(3S,3aS,7S,8aS)-3-hydroxy-3-(hydroxymethyl)-7-methyl-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: da9582de-7a24-49a1-a321-9feb0565de4f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3S,3aS,7S,8aS)-3-hydroxy-3-(hydroxymethyl)-7-methyl-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• InChI: InChI=1S/C15H20O5/c1-9-7-13-12(15(19,8-16)14(18)20-13)6-5-11(9)4-3-10(2)17/h3-5,9,12-13,16,19H,6-8H2,1-2H3/b4-3+/t9-,12-,13-,15+/m0/s1
• InChI Key: JMWTXWWQGSJXAM-WNSJDEPSSA-N
• Popularity: 2 references 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): 83.80 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9271	92.71%
Caco-2	-	0.7957	79.57%
Blood Brain Barrier	+	0.5781	57.81%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7106	71.06%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9083	90.83%
OATP1B3 inhibitior	+	0.9679	96.79%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6497	64.97%
P-glycoprotein inhibitior	-	0.9419	94.19%
P-glycoprotein substrate	-	0.7215	72.15%
CYP3A4 substrate	+	0.5967	59.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	-	0.6805	68.05%
CYP2C9 inhibition	-	0.8029	80.29%
CYP2C19 inhibition	-	0.8485	84.85%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.8055	80.55%
CYP2C8 inhibition	-	0.7937	79.37%
CYP inhibitory promiscuity	-	0.9637	96.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5526	55.26%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9489	94.89%
Skin irritation	-	0.6172	61.72%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6173	61.73%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8741	87.41%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6549	65.49%
Acute Oral Toxicity (c)	III	0.4491	44.91%
Estrogen receptor binding	+	0.5595	55.95%
Androgen receptor binding	-	0.5788	57.88%
Thyroid receptor binding	-	0.5436	54.36%
Glucocorticoid receptor binding	+	0.6504	65.04%
Aromatase binding	-	0.7339	73.39%
PPAR gamma	-	0.7940	79.40%
Honey bee toxicity	-	0.8590	85.90%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9409	94.09%

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	97.40%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.17%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.85%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.49%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.33%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.77%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.24%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.47%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.68%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.44%	95.56%

Plants that contains it

• Xanthium strumarium

Cross-Links

• PubChem: 100937080
• NPASS: NPC263983
• LOTUS: LTS0150658
• wikiData: Q105131719