N2-[(Benzyloxy)carbonyl]-N-[(3R)-1-{N-[(benzyloxy)carbonyl]-L-leucyl}-4-oxo-3-pyrrolidinyl]-L-leucinamide

Identification

Generic Name
N2-[(Benzyloxy)carbonyl]-N-[(3R)-1-{N-[(benzyloxy)carbonyl]-L-leucyl}-4-oxo-3-pyrrolidinyl]-L-leucinamide
DrugBank Accession Number
DB03405
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 594.6985
Monoisotopic: 594.305349718
Chemical Formula
C32H42N4O7
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCathepsin KNot 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
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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 leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Leucine and derivatives
Alternative Parents
Alpha amino acid amides / Benzyloxycarbonyls / N-acylpyrrolidines / Pyrrolidine-3-ones / N-acyl amines / Tertiary carboxylic acid amides / Carbamate esters / Secondary carboxylic acid amides / Cyclic ketones / Azacyclic compounds
show 3 more
Substituents
3-pyrrolidone / Alpha-amino acid amide / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbamic acid ester / Carbonyl group / Carboxamide group / Cyclic ketone
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrrolidinone, N-acylpyrrolidine, L-leucine derivative (CHEBI:44954)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
GXENQLUSOCKXDN-GMQQYTKMSA-N
InChI
InChI=1S/C32H42N4O7/c1-21(2)15-25(34-31(40)42-19-23-11-7-5-8-12-23)29(38)33-27-17-36(18-28(27)37)30(39)26(16-22(3)4)35-32(41)43-20-24-13-9-6-10-14-24/h5-14,21-22,25-27H,15-20H2,1-4H3,(H,33,38)(H,34,40)(H,35,41)/t25-,26-,27+/m0/s1
IUPAC Name
benzyl N-[(2S)-1-[(3R)-3-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-4-oxopyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]carbamate
SMILES
[H]N([C@@H](CC(C)C)C(=O)N([H])[C@@H]1CN(CC1=O)C(=O)[C@H](CC(C)C)N([H])C(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
5289122
PubChem Substance
46506182
ChemSpider
4451150
ZINC
ZINC000014096696
PDBe Ligand
PCM
PDB Entries
1au3

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 Solubility0.0045 mg/mLALOGPS
logP2.89ALOGPS
logP4.28Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)12.3Chemaxon
pKa (Strongest Basic)-3.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area143.14 Å2Chemaxon
Rotatable Bond Count15Chemaxon
Refractivity158.89 m3·mol-1Chemaxon
Polarizability64.46 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.981
Blood Brain Barrier-0.9339
Caco-2 permeable-0.7536
P-glycoprotein substrateSubstrate0.8011
P-glycoprotein inhibitor IInhibitor0.9385
P-glycoprotein inhibitor IIInhibitor0.6834
Renal organic cation transporterNon-inhibitor0.8733
CYP450 2C9 substrateNon-substrate0.7713
CYP450 2D6 substrateNon-substrate0.7868
CYP450 3A4 substrateSubstrate0.737
CYP450 1A2 substrateNon-inhibitor0.9086
CYP450 2C9 inhibitorNon-inhibitor0.8324
CYP450 2D6 inhibitorNon-inhibitor0.8553
CYP450 2C19 inhibitorInhibitor0.5712
CYP450 3A4 inhibitorNon-inhibitor0.67
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5816
Ames testNon AMES toxic0.8406
CarcinogenicityNon-carcinogens0.8515
BiodegradationNot ready biodegradable0.9268
Rat acute toxicity2.7478 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8964
hERG inhibition (predictor II)Inhibitor0.5704
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

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Details
1. Cathepsin K
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Proteoglycan binding
Specific Function
Closely involved in osteoclastic bone resorption and may participate partially in the disorder of bone remodeling. Displays potent endoprotease activity against fibrinogen at acid pH. May play an i...
Gene Name
CTSK
Uniprot ID
P43235
Uniprot Name
Cathepsin K
Molecular Weight
36965.82 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52