N-({(2S)-1-[(3R)-3-amino-4-(3-chlorophenyl)butanoyl]pyrrolidin-2-yl}methyl)-3-(methylsulfonyl)benzamide

Identification

Name
N-({(2S)-1-[(3R)-3-amino-4-(3-chlorophenyl)butanoyl]pyrrolidin-2-yl}methyl)-3-(methylsulfonyl)benzamide
Accession Number
DB08429
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: 478.004
Monoisotopic: 477.148904796
Chemical Formula
C23H28ClN3O4S
InChI Key
QRGBOABBMKYMLG-UXHICEINSA-N
InChI
InChI=1S/C23H28ClN3O4S/c1-32(30,31)21-9-3-6-17(13-21)23(29)26-15-20-8-4-10-27(20)22(28)14-19(25)12-16-5-2-7-18(24)11-16/h2-3,5-7,9,11,13,19-20H,4,8,10,12,14-15,25H2,1H3,(H,26,29)/t19-,20+/m1/s1
IUPAC Name
N-{[(2S)-1-[(3R)-3-amino-4-(3-chlorophenyl)butanoyl]pyrrolidin-2-yl]methyl}-3-methanesulfonylbenzamide
SMILES
[H][[email protected]](N)(CC(=O)N1CCC[[email protected]@]1([H])CNC(=O)C1=CC=CC(=C1)S(C)(=O)=O)CC1=CC(Cl)=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDipeptidyl peptidase 4Not AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
42608447
PubChem Substance
99444900
ChemSpider
24629791
BindingDB
50296131
ChEMBL
CHEMBL564249
HET
PS4
PDB Entries
3h0c

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 Solubility0.0105 mg/mLALOGPS
logP1.97ALOGPS
logP1.59ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)14.03ChemAxon
pKa (Strongest Basic)8.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area109.57 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity125.44 m3·mol-1ChemAxon
Polarizability49.35 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8367
Blood Brain Barrier+0.745
Caco-2 permeable-0.7022
P-glycoprotein substrateSubstrate0.5976
P-glycoprotein inhibitor INon-inhibitor0.7538
P-glycoprotein inhibitor IINon-inhibitor0.9498
Renal organic cation transporterNon-inhibitor0.6482
CYP450 2C9 substrateNon-substrate0.7004
CYP450 2D6 substrateNon-substrate0.8167
CYP450 3A4 substrateSubstrate0.5334
CYP450 1A2 substrateNon-inhibitor0.9024
CYP450 2C9 inhibitorNon-inhibitor0.7701
CYP450 2D6 inhibitorNon-inhibitor0.6629
CYP450 2C19 inhibitorNon-inhibitor0.6852
CYP450 3A4 inhibitorInhibitor0.7186
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6665
Ames testNon AMES toxic0.6374
CarcinogenicityNon-carcinogens0.6693
BiodegradationNot ready biodegradable0.9702
Rat acute toxicity2.4702 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9706
hERG inhibition (predictor II)Inhibitor0.6877
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 / Benzenesulfonyl compounds / N-acylpyrrolidines / Benzoyl derivatives / Aralkylamines / Chlorobenzenes / Aryl chlorides / Tertiary carboxylic acid amides / Sulfones
show 8 more
Substituents
Beta amino acid or derivatives / Amphetamine or derivatives / Benzamide / Benzoic acid or derivatives / Benzenesulfonyl group / Benzoyl / N-acylpyrrolidine / Chlorobenzene / Aralkylamine / Halobenzene
show 27 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Dipeptidyl peptidase 4
Kind
Protein
Organism
Human
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 15:31 / Updated on December 01, 2017 16:04