NALPHA-[(BENZYLOXY)CARBONYL]-N-[(1R)-4-HYDROXY-1-METHYL-2-OXOBUTYL]-L-PHENYLALANINAMIDE
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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
Target Actions Organism UReplicase polyprotein 1ab Not Available SARS-CoV UReplicase polyprotein 1a Not Available SARS-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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- PubChem Compound
- 16220131
- PubChem Substance
- 99445203
- ChemSpider
- 17347435
- ZINC
- ZINC000016052314
- PDBe Ligand
- WR1
- PDB Entries
- 2op9
Clinical Trials
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
Property Value Source Water Solubility 0.0146 mg/mL ALOGPS logP 1.55 ALOGPS logP 2.45 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 12.7 Chemaxon pKa (Strongest Basic) -2.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 104.73 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 108.05 m3·mol-1 Chemaxon Polarizability 42.27 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7715 Blood Brain Barrier + 0.7761 Caco-2 permeable - 0.727 P-glycoprotein substrate Substrate 0.7207 P-glycoprotein inhibitor I Non-inhibitor 0.6804 P-glycoprotein inhibitor II Non-inhibitor 0.8087 Renal organic cation transporter Non-inhibitor 0.8491 CYP450 2C9 substrate Non-substrate 0.7416 CYP450 2D6 substrate Non-substrate 0.8297 CYP450 3A4 substrate Non-substrate 0.6133 CYP450 1A2 substrate Non-inhibitor 0.79 CYP450 2C9 inhibitor Non-inhibitor 0.7418 CYP450 2D6 inhibitor Non-inhibitor 0.6785 CYP450 2C19 inhibitor Non-inhibitor 0.7084 CYP450 3A4 inhibitor Inhibitor 0.7267 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5848 Ames test Non AMES toxic 0.807 Carcinogenicity Non-carcinogens 0.9152 Biodegradation Not ready biodegradable 0.6491 Rat acute toxicity 2.1123 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9551 hERG inhibition (predictor II) Non-inhibitor 0.7645
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0ue9-1694000000-1affede0a1e64e044ba7 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0229-1290000000-60b55b10813e5fe28229 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f6y-9651000000-7e512c9e46215acfc22a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-006w-2890000000-ff732af957962347545f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9500000000-1c6de5f7c16f0c67d0a8 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-052e-2910000000-020f684cab23d6347e90 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.59825 predictedDeepCCS 1.0 (2019) [M+H]+ 189.99382 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.90636 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsReplicase polyprotein 1ab
- 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
- 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]
2. DetailsReplicase polyprotein 1a
- 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
- 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