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

Details

• Internal ID: e5b921ce-5169-4840-a38e-56b561f5ab3a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3S,3aS,4R,7S,8aR)-4-hydroxy-3,7-dimethyl-6-(3-oxobutyl)-3,3a,4,7,8,8a-hexahydrocyclohepta[b]furan-2-one
• SMILES (Canonical): CC1CC2C(C(C(=O)O2)C)C(C=C1CCC(=O)C)O
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@@H]([C@@H](C(=O)O2)C)[C@@H](C=C1CCC(=O)C)O
• InChI: InChI=1S/C15H22O4/c1-8-6-13-14(10(3)15(18)19-13)12(17)7-11(8)5-4-9(2)16/h7-8,10,12-14,17H,4-6H2,1-3H3/t8-,10-,12+,13+,14-/m0/s1
• InChI Key: JTJGUCQHALEULJ-ZVFRIGBMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 4
• 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	+	0.9713	97.13%
Caco-2	+	0.6535	65.35%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6331	63.31%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9041	90.41%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8271	82.71%
P-glycoprotein inhibitior	-	0.9225	92.25%
P-glycoprotein substrate	-	0.7234	72.34%
CYP3A4 substrate	+	0.5124	51.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8344	83.44%
CYP3A4 inhibition	-	0.6927	69.27%
CYP2C9 inhibition	-	0.8338	83.38%
CYP2C19 inhibition	-	0.8076	80.76%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	+	0.7016	70.16%
CYP2C8 inhibition	-	0.9311	93.11%
CYP inhibitory promiscuity	-	0.9350	93.50%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6349	63.49%
Eye corrosion	-	0.9774	97.74%
Eye irritation	-	0.9304	93.04%
Skin irritation	+	0.5398	53.98%
Skin corrosion	-	0.9181	91.81%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4509	45.09%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.7431	74.31%
skin sensitisation	-	0.8142	81.42%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5218	52.18%
Acute Oral Toxicity (c)	II	0.4842	48.42%
Estrogen receptor binding	-	0.6342	63.42%
Androgen receptor binding	-	0.7081	70.81%
Thyroid receptor binding	-	0.6811	68.11%
Glucocorticoid receptor binding	-	0.5654	56.54%
Aromatase binding	-	0.8798	87.98%
PPAR gamma	-	0.8363	83.63%
Honey bee toxicity	-	0.8803	88.03%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.96%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.06%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.19%	85.14%
CHEMBL2581	P07339	Cathepsin D	86.72%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.75%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.85%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.41%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.97%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.24%	99.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 57391114
• LOTUS: LTS0132837
• wikiData: Q105134794