NAV

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

Identification

Generic Name
N-{[(2S,3S)-3-(ETHOXYCARBONYL)OXIRAN-2-YL]CARBONYL}-L-ISOLEUCINE
DrugBank Accession Number
DB07160
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 273.2824
Monoisotopic: 273.121237345
Chemical Formula
C12H19NO6
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCathepsin BNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
Aliphatic heteromonocyclic compound / Branched fatty acid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid ester / Dialkyl ether / Dicarboxylic acid or derivatives / Epoxy fatty acid / Ether
show 21 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@](C)(CC)[C@]([H])(NC(=O)[C@@]1([H])O[C@]1([H])C(=O)OCC)C(O)=O

References

General References
Not Available
PubChem Compound
23647357
PubChem Substance
99443631
ChemSpider
25057004
BindingDB
16497
ZINC
ZINC000014961462
PDBe Ligand
59A
PDB Entries
2dc8

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-100s-9640000000-4423244b08e849ae93a5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9770000000-057693e94b674c74f57a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0g59-2790000000-637d513d5b6e0fc853c1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-7910000000-3b398cf6746b0b1ef118
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-9500000000-18605ca65c75a173157c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9310000000-0f2c035674a1bc0603a9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9310000000-05c5812b754aabe667b5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-162.50648
predicted
DeepCCS 1.0 (2019)
[M+H]+164.90204
predicted
DeepCCS 1.0 (2019)
[M+Na]+172.16588
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cathepsin B
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:19 / Updated at June 12, 2020 16:52