Identification
- Generic Name
- N-(4-MORPHOLINE)CARBONYL-B-(1-NAPHTHYL)-L-ALANINE-L-LEUCINE BORONIC ACID
- DrugBank Accession Number
- DB04732
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for N-(4-MORPHOLINE)CARBONYL-B-(1-NAPHTHYL)-L-ALANINE-L-LEUCINE BORONIC ACID (DB04732)
- Weight
- Average: 441.328
Monoisotopic: 441.243501615 - Chemical Formula
- C23H32BN3O5
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UProteasome subunit beta Not Available Mycobacterium tuberculosis UProteasome subunit alpha Not Available Mycobacterium tuberculosis - 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 n-carbamoyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an carbamoyl group at its terminal nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- N-carbamoyl-alpha amino acids and derivatives
- Alternative Parents
- Alpha amino acid amides / Naphthalenes / Morpholine carboxylic acids and derivatives / Fatty amides / Ureas / Secondary carboxylic acid amides / Boronic acids / Oxacyclic compounds / Azacyclic compounds / Dialkyl ethers show 7 more
- Substituents
- Alkylborane / Alpha-amino acid amide / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Boronic acid / Boronic acid derivative / Carbonic acid derivative / Carbonyl group / Carboxamide group show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- ureas, naphthalenes, morpholines, boronic acids (CHEBI:43809)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- MQMHIOPMTAJOHV-RTWAWAEBSA-N
- InChI
- InChI=1S/C23H32BN3O5/c1-16(2)14-21(24(30)31)26-22(28)20(25-23(29)27-10-12-32-13-11-27)15-18-8-5-7-17-6-3-4-9-19(17)18/h3-9,16,20-21,30-31H,10-15H2,1-2H3,(H,25,29)(H,26,28)/t20-,21+/m1/s1
- IUPAC Name
- [(1R)-3-methyl-1-[(2R)-2-[(morpholine-4-carbonyl)amino]-3-(naphthalen-1-yl)propanamido]butyl]boronic acid
- SMILES
- [H][C@@](CC(C)C)(NC(=O)[C@@]([H])(CC1=C2C=CC=CC2=CC=C1)NC(=O)N1CCOCC1)B(O)O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 387442
- PubChem Substance
- 46505262
- ChemSpider
- 343397
- ChEMBL
- CHEMBL1234151
- ZINC
- ZINC000169748489
- PDBe Ligand
- M1N
- PDB Entries
- 2fhh
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 0.0313 mg/mL ALOGPS logP 1.89 ALOGPS logP 2.91 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 8.64 Chemaxon pKa (Strongest Basic) -2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 111.13 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 117.38 m3·mol-1 Chemaxon Polarizability 46.91 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5 Blood Brain Barrier - 0.8144 Caco-2 permeable - 0.7438 P-glycoprotein substrate Substrate 0.9166 P-glycoprotein inhibitor I Inhibitor 0.6523 P-glycoprotein inhibitor II Non-inhibitor 0.9969 Renal organic cation transporter Non-inhibitor 0.9053 CYP450 2C9 substrate Non-substrate 0.7401 CYP450 2D6 substrate Non-substrate 0.7362 CYP450 3A4 substrate Substrate 0.5755 CYP450 1A2 substrate Non-inhibitor 0.9008 CYP450 2C9 inhibitor Non-inhibitor 0.7776 CYP450 2D6 inhibitor Non-inhibitor 0.9086 CYP450 2C19 inhibitor Non-inhibitor 0.7142 CYP450 3A4 inhibitor Non-inhibitor 0.5994 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9737 Ames test Non AMES toxic 0.6212 Carcinogenicity Non-carcinogens 0.8663 Biodegradation Not ready biodegradable 0.8033 Rat acute toxicity 2.4890 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6528 hERG inhibition (predictor II) Inhibitor 0.5
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
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- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Component of the proteasome core, a large protease complex with broad specificity involved in protein degradation. The M.tuberculosis proteasome is able to cleave oligopeptides not only after hydrophobic but also after basic, acidic and small neutral residues (PubMed:16468985). In complex with the ATPase Mpa, degrades protein targets conjugated to a prokaryotic ubiquitin-like protein (Pup). Among the identified substrates of the M.tuberculosis proteasome are the pupylated FabD, PanB and Mpa proteins (PubMed:17082771). One function of the proteasome is to contribute to M.tuberculosis ability to resist killing by host macrophages, since the core proteasome is essential for persistence of the pathogen during the chronic phase of infection in mice (PubMed:18059281). Likely functions to recycle amino acids under nutrient starvation, thereby enabling the cell to maintain basal metabolic activities (PubMed:20711362) (By similarity). The mechanism of protection against bactericidal chemistries of the host's immune response probably involves the degradation of proteins that are irreversibly oxidized, nitrated, or nitrosated. A proteolysis-independent activity of the proteasome core is required for optimal growth of M.tuberculosis in mouse lungs and for RNI resistance; in contrast, long-term survival of M.tuberculosis in stationary phase and during starvation in vitro and in the chronic phase of mouse infection required a proteolytically active proteasome (PubMed:20711362).
- Specific Function
- Threonine-type endopeptidase activity
- Gene Name
- prcB
- Uniprot ID
- P9WHT9
- Uniprot Name
- Proteasome subunit beta
- Molecular Weight
- 30304.72 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]
- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Component of the proteasome core, a large protease complex with broad specificity involved in protein degradation. The M.tuberculosis proteasome is able to cleave oligopeptides not only after hydrophobic but also after basic, acidic and small neutral residues (PubMed:16468985). In complex with the ATPase Mpa, degrades protein targets conjugated to a prokaryotic ubiquitin-like protein (Pup). Among the identified substrates of the M.tuberculosis proteasome are the pupylated FabD, PanB and Mpa proteins (PubMed:17082771). One function of the proteasome is to contribute to M.tuberculosis ability to resist killing by host macrophages, since the core proteasome is essential for persistence of the pathogen during the chronic phase of infection in mice (PubMed:18059281). Likely functions to recycle amino acids under nutrient starvation, thereby enabling the cell to maintain basal metabolic activities (PubMed:20711362) (By similarity). The mechanism of protection against bactericidal chemistries of the host's immune response probably involves the degradation of proteins that are irreversibly oxidized, nitrated, or nitrosated. A proteolysis-independent activity of the proteasome core is required for optimal growth of M.tuberculosis in mouse lungs and for RNI resistance; in contrast, long-term survival of M.tuberculosis in stationary phase and during starvation in vitro and in the chronic phase of mouse infection required a proteolytically active proteasome (PubMed:20711362).
- Specific Function
- Threonine-type endopeptidase activity
- Gene Name
- prcA
- Uniprot ID
- P9WHU1
- Uniprot Name
- Proteasome subunit alpha
- Molecular Weight
- 26880.775 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 11, 2007 17:49 / Updated at June 12, 2020 16:52