(3aR,7S,8aR)-6-[(E)-3-hydroxybut-1-enyl]-7-methyl-3-methylidene-4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: 7001fc8b-ccf1-42b3-bd35-d694971f7257
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3aR,7S,8aR)-6-[(E)-3-hydroxybut-1-enyl]-7-methyl-3-methylidene-4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[b]furan-2-one
• SMILES (Canonical): CC1CC2C(CCC1C=CC(C)O)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@H](CCC1/C=C/C(C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H22O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-5,9-10,12-14,16H,3,6-8H2,1-2H3/b5-4+/t9-,10?,12?,13+,14+/m0/s1
• InChI Key: WZXLMGPZPXPPPZ-QLVYERCOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.8092	80.92%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4876	48.76%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.9302	93.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.9022	90.22%
P-glycoprotein inhibitior	-	0.8999	89.99%
P-glycoprotein substrate	-	0.8147	81.47%
CYP3A4 substrate	+	0.5358	53.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8349	83.49%
CYP3A4 inhibition	-	0.6865	68.65%
CYP2C9 inhibition	-	0.9350	93.50%
CYP2C19 inhibition	-	0.8228	82.28%
CYP2D6 inhibition	-	0.9360	93.60%
CYP1A2 inhibition	+	0.7612	76.12%
CYP2C8 inhibition	-	0.8551	85.51%
CYP inhibitory promiscuity	-	0.9425	94.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6283	62.83%
Eye corrosion	-	0.9529	95.29%
Eye irritation	-	0.8817	88.17%
Skin irritation	-	0.5286	52.86%
Skin corrosion	-	0.9261	92.61%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6260	62.60%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.5683	56.83%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4924	49.24%
Estrogen receptor binding	-	0.6987	69.87%
Androgen receptor binding	-	0.6839	68.39%
Thyroid receptor binding	+	0.5543	55.43%
Glucocorticoid receptor binding	+	0.6947	69.47%
Aromatase binding	-	0.8287	82.87%
PPAR gamma	-	0.7811	78.11%
Honey bee toxicity	-	0.8148	81.48%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9871	98.71%

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	96.87%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.12%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.24%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.39%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.31%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.89%	91.11%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.13%	93.03%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.08%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.99%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.55%	96.47%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.88%	89.34%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.68%	93.56%

Plants that contains it

• Dittrichia graveolens
• Salvia candicans

Cross-Links

• PubChem: 162816932
• LOTUS: LTS0088905
• wikiData: Q105176372