(3aR,6R,7S,8aS)-7-methyl-3-methylidene-6-(3-oxobutyl)-4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: e0dcdb42-d624-4460-8dcc-385af1601f6d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3aR,6R,7S,8aS)-7-methyl-3-methylidene-6-(3-oxobutyl)-4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[b]furan-2-one
• SMILES (Canonical): CC1CC2C(CCC1CCC(=O)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@H]2[C@H](CC[C@@H]1CCC(=O)C)C(=C)C(=O)O2
• InChI: InChI=1S/C15H22O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h9,12-14H,3-8H2,1-2H3/t9-,12-,13+,14-/m0/s1
• InChI Key: BOTVFTZDPPJPBG-WTDIUWLJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.8148	81.48%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5854	58.54%
OATP2B1 inhibitior	-	0.8531	85.31%
OATP1B1 inhibitior	+	0.8994	89.94%
OATP1B3 inhibitior	+	0.9098	90.98%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.9107	91.07%
P-glycoprotein inhibitior	-	0.8195	81.95%
P-glycoprotein substrate	-	0.8147	81.47%
CYP3A4 substrate	+	0.5237	52.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8760	87.60%
CYP3A4 inhibition	-	0.7891	78.91%
CYP2C9 inhibition	-	0.9042	90.42%
CYP2C19 inhibition	-	0.7932	79.32%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	+	0.7012	70.12%
CYP2C8 inhibition	-	0.8198	81.98%
CYP inhibitory promiscuity	-	0.8802	88.02%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6586	65.86%
Eye corrosion	-	0.9492	94.92%
Eye irritation	+	0.5800	58.00%
Skin irritation	-	0.5363	53.63%
Skin corrosion	-	0.9092	90.92%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5107	51.07%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.5743	57.43%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6024	60.24%
Acute Oral Toxicity (c)	III	0.6147	61.47%
Estrogen receptor binding	-	0.6119	61.19%
Androgen receptor binding	-	0.6236	62.36%
Thyroid receptor binding	-	0.6540	65.40%
Glucocorticoid receptor binding	+	0.7226	72.26%
Aromatase binding	-	0.7544	75.44%
PPAR gamma	-	0.7261	72.61%
Honey bee toxicity	-	0.8796	87.96%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9947	99.47%

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	96.79%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.69%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.21%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.12%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.06%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.53%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.49%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.67%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.55%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.34%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.04%	92.50%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.53%	98.46%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.32%	93.03%

Plants that contains it

• Dittrichia graveolens

Cross-Links

• PubChem: 163037400
• LOTUS: LTS0244965
• wikiData: Q104939701