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Identification
NameN-({(2S)-1-[(3R)-3-amino-4-(3-chlorophenyl)butanoyl]pyrrolidin-2-yl}methyl)-3-(methylsulfonyl)benzamide
Accession NumberDB08429
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 478.004
Monoisotopic: 477.148904796
Chemical FormulaC23H28ClN3O4S
InChI KeyInChIKey=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][C@](N)(CC(=O)N1CCC[C@@]1([H])CNC(=O)C1=CC=CC(=C1)S(C)(=O)=O)CC1=CC(Cl)=CC=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Amphetamine or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • N-acylpyrrolidine
  • Benzoyl
  • Aralkylamine
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Tertiary carboxylic acid amide
  • Sulfonyl
  • Sulfone
  • Pyrrolidine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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 binding at least ADA, CAV1, IGF2R, and PTPRC. Its binding to CAV1 and CARD11 induces T-cell proliferation and NF-kappa-B activation in a T-cell receptor/CD3-dependent manner. Its interaction with ADA also ...
Gene Name:
DPP4
Uniprot ID:
P27487
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 ]
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Drug created on September 15, 2010 15:31 / Updated on September 16, 2013 18:09