(4S)-4-[(2R)-2-hydroperoxy-3-[[(2S,4R)-4-methyl-5-oxooxolan-2-yl]methyl]but-3-enyl]-3-methylideneoxolan-2-one

Details

• Internal ID: 8104f361-c3c0-4b4d-a323-6b2c45193b78
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (4S)-4-[(2R)-2-hydroperoxy-3-[[(2S,4R)-4-methyl-5-oxooxolan-2-yl]methyl]but-3-enyl]-3-methylideneoxolan-2-one
• SMILES (Canonical): CC1CC(OC1=O)CC(=C)C(CC2COC(=O)C2=C)OO
• SMILES (Isomeric): C[C@@H]1C[C@H](OC1=O)CC(=C)[C@@H](C[C@@H]2COC(=O)C2=C)OO
• InChI: InChI=1S/C15H20O6/c1-8(4-12-5-9(2)14(16)20-12)13(21-18)6-11-7-19-15(17)10(11)3/h9,11-13,18H,1,3-7H2,2H3/t9-,11-,12-,13-/m1/s1
• InChI Key: RVCYZETYOBPXIA-OJAKKHQRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₆
• Molecular Weight: 296.31 g/mol
• Exact Mass: 296.12598835 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9096	90.96%
Caco-2	-	0.6079	60.79%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8173	81.73%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.9107	91.07%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8268	82.68%
P-glycoprotein inhibitior	-	0.8690	86.90%
P-glycoprotein substrate	-	0.5699	56.99%
CYP3A4 substrate	+	0.5882	58.82%
CYP2C9 substrate	-	0.5839	58.39%
CYP2D6 substrate	-	0.8850	88.50%
CYP3A4 inhibition	-	0.8237	82.37%
CYP2C9 inhibition	-	0.7268	72.68%
CYP2C19 inhibition	-	0.7643	76.43%
CYP2D6 inhibition	-	0.9138	91.38%
CYP1A2 inhibition	-	0.7454	74.54%
CYP2C8 inhibition	-	0.8278	82.78%
CYP inhibitory promiscuity	-	0.8211	82.11%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8078	80.78%
Carcinogenicity (trinary)	Non-required	0.5724	57.24%
Eye corrosion	-	0.9542	95.42%
Eye irritation	-	0.6814	68.14%
Skin irritation	-	0.6985	69.85%
Skin corrosion	-	0.8691	86.91%
Ames mutagenesis	-	0.5324	53.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.7263	72.63%
Micronuclear	-	0.6541	65.41%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7521	75.21%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.6301	63.01%
Acute Oral Toxicity (c)	III	0.6430	64.30%
Estrogen receptor binding	+	0.7766	77.66%
Androgen receptor binding	+	0.5578	55.78%
Thyroid receptor binding	+	0.6453	64.53%
Glucocorticoid receptor binding	+	0.7784	77.84%
Aromatase binding	+	0.5899	58.99%
PPAR gamma	-	0.5146	51.46%
Honey bee toxicity	-	0.7599	75.99%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9795	97.95%

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	95.52%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.44%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	92.36%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.51%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.46%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.00%	98.95%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.15%	90.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.44%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.45%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.08%	86.33%

Plants that contains it

• Anthemis auriculata

Cross-Links

• PubChem: 163105879
• LOTUS: LTS0223277
• wikiData: Q105245974