METHYL N-({(2S,3S)-3-[(PROPYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINATE

Identification

Name
METHYL N-({(2S,3S)-3-[(PROPYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINATE
Accession Number
DB07223
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: 397.4659
Monoisotopic: 397.221285739
Chemical Formula
C19H31N3O6
InChI Key
XGWSRLSPWIEMLQ-YTFOTSKYSA-N
InChI
InChI=1S/C19H31N3O6/c1-5-9-20-16(23)14-15(28-14)17(24)21-13(11(3)6-2)18(25)22-10-7-8-12(22)19(26)27-4/h11-15H,5-10H2,1-4H3,(H,20,23)(H,21,24)/t11-,12-,13-,14-,15-/m0/s1
IUPAC Name
methyl (2S)-1-[(2S,3S)-3-methyl-2-{[(2S,3S)-3-(propylcarbamoyl)oxiran-2-yl]formamido}pentanoyl]pyrrolidine-2-carboxylate
SMILES
[H][[email protected]](C)(CC)[[email protected]]([H])(NC(=O)[[email protected]@]1([H])O[[email protected]]1([H])C(=O)NCCC)C(=O)N1CCC[[email protected]@]1([H])C(=O)OC

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
6610318
PubChem Substance
99443694
ChemSpider
5042571
BindingDB
16503
ChEMBL
CHEMBL262103
HET
74M
PDB Entries
2dc9

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 Solubility2.9 mg/mLALOGPS
logP0.76ALOGPS
logP0.31ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.34 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity99.34 m3·mol-1ChemAxon
Polarizability41.9 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8421
Blood Brain Barrier-0.7765
Caco-2 permeable-0.6654
P-glycoprotein substrateSubstrate0.7129
P-glycoprotein inhibitor IInhibitor0.5386
P-glycoprotein inhibitor IIInhibitor0.506
Renal organic cation transporterNon-inhibitor0.9269
CYP450 2C9 substrateNon-substrate0.9096
CYP450 2D6 substrateNon-substrate0.8197
CYP450 3A4 substrateSubstrate0.5243
CYP450 1A2 substrateNon-inhibitor0.7625
CYP450 2C9 inhibitorNon-inhibitor0.775
CYP450 2D6 inhibitorNon-inhibitor0.8701
CYP450 2C19 inhibitorNon-inhibitor0.7213
CYP450 3A4 inhibitorInhibitor0.5831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7654
Ames testNon AMES toxic0.6917
CarcinogenicityNon-carcinogens0.8652
BiodegradationNot ready biodegradable0.8975
Rat acute toxicity2.4300 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9853
hERG inhibition (predictor II)Non-inhibitor0.7976
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/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 peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Peptides
Alternative Parents
Isoleucine and derivatives / Alpha amino acid esters / Proline and derivatives / N-acyl-alpha amino acids / Alpha amino acid amides / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Oxirane carboxylic acids and derivatives / Methyl esters / Tertiary carboxylic acid amides
show 10 more
Substituents
Alpha peptide / Isoleucine or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / Alpha-amino acid ester / Proline or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / N-acylpyrrolidine / Pyrrolidine carboxylic acid
show 24 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Cathepsin B
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