N-({(2S)-1-[(3R)-3-AMINO-4-(2-FLUOROPHENYL)BUTANOYL]PYRROLIDIN-2-YL}METHYL)BENZAMIDE

Identification

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Name
N-({(2S)-1-[(3R)-3-AMINO-4-(2-FLUOROPHENYL)BUTANOYL]PYRROLIDIN-2-YL}METHYL)BENZAMIDE
Accession Number
DB07779
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: 383.4591
Monoisotopic: 383.200905296
Chemical Formula
C22H26FN3O2
InChI Key
ANQHSFFUNMTTRS-MOPGFXCFSA-N
InChI
InChI=1S/C22H26FN3O2/c23-20-11-5-4-9-17(20)13-18(24)14-21(27)26-12-6-10-19(26)15-25-22(28)16-7-2-1-3-8-16/h1-5,7-9,11,18-19H,6,10,12-15,24H2,(H,25,28)/t18-,19+/m1/s1
IUPAC Name
N-{[(2S)-1-[(3R)-3-amino-4-(2-fluorophenyl)butanoyl]pyrrolidin-2-yl]methyl}benzamide
SMILES
[H][C@](N)(CC(=O)N1CCC[C@@]1([H])CNC(=O)C1=CC=CC=C1)CC1=C(F)C=CC=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
5494422
PubChem Substance
99444250
ChemSpider
4591871
BindingDB
11559
ChEMBL
CHEMBL425584
HET
FPB
PDB Entries
2bub

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 Solubility0.0241 mg/mLALOGPS
logP2.05ALOGPS
logP2.29ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)14.99ChemAxon
pKa (Strongest Basic)8.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.43 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.85 m3·mol-1ChemAxon
Polarizability40.87 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9797
Blood Brain Barrier+0.9181
Caco-2 permeable-0.6822
P-glycoprotein substrateSubstrate0.5981
P-glycoprotein inhibitor IInhibitor0.7772
P-glycoprotein inhibitor IINon-inhibitor0.7569
Renal organic cation transporterInhibitor0.5205
CYP450 2C9 substrateNon-substrate0.8905
CYP450 2D6 substrateNon-substrate0.7705
CYP450 3A4 substrateNon-substrate0.5659
CYP450 1A2 substrateNon-inhibitor0.7235
CYP450 2C9 inhibitorNon-inhibitor0.6081
CYP450 2D6 inhibitorInhibitor0.6215
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorInhibitor0.6845
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7761
Ames testNon AMES toxic0.7357
CarcinogenicityNon-carcinogens0.8124
BiodegradationNot ready biodegradable0.9963
Rat acute toxicity2.5616 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9393
hERG inhibition (predictor II)Inhibitor0.9044
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 beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Beta amino acids and derivatives
Alternative Parents
Amphetamines and derivatives / Benzamides / N-acylpyrrolidines / Benzoyl derivatives / Aralkylamines / Fluorobenzenes / Aryl fluorides / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azacyclic compounds
show 6 more
Substituents
Beta amino acid or derivatives / Amphetamine or derivatives / Benzamide / Benzoic acid or derivatives / Benzoyl / N-acylpyrrolidine / Fluorobenzene / Aralkylamine / Halobenzene / Aryl fluoride
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
benzamides, N-acylpyrrolidine (CHEBI:42621)

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 15:25 / Updated on December 02, 2019 07:53