N-{[(2S,3S)-3-(ETHOXYCARBONYL)OXIRAN-2-YL]CARBONYL}-L-ISOLEUCINE

Identification

Name
N-{[(2S,3S)-3-(ETHOXYCARBONYL)OXIRAN-2-YL]CARBONYL}-L-ISOLEUCINE
Accession Number
DB07160
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 273.2824
Monoisotopic: 273.121237345
Chemical Formula
C12H19NO6
InChI Key
MZJYLQZZISBOTF-JBDRJPRFSA-N
InChI
InChI=1S/C12H19NO6/c1-4-6(3)7(11(15)16)13-10(14)8-9(19-8)12(17)18-5-2/h6-9H,4-5H2,1-3H3,(H,13,14)(H,15,16)/t6-,7-,8-,9-/m0/s1
IUPAC Name
(2S,3S)-2-{[(2S,3S)-3-(ethoxycarbonyl)oxiran-2-yl]formamido}-3-methylpentanoic acid
SMILES
[H][[email protected]](C)(CC)[[email protected]]([H])(NC(=O)[[email protected]@]1([H])O[[email protected]]1([H])C(=O)OCC)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCathepsin BNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
23647357
PubChem Substance
99443631
ChemSpider
25057004
BindingDB
16497
HET
59A
PDB Entries
2dc8

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility27.6 mg/mLALOGPS
logP0.88ALOGPS
logP0.63ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.23 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity63.12 m3·mol-1ChemAxon
Polarizability27.57 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6162
Blood Brain Barrier-0.6968
Caco-2 permeable-0.6815
P-glycoprotein substrateNon-substrate0.631
P-glycoprotein inhibitor INon-inhibitor0.635
P-glycoprotein inhibitor IINon-inhibitor0.6945
Renal organic cation transporterNon-inhibitor0.973
CYP450 2C9 substrateNon-substrate0.8339
CYP450 2D6 substrateNon-substrate0.8333
CYP450 3A4 substrateNon-substrate0.5554
CYP450 1A2 substrateNon-inhibitor0.7762
CYP450 2C9 inhibitorNon-inhibitor0.7598
CYP450 2D6 inhibitorNon-inhibitor0.8794
CYP450 2C19 inhibitorNon-inhibitor0.786
CYP450 3A4 inhibitorNon-inhibitor0.5769
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8868
Ames testNon AMES toxic0.6672
CarcinogenicityNon-carcinogens0.873
BiodegradationReady biodegradable0.5
Rat acute toxicity2.2891 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.998
hERG inhibition (predictor II)Non-inhibitor0.959
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as isoleucine and derivatives. These are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Isoleucine and derivatives
Alternative Parents
N-acyl-L-alpha-amino acids / Methyl-branched fatty acids / Epoxy fatty acids / Oxirane carboxylic acids / Dicarboxylic acids and derivatives / Secondary carboxylic acid amides / Carboxylic acid esters / Oxacyclic compounds / Dialkyl ethers / Carboxylic acids
show 5 more
Substituents
Isoleucine or derivatives / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / N-acyl-l-alpha-amino acid / Branched fatty acid / Epoxy fatty acid / Heterocyclic fatty acid / Methyl-branched fatty acid / Dicarboxylic acid or derivatives / Oxirane carboxylic acid
show 21 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Proteoglycan binding
Specific Function
Thiol protease which is believed to participate in intracellular degradation and turnover of proteins. Has also been implicated in tumor invasion and metastasis.
Gene Name
CTSB
Uniprot ID
P07858
Uniprot Name
Cathepsin B
Molecular Weight
37821.35 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:19 / Updated on December 01, 2017 15:47