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

Identification

Name
BENZYL N-({(2S,3S)-3-[(PROPYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINATE
Accession Number
DB07219
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: 473.5619
Monoisotopic: 473.252585867
Chemical Formula
C25H35N3O6
InChI Key
OMQNYWZURFTFHE-MQBSTWLZSA-N
InChI
InChI=1S/C25H35N3O6/c1-4-13-26-22(29)20-21(34-20)23(30)27-19(16(3)5-2)24(31)28-14-9-12-18(28)25(32)33-15-17-10-7-6-8-11-17/h6-8,10-11,16,18-21H,4-5,9,12-15H2,1-3H3,(H,26,29)(H,27,30)/t16-,18-,19-,20-,21-/m0/s1
IUPAC Name
benzyl (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)OCC1=CC=CC=C1

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
22850133
PubChem Substance
99443690
ChemSpider
18741757
BindingDB
16504
HET
73V
PDB Entries
2dc6

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 Solubility0.1 mg/mLALOGPS
logP2.38ALOGPS
logP2.03ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)12.15ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.34 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity123.96 m3·mol-1ChemAxon
Polarizability51.15 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.971
Blood Brain Barrier-0.8943
Caco-2 permeable-0.6941
P-glycoprotein substrateSubstrate0.731
P-glycoprotein inhibitor IInhibitor0.6101
P-glycoprotein inhibitor IINon-inhibitor0.6769
Renal organic cation transporterNon-inhibitor0.9074
CYP450 2C9 substrateNon-substrate0.8907
CYP450 2D6 substrateNon-substrate0.8387
CYP450 3A4 substrateNon-substrate0.5255
CYP450 1A2 substrateNon-inhibitor0.7815
CYP450 2C9 inhibitorNon-inhibitor0.7716
CYP450 2D6 inhibitorNon-inhibitor0.8144
CYP450 2C19 inhibitorNon-inhibitor0.5348
CYP450 3A4 inhibitorInhibitor0.8817
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5923
Ames testNon AMES toxic0.7133
CarcinogenicityNon-carcinogens0.8403
BiodegradationNot ready biodegradable0.9472
Rat acute toxicity2.3991 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9723
hERG inhibition (predictor II)Non-inhibitor0.7313
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 / Proline and derivatives / Alpha amino acid esters / N-acyl-alpha amino acids / Alpha amino acid amides / Benzyloxycarbonyls / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Oxirane carboxylic acids and derivatives / Tertiary carboxylic acid amides
show 11 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 / Benzyloxycarbonyl / Alpha-amino acid or derivatives / N-acylpyrrolidine
show 26 more
Molecular Framework
Aromatic 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