NALPHA-[(BENZYLOXY)CARBONYL]-N-[(1R)-4-HYDROXY-1-METHYL-2-OXOBUTYL]-L-PHENYLALANINAMIDE

Identification

Generic Name
NALPHA-[(BENZYLOXY)CARBONYL]-N-[(1R)-4-HYDROXY-1-METHYL-2-OXOBUTYL]-L-PHENYLALANINAMIDE
DrugBank Accession Number
DB08732
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 398.4522
Monoisotopic: 398.184171952
Chemical Formula
C22H26N2O5
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UReplicase polyprotein 1abNot AvailableSARS-CoV
UReplicase polyprotein 1aNot AvailableSARS-CoV
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 / Beta-hydroxy ketones / Carbamate esters / Secondary carboxylic acid amides / Organic carbonic acids and derivatives / Primary alcohols / Organopnictogen compounds
show 3 more
Substituents
Alcohol / Alpha-amino acid amide / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid / Benzyloxycarbonyl / Beta-hydroxy ketone / Carbamic acid ester / Carbonic acid derivative / Carbonyl group
show 15 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
UUOOAGBWJUGBMV-APWZRJJASA-N
InChI
InChI=1S/C22H26N2O5/c1-16(20(26)12-13-25)23-21(27)19(14-17-8-4-2-5-9-17)24-22(28)29-15-18-10-6-3-7-11-18/h2-11,16,19,25H,12-15H2,1H3,(H,23,27)(H,24,28)/t16-,19+/m1/s1
IUPAC Name
benzyl N-[(1S)-1-{[(2R)-5-hydroxy-3-oxopentan-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(=O)CCO

References

General References
Not Available
PubChem Compound
16220131
PubChem Substance
99445203
ChemSpider
17347435
ZINC
ZINC000016052314
PDBe Ligand
WR1
PDB Entries
2op9

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 Solubility0.0146 mg/mLALOGPS
logP1.55ALOGPS
logP2.45Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.7Chemaxon
pKa (Strongest Basic)-2.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area104.73 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity108.05 m3·mol-1Chemaxon
Polarizability42.27 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7715
Blood Brain Barrier+0.7761
Caco-2 permeable-0.727
P-glycoprotein substrateSubstrate0.7207
P-glycoprotein inhibitor INon-inhibitor0.6804
P-glycoprotein inhibitor IINon-inhibitor0.8087
Renal organic cation transporterNon-inhibitor0.8491
CYP450 2C9 substrateNon-substrate0.7416
CYP450 2D6 substrateNon-substrate0.8297
CYP450 3A4 substrateNon-substrate0.6133
CYP450 1A2 substrateNon-inhibitor0.79
CYP450 2C9 inhibitorNon-inhibitor0.7418
CYP450 2D6 inhibitorNon-inhibitor0.6785
CYP450 2C19 inhibitorNon-inhibitor0.7084
CYP450 3A4 inhibitorInhibitor0.7267
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5848
Ames testNon AMES toxic0.807
CarcinogenicityNon-carcinogens0.9152
BiodegradationNot ready biodegradable0.6491
Rat acute toxicity2.1123 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9551
hERG inhibition (predictor II)Non-inhibitor0.7645
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/MSsplash10-0ue9-1694000000-1affede0a1e64e044ba7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0229-1290000000-60b55b10813e5fe28229
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6y-9651000000-7e512c9e46215acfc22a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-006w-2890000000-ff732af957962347545f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9500000000-1c6de5f7c16f0c67d0a8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052e-2910000000-020f684cab23d6347e90
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]-187.59825
predicted
DeepCCS 1.0 (2019)
[M+H]+189.99382
predicted
DeepCCS 1.0 (2019)
[M+Na]+195.90636
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
SARS-CoV
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Replicase polyprotein 1ab: Multifunctional protein involved in the transcription and replication of viral RNAs. Contains the proteinases responsible for the cleavages of the polyprotein.Host transl...
Gene Name
rep
Uniprot ID
P0C6X7
Uniprot Name
Replicase polyprotein 1ab
Molecular Weight
790241.63 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]
Kind
Protein
Organism
SARS-CoV
Pharmacological action
Unknown
General Function
The papain-like proteinase (PL-PRO) is responsible for the cleavages located at the N-terminus of replicase polyprotein. In addition, PL-PRO possesses a deubiquitinating/deISGylating activity and processes both 'Lys-48'- and 'Lys-63'-linked polyubiquitin chains from cellular substrates. Antagonizes innate immune induction of type I interferon by blocking the phosphorylation, dimerization and subsequent nuclear translocation of host IRF-3.
Specific Function
Cysteine-type endopeptidase activity
Gene Name
Not Available
Uniprot ID
P0C6U8
Uniprot Name
Replicase polyprotein 1a
Molecular Weight
486368.515 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 September 15, 2010 21:34 / Updated at June 12, 2020 16:52