NAV

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

Identification

Generic Name
N-{[(2S,3S)-3-(ETHOXYCARBONYL)OXIRAN-2-YL]CARBONYL}-L-ISOLEUCYL-L-ISOLEUCINE
DrugBank Accession Number
DB07225
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 386.44
Monoisotopic: 386.205301324
Chemical Formula
C18H30N2O7
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 / Epoxy fatty acids / Methyl-branched fatty acids / Oxirane carboxylic acids / Dicarboxylic acids and derivatives / N-acyl amines / Secondary carboxylic acid amides / Carboxylic acid esters
show 8 more
Substituents
Aliphatic heteromonocyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Branched fatty acid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid ester / Dialkyl ether
show 27 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
CFABOFMUPCWOPC-LHEWDLALSA-N
InChI
InChI=1S/C18H30N2O7/c1-6-9(4)11(15(21)20-12(17(23)24)10(5)7-2)19-16(22)13-14(27-13)18(25)26-8-3/h9-14H,6-8H2,1-5H3,(H,19,22)(H,20,21)(H,23,24)/t9-,10-,11-,12-,13-,14-/m0/s1
IUPAC Name
(2S,3S)-2-[(2S,3S)-2-{[(2S,3S)-3-(ethoxycarbonyl)oxiran-2-yl]formamido}-3-methylpentanamido]-3-methylpentanoic acid
SMILES
[H][C@](C)(CC)[C@]([H])(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
46937062
PubChem Substance
99443696
ChemSpider
25060305
ZINC
ZINC000014961474
PDBe Ligand
76V
PDB Entries
2dcb

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 Solubility1.83 mg/mLALOGPS
logP1.65ALOGPS
logP1.43Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.97Chemaxon
pKa (Strongest Basic)-3.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area134.33 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity94.01 m3·mol-1Chemaxon
Polarizability40.17 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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01p6-4679000000-a7ea111e14706819c33b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014r-1598000000-f13f5ebefadb2bd734fd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ql-5922000000-a9e4be7543c4be2ac502
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-017j-8691000000-8f72bb18a340391322e0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ir9-6913000000-df05aad772671780565a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6921000000-a62b1b8c40f450f97ecc
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]-192.71411
predicted
DeepCCS 1.0 (2019)
[M+H]+194.539
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.17035
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