NAV

(4R,5R)-5-AMINO-1-[2-(1,3-BENZODIOXOL-5-YL)ETHYL]-4-(2,4,5-TRIFLUOROPHENYL)PIPERIDIN-2-ONE

Identification

Generic Name
(4R,5R)-5-AMINO-1-[2-(1,3-BENZODIOXOL-5-YL)ETHYL]-4-(2,4,5-TRIFLUOROPHENYL)PIPERIDIN-2-ONE
DrugBank Accession Number
DB07830
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 392.3717
Monoisotopic: 392.134777099
Chemical Formula
C20H19F3N2O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDipeptidyl peptidase 4Not AvailableHumans
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 phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Benzodioxoles / Aminopiperidines / Piperidinones / Aralkylamines / Delta lactams / Fluorobenzenes / Aryl fluorides / Tertiary carboxylic acid amides / Amino acids and derivatives / Azacyclic compounds
show 8 more
Substituents
3-aminopiperidine / Acetal / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, benzodioxoles, aminopiperidine, piperidones (CHEBI:42903)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DIRIFWIKLRTNMB-DYVFJYSZSA-N
InChI
InChI=1S/C20H19F3N2O3/c21-14-8-16(23)15(22)6-12(14)13-7-20(26)25(9-17(13)24)4-3-11-1-2-18-19(5-11)28-10-27-18/h1-2,5-6,8,13,17H,3-4,7,9-10,24H2/t13-,17+/m1/s1
IUPAC Name
(4R,5R)-5-amino-1-[2-(2H-1,3-benzodioxol-5-yl)ethyl]-4-(2,4,5-trifluorophenyl)piperidin-2-one
SMILES
[H][C@]1(N)CN(CCC2=CC=C3OCOC3=C2)C(=O)C[C@]1([H])C1=CC(F)=C(F)C=C1F

References

General References
Not Available
PubChem Compound
16040279
PubChem Substance
99444301
ChemSpider
13168826
BindingDB
15510
ChEMBL
CHEMBL225210
ZINC
ZINC000014958799
PDBe Ligand
GGO
PDB Entries
2oqi

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 Solubility0.113 mg/mLALOGPS
logP2.38ALOGPS
logP2.47Chemaxon
logS-3.5ALOGPS
pKa (Strongest Basic)8.86Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area64.79 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity95.12 m3·mol-1Chemaxon
Polarizability37.48 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9942
Blood Brain Barrier+0.9826
Caco-2 permeable-0.5875
P-glycoprotein substrateSubstrate0.7129
P-glycoprotein inhibitor IInhibitor0.6774
P-glycoprotein inhibitor IINon-inhibitor0.7155
Renal organic cation transporterNon-inhibitor0.6488
CYP450 2C9 substrateNon-substrate0.9361
CYP450 2D6 substrateNon-substrate0.6426
CYP450 3A4 substrateSubstrate0.6348
CYP450 1A2 substrateInhibitor0.5974
CYP450 2C9 inhibitorNon-inhibitor0.7917
CYP450 2D6 inhibitorInhibitor0.7009
CYP450 2C19 inhibitorInhibitor0.6513
CYP450 3A4 inhibitorInhibitor0.7372
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7408
Ames testNon AMES toxic0.6431
CarcinogenicityNon-carcinogens0.8914
BiodegradationNot ready biodegradable0.9963
Rat acute toxicity2.6958 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9496
hERG inhibition (predictor II)Inhibitor0.7208
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/MSsplash10-0006-0009000000-cb6dd803353807949257
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-c98cb41069f38a465045
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01oy-0019000000-e99fce6890e68d30f655
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-40fb71baf82b95d0d2f4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03fs-0898000000-827030dae175de9847a3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fmm-0593000000-af5088bda4ac710b136f
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]-190.94698
predicted
DeepCCS 1.0 (2019)
[M+H]+193.80713
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.7447
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dipeptidyl peptidase 4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by bindi...
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 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 21:26 / Updated at June 12, 2020 16:52