Identification
- Generic Name
- (3S)-1-CYCLOHEXYL-N-(3,5-DICHLOROPHENYL)-5-OXOPYRROLIDINE-3-CARBOXAMIDE
- DrugBank Accession Number
- DB07188
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (3S)-1-CYCLOHEXYL-N-(3,5-DICHLOROPHENYL)-5-OXOPYRROLIDINE-3-CARBOXAMIDE (DB07188)
- Weight
- Average: 355.259
Monoisotopic: 354.090183308 - Chemical Formula
- C17H20Cl2N2O2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.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 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 / Dichlorobenzenes / Pyrrolidine-2-ones / N-alkylpyrrolidines / Aryl chlorides / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Lactams / Azacyclic compounds show 5 more
- Substituents
- 1,3-dichlorobenzene / 2-pyrrolidone / Anilide / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative show 21 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrrolidinecarboxamide, dichlorobenzene, pyrrolidin-2-ones (CHEBI:47145)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- YUFADRZDHJKVOT-NSHDSACASA-N
- InChI
- InChI=1S/C17H20Cl2N2O2/c18-12-7-13(19)9-14(8-12)20-17(23)11-6-16(22)21(10-11)15-4-2-1-3-5-15/h7-9,11,15H,1-6,10H2,(H,20,23)/t11-/m0/s1
- IUPAC Name
- (3S)-1-cyclohexyl-N-(3,5-dichlorophenyl)-5-oxopyrrolidine-3-carboxamide
- SMILES
- [H][C@]1(CN(C2CCCCC2)C(=O)C1)C(=O)NC1=CC(Cl)=CC(Cl)=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 1283969
- PubChem Substance
- 99443659
- ChemSpider
- 1077055
- ZINC
- ZINC000001103943
- PDBe Ligand
- 641
- PDB Entries
- 4tzk
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 0.0178 mg/mL ALOGPS logP 4.01 ALOGPS logP 3.46 ChemAxon logS -4.3 ALOGPS pKa (Strongest Acidic) 13.36 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 92.14 m3·mol-1 ChemAxon Polarizability 36.84 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 + 0.9951 Caco-2 permeable + 0.5 P-glycoprotein substrate Non-substrate 0.7416 P-glycoprotein inhibitor I Inhibitor 0.5536 P-glycoprotein inhibitor II Inhibitor 0.5357 Renal organic cation transporter Inhibitor 0.5 CYP450 2C9 substrate Non-substrate 0.7947 CYP450 2D6 substrate Non-substrate 0.8067 CYP450 3A4 substrate Substrate 0.6882 CYP450 1A2 substrate Inhibitor 0.5982 CYP450 2C9 inhibitor Non-inhibitor 0.5475 CYP450 2D6 inhibitor Non-inhibitor 0.7341 CYP450 2C19 inhibitor Inhibitor 0.7679 CYP450 3A4 inhibitor Non-inhibitor 0.5632 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6619 Ames test Non AMES toxic 0.7517 Carcinogenicity Non-carcinogens 0.8512 Biodegradation Not ready biodegradable 0.9916 Rat acute toxicity 2.3018 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8949 hERG inhibition (predictor II) Inhibitor 0.581
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
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 21:19 / Updated at June 12, 2020 16:52