N-[(benzyloxy)carbonyl]-L-leucyl-N-[(1S)-3-fluoro-1-(4-hydroxybenzyl)-2-oxopropyl]-L-leucinamide

Identification

Generic Name
N-[(benzyloxy)carbonyl]-L-leucyl-N-[(1S)-3-fluoro-1-(4-hydroxybenzyl)-2-oxopropyl]-L-leucinamide
DrugBank Accession Number
DB04653
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 557.6535
Monoisotopic: 557.290114232
Chemical Formula
C30H40FN3O6
Synonyms
  • Calpain inhibitor IV
  • CBZ-LEU-LEU-TYR-CH2F
  • N-[(benzyloxy)carbonyl]leucyl-N(1)-[3-fluoro-1-(4-hydroxybenzyl)-2-oxopropyl]leucinamide

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCalpain-1 catalytic subunitNot 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
Medicalerrors
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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
Leucine and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Benzyloxycarbonyls / Amphetamines and derivatives / 1-hydroxy-2-unsubstituted benzenoids / N-acyl amines / Carbamate esters / Alpha-haloketones / Secondary carboxylic acid amides
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Substituents
1-hydroxy-2-unsubstituted benzenoid / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Alpha-haloketone / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid
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Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
133410-84-1
InChI Key
JCRSHQCFRMCMOC-GSDHBNRESA-N
InChI
InChI=1S/C30H40FN3O6/c1-19(2)14-25(28(37)32-24(27(36)17-31)16-21-10-12-23(35)13-11-21)33-29(38)26(15-20(3)4)34-30(39)40-18-22-8-6-5-7-9-22/h5-13,19-20,24-26,35H,14-18H2,1-4H3,(H,32,37)(H,33,38)(H,34,39)/t24-,25-,26-/m0/s1
IUPAC Name
benzyl N-[(1S)-1-{[(1S)-1-{[(2S)-4-fluoro-1-(4-hydroxyphenyl)-3-oxobutan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamate
SMILES
[H]N([C@@H](CC(C)C)C(=O)N([H])[C@@H](CC(C)C)C(=O)N([H])[C@@H](CC1=CC=C(O)C=C1)C(=O)CF)C(=O)OCC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
11505008
PubChem Substance
46507912
ChemSpider
9679808
ChEMBL
CHEMBL72006
ZINC
ZINC000026289134
PDBe Ligand
C1N
PDB Entries
1zcm

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 Solubility0.00384 mg/mLALOGPS
logP3.84ALOGPS
logP4.78ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.83 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity148.28 m3·mol-1ChemAxon
Polarizability59.42 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8774
Blood Brain Barrier-0.7493
Caco-2 permeable-0.7693
P-glycoprotein substrateSubstrate0.7795
P-glycoprotein inhibitor INon-inhibitor0.7683
P-glycoprotein inhibitor IINon-inhibitor0.874
Renal organic cation transporterNon-inhibitor0.9234
CYP450 2C9 substrateNon-substrate0.6536
CYP450 2D6 substrateNon-substrate0.7682
CYP450 3A4 substrateSubstrate0.5591
CYP450 1A2 substrateNon-inhibitor0.5997
CYP450 2C9 inhibitorNon-inhibitor0.7022
CYP450 2D6 inhibitorNon-inhibitor0.8203
CYP450 2C19 inhibitorInhibitor0.6096
CYP450 3A4 inhibitorNon-inhibitor0.5923
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7581
Ames testNon AMES toxic0.8052
CarcinogenicityNon-carcinogens0.8901
BiodegradationNot ready biodegradable0.9605
Rat acute toxicity2.5586 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9928
hERG inhibition (predictor II)Non-inhibitor0.9206
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

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Calcium-dependent cysteine-type endopeptidase activity
Specific Function
Calcium-regulated non-lysosomal thiol-protease which catalyze limited proteolysis of substrates involved in cytoskeletal remodeling and signal transduction.
Gene Name
CAPN1
Uniprot ID
P07384
Uniprot Name
Calpain-1 catalytic subunit
Molecular Weight
81889.325 Da

Drug created on September 11, 2007 17:49 / Updated on June 12, 2020 16:52