(3R,3aS,6aR,9aR,9bS)-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 660a582a-68c2-4c14-b88f-98401097eb75
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3R,3aS,6aR,9aR,9bS)-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C2CCC(=C)C3CCC(=C)C3C2OC1=O
• SMILES (Isomeric): C[C@@H]1[C@@H]2CCC(=C)[C@@H]3CCC(=C)[C@@H]3[C@H]2OC1=O
• InChI: InChI=1S/C15H20O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h10-14H,1-2,4-7H2,3H3/t10-,11+,12+,13+,14+/m1/s1
• InChI Key: UJADCNYXDHHISU-QMVSFRDZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 2
• 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	+	0.9974	99.74%
Caco-2	+	0.7444	74.44%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.3746	37.46%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.9040	90.40%
OATP1B3 inhibitior	+	0.9350	93.50%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.8964	89.64%
P-glycoprotein inhibitior	-	0.9043	90.43%
P-glycoprotein substrate	-	0.8696	86.96%
CYP3A4 substrate	+	0.5124	51.24%
CYP2C9 substrate	-	0.7874	78.74%
CYP2D6 substrate	-	0.8423	84.23%
CYP3A4 inhibition	-	0.8656	86.56%
CYP2C9 inhibition	-	0.9204	92.04%
CYP2C19 inhibition	-	0.5187	51.87%
CYP2D6 inhibition	-	0.9285	92.85%
CYP1A2 inhibition	+	0.8025	80.25%
CYP2C8 inhibition	-	0.9524	95.24%
CYP inhibitory promiscuity	-	0.8080	80.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5678	56.78%
Eye corrosion	-	0.7916	79.16%
Eye irritation	+	0.5815	58.15%
Skin irritation	-	0.5376	53.76%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6808	68.08%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	+	0.5436	54.36%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.6333	63.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4713	47.13%
Acute Oral Toxicity (c)	III	0.6273	62.73%
Estrogen receptor binding	-	0.6417	64.17%
Androgen receptor binding	+	0.5247	52.47%
Thyroid receptor binding	-	0.5979	59.79%
Glucocorticoid receptor binding	-	0.5074	50.74%
Aromatase binding	-	0.8329	83.29%
PPAR gamma	-	0.8047	80.47%
Honey bee toxicity	-	0.8492	84.92%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9846	98.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.80%	97.25%
CHEMBL1978	P11511	Cytochrome P450 19A1	88.14%	91.76%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.51%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.18%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.11%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.72%	94.80%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.67%	91.11%
CHEMBL1871	P10275	Androgen Receptor	81.08%	96.43%

Plants that contains it

• Aucklandia costus

Cross-Links

• PubChem: 10704750
• LOTUS: LTS0116967
• wikiData: Q105273810