(3S)-1-CYCLOHEXYL-N-(3,5-DICHLOROPHENYL)-5-OXOPYRROLIDINE-3-CARBOXAMIDE

Identification

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Name
(3S)-1-CYCLOHEXYL-N-(3,5-DICHLOROPHENYL)-5-OXOPYRROLIDINE-3-CARBOXAMIDE
Accession Number
DB07188
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 355.259
Monoisotopic: 354.090183308
Chemical Formula
C17H20Cl2N2O2
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
1283969
PubChem Substance
99443659
ChemSpider
1077055
HET
641
PDB Entries
4tzk

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0178 mg/mLALOGPS
logP4.01ALOGPS
logP3.46ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.36ChemAxon
pKa (Strongest Basic)-0.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.14 m3·mol-1ChemAxon
Polarizability36.84 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+0.9951
Caco-2 permeable+0.5
P-glycoprotein substrateNon-substrate0.7416
P-glycoprotein inhibitor IInhibitor0.5536
P-glycoprotein inhibitor IIInhibitor0.5357
Renal organic cation transporterInhibitor0.5
CYP450 2C9 substrateNon-substrate0.7947
CYP450 2D6 substrateNon-substrate0.8067
CYP450 3A4 substrateSubstrate0.6882
CYP450 1A2 substrateInhibitor0.5982
CYP450 2C9 inhibitorNon-inhibitor0.5475
CYP450 2D6 inhibitorNon-inhibitor0.7341
CYP450 2C19 inhibitorInhibitor0.7679
CYP450 3A4 inhibitorNon-inhibitor0.5632
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6619
Ames testNon AMES toxic0.7517
CarcinogenicityNon-carcinogens0.8512
BiodegradationNot ready biodegradable0.9916
Rat acute toxicity2.3018 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8949
hERG inhibition (predictor II)Inhibitor0.581
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Anilide / 1,3-dichlorobenzene / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-3-carboxamide / N-arylamide / Chlorobenzene / Halobenzene / Aryl chloride / N-alkylpyrrolidine / Aryl halide
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrrolidinecarboxamide, dichlorobenzene, pyrrolidin-2-ones (CHEBI:47145)

Targets

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. [PubMed:10592235]

Drug created on September 15, 2010 15:19 / Updated on June 04, 2019 06:35