(5S)-3-methylidene-5-[(Z)-2-methyl-4-(4-methylidene-5-oxooxolan-3-yl)but-2-enyl]oxolan-2-one

Details

• Internal ID: 4adbdd18-ed91-4944-828a-39313bb589a5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (5S)-3-methylidene-5-[(Z)-2-methyl-4-(4-methylidene-5-oxooxolan-3-yl)but-2-enyl]oxolan-2-one
• SMILES (Canonical): CC(=CCC1COC(=O)C1=C)CC2CC(=C)C(=O)O2
• SMILES (Isomeric): C/C(=C/CC1COC(=O)C1=C)/C[C@H]2CC(=C)C(=O)O2
• InChI: InChI=1S/C15H18O4/c1-9(6-13-7-10(2)14(16)19-13)4-5-12-8-18-15(17)11(12)3/h4,12-13H,2-3,5-8H2,1H3/b9-4-/t12?,13-/m0/s1
• InChI Key: KHEYJBCVWLIDAG-HNINGHOPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.31
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9857	98.57%
Caco-2	+	0.4898	48.98%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7370	73.70%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8854	88.54%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9075	90.75%
P-glycoprotein inhibitior	-	0.8783	87.83%
P-glycoprotein substrate	-	0.7879	78.79%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	+	0.5973	59.73%
CYP2D6 substrate	-	0.8555	85.55%
CYP3A4 inhibition	-	0.8676	86.76%
CYP2C9 inhibition	-	0.8168	81.68%
CYP2C19 inhibition	-	0.7970	79.70%
CYP2D6 inhibition	-	0.9214	92.14%
CYP1A2 inhibition	-	0.6215	62.15%
CYP2C8 inhibition	-	0.8508	85.08%
CYP inhibitory promiscuity	-	0.8507	85.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8351	83.51%
Carcinogenicity (trinary)	Non-required	0.5897	58.97%
Eye corrosion	-	0.9266	92.66%
Eye irritation	-	0.5851	58.51%
Skin irritation	-	0.5136	51.36%
Skin corrosion	-	0.8550	85.50%
Ames mutagenesis	+	0.5230	52.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.4657	46.57%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.6782	67.82%
skin sensitisation	-	0.6700	67.00%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	+	0.8030	80.30%
Acute Oral Toxicity (c)	III	0.7143	71.43%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5171	51.71%
Thyroid receptor binding	-	0.6144	61.44%
Glucocorticoid receptor binding	+	0.6541	65.41%
Aromatase binding	+	0.7592	75.92%
PPAR gamma	-	0.6145	61.45%
Honey bee toxicity	-	0.8381	83.81%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9885	98.85%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.90%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.19%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.84%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	88.12%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.03%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.26%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.88%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.46%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.90%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.10%	100.00%

Plants that contains it

• Anthemis pseudocotula

Cross-Links

• PubChem: 162817352
• LOTUS: LTS0014326
• wikiData: Q105141105