NAV

N2-[(benzyloxy)carbonyl]-n1-[(3S)-1-cyanopyrrolidin-3-yl]-l-leucinamide

Identification

Generic Name
N2-[(benzyloxy)carbonyl]-n1-[(3S)-1-cyanopyrrolidin-3-yl]-l-leucinamide
DrugBank Accession Number
DB03456
Background

N2-[(benzyloxy)carbonyl]-n1-[(3S)-1-cyanopyrrolidin-3-yl]-l-leucinamide is a solid. This compound belongs to the n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. It is known to target cathepsin K.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 358.4347
Monoisotopic: 358.200490718
Chemical Formula
C19H26N4O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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-acyl amines / Pyrrolidines / Carbamate esters / Secondary carboxylic acid amides / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Alpha-amino acid amide / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboxamide group / Fatty acyl
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
L-leucine derivative, pyrrolidinecarbonitrile (CHEBI:44309)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
IMTUSTXBVIALBC-SJORKVTESA-N
InChI
InChI=1S/C19H26N4O3/c1-14(2)10-17(18(24)21-16-8-9-23(11-16)13-20)22-19(25)26-12-15-6-4-3-5-7-15/h3-7,14,16-17H,8-12H2,1-2H3,(H,21,24)(H,22,25)/t16-,17+/m1/s1
IUPAC Name
benzyl N-[(1S)-1-{[(3R)-1-cyanopyrrolidin-3-yl]carbamoyl}-3-methylbutyl]carbamate
SMILES
[H][C@@](CC(C)C)(NC(=O)OCC1=CC=CC=C1)C(=O)N[C@]1([H])CCN(C1)C#N

References

General References
Not Available
PubChem Compound
5288988
PubChem Substance
46504451
ChemSpider
4451045
ZINC
ZINC000012503669
PDBe Ligand
NBL
PDB Entries
1yk7

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 Solubility0.137 mg/mLALOGPS
logP1.58ALOGPS
logP2.2Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.45Chemaxon
pKa (Strongest Basic)-3.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area94.46 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity98.11 m3·mol-1Chemaxon
Polarizability38.51 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9784
Blood Brain Barrier-0.6998
Caco-2 permeable-0.7086
P-glycoprotein substrateSubstrate0.7864
P-glycoprotein inhibitor IInhibitor0.5702
P-glycoprotein inhibitor IINon-inhibitor0.7772
Renal organic cation transporterNon-inhibitor0.8788
CYP450 2C9 substrateNon-substrate0.7836
CYP450 2D6 substrateNon-substrate0.804
CYP450 3A4 substrateSubstrate0.511
CYP450 1A2 substrateNon-inhibitor0.7235
CYP450 2C9 inhibitorNon-inhibitor0.7789
CYP450 2D6 inhibitorNon-inhibitor0.9043
CYP450 2C19 inhibitorInhibitor0.5422
CYP450 3A4 inhibitorNon-inhibitor0.6574
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7727
Ames testNon AMES toxic0.7491
CarcinogenicityNon-carcinogens0.9297
BiodegradationReady biodegradable0.6335
Rat acute toxicity2.4411 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9146
hERG inhibition (predictor II)Non-inhibitor0.6537
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/MSsplash10-0a4l-4093000000-1175356b9ce1284971dd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bt9-1930000000-9c696cea7b8e60f4f2ec
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9683000000-e22b332b0036c832759a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-3490000000-c3729c84f9a302909dcd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-9410000000-f2d33904c14c456d4ebd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-5901000000-41df47a17adefe959f97
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-186.23457
predicted
DeepCCS 1.0 (2019)
[M+H]+188.64629
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.92853
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 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. 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