NAV

(3S)-N-(3-BROMOPHENYL)-1-CYCLOHEXYL-5-OXOPYRROLIDINE-3-CARBOXAMIDE

Identification

Generic Name
(3S)-N-(3-BROMOPHENYL)-1-CYCLOHEXYL-5-OXOPYRROLIDINE-3-CARBOXAMIDE
DrugBank Accession Number
DB07192
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 365.265
Monoisotopic: 364.078640573
Chemical Formula
C17H21BrN2O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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 / Bromobenzenes / Pyrrolidine-2-ones / N-alkylpyrrolidines / Aryl bromides / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Lactams / Azacyclic compounds
show 5 more
Substituents
2-pyrrolidone / Anilide / Aromatic heteromonocyclic compound / Aryl bromide / Aryl halide / Azacycle / Bromobenzene / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organobromine compound, pyrrolidinecarboxamide, pyrrolidin-2-ones (CHEBI:47150)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MVPIURCUINFSAB-LBPRGKRZSA-N
InChI
InChI=1S/C17H21BrN2O2/c18-13-5-4-6-14(10-13)19-17(22)12-9-16(21)20(11-12)15-7-2-1-3-8-15/h4-6,10,12,15H,1-3,7-9,11H2,(H,19,22)/t12-/m0/s1
IUPAC Name
(3S)-N-(3-bromophenyl)-1-cyclohexyl-5-oxopyrrolidine-3-carboxamide
SMILES
[H][C@]1(CN(C2CCCCC2)C(=O)C1)C(=O)NC1=CC=CC(Br)=C1

References

General References
Not Available
PubChem Compound
1116191
PubChem Substance
99443663
ChemSpider
950568
ZINC
ZINC000000851723
PDBe Ligand
665
PDB Entries
4trj

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 Solubility0.0539 mg/mLALOGPS
logP3.63ALOGPS
logP3.03Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)13.69Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area49.41 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity90.15 m3·mol-1Chemaxon
Polarizability35.2 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9972
Blood Brain Barrier+0.9943
Caco-2 permeable+0.5
P-glycoprotein substrateNon-substrate0.7334
P-glycoprotein inhibitor IInhibitor0.6522
P-glycoprotein inhibitor IIInhibitor0.6149
Renal organic cation transporterInhibitor0.5
CYP450 2C9 substrateNon-substrate0.8279
CYP450 2D6 substrateNon-substrate0.7996
CYP450 3A4 substrateSubstrate0.6462
CYP450 1A2 substrateInhibitor0.55
CYP450 2C9 inhibitorInhibitor0.508
CYP450 2D6 inhibitorNon-inhibitor0.8384
CYP450 2C19 inhibitorInhibitor0.5825
CYP450 3A4 inhibitorNon-inhibitor0.6044
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6909
Ames testNon AMES toxic0.7396
CarcinogenicityNon-carcinogens0.8768
BiodegradationNot ready biodegradable0.9925
Rat acute toxicity2.3368 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9301
hERG inhibition (predictor II)Inhibitor0.621
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/MSsplash10-014i-2509000000-f9eec6f6ca98f3307d51
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0109000000-539c1461f612a3434f19
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lu-5922000000-fad8c60d31c84165b96d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-3249000000-4cdb53606fa030eb1756
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03yi-3921000000-b50876a8b7f676fb2825
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9231000000-d82a8abeb3231e33e4c6
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]-172.69194
predicted
DeepCCS 1.0 (2019)
[M+H]+175.04996
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.15402
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 21:19 / Updated at June 12, 2020 16:52