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

Identification

Name
N-{[(2S,3S)-3-(ETHOXYCARBONYL)OXIRAN-2-YL]CARBONYL}-L-ISOLEUCYL-L-ALANINE
Accession Number
DB07224
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: 344.3603
Monoisotopic: 344.158351132
Chemical Formula
C15H24N2O7
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][[email protected]@](C)(NC(=O)[[email protected]@]([H])(NC(=O)[[email protected]@]1([H])O[[email protected]]1([H])C(=O)OCC)[[email protected]@]([H])(C)CC)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
23647358
PubChem Substance
99443695
ChemSpider
25056578
BindingDB
16499
HET
75V
PDB Entries
2dca

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 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-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 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
Alpha-dipeptide / Isoleucine or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / N-acyl-l-alpha-amino acid / Alpha-amino acid amide / Alanine or derivatives / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / N-acyl-amine
show 23 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