6-(4-{(1S,2S)-2-AMINO-1-[(DIMETHYLAMINO)CARBONYL]-3-[(3S)-3-FLUOROPYRROLIDIN-1-YL]-3-OXOPROPYL}PHENYL)-1H-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-4-IUM

Identification

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Name
6-(4-{(1S,2S)-2-AMINO-1-[(DIMETHYLAMINO)CARBONYL]-3-[(3S)-3-FLUOROPYRROLIDIN-1-YL]-3-OXOPROPYL}PHENYL)-1H-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-4-IUM
Accession Number
DB08504
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: 424.4713
Monoisotopic: 424.202302279
Chemical Formula
C22H25FN6O2
InChI Key
ZNHVIJAGMFQGMS-IHPCNDPISA-N
InChI
InChI=1S/C22H25FN6O2/c1-27(2)21(30)19(20(24)22(31)28-10-9-17(23)12-28)15-5-3-14(4-6-15)16-7-8-18-25-13-26-29(18)11-16/h3-8,11,13,17,19-20H,9-10,12,24H2,1-2H3/t17-,19-,20-/m0/s1
IUPAC Name
(2S,3S)-3-amino-4-[(3S)-3-fluoropyrrolidin-1-yl]-N,N-dimethyl-4-oxo-2-(4-{[1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)butanamide
SMILES
[H][C@@](N)(C(=O)N1CC[C@]([H])(F)C1)[C@@]([H])(C(=O)N(C)C)C1=CC=C(C=C1)C1=CN2N=CN=C2C=C1

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
10320144
PubChem Substance
99444975
ChemSpider
8495608
BindingDB
50221972
ChEMBL
CHEMBL237337
HET
S14
PDB Entries
2fjp

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 Solubility0.109 mg/mLALOGPS
logP1.3ALOGPS
logP0.73ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)18.09ChemAxon
pKa (Strongest Basic)6.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area96.83 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.43 m3·mol-1ChemAxon
Polarizability44.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9475
Caco-2 permeable-0.6656
P-glycoprotein substrateSubstrate0.7279
P-glycoprotein inhibitor INon-inhibitor0.5625
P-glycoprotein inhibitor IINon-inhibitor0.7761
Renal organic cation transporterNon-inhibitor0.5269
CYP450 2C9 substrateNon-substrate0.8861
CYP450 2D6 substrateNon-substrate0.7442
CYP450 3A4 substrateSubstrate0.6909
CYP450 1A2 substrateNon-inhibitor0.7997
CYP450 2C9 inhibitorInhibitor0.6659
CYP450 2D6 inhibitorNon-inhibitor0.9149
CYP450 2C19 inhibitorNon-inhibitor0.5094
CYP450 3A4 inhibitorNon-inhibitor0.9477
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5433
Ames testNon AMES toxic0.5353
CarcinogenicityNon-carcinogens0.802
BiodegradationNot ready biodegradable0.9967
Rat acute toxicity2.6436 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9372
hERG inhibition (predictor II)Inhibitor0.7776
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 phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Phenylpyridines
Direct Parent
Phenylpyridines
Alternative Parents
Alpha amino acid amides / Phenylacetamides / Aromatic monoterpenoids / Bicyclic monoterpenoids / Triazolopyridines / N-acylpyrrolidines / Aralkylamines / N-acyl amines / Triazoles / Tertiary carboxylic acid amides
show 9 more
Substituents
Alpha-amino acid amide / 3-phenylpyridine / Alpha-amino acid or derivatives / P-cymene / Aromatic monoterpenoid / Bicyclic monoterpenoid / Monoterpenoid / Phenylacetamide / Triazolopyridine / N-acylpyrrolidine
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. 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. [PubMed:10592235]

Drug created on September 15, 2010 15:32 / Updated on December 02, 2019 08:14