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

Identification

Generic Name
BENZYL N-({(2S,3S)-3-[(PROPYLAMINO)CARBONYL]OXIRAN-2-YL}CARBONYL)-L-ISOLEUCYL-L-PROLINATE
DrugBank Accession Number
DB07219
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 473.5619
Monoisotopic: 473.252585867
Chemical Formula
C25H35N3O6
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
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 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 / Alpha-amino acid amide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbonyl group / Carboxamide group
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@](C)(CC)[C@]([H])(NC(=O)[C@@]1([H])O[C@]1([H])C(=O)NCCC)C(=O)N1CCC[C@@]1([H])C(=O)OCC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
22850133
PubChem Substance
99443690
ChemSpider
18741757
BindingDB
16504
ZINC
ZINC000014961495
PDBe Ligand
73V
PDB Entries
2dc6

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 Solubility0.097 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
Polarizability50.97 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

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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