(3aS,6aS,9aR,9bS)-6a-hydroxy-6,9-dimethyl-3-methylidene-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 5d921498-211c-4e1c-b959-178c9bea0f64
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aS,9aR,9bS)-6a-hydroxy-6,9-dimethyl-3-methylidene-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2C(C3C1(CC=C3C)O)OC(=O)C2=C
• SMILES (Isomeric): CC1=CC[C@@H]2[C@@H]([C@@H]3[C@]1(CC=C3C)O)OC(=O)C2=C
• InChI: InChI=1S/C15H18O3/c1-8-6-7-15(17)9(2)4-5-11-10(3)14(16)18-13(11)12(8)15/h4,6,11-13,17H,3,5,7H2,1-2H3/t11-,12+,13-,15+/m0/s1
• InChI Key: KAMPINJSJRYFGQ-SFDCQRBFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.5077	50.77%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4626	46.26%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9040	90.40%
OATP1B3 inhibitior	+	0.9412	94.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9482	94.82%
P-glycoprotein inhibitior	-	0.9333	93.33%
P-glycoprotein substrate	-	0.8981	89.81%
CYP3A4 substrate	+	0.5580	55.80%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.8299	82.99%
CYP2C9 inhibition	-	0.9129	91.29%
CYP2C19 inhibition	-	0.8356	83.56%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.6626	66.26%
CYP2C8 inhibition	-	0.7939	79.39%
CYP inhibitory promiscuity	-	0.9364	93.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5233	52.33%
Eye corrosion	-	0.9675	96.75%
Eye irritation	-	0.8835	88.35%
Skin irritation	+	0.5178	51.78%
Skin corrosion	-	0.8402	84.02%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6031	60.31%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.7699	76.99%
skin sensitisation	-	0.5969	59.69%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6501	65.01%
Acute Oral Toxicity (c)	II	0.4203	42.03%
Estrogen receptor binding	-	0.5187	51.87%
Androgen receptor binding	+	0.5934	59.34%
Thyroid receptor binding	-	0.5668	56.68%
Glucocorticoid receptor binding	-	0.5710	57.10%
Aromatase binding	-	0.6143	61.43%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8647	86.47%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9311	93.11%

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	94.23%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.11%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.32%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.09%	97.25%
CHEMBL4530	P00488	Coagulation factor XIII	86.52%	96.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.16%	93.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.92%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.00%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.74%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.04%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.03%	86.33%

Plants that contains it

• Kaunia lasiophthalma

Cross-Links

• PubChem: 14589130
• LOTUS: LTS0202128
• wikiData: Q105137910