Vildagliptin (CED0003886)

Record Information
Version1.0
Creation Date2016-05-25 18:28:51 UTC
Update Date2026-08-19 21:33:12 UTC
Accession NumberCHEM022341
Identification
Common NameVildagliptin
ClassSmall Molecule
Description
Vildagliptin is an organic compound with the formula C17H25N3O2 and an average molecular weight of 303.40 g/mol. Vildagliptin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. In terms of its biological activity, it acts as an inhibitor of the protein target Dipeptidyl peptidase 4 (DPP4). The compound is utilized within healthcare, pharmaceuticals, and veterinary products as a blood glucose lowering drug, excluding insulins. The recorded route of exposure for this substance is oral. Vildagliptin has been found in or released from 27 recorded sources. These include building and construction materials such as floors, roofs, fencing, and tents or canopies. It is also associated with household cleaning and consumer products, specifically soap dispensers, pipe accessories, and match receptacles or boxes. Within the food and cookware sector, it is linked to molasses and the treatment of molasses. Additionally, it is found in electrical and electronic equipment, including amplifiers, antennas, coils, auxiliary devices, adjustable resistors, and 13 other sources.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
NVP-LAF237HMDB
EQUAHMDB
GalvusHMDB
JalraHMDB
LAF 237HMDB
LAF237HMDB
NVP-LAF-237HMDB
XiliarxHMDB
(2S)-(((3-Hydroxyadamantan-1-yl)amino)acetyl)pyrrolidine-2-carbonitrileHMDB
NVP LAF237MeSH
VildagliptinMeSH
Chemical FormulaC17H25N3O2
Average Molecular Mass303.399 g/mol
Monoisotopic Mass303.195 g/mol
CAS Registry Number274901-16-5
IUPAC Name(2S)-1-{2-[(3-hydroxyadamantan-1-yl)amino]acetyl}pyrrolidine-2-carbonitrile
Traditional NameEQUA
SMILESOC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N
InChI IdentifierInChI=1S/C17H25N3O2/c18-9-14-2-1-3-20(14)15(21)10-19-16-5-12-4-13(6-16)8-17(22,7-12)11-16/h12-14,19,22H,1-8,10-11H2/t12?,13?,14-,16?,17?/m0/s1
InChI KeySYOKIDBDQMKNDQ-XWTIBIIYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • N-acylpyrrolidine
  • Cyclic alcohol
  • Pyrrolidine
  • Tertiary alcohol
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Secondary aliphatic amine
  • Carbonitrile
  • Nitrile
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.75 g/LALOGPS
logP1.12ALOGPS
logP-0.22ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)14.71ChemAxon
pKa (Strongest Basic)9.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82 m³·mol⁻¹ChemAxon
Polarizability33.17 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-9640000000-8d45705b266a6c8e72b7Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fk9-8924000000-5ae92687d7574a071316Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0049000000-467b8774aceed12b4d58Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0109000000-f6f13525e0841cb9a0ceNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0902000000-39449b9fce86086b9f42Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-e42a57f8c41f08f0fe2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-bdf96b3bb5758ccb2ee2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ue9-0900000000-813cd0c1f6616a3aac1aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0309000000-4cc7261ec4a8a5eb3c50Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0901000000-2828160e08a306467998Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-5900000000-797e5126c08d2be98d02Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f6t-9600000000-55a58d88d2018c5adff8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9200000000-b511fd9b2243cdaf69ccNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0005-9100000000-5c5cb1119f70d6852572Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1709000000-d62dc38a0bb019fd4bedNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0902000000-fb003533761fa4eb101cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0109000000-9e22f780279800f79e8cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-70a44e1224e6ccd6e6cfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-8aee1e33231f7ccb116eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ue9-0900000000-813cd0c1f6616a3aac1aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0109000000-245ea3783939a252f52cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9200000000-e280cd752fa27ea32bb4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f6t-9600000000-0893164552131a4795b3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0005-9100000000-59af6bd449ca2b41f97aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-5900000000-a50be87bdbed9a599dedNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0901000000-3e28f1f03fca944153eeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0309