NAV

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

Identification

Generic Name
N-{[(2S,3S)-3-(ETHOXYCARBONYL)OXIRAN-2-YL]CARBONYL}-L-ISOLEUCYL-L-ALANINE
DrugBank Accession Number
DB07224
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 344.3603
Monoisotopic: 344.158351132
Chemical Formula
C15H24N2O7
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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Isoleucine and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Alanine and derivatives / Oxirane carboxylic acids / Dicarboxylic acids and derivatives / N-acyl amines / Secondary carboxylic acid amides / Carboxylic acid esters / Oxacyclic compounds
show 7 more
Substituents
Alanine or derivatives / Aliphatic heteromonocyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid ester / Dialkyl ether
show 23 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
FCCIQOJEDMDETP-QHZLYTNSSA-N
InChI
InChI=1S/C15H24N2O7/c1-5-7(3)9(12(18)16-8(4)14(20)21)17-13(19)10-11(24-10)15(22)23-6-2/h7-11H,5-6H2,1-4H3,(H,16,18)(H,17,19)(H,20,21)/t7-,8-,9-,10-,11-/m0/s1
IUPAC Name
(2S)-2-[(2S,3S)-2-{[(2S,3S)-3-(ethoxycarbonyl)oxiran-2-yl]formamido}-3-methylpentanamido]propanoic acid
SMILES
[H][C@@](C)(NC(=O)[C@@]([H])(NC(=O)[C@@]1([H])O[C@]1([H])C(=O)OCC)[C@@]([H])(C)CC)C(O)=O

References

General References
Not Available
PubChem Compound
23647358
PubChem Substance
99443695
ChemSpider
25056578
BindingDB
16499
ZINC
ZINC000014961470
PDBe Ligand
75V
PDB Entries
2dca

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 Solubility5.49 mg/mLALOGPS
logP1.04ALOGPS
logP0.095Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.8Chemaxon
pKa (Strongest Basic)-3.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area134.33 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity80.41 m3·mol-1Chemaxon
Polarizability34.47 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6491
Blood Brain Barrier-0.8263
Caco-2 permeable-0.6975
P-glycoprotein substrateSubstrate0.5114
P-glycoprotein inhibitor INon-inhibitor0.5328
P-glycoprotein inhibitor IINon-inhibitor0.8294
Renal organic cation transporterNon-inhibitor0.9763
CYP450 2C9 substrateNon-substrate0.8546
CYP450 2D6 substrateNon-substrate0.8373
CYP450 3A4 substrateNon-substrate0.6041
CYP450 1A2 substrateNon-inhibitor0.7783
CYP450 2C9 inhibitorNon-inhibitor0.8064
CYP450 2D6 inhibitorNon-inhibitor0.876
CYP450 2C19 inhibitorNon-inhibitor0.777
CYP450 3A4 inhibitorInhibitor0.5192
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9017
Ames testNon AMES toxic0.6865
CarcinogenicityNon-carcinogens0.8488
BiodegradationNot ready biodegradable0.8361
Rat acute toxicity2.2711 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9984
hERG inhibition (predictor II)Non-inhibitor0.9651
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-MSsplash10-00vs-7291000000-1fd72ecfd3479bc3d7ad
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a73-1494000000-19051b3a2a82f1050e2a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-06r5-2593000000-0fbee5d35bb1db19a3e2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ec-4921000000-3bd515500ac48899d9b0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uyj-9650000000-c286272a315250e1f79c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-6930000000-d626f3ba982d6aaa2d4e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uyl-7920000000-83519941a60199061ce9
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]-175.26079
predicted
DeepCCS 1.0 (2019)
[M+H]+177.13841
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.74425
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