[1-(1-Benzyl-3-Hydroxy-2-Oxo-Propylcarbamoyl)-2-Phenyl-Ethyl]-Carbamic Acid Benzyl Ester

Identification

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Name
[1-(1-Benzyl-3-Hydroxy-2-Oxo-Propylcarbamoyl)-2-Phenyl-Ethyl]-Carbamic Acid Benzyl Ester
Accession Number
DB01871  (EXPT02989)
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: 460.5216
Monoisotopic: 460.199822016
Chemical Formula
C27H28N2O5
InChI Key
OACUXIVGLLCILS-ZEQRLZLVSA-N
InChI
InChI=1S/C27H28N2O5/c30-18-25(31)23(16-20-10-4-1-5-11-20)28-26(32)24(17-21-12-6-2-7-13-21)29-27(33)34-19-22-14-8-3-9-15-22/h1-15,23-24,30H,16-19H2,(H,28,32)(H,29,33)/t23-,24-/m0/s1
IUPAC Name
benzyl N-[(1S)-1-{[(2S)-4-hydroxy-3-oxo-1-phenylbutan-2-yl]carbamoyl}-2-phenylethyl]carbamate
SMILES
[H][C@@](CC1=CC=CC=C1)(NC(=O)[C@]([H])(CC1=CC=CC=C1)NC(=O)OCC1=CC=CC=C1)C(=O)CO

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCruzipainNot AvailableTrypanosoma cruzi
UCathepsin FNot 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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
5289424
PubChem Substance
46507866
ChemSpider
4451401
ChEMBL
CHEMBL261723
HET
T10
PDB Entries
1me4

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 Solubility0.00155 mg/mLALOGPS
logP2.72ALOGPS
logP3.87ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)12.54ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.73 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity127.97 m3·mol-1ChemAxon
Polarizability48.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.515
Blood Brain Barrier-0.6196
Caco-2 permeable-0.7901
P-glycoprotein substrateSubstrate0.6109
P-glycoprotein inhibitor INon-inhibitor0.5841
P-glycoprotein inhibitor IINon-inhibitor0.6795
Renal organic cation transporterNon-inhibitor0.9189
CYP450 2C9 substrateNon-substrate0.782
CYP450 2D6 substrateNon-substrate0.831
CYP450 3A4 substrateNon-substrate0.6564
CYP450 1A2 substrateNon-inhibitor0.8117
CYP450 2C9 inhibitorNon-inhibitor0.8584
CYP450 2D6 inhibitorNon-inhibitor0.8277
CYP450 2C19 inhibitorNon-inhibitor0.8526
CYP450 3A4 inhibitorNon-inhibitor0.6981
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6806
Ames testNon AMES toxic0.7289
CarcinogenicityNon-carcinogens0.9038
BiodegradationNot ready biodegradable0.7038
Rat acute toxicity2.1984 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.981
hERG inhibition (predictor II)Non-inhibitor0.6381
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 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 / Benzyloxycarbonyls / Amphetamines and derivatives / Monosaccharides / Fatty amides / Carbamate esters / Alpha-hydroxy ketones / Secondary carboxylic acid amides / Organic carbonic acids and derivatives / Primary alcohols
show 4 more
Substituents
Phenylalanine or derivatives / Alpha-amino acid amide / Amphetamine or derivatives / Benzyloxycarbonyl / Monocyclic benzene moiety / Fatty amide / Monosaccharide / Benzenoid / Fatty acyl / Carbamic acid ester
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

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. [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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Cysteine-type endopeptidase activity
Specific Function
Thiol protease which is believed to participate in intracellular degradation and turnover of proteins. Has also been implicated in tumor invasion and metastasis.
Gene Name
CTSF
Uniprot ID
Q9UBX1
Uniprot Name
Cathepsin F
Molecular Weight
53365.455 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on January 02, 2020 04:53