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

Identification

Generic Name
N-({(2S)-1-[(3R)-3-AMINO-4-(2-FLUOROPHENYL)BUTANOYL]PYRROLIDIN-2-YL}METHYL)BENZAMIDE
DrugBank Accession Number
DB07779
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 383.4591
Monoisotopic: 383.200905296
Chemical Formula
C22H26FN3O2
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 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
Amine / Amphetamine or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzamide / Benzenoid / Benzoic acid or derivatives
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
benzamides, N-acylpyrrolidine (CHEBI:42621)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
5494422
PubChem Substance
99444250
ChemSpider
4591871
BindingDB
11559
ChEMBL
CHEMBL425584
ZINC
ZINC000014948268
PDBe Ligand
FPB
PDB Entries
2bub

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 Solubility0.0241 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/MSsplash10-06si-1975000000-a844419cdfa48bfd25f9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fc0-1953000000-629809c1a64f43c692a2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4j-1924000000-c65c5480cdf97ef4bb77
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9330000000-95f986d21b4b21eb5b2e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9530000000-a453a3d1a75f967c630a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-3911000000-aa8ac4b3c811948da1e2
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]-182.60365
predicted
DeepCCS 1.0 (2019)
[M+H]+184.99922
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.91174
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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. [Article]

Drug created at September 15, 2010 21:25 / Updated at June 12, 2020 16:52