NAV

(3S)-N-(3-CHLORO-2-METHYLPHENYL)-1-CYCLOHEXYL-5-OXOPYRROLIDINE-3-CARBOXAMIDE

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
3D
Similar Structures
Weight
Average: 334.84
Monoisotopic: 334.144805697
Chemical Formula
C18H23ClN2O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEnoyl-[acyl-carrier-protein] reductase [NADH]Not AvailableMycobacterium 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
PubChem Compound
40636608
PubChem Substance
99443561
ChemSpider
25058539
ZINC
ZINC000006700734
PDBe Ligand
468
PDB Entries
4tzt

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 Solubility0.0406 mg/mLALOGPS
logP3.55ALOGPS
logP3.37Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.81Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area49.41 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity92.38 m3·mol-1Chemaxon
Polarizability36.26 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.994
Caco-2 permeable+0.5452
P-glycoprotein substrateNon-substrate0.6542
P-glycoprotein inhibitor IInhibitor0.5801
P-glycoprotein inhibitor IINon-inhibitor0.6002
Renal organic cation transporterNon-inhibitor0.5346
CYP450 2C9 substrateNon-substrate0.7146
CYP450 2D6 substrateNon-substrate0.8328
CYP450 3A4 substrateSubstrate0.7328
CYP450 1A2 substrateInhibitor0.659
CYP450 2C9 inhibitorNon-inhibitor0.5414
CYP450 2D6 inhibitorNon-inhibitor0.8032
CYP450 2C19 inhibitorInhibitor0.8
CYP450 3A4 inhibitorInhibitor0.6524
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7583
Ames testNon AMES toxic0.774
CarcinogenicityNon-carcinogens0.8446
BiodegradationNot ready biodegradable0.9907
Rat acute toxicity2.2611 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9106
hERG inhibition (predictor II)Inhibitor0.6376
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/MSsplash10-000l-2907000000-269d0d55ca9d55456c9d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-3009000000-59fb1bdfadce2d5c6c97
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9666000000-24048a6fa490cbe7779b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-2719000000-2e7998812e5d9ef9a21d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-4941000000-0bc6a7681578c1efe612
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9100000000-094f5433af720e4db1eb
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]-177.40553
predicted
DeepCCS 1.0 (2019)
[M+H]+179.76353
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.32207
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Enoyl-[acyl-carrier-protein] reductase [NADH]
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
  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 21:18 / Updated at June 12, 2020 16:52