NAV

(3S)-1-CYCLOHEXYL-5-OXO-N-PHENYLPYRROLIDINE-3-CARBOXAMIDE

Identification

Generic Name
(3S)-1-CYCLOHEXYL-5-OXO-N-PHENYLPYRROLIDINE-3-CARBOXAMIDE
DrugBank Accession Number
DB07155
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 286.3688
Monoisotopic: 286.168127958
Chemical Formula
C17H22N2O2
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 / Pyrrolidine-2-ones / N-alkylpyrrolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
2-pyrrolidone / Anilide / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / Lactam / N-alkylpyrrolidine
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrrolidinecarboxamide (CHEBI:40149)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
BVUSHGJZBZMDML-ZDUSSCGKSA-N
InChI
InChI=1S/C17H22N2O2/c20-16-11-13(12-19(16)15-9-5-2-6-10-15)17(21)18-14-7-3-1-4-8-14/h1,3-4,7-8,13,15H,2,5-6,9-12H2,(H,18,21)/t13-/m0/s1
IUPAC Name
(3S)-1-cyclohexyl-5-oxo-N-phenylpyrrolidine-3-carboxamide
SMILES
[H][C@]1(CN(C2CCCCC2)C(=O)C1)C(=O)NC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
2266114
PubChem Substance
99443626
ChemSpider
1694059
ChEBI
40149
ZINC
ZINC000002943677
PDBe Ligand
566
PDB Entries
4u0j

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 Solubility0.31 mg/mLALOGPS
logP2.95ALOGPS
logP2.26Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)13.96Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area49.41 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity82.53 m3·mol-1Chemaxon
Polarizability31.61 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+0.9964
Caco-2 permeable+0.5825
P-glycoprotein substrateNon-substrate0.7405
P-glycoprotein inhibitor IInhibitor0.5926
P-glycoprotein inhibitor IIInhibitor0.5178
Renal organic cation transporterNon-inhibitor0.5238
CYP450 2C9 substrateNon-substrate0.7878
CYP450 2D6 substrateNon-substrate0.8051
CYP450 3A4 substrateSubstrate0.6249
CYP450 1A2 substrateNon-inhibitor0.7166
CYP450 2C9 inhibitorNon-inhibitor0.5955
CYP450 2D6 inhibitorNon-inhibitor0.866
CYP450 2C19 inhibitorNon-inhibitor0.6573
CYP450 3A4 inhibitorNon-inhibitor0.7032
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5754
Ames testNon AMES toxic0.7722
CarcinogenicityNon-carcinogens0.9062
BiodegradationNot ready biodegradable0.9433
Rat acute toxicity2.3941 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.924
hERG inhibition (predictor II)Non-inhibitor0.537
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000x-9740000000-7688929931daba5b50d6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-3790000000-e8ad69abcc7e3fc3b8df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0390000000-3daaf6e3cd5649c3af80
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lu-4910000000-9f7a1b16c45ed0cf2215
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0390000000-0ad89eafe499fcc47fdf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ei-3920000000-ba1591a0c32994055ee7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9410000000-200a9354e1d89ce32dc9
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]-164.33983
predicted
DeepCCS 1.0 (2019)
[M+H]+166.69785
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.48193
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