NAV

[1-(3-hydroxy-2-oxo-1-phenethyl-propylcarbamoyl)2-phenyl-ethyl]-carbamic acid pyridin-4-ylmethyl ester

Identification

Generic Name
[1-(3-hydroxy-2-oxo-1-phenethyl-propylcarbamoyl)2-phenyl-ethyl]-carbamic acid pyridin-4-ylmethyl ester
DrugBank Accession Number
DB02128
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 475.5363
Monoisotopic: 475.210721053
Chemical Formula
C27H29N3O5
Synonyms
  • N-[(3S)-1-hydroxy-2-oxo-5-phenyl-3-pentanyl]-Nα-[(3-pyridinylmethoxy)carbonyl]-L-phenylalaninamide
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCruzipainNot AvailableTrypanosoma cruzi
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 phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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
Phenylalanine and derivatives
Alternative Parents
Alpha amino acid amides / Amphetamines and derivatives / Pyridines and derivatives / Monosaccharides / Fatty amides / Heteroaromatic compounds / Carbamate esters / Alpha-hydroxy ketones / Secondary carboxylic acid amides / Azacyclic compounds
show 4 more
Substituents
Alcohol / Alpha-amino acid amide / Alpha-hydroxy ketone / Amphetamine or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbamic acid ester / Carbonyl group / Carboxamide group
show 17 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
QCUBCTPTNWPFBC-ZEQRLZLVSA-N
InChI
InChI=1S/C27H29N3O5/c31-18-25(32)23(14-13-20-8-3-1-4-9-20)29-26(33)24(16-21-10-5-2-6-11-21)30-27(34)35-19-22-12-7-15-28-17-22/h1-12,15,17,23-24,31H,13-14,16,18-19H2,(H,29,33)(H,30,34)/t23-,24-/m0/s1
IUPAC Name
(pyridin-3-yl)methyl N-[(1S)-1-{[(3S)-1-hydroxy-2-oxo-5-phenylpentan-3-yl]carbamoyl}-2-phenylethyl]carbamate
SMILES
[H]N([C@@H](CC1=CC=CC=C1)C(=O)N([H])[C@@H](CCC1=CC=CC=C1)C(=O)CO)C(=O)OCC1=CN=CC=C1

References

General References
Not Available
PubChem Compound
5289091
PubChem Substance
46507860
ChemSpider
4451125
ZINC
ZINC000012501625
PDBe Ligand
P10
PDB Entries
1me3

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 Solubility0.00492 mg/mLALOGPS
logP1.58ALOGPS
logP3.1Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)12.42Chemaxon
pKa (Strongest Basic)4.72Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area117.62 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity130.41 m3·mol-1Chemaxon
Polarizability50.03 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6715
Blood Brain Barrier-0.8181
Caco-2 permeable-0.7618
P-glycoprotein substrateSubstrate0.6483
P-glycoprotein inhibitor INon-inhibitor0.6093
P-glycoprotein inhibitor IINon-inhibitor0.6991
Renal organic cation transporterNon-inhibitor0.859
CYP450 2C9 substrateNon-substrate0.8303
CYP450 2D6 substrateNon-substrate0.8294
CYP450 3A4 substrateNon-substrate0.6253
CYP450 1A2 substrateNon-inhibitor0.8006
CYP450 2C9 inhibitorNon-inhibitor0.802
CYP450 2D6 inhibitorNon-inhibitor0.8338
CYP450 2C19 inhibitorNon-inhibitor0.7393
CYP450 3A4 inhibitorInhibitor0.5162
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7409
Ames testNon AMES toxic0.7612
CarcinogenicityNon-carcinogens0.9535
BiodegradationNot ready biodegradable0.8446
Rat acute toxicity2.2646 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9409
hERG inhibition (predictor II)Inhibitor0.5744
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/MSsplash10-0550-1269700000-74fdf04d497c4b7c4de9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bt9-2149000000-c0b7b484fbae179a5fa5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-1109000000-0dae07a93a22be7deeb0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-06u6-3904400000-058509cc251ed24ea79c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-08fr-2913000000-995cc5b7df2c83600a8e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kf-6903200000-3f3cf89272008adf2f03
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]-202.43846
predicted
DeepCCS 1.0 (2019)
[M+H]+204.83403
predicted
DeepCCS 1.0 (2019)
[M+Na]+210.74702
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cruzipain
Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
Unknown
General Function
Cysteine-type endopeptidase activity
Specific Function
Hydrolyzes chromogenic peptides at the carboxyl Arg or Lys; requires at least one more amino acid, preferably Arg, Phe, Val or Leu, between the terminal Arg or Lys and the amino-blocking group.The ...
Gene Name
Not Available
Uniprot ID
P25779
Uniprot Name
Cruzipain
Molecular Weight
49835.59 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]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52