZIGOOCZRGU-ZBINZKHDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.28 g/mol
• Exact Mass: 244.109944368 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.34
• 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	+	0.9933	99.33%
Caco-2	+	0.7437	74.37%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5051	50.51%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9045	90.45%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.9342	93.42%
P-glycoprotein inhibitior	-	0.8773	87.73%
P-glycoprotein substrate	-	0.8630	86.30%
CYP3A4 substrate	+	0.5881	58.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	-	0.8681	86.81%
CYP2C9 inhibition	-	0.8738	87.38%
CYP2C19 inhibition	-	0.8790	87.90%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	+	0.8754	87.54%
CYP2C8 inhibition	-	0.8505	85.05%
CYP inhibitory promiscuity	-	0.8846	88.46%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4963	49.63%
Eye corrosion	-	0.9399	93.99%
Eye irritation	-	0.8788	87.88%
Skin irritation	+	0.5658	56.58%
Skin corrosion	-	0.6929	69.29%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6199	61.99%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.8375	83.75%
skin sensitisation	-	0.5657	56.57%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6456	64.56%
Acute Oral Toxicity (c)	III	0.4607	46.07%
Estrogen receptor binding	-	0.7381	73.81%
Androgen receptor binding	-	0.5444	54.44%
Thyroid receptor binding	-	0.6661	66.61%
Glucocorticoid receptor binding	-	0.6176	61.76%
Aromatase binding	-	0.6106	61.06%
PPAR gamma	-	0.5063	50.63%
Honey bee toxicity	-	0.8923	89.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9841	98.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.62%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.54%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.85%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.63%	97.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.17%	93.40%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.72%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.00%	100.00%
CHEMBL1871	P10275	Androgen Receptor	82.51%	96.43%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.47%	97.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.12%	93.03%

Plants that contains it

• Artemisia mesatlantica

Cross-Links

• PubChem: 10988516
• LOTUS: LTS0263566
• wikiData: Q104397406