NAV

(3R,4R)-1-{6-[3-(METHYLSULFONYL)PHENYL]PYRIMIDIN-4-YL}-4-(2,4,5-TRIFLUOROPHENYL)PIPERIDIN-3-AMINE

Identification

Generic Name
(3R,4R)-1-{6-[3-(METHYLSULFONYL)PHENYL]PYRIMIDIN-4-YL}-4-(2,4,5-TRIFLUOROPHENYL)PIPERIDIN-3-AMINE
DrugBank Accession Number
DB08164
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 462.488
Monoisotopic: 462.133731241
Chemical Formula
C22H21F3N4O2S
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 phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Phenylpyrimidines
Alternative Parents
Phenylpiperidines / Benzenesulfonyl compounds / Dialkylarylamines / Aminopiperidines / Aminopyrimidines and derivatives / Aralkylamines / Fluorobenzenes / Aryl fluorides / Imidolactams / Sulfones
show 7 more
Substituents
3-aminopiperidine / 4-phenylpyrimidine / 5-phenylpyrimidine / Amine / Aminopyrimidine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, aminopyrimidine, aminopiperidine, heteroarylpiperidine (CHEBI:43835)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
GOBIXGZJSMAOFV-QRWLVFNGSA-N
InChI
InChI=1S/C22H21F3N4O2S/c1-32(30,31)14-4-2-3-13(7-14)21-10-22(28-12-27-21)29-6-5-15(20(26)11-29)16-8-18(24)19(25)9-17(16)23/h2-4,7-10,12,15,20H,5-6,11,26H2,1H3/t15-,20+/m1/s1
IUPAC Name
(3R,4R)-1-[6-(3-methanesulfonylphenyl)pyrimidin-4-yl]-4-(2,4,5-trifluorophenyl)piperidin-3-amine
SMILES
[H][C@]1(N)CN(CC[C@]1([H])C1=CC(F)=C(F)C=C1F)C1=NC=NC(=C1)C1=CC=CC(=C1)S(C)(=O)=O

References

General References
Not Available
PubChem Compound
16058650
PubChem Substance
99444635
ChemSpider
17218369
BindingDB
15518
ChEMBL
CHEMBL1234200
ZINC
ZINC000014958825
PDBe Ligand
MA9
PDB Entries
2oqv

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 Solubility0.0119 mg/mLALOGPS
logP2.52ALOGPS
logP3.22Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.19Chemaxon
pKa (Strongest Basic)9.48Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area89.18 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity116.61 m3·mol-1Chemaxon
Polarizability44.84 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9773
Blood Brain Barrier+0.9343
Caco-2 permeable-0.5689
P-glycoprotein substrateSubstrate0.6597
P-glycoprotein inhibitor INon-inhibitor0.7634
P-glycoprotein inhibitor IINon-inhibitor0.9745
Renal organic cation transporterNon-inhibitor0.6149
CYP450 2C9 substrateNon-substrate0.759
CYP450 2D6 substrateNon-substrate0.7417
CYP450 3A4 substrateNon-substrate0.5128
CYP450 1A2 substrateNon-inhibitor0.6395
CYP450 2C9 inhibitorNon-inhibitor0.6467
CYP450 2D6 inhibitorNon-inhibitor0.6891
CYP450 2C19 inhibitorNon-inhibitor0.5119
CYP450 3A4 inhibitorInhibitor0.507
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5272
Ames testNon AMES toxic0.6223
CarcinogenicityNon-carcinogens0.8343
BiodegradationNot ready biodegradable0.9965
Rat acute toxicity2.5731 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9208
hERG inhibition (predictor II)Inhibitor0.8035
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/MSsplash10-03di-0000900000-be7715e4f93935cecf96
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1020900000-b397f9d0e83415ec5ab9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dj-0002900000-5f17a329be40fb224e43
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-3000900000-390059851b9ac7d8ea23
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-07bb-0195600000-561180b415476ede3711
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fs-3592500000-dc3d94293faf7bd5dd1f
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]-203.27318
predicted
DeepCCS 1.0 (2019)
[M+H]+205.66875
predicted
DeepCCS 1.0 (2019)
[M+Na]+211.58128
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 21:29 / Updated at June 12, 2020 16:52