NAV

N-(4-bromo-2-{[(3R,5S)-3,5-dimethylpiperidin-1-yl]carbonyl}phenyl)-4-morpholin-4-yl-4-oxobutanamide

Identification

Generic Name
N-(4-bromo-2-{[(3R,5S)-3,5-dimethylpiperidin-1-yl]carbonyl}phenyl)-4-morpholin-4-yl-4-oxobutanamide
DrugBank Accession Number
DB08582
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 480.395
Monoisotopic: 479.14196911
Chemical Formula
C22H30BrN3O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot AvailableHepatitis C virus genotype 1b (isolate BK)
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 1-benzoylpiperidines. These are compounds containing a piperidine ring substituted at the 1-position with a benzoyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoyl derivatives
Direct Parent
1-benzoylpiperidines
Alternative Parents
N-benzoylpiperidines / Acylaminobenzoic acid and derivatives / 3-halobenzoic acids and derivatives / Anilides / Benzamides / N-arylamides / Bromobenzenes / Morpholines / Aryl bromides / Fatty amides
show 11 more
Substituents
1-benzoylpiperidine / 3-halobenzoic acid or derivatives / Acylaminobenzoic acid or derivatives / Anilide / Aromatic heteromonocyclic compound / Aryl bromide / Aryl halide / Azacycle / Benzamide / Benzoic acid or derivatives
show 30 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DELARNBPJXTDBD-IYBDPMFKSA-N
InChI
InChI=1S/C22H30BrN3O4/c1-15-11-16(2)14-26(13-15)22(29)18-12-17(23)3-4-19(18)24-20(27)5-6-21(28)25-7-9-30-10-8-25/h3-4,12,15-16H,5-11,13-14H2,1-2H3,(H,24,27)/t15-,16+
IUPAC Name
N-{4-bromo-2-[(3R,5S)-3,5-dimethylpiperidine-1-carbonyl]phenyl}-4-(morpholin-4-yl)-4-oxobutanamide
SMILES
[H][C@]1(C)CN(C[C@@]([H])(C)C1)C(=O)C1=C(NC(=O)CCC(=O)N2CCOCC2)C=CC(Br)=C1

References

General References
Not Available
PubChem Compound
24764443
PubChem Substance
99445053
ChemSpider
23315452
ChEMBL
CHEMBL402315
ZINC
ZINC000024978180
PDBe Ligand
SX6
PDB Entries
3cj5

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 Solubility0.108 mg/mLALOGPS
logP2.59ALOGPS
logP2.75Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)13Chemaxon
pKa (Strongest Basic)-0.93Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area78.95 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity120.08 m3·mol-1Chemaxon
Polarizability48.04 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9316
Blood Brain Barrier+0.7056
Caco-2 permeable-0.5112
P-glycoprotein substrateSubstrate0.6505
P-glycoprotein inhibitor IInhibitor0.8466
P-glycoprotein inhibitor IINon-inhibitor0.5145
Renal organic cation transporterNon-inhibitor0.8012
CYP450 2C9 substrateNon-substrate0.8707
CYP450 2D6 substrateNon-substrate0.7871
CYP450 3A4 substrateSubstrate0.6457
CYP450 1A2 substrateNon-inhibitor0.9341
CYP450 2C9 inhibitorNon-inhibitor0.786
CYP450 2D6 inhibitorNon-inhibitor0.9075
CYP450 2C19 inhibitorNon-inhibitor0.7457
CYP450 3A4 inhibitorInhibitor0.5
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.602
Ames testNon AMES toxic0.7035
CarcinogenicityNon-carcinogens0.8656
BiodegradationNot ready biodegradable0.9874
Rat acute toxicity2.2141 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9003
hERG inhibition (predictor II)Inhibitor0.6384
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/MSsplash10-001l-0018900000-146cf127b16277a30610
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0003900000-3e5862efc324772586b5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-2329700000-aa357285bb5460cec7f3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05r0-3906400000-8488b4ce11a52beef390
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-5922300000-24085080524f04c4034c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9444400000-ddeb57e9b4c70d3f23ae
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]-197.4287
predicted
DeepCCS 1.0 (2019)
[M+H]+199.82426
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.73677
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Genome polyprotein
Kind
Protein
Organism
Hepatitis C virus genotype 1b (isolate BK)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Core protein packages viral RNA to form a viral nucleocapsid, and promotes virion budding. Modulates viral translation initiation by interacting with HCV IRES and 40S ribosomal subunit. Also regula...
Gene Name
Not Available
Uniprot ID
P26663
Uniprot Name
Genome polyprotein
Molecular Weight
327190.435 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 21:33 / Updated at June 12, 2020 16:52