Valilactone

Details

• Internal ID: f6884f0f-fcf1-494d-8925-5e5aa07453cb
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acid esters
• IUPAC Name: [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]heptan-2-yl] (2S)-2-formamido-3-methylbutanoate
• InChI: InChI=1S/C22H39NO5/c1-5-7-9-11-13-18-19(28-21(18)25)14-17(12-10-8-6-2)27-22(26)20(16(3)4)23-15-24/h15-20H,5-14H2,1-4H3,(H,23,24)/t17-,18-,19-,20-/m0/s1
• InChI Key: WWGVIIVMPMBQFV-MUGJNUQGSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₉NO₅
• Molecular Weight: 397.50 g/mol
• Exact Mass: 397.28282334 g/mol
• Topological Polar Surface Area (TPSA): 81.70 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 4.15
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 16

Synonyms

• 113276-96-3
• (-)-Valilactone
• [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]heptan-2-yl] (2S)-2-formamido-3-methylbutanoate
• CHEMBL492253
• SCHEMBL4121010
• BDBM24571
• DTXSID80921027
• 5-(N-Formyl-L-valinyloxy)-2-hexyl-3-hydroxydecanoic lactone
• AKOS040749737
• L-Valine, N-formyl-, 1-((3-hexyl-4-oxo-2-oxetanyl)methyl)hexyl ester, (2S-(2alpha(R*),3beta))-
• HY-124258
• CS-0086049
• 1-(3-Hexyl-4-oxooxetan-2-yl)heptan-2-yl N-(hydroxymethylidene)valinate
• (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]heptan-2-yl (2S)-2-formamido-3-methylbutanoate
• (S)-(S)-1-((2S,3S)-3-Hexyl-4-oxooxetan-2-yl)heptan-2-yl 2-formamido-3-methylbutanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9438	94.38%
Caco-2	-	0.5461	54.61%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6065	60.65%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9259	92.59%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6178	61.78%
BSEP inhibitior	-	0.4922	49.22%
P-glycoprotein inhibitior	-	0.4568	45.68%
P-glycoprotein substrate	-	0.5465	54.65%
CYP3A4 substrate	+	0.6131	61.31%
CYP2C9 substrate	-	0.6017	60.17%
CYP2D6 substrate	-	0.8690	86.90%
CYP3A4 inhibition	-	0.7364	73.64%
CYP2C9 inhibition	-	0.7915	79.15%
CYP2C19 inhibition	-	0.6580	65.80%
CYP2D6 inhibition	-	0.8944	89.44%
CYP1A2 inhibition	-	0.8243	82.43%
CYP2C8 inhibition	-	0.7486	74.86%
CYP inhibitory promiscuity	-	0.9042	90.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6157	61.57%
Eye corrosion	-	0.9749	97.49%
Eye irritation	-	0.9101	91.01%
Skin irritation	-	0.7911	79.11%
Skin corrosion	-	0.9368	93.68%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6738	67.38%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.5341	53.41%
skin sensitisation	-	0.8708	87.08%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	-	0.6830	68.30%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.8673	86.73%
Acute Oral Toxicity (c)	III	0.6839	68.39%
Estrogen receptor binding	+	0.5641	56.41%
Androgen receptor binding	-	0.5269	52.69%
Thyroid receptor binding	+	0.6218	62.18%
Glucocorticoid receptor binding	+	0.7454	74.54%
Aromatase binding	-	0.5452	54.52%
PPAR gamma	-	0.5625	56.25%
Honey bee toxicity	-	0.8371	83.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.7290	72.90%
Fish aquatic toxicity	+	0.9270	92.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5545	Q9Y4D2	Sn1-specific diacylglycerol lipase alpha	35 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL230	P35354	Cyclooxygenase-2	98.47%	89.63%
CHEMBL299	P17252	Protein kinase C alpha	96.51%	98.03%
CHEMBL4072	P07858	Cathepsin B	96.42%	93.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.51%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.08%	98.95%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	92.34%	97.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.28%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.77%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.63%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.60%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.34%	97.25%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.70%	95.17%
CHEMBL2996	Q05655	Protein kinase C delta	89.63%	97.79%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	89.33%	92.86%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	88.60%	90.24%
CHEMBL4040	P28482	MAP kinase ERK2	88.37%	83.82%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.51%	85.31%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.22%	96.77%
CHEMBL4588	P22894	Matrix metalloproteinase 8	86.05%	94.66%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	84.46%	95.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.60%	96.90%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.47%	89.34%
CHEMBL2514	O95665	Neurotensin receptor 2	83.33%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.20%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	83.06%	92.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.62%	90.08%
CHEMBL3401	O75469	Pregnane X receptor	82.47%	94.73%
CHEMBL3891	P07384	Calpain 1	82.40%	93.04%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.25%	94.80%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.06%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.94%	95.56%
CHEMBL3776	Q14790	Caspase-8	81.70%	97.06%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.43%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.67%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.50%	96.00%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.19%	92.32%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 195004
• LOTUS: LTS0033303
• wikiData: Q82893755