(4S)-4-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dienyl]-3-methylideneoxolan-2-one

Details

• Internal ID: 326c3d2f-fa68-4236-a291-e4e09ef388b9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4S)-4-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dienyl]-3-methylideneoxolan-2-one
• SMILES (Canonical): CC(=CC(=O)CC(=CCC1COC(=O)C1=C)C)C
• SMILES (Isomeric): CC(=CC(=O)C/C(=C/C[C@@H]1COC(=O)C1=C)/C)C
• InChI: InChI=1S/C15H20O3/c1-10(2)7-14(16)8-11(3)5-6-13-9-18-15(17)12(13)4/h5,7,13H,4,6,8-9H2,1-3H3/b11-5+/t13-/m1/s1
• InChI Key: WSKLYRKBPFVGEJ-HQIZRNBFSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.98
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9920	99.20%
Caco-2	+	0.8005	80.05%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7626	76.26%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9231	92.31%
OATP1B3 inhibitior	+	0.9221	92.21%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7273	72.73%
P-glycoprotein inhibitior	-	0.9171	91.71%
P-glycoprotein substrate	-	0.7408	74.08%
CYP3A4 substrate	+	0.5137	51.37%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9047	90.47%
CYP3A4 inhibition	-	0.7530	75.30%
CYP2C9 inhibition	-	0.8005	80.05%
CYP2C19 inhibition	-	0.7594	75.94%
CYP2D6 inhibition	-	0.9257	92.57%
CYP1A2 inhibition	-	0.6127	61.27%
CYP2C8 inhibition	-	0.9330	93.30%
CYP inhibitory promiscuity	-	0.8003	80.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8344	83.44%
Carcinogenicity (trinary)	Non-required	0.5807	58.07%
Eye corrosion	-	0.9246	92.46%
Eye irritation	+	0.6719	67.19%
Skin irritation	-	0.5539	55.39%
Skin corrosion	-	0.9113	91.13%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4769	47.69%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5431	54.31%
skin sensitisation	+	0.5338	53.38%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	+	0.6980	69.80%
Acute Oral Toxicity (c)	III	0.5990	59.90%
Estrogen receptor binding	-	0.7276	72.76%
Androgen receptor binding	-	0.5800	58.00%
Thyroid receptor binding	-	0.7240	72.40%
Glucocorticoid receptor binding	-	0.4680	46.80%
Aromatase binding	-	0.7256	72.56%
PPAR gamma	-	0.5287	52.87%
Honey bee toxicity	-	0.8738	87.38%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9918	99.18%

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	96.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.21%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.54%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.66%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.29%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.24%	89.34%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.00%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.86%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.74%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.96%	95.50%

Plants that contains it

• Anthemis auriculata
• Anthemis cotula

Cross-Links

• PubChem: 12050675
• LOTUS: LTS0267297
• wikiData: Q105311918