NAV

[1-(1-Methyl-4,5-Dioxo-Pent-2-Enylcarbamoyl)-2-Phenyl-Ethyl]-Carbamic Acid Benzyl Ester

Identification

Generic Name
[1-(1-Methyl-4,5-Dioxo-Pent-2-Enylcarbamoyl)-2-Phenyl-Ethyl]-Carbamic Acid Benzyl Ester
DrugBank Accession Number
DB01810
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 408.4471
Monoisotopic: 408.168521888
Chemical Formula
C23H24N2O5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCathepsin FNot AvailableHumans
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 / Benzyloxycarbonyls / Amphetamines and derivatives / Fatty amides / Enones / Carbamate esters / Alpha ketoaldehydes / Acryloyl compounds / Secondary carboxylic acid amides / Organic carbonic acids and derivatives
show 5 more
Substituents
Acryloyl-group / Aldehyde / Alpha,beta-unsaturated ketone / Alpha-amino acid amide / Alpha-ketoaldehyde / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid / Benzyloxycarbonyl / Carbamic acid ester
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NOXVWFAAXREWMI-GURWAVDKSA-N
InChI
InChI=1S/C23H24N2O5/c1-17(12-13-20(27)15-26)24-22(28)21(14-18-8-4-2-5-9-18)25-23(29)30-16-19-10-6-3-7-11-19/h2-13,15,17,21H,14,16H2,1H3,(H,24,28)(H,25,29)/b13-12+/t17-,21+/m0/s1
IUPAC Name
benzyl N-[(1R)-1-{[(2S,3E)-5,6-dioxohex-3-en-2-yl]carbamoyl}-2-phenylethyl]carbamate
SMILES
[H][C@@](C)(NC(=O)[C@@]([H])(CC1=CC=CC=C1)NC(=O)OCC1=CC=CC=C1)\C=C\C(=O)C=O

References

General References
Not Available
PubChem Compound
5287438
PubChem Substance
46507094
ChemSpider
4449820
ZINC
ZINC000012501121
PDBe Ligand
186
PDB Entries
1u9q

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 Solubility0.0017 mg/mLALOGPS
logP2.49ALOGPS
logP3.65Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.43Chemaxon
pKa (Strongest Basic)-4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area101.57 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity112.82 m3·mol-1Chemaxon
Polarizability42.65 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9879
Blood Brain Barrier+0.7633
Caco-2 permeable-0.7194
P-glycoprotein substrateSubstrate0.6092
P-glycoprotein inhibitor IInhibitor0.5446
P-glycoprotein inhibitor IINon-inhibitor0.7117
Renal organic cation transporterNon-inhibitor0.9196
CYP450 2C9 substrateNon-substrate0.7828
CYP450 2D6 substrateNon-substrate0.8317
CYP450 3A4 substrateNon-substrate0.5713
CYP450 1A2 substrateNon-inhibitor0.7539
CYP450 2C9 inhibitorNon-inhibitor0.6994
CYP450 2D6 inhibitorNon-inhibitor0.8605
CYP450 2C19 inhibitorNon-inhibitor0.7792
CYP450 3A4 inhibitorInhibitor0.8422
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6398
Ames testNon AMES toxic0.5671
CarcinogenicityNon-carcinogens0.874
BiodegradationNot ready biodegradable0.8732
Rat acute toxicity2.0880 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9882
hERG inhibition (predictor II)Non-inhibitor0.9097
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, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1981000000-2b6a66fd830bdf66cb7b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00gi-6792100000-140b0fe81a59ebfd89cd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05i4-2910000000-6b8c0a5d561d77338d58
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f97-9550000000-4ef95995e28eb6531adc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052e-3910000000-84e4e219e25dd5fecae1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9400000000-37b5895355e07ce2df02
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]-191.40132
predicted
DeepCCS 1.0 (2019)
[M+H]+193.79689
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.70943
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cathepsin F
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. [Article]
Details2. 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