1-[N[(Phenylmethoxy)Carbonyl]-L-Leucyl-4-[[N/N-[(Phenylmethoxy)Carbonyl]-/Nl-Leucyl]Amino]-3-Pyrrolidinone/N

Identification

Name
1-[N[(Phenylmethoxy)Carbonyl]-L-Leucyl-4-[[N/N-[(Phenylmethoxy)Carbonyl]-/Nl-Leucyl]Amino]-3-Pyrrolidinone/N
Accession Number
DB03405  (EXPT02520)
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: 594.6985
Monoisotopic: 594.305349718
Chemical Formula
C32H42N4O7
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
(2S)-2-{[(benzyloxy)(hydroxy)methylidene]amino}-N-[(3R)-1-[(2S)-2-{[(benzyloxy)(hydroxy)methylidene]amino}-4-methylpentanoyl]-4-oxopyrrolidin-3-yl]-4-methylpentanimidic acid
SMILES
[H][[email protected]@](CC(C)C)(N=C(O)OCC1=CC=CC=C1)C(O)=N[[email protected]]1([H])CN(CC1=O)C(=O)[[email protected]]([H])(CC(C)C)N=C(O)OCC1=CC=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCathepsin KNot 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
5289122
PubChem Substance
46506182
ChemSpider
4451150
HET
PCM
PDB Entries
1au3

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 Solubility0.00489 mg/mLALOGPS
logP3.49ALOGPS
logP6.68ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)5.29ChemAxon
pKa (Strongest Basic)1.1ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area153.61 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity160.99 m3·mol-1ChemAxon
Polarizability64.83 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

Taxonomy

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
Leucine or derivatives / Alpha-amino acid amide / Benzyloxycarbonyl / N-acylpyrrolidine / Monocyclic benzene moiety / Fatty amide / N-acyl-amine / Pyrrolidone / 3-pyrrolidone / Benzenoid
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrrolidinone, N-acylpyrrolidine, L-leucine derivative (CHEBI:44954)

Targets

Details
1. Cathepsin K
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:13