(6aR,9S,9bR)-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione

Details

• Internal ID: 0d9031ee-cb7e-4311-9bd6-a13fc52e4cfc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (6aR,9S,9bR)-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): CC1C2C(CC1=O)C(=C)CCC3C2OC(=O)C3=C
• SMILES (Isomeric): C[C@H]1C2[C@@H](CC1=O)C(=C)CCC3[C@@H]2OC(=O)C3=C
• InChI: InChI=1S/C15H18O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h9-11,13-14H,1-2,4-6H2,3H3/t9-,10?,11+,13?,14+/m1/s1
• InChI Key: PVRPBMBRMSXIHM-ZNFKVZEKSA-N
• Popularity: 2 references 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): 43.40 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.28
• 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	+	0.9952	99.52%
Caco-2	+	0.6959	69.59%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6206	62.06%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.8492	84.92%
OATP1B3 inhibitior	+	0.9367	93.67%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.9431	94.31%
P-glycoprotein inhibitior	-	0.8858	88.58%
P-glycoprotein substrate	-	0.9210	92.10%
CYP3A4 substrate	+	0.5163	51.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8743	87.43%
CYP3A4 inhibition	-	0.9031	90.31%
CYP2C9 inhibition	-	0.9221	92.21%
CYP2C19 inhibition	-	0.7281	72.81%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	+	0.6759	67.59%
CYP2C8 inhibition	-	0.8222	82.22%
CYP inhibitory promiscuity	-	0.9276	92.76%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6389	63.89%
Eye corrosion	-	0.8782	87.82%
Eye irritation	+	0.8611	86.11%
Skin irritation	-	0.5284	52.84%
Skin corrosion	-	0.8939	89.39%
Ames mutagenesis	-	0.7224	72.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4729	47.29%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.5967	59.67%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6190	61.90%
Acute Oral Toxicity (c)	III	0.6322	63.22%
Estrogen receptor binding	-	0.5136	51.36%
Androgen receptor binding	+	0.5894	58.94%
Thyroid receptor binding	-	0.6682	66.82%
Glucocorticoid receptor binding	-	0.5654	56.54%
Aromatase binding	-	0.8093	80.93%
PPAR gamma	-	0.8229	82.29%
Honey bee toxicity	-	0.7775	77.75%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9856	98.56%

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	90.71%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.68%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.44%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.47%	98.95%
CHEMBL1902	P62942	FK506-binding protein 1A	83.04%	97.05%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.74%	99.23%

Plants that contains it

• Ainsliaea acerifolia
• Eremanthus erythropappus

Cross-Links

• PubChem: 101238032
• LOTUS: LTS0082252
• wikiData: Q105215578