(3S)-N-(3-CHLORO-2-METHYLPHENYL)-1-CYCLOHEXYL-5-OXOPYRROLIDINE-3-CARBOXAMIDE
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Identification
- Generic Name
- (3S)-N-(3-CHLORO-2-METHYLPHENYL)-1-CYCLOHEXYL-5-OXOPYRROLIDINE-3-CARBOXAMIDE
- DrugBank Accession Number
- DB07090
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 334.84
Monoisotopic: 334.144805697 - Chemical Formula
- C18H23ClN2O2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UEnoyl-[acyl-carrier-protein] reductase [NADH] 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
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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 anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Anilides
- Direct Parent
- Anilides
- Alternative Parents
- Pyrrolidinecarboxamides / N-arylamides / Toluenes / Chlorobenzenes / Pyrrolidine-2-ones / Aryl chlorides / N-alkylpyrrolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Lactams show 6 more
- Substituents
- 2-pyrrolidone / Anilide / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Chlorobenzene show 21 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrrolidinecarboxamide, monochlorobenzenes, pyrrolidin-2-ones (CHEBI:47116)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- NJNMAZNXKKBTPS-ZDUSSCGKSA-N
- InChI
- InChI=1S/C18H23ClN2O2/c1-12-15(19)8-5-9-16(12)20-18(23)13-10-17(22)21(11-13)14-6-3-2-4-7-14/h5,8-9,13-14H,2-4,6-7,10-11H2,1H3,(H,20,23)/t13-/m0/s1
- IUPAC Name
- (3S)-N-(3-chloro-2-methylphenyl)-1-cyclohexyl-5-oxopyrrolidine-3-carboxamide
- SMILES
- [H][C@]1(CN(C2CCCCC2)C(=O)C1)C(=O)NC1=C(C)C(Cl)=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 40636608
- PubChem Substance
- 99443561
- ChemSpider
- 25058539
- ZINC
- ZINC000006700734
- PDBe Ligand
- 468
- PDB Entries
- 4tzt
Clinical Trials
- Clinical Trials
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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 0.0406 mg/mL ALOGPS logP 3.55 ALOGPS logP 3.37 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 13.81 Chemaxon pKa (Strongest Basic) -1.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 49.41 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 92.38 m3·mol-1 Chemaxon Polarizability 36.26 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.994 Caco-2 permeable + 0.5452 P-glycoprotein substrate Non-substrate 0.6542 P-glycoprotein inhibitor I Inhibitor 0.5801 P-glycoprotein inhibitor II Non-inhibitor 0.6002 Renal organic cation transporter Non-inhibitor 0.5346 CYP450 2C9 substrate Non-substrate 0.7146 CYP450 2D6 substrate Non-substrate 0.8328 CYP450 3A4 substrate Substrate 0.7328 CYP450 1A2 substrate Inhibitor 0.659 CYP450 2C9 inhibitor Non-inhibitor 0.5414 CYP450 2D6 inhibitor Non-inhibitor 0.8032 CYP450 2C19 inhibitor Inhibitor 0.8 CYP450 3A4 inhibitor Inhibitor 0.6524 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7583 Ames test Non AMES toxic 0.774 Carcinogenicity Non-carcinogens 0.8446 Biodegradation Not ready biodegradable 0.9907 Rat acute toxicity 2.2611 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9106 hERG inhibition (predictor II) Inhibitor 0.6376
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000l-2907000000-269d0d55ca9d55456c9d Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-3009000000-59fb1bdfadce2d5c6c97 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9666000000-24048a6fa490cbe7779b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000l-2719000000-2e7998812e5d9ef9a21d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-4941000000-0bc6a7681578c1efe612 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9100000000-094f5433af720e4db1eb 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]- 177.40553 predictedDeepCCS 1.0 (2019) [M+H]+ 179.76353 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.32207 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Enoyl-ACP reductase of the type II fatty acid syntase (FAS-II) system, which is involved in the biosynthesis of mycolic acids, a major component of mycobacterial cell walls (PubMed:25227413). Catalyzes the NADH-dependent reduction of the double bond of 2-trans-enoyl-[acyl-carrier protein], an essential step in the fatty acid elongation cycle of the FAS-II pathway (PubMed:7599116). Shows preference for long-chain fatty acyl thioester substrates (>C16), and can also use 2-trans-enoyl-CoAs as alternative substrates (PubMed:7599116). The mycobacterial FAS-II system utilizes the products of the FAS-I system as primers to extend fatty acyl chain lengths up to C56, forming the meromycolate chain that serves as the precursor for final mycolic acids (PubMed:25227413).
- Specific Function
- enoyl-[acyl-carrier-protein] reductase (NADH) activity
- Gene Name
- inhA
- Uniprot ID
- P9WGR1
- Uniprot Name
- Enoyl-[acyl-carrier-protein] reductase [NADH]
- Molecular Weight
- 28527.55 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 21:18 / Updated at June 12, 2020 16:52