5-(1-Hydroxy-3-oxobutyl)-6-methyl-11-methylidene-4,9-dioxatricyclo[6.3.0.03,5]undecan-10-one

Details

• Internal ID: c3997903-b688-4ade-a1a1-7f2b85c63aad
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: 5-(1-hydroxy-3-oxobutyl)-6-methyl-11-methylidene-4,9-dioxatricyclo[6.3.0.03,5]undecan-10-one
• SMILES (Canonical): CC1CC2C(CC3C1(O3)C(CC(=O)C)O)C(=C)C(=O)O2
• SMILES (Isomeric): CC1CC2C(CC3C1(O3)C(CC(=O)C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O5/c1-7-4-11-10(9(3)14(18)19-11)6-13-15(7,20-13)12(17)5-8(2)16/h7,10-13,17H,3-6H2,1-2H3
• InChI Key: BTERVGRTNQJMQT-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.99
• H-Bond Acceptor: 5
• 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	+	0.9507	95.07%
Caco-2	+	0.5066	50.66%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6029	60.29%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.9027	90.27%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9097	90.97%
P-glycoprotein inhibitior	-	0.8620	86.20%
P-glycoprotein substrate	-	0.6375	63.75%
CYP3A4 substrate	+	0.5843	58.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8723	87.23%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8454	84.54%
CYP2C19 inhibition	-	0.8566	85.66%
CYP2D6 inhibition	-	0.9452	94.52%
CYP1A2 inhibition	-	0.7651	76.51%
CYP2C8 inhibition	-	0.8320	83.20%
CYP inhibitory promiscuity	-	0.9528	95.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4648	46.48%
Eye corrosion	-	0.9793	97.93%
Eye irritation	-	0.7616	76.16%
Skin irritation	-	0.5574	55.74%
Skin corrosion	-	0.8949	89.49%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5917	59.17%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.7199	71.99%
skin sensitisation	-	0.7269	72.69%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.4792	47.92%
Acute Oral Toxicity (c)	II	0.3668	36.68%
Estrogen receptor binding	+	0.6740	67.40%
Androgen receptor binding	-	0.4935	49.35%
Thyroid receptor binding	+	0.6001	60.01%
Glucocorticoid receptor binding	+	0.7613	76.13%
Aromatase binding	-	0.6323	63.23%
PPAR gamma	-	0.5312	53.12%
Honey bee toxicity	-	0.7526	75.26%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9771	97.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.26%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.61%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.09%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	87.78%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.56%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.12%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.52%	96.61%
CHEMBL2581	P07339	Cathepsin D	83.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.33%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.89%	99.23%
CHEMBL299	P17252	Protein kinase C alpha	81.57%	98.03%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.57%	95.50%

Plants that contains it

• Xanthium strumarium

Cross-Links

• PubChem: 163049406
• LOTUS: LTS0017496
• wikiData: Q104945562