000000-f7d3097413bf35d00a6aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f79-1975000000-6db3cd2ad45cf37d3b43Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-1930000000-3e7f36dc245475385bfaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0il0-4900000000-1ce29a450de87e7c1becNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0119000000-033d575b95152dc083baNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udj-9768000000-d519b4fc4f6961772f76Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00tg-9310000000-fa47fa8e44cd03fddfb2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0029000000-07c314705464c52849caNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2905000000-925d7c8dfcef9600b6d4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1900000000-3b0e5c30bff39a9c4d54Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-481f847369c25877150eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1029000000-6f63cd2f3377aaca2604Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-5491000000-91d563f3cd51e39d6f64Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
242.0Log mg/kg[140:430]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
263Blood glucose lowering drugs, excl. insulinsHealthcare, pharmaceuticals & veterinary productsNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
528MicrophonesElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
558Match Receptables Or BoxesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
577Watch ChainsHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
590Lifeboat EquipmentMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Dipeptidyl peptidase 4 structureClick to view 3D structureDipeptidyl peptidase 4P27487HumansPredicted (SEA)2.25763
Dipeptidyl peptidase 2 structureClick to view 3D structureDipeptidyl peptidase 2Q9UHL4HumansPredicted (SEA)0.311397
Glomulin structureClick to view 3D structureGlomulinQ92990HumansPredicted (SEA)0.0778492
Prolyl endopeptidase structureClick to view 3D structureProlyl endopeptidaseP48147HumansPredicted (SEA)0.389246
Dipeptidyl peptidase 8 structureClick to view 3D structureDipeptidyl peptidase 8Q6V1X1HumansPredicted (SEA)1.01204
Dipeptidyl peptidase 9 structureClick to view 3D structureDipeptidyl peptidase 9Q86TI2HumansPredicted (SEA)2.02408
Prolyl endopeptidase FAP structureClick to view 3D structureProlyl endopeptidase FAPQ12884HumansPredicted (SEA)3.11397
Click to view 3D structureProlyl endopeptidase FAPP97321Mus musculusPredicted (SEA)1.94623
Click to view 3D structureDipeptidyl peptidase 4P28843Mus musculusPredicted (SEA)2.41333
Click to view 3D structureDipeptidyl peptidase 9E1BI31Bos taurusPredicted (SEA)0.155698
Click to view 3D structureDipeptidyl peptidase IVO31048Porphyromonas gingivalisPredicted (SEA)0.155698
Click to view 3D structureProlyl endopeptidaseP23687Sus scrofaPredicted (SEA)116.852
Bifunctional epoxide hydrolase 2 structureClick to view 3D structureBifunctional epoxide hydrolase 2P34913HumansPredicted (SEA)839.837
Click to view 3D structureDipeptidyl peptidase 4P14740Rattus norvegicusPredicted (SEA)8.71911
Click to view 3D structureProlyl endopeptidaseQ9QUR6Mus musculusPredicted (SEA)75.903
Presequence protease, mitochondrial structureClick to view 3D structurePresequence protease, mitochondrialQ5JRX3HumansPredicted (SEA)8.01847
Click to view 3D structureEnvelope phospholipase OPG057P04021Vaccinia virus (strain Western Reserve) (VACV) (Vaccinia virus (strainWR))Predicted (SEA)86.8019
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)6485.93
Click to view 3D structureEpoxide hydrolase 1P07099HumansPredicted (SEA)428.093
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)6980.9
Diphosphomevalonate decarboxylase structureClick to view 3D structureDiphosphomevalonate decarboxylaseP53602HumansPredicted (SEA)17.4382
Click to view 3D structureBifunctional epoxide hydrolase 2P34914Mus musculusPredicted (SEA)827.459
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)6622.01
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)7071.75
Click to view 3D structureProlyl endopeptidaseO70196Rattus norvegicusPredicted (SEA)227.398
Concentrations
Not Available
External Links
DrugBank IDDB04876
HMDB IDHMDB0015596
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVildagliptin
Chemspider ID5293734
ChEBI ID334541
PubChem Compound ID6918537
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Balas B, Baig MR, Watson C, Dunning BE, Ligueros-Saylan M, Wang Y, He YL, Darland C, Holst JJ, Deacon CF, Cusi K, Mari A, Foley JE, DeFronzo RA: The dipeptidyl peptidase IV inhibitor vildagliptin suppresses endogenous glucose production and enhances islet function after single-dose administration in type 2 diabetic patients. J Clin Endocrinol Metab. 2007 Apr;92(4):1249-55. Epub 2007 Jan 23.