(3R,3aR,8aR)-3,7-dimethyl-6-(3-oxobutyl)-3a,4,8,8a-tetrahydro-3H-cyclohepta[b]furan-2,5-dione

Details

• Internal ID: 1e33751c-0e95-4fa8-9f68-5268d505f97f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3R,3aR,8aR)-3,7-dimethyl-6-(3-oxobutyl)-3a,4,8,8a-tetrahydro-3H-cyclohepta[b]furan-2,5-dione
• SMILES (Canonical): CC1C2CC(=O)C(=C(CC2OC1=O)C)CCC(=O)C
• SMILES (Isomeric): C[C@@H]1[C@H]2CC(=O)C(=C(C[C@H]2OC1=O)C)CCC(=O)C
• InChI: InChI=1S/C15H20O4/c1-8-6-14-12(10(3)15(18)19-14)7-13(17)11(8)5-4-9(2)16/h10,12,14H,4-7H2,1-3H3/t10-,12-,14-/m1/s1
• InChI Key: UUKUKOWRPZPCIE-MPKXVKKWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 60.40 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 4
• 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	+	0.9900	99.00%
Caco-2	+	0.7583	75.83%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6147	61.47%
OATP2B1 inhibitior	-	0.8502	85.02%
OATP1B1 inhibitior	+	0.8808	88.08%
OATP1B3 inhibitior	+	0.9449	94.49%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.6425	64.25%
P-glycoprotein inhibitior	-	0.7883	78.83%
P-glycoprotein substrate	-	0.7015	70.15%
CYP3A4 substrate	+	0.5120	51.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9001	90.01%
CYP3A4 inhibition	-	0.7636	76.36%
CYP2C9 inhibition	-	0.8916	89.16%
CYP2C19 inhibition	-	0.8411	84.11%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	+	0.6387	63.87%
CYP2C8 inhibition	-	0.9486	94.86%
CYP inhibitory promiscuity	-	0.9057	90.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6816	68.16%
Eye corrosion	-	0.9696	96.96%
Eye irritation	-	0.6182	61.82%
Skin irritation	-	0.5190	51.90%
Skin corrosion	-	0.9339	93.39%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5950	59.50%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.8306	83.06%
skin sensitisation	-	0.7272	72.72%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6201	62.01%
Acute Oral Toxicity (c)	III	0.5906	59.06%
Estrogen receptor binding	-	0.7027	70.27%
Androgen receptor binding	-	0.5794	57.94%
Thyroid receptor binding	-	0.7294	72.94%
Glucocorticoid receptor binding	-	0.5163	51.63%
Aromatase binding	-	0.9260	92.60%
PPAR gamma	-	0.7571	75.71%
Honey bee toxicity	-	0.8349	83.49%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9903	99.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4481	P35228	Nitric oxide synthase, inducible	92.37%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.70%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.95%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.03%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.56%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.27%	97.21%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.50%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.25%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.97%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.20%	99.23%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.54%	96.95%

Plants that contains it

• Dittrichia graveolens

Cross-Links

• PubChem: 10706730
• LOTUS: LTS0137682
• wikiData: Q105279390