(2S,3S)-3-AMINO-4-[(3S)-3-FLUOROPYRROLIDIN-1-YL]-N,N-DIMETHYL-4-OXO-2-(TRANS-4-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-5-YLCYCLOHEXYL)BUTANAMIDE

Identification

Name
(2S,3S)-3-AMINO-4-[(3S)-3-FLUOROPYRROLIDIN-1-YL]-N,N-DIMETHYL-4-OXO-2-(TRANS-4-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-5-YLCYCLOHEXYL)BUTANAMIDE
Accession Number
DB07135
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: 430.5189
Monoisotopic: 430.249252471
Chemical Formula
C22H31FN6O2
InChI Key
ZPWDKZWKUOYOHA-UKSSEWCLSA-N
InChI
InChI=1S/C22H31FN6O2/c1-27(2)21(30)19(20(24)22(31)28-11-10-16(23)12-28)15-8-6-14(7-9-15)17-4-3-5-18-25-13-26-29(17)18/h3-5,13-16,19-20H,6-12,24H2,1-2H3/t14-,15-,16-,19-,20-/m0/s1
IUPAC Name
(2S,3S)-3-amino-4-[(3S)-3-fluoropyrrolidin-1-yl]-N,N-dimethyl-4-oxo-2-[(1r,4S)-4-{[1,2,4]triazolo[1,5-a]pyridin-5-yl}cyclohexyl]butanamide
SMILES
[H][C@@](N)(C(=O)N1CC[C@]([H])(F)C1)[C@@]([H])(C(=O)N(C)C)[C@@]1([H])CC[C@@]([H])(CC1)C1=CC=CC2=NC=NN12

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
11495704
PubChem Substance
99443606
ChemSpider
24684686
BindingDB
50221979
ChEMBL
CHEMBL400841
ZINC
ZINC000100071163
PDBe Ligand
524
PDB Entries
2qt9

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 Solubility0.152 mg/mLALOGPS
logP1.2ALOGPS
logP0.81ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)18.94ChemAxon
pKa (Strongest Basic)7.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area96.83 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.95 m3·mol-1ChemAxon
Polarizability45.57 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+0.9397
Caco-2 permeable-0.6864
P-glycoprotein substrateSubstrate0.7134
P-glycoprotein inhibitor IInhibitor0.5365
P-glycoprotein inhibitor IINon-inhibitor0.698
Renal organic cation transporterInhibitor0.5
CYP450 2C9 substrateNon-substrate0.8951
CYP450 2D6 substrateNon-substrate0.7271
CYP450 3A4 substrateSubstrate0.6866
CYP450 1A2 substrateNon-inhibitor0.864
CYP450 2C9 inhibitorInhibitor0.733
CYP450 2D6 inhibitorNon-inhibitor0.9137
CYP450 2C19 inhibitorNon-inhibitor0.5125
CYP450 3A4 inhibitorNon-inhibitor0.9233
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5118
Ames testNon AMES toxic0.5233
CarcinogenicityNon-carcinogens0.7922
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.6631 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9101
hERG inhibition (predictor II)Inhibitor0.7722
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 alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Aromatic monoterpenoids / Bicyclic monoterpenoids / Menthane monoterpenoids / Triazolopyridines / N-acylpyrrolidines / Aralkylamines / Pyridines and derivatives / N-acyl amines / Triazoles / Tertiary carboxylic acid amides
show 9 more
Substituents
1,2,4-triazole / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aromatic monoterpenoid / Azacycle / Azole
show 24 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 15:19 / Updated on June 12, 2020 10:52

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