(1R,3aR,5aR,8aR,9aR)-1,8-dimethyl-5-methylidene-1,3a,4,5a,6,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: 72d47986-3330-49e9-afb1-a99a45e0c228
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (1R,3aR,5aR,8aR,9aR)-1,8-dimethyl-5-methylidene-1,3a,4,5a,6,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1C2CC3C(CC=C3C)C(=C)CC2OC1=O
• SMILES (Isomeric): C[C@@H]1[C@H]2C[C@@H]3[C@@H](CC=C3C)C(=C)C[C@H]2OC1=O
• InChI: InChI=1S/C15H20O2/c1-8-4-5-11-9(2)6-14-13(7-12(8)11)10(3)15(16)17-14/h4,10-14H,2,5-7H2,1,3H3/t10-,11+,12+,13-,14-/m1/s1
• InChI Key: ZBWWLHSOPWQYSL-MBJXGIAVSA-N
• Popularity: 2 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: 2.50
• 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	+	1.0000	100.00%
Caco-2	+	0.7465	74.65%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4279	42.79%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9148	91.48%
OATP1B3 inhibitior	+	0.9300	93.00%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8995	89.95%
P-glycoprotein inhibitior	-	0.8915	89.15%
P-glycoprotein substrate	-	0.7941	79.41%
CYP3A4 substrate	+	0.5544	55.44%
CYP2C9 substrate	-	0.7874	78.74%
CYP2D6 substrate	-	0.8423	84.23%
CYP3A4 inhibition	-	0.7926	79.26%
CYP2C9 inhibition	-	0.9476	94.76%
CYP2C19 inhibition	-	0.6982	69.82%
CYP2D6 inhibition	-	0.9536	95.36%
CYP1A2 inhibition	-	0.5059	50.59%
CYP2C8 inhibition	-	0.8880	88.80%
CYP inhibitory promiscuity	-	0.8608	86.08%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9317	93.17%
Carcinogenicity (trinary)	Non-required	0.6018	60.18%
Eye corrosion	-	0.8789	87.89%
Eye irritation	-	0.7146	71.46%
Skin irritation	-	0.5534	55.34%
Skin corrosion	-	0.9417	94.17%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5946	59.46%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	+	0.5971	59.71%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5900	59.00%
Acute Oral Toxicity (c)	III	0.6348	63.48%
Estrogen receptor binding	-	0.7485	74.85%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.6924	69.24%
Glucocorticoid receptor binding	-	0.4711	47.11%
Aromatase binding	-	0.7836	78.36%
PPAR gamma	-	0.7829	78.29%
Honey bee toxicity	-	0.6867	68.67%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9822	98.22%

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	91.02%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	91.00%	86.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.93%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.74%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.49%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.44%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.36%	96.95%

Plants that contains it

• Stevia samaipatensis
• Xanthium spinosum subsp. spinosum

Cross-Links

• PubChem: 102239789
• LOTUS: LTS0183640
• wikiData: Q105370884