(3S,6aR,9S,9aR,9bS)-3,9-dimethyl-6-methylidene-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione

Details

• Internal ID: 0acc3f42-20f5-46ca-b6d9-07bb51d94e4d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,6aR,9S,9aR,9bS)-3,9-dimethyl-6-methylidene-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): CC1C2CCC(=C)C3CC(=O)C(C3C2OC1=O)C
• SMILES (Isomeric): C[C@H]1[C@H]2[C@@H](CC1=O)C(=C)CCC3[C@@H]2OC(=O)[C@H]3C
• InChI: InChI=1S/C15H20O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h8-11,13-14H,1,4-6H2,2-3H3/t8-,9+,10?,11-,13-,14-/m0/s1
• InChI Key: QEFUTRKIARMBLC-GTBOYDOOSA-N
• Popularity: 0 references 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: 1.90
• Atomic LogP (AlogP): 2.36
• 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	+	0.9940	99.40%
Caco-2	+	0.8479	84.79%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6391	63.91%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	+	0.8543	85.43%
OATP1B3 inhibitior	+	0.9259	92.59%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.9114	91.14%
P-glycoprotein inhibitior	-	0.8649	86.49%
P-glycoprotein substrate	-	0.8834	88.34%
CYP3A4 substrate	+	0.5466	54.66%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8432	84.32%
CYP3A4 inhibition	-	0.8388	83.88%
CYP2C9 inhibition	-	0.9283	92.83%
CYP2C19 inhibition	-	0.8080	80.80%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	+	0.6537	65.37%
CYP2C8 inhibition	-	0.8551	85.51%
CYP inhibitory promiscuity	-	0.9252	92.52%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6706	67.06%
Eye corrosion	-	0.9148	91.48%
Eye irritation	+	0.6807	68.07%
Skin irritation	-	0.5637	56.37%
Skin corrosion	-	0.9037	90.37%
Ames mutagenesis	-	0.7395	73.95%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.5806	58.06%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5570	55.70%
Acute Oral Toxicity (c)	III	0.6252	62.52%
Estrogen receptor binding	-	0.6990	69.90%
Androgen receptor binding	+	0.5719	57.19%
Thyroid receptor binding	-	0.5802	58.02%
Glucocorticoid receptor binding	-	0.6425	64.25%
Aromatase binding	-	0.8378	83.78%
PPAR gamma	-	0.8982	89.82%
Honey bee toxicity	-	0.7683	76.83%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9877	98.77%

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	95.01%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	89.73%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.33%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.06%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.50%	97.25%
CHEMBL2581	P07339	Cathepsin D	85.40%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.67%	94.80%
CHEMBL1902	P62942	FK506-binding protein 1A	83.01%	97.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.92%	100.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.30%	93.40%

Plants that contains it

• Arctotis stoechadifolia

Cross-Links

• PubChem: 162872678
• LOTUS: LTS0203242
• wikiData: Q105219168