(3S,3aR,7S,8aR)-6-[(3S)-3-hydroxybutyl]-3,7-dimethyl-3,3a,4,7,8,8a-hexahydrocyclohepta[b]furan-2-one

Details

• Internal ID: 2c01690d-ce9e-4482-87ca-5bfde89e4ff6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3S,3aR,7S,8aR)-6-[(3S)-3-hydroxybutyl]-3,7-dimethyl-3,3a,4,7,8,8a-hexahydrocyclohepta[b]furan-2-one
• InChI: InChI=1S/C15H24O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h6,9-11,13-14,16H,4-5,7-8H2,1-3H3/t9-,10-,11-,13+,14+/m0/s1
• InChI Key: GVKRUTFARUBHKM-FFNLUWKOSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	+	0.8386	83.86%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5816	58.16%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.9411	94.11%
OATP1B3 inhibitior	+	0.9589	95.89%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8618	86.18%
P-glycoprotein inhibitior	-	0.9332	93.32%
P-glycoprotein substrate	-	0.6609	66.09%
CYP3A4 substrate	+	0.5326	53.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8315	83.15%
CYP3A4 inhibition	-	0.5876	58.76%
CYP2C9 inhibition	-	0.8925	89.25%
CYP2C19 inhibition	-	0.8439	84.39%
CYP2D6 inhibition	-	0.9456	94.56%
CYP1A2 inhibition	-	0.5297	52.97%
CYP2C8 inhibition	-	0.9569	95.69%
CYP inhibitory promiscuity	-	0.9219	92.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6478	64.78%
Eye corrosion	-	0.9786	97.86%
Eye irritation	-	0.7662	76.62%
Skin irritation	-	0.5121	51.21%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4007	40.07%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.6436	64.36%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.5951	59.51%
Acute Oral Toxicity (c)	III	0.4456	44.56%
Estrogen receptor binding	-	0.6410	64.10%
Androgen receptor binding	-	0.5444	54.44%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6701	67.01%
Aromatase binding	-	0.8454	84.54%
PPAR gamma	-	0.7462	74.62%
Honey bee toxicity	-	0.8923	89.23%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.9664	96.64%

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	98.89%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.67%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.43%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.40%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.74%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.01%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	84.47%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.33%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.22%	89.34%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.81%	90.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.63%	97.21%

Plants that contains it

• Arnica lanceolata subsp. prima
• Stevia isomeca

Cross-Links

• PubChem: 163072307
• LOTUS: LTS0003446
• wikiData: Q105021361