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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:02 UTC
HMDB IDHMDB0015596
Secondary Accession Numbers
  • HMDB15596
Metabolite Identification
Common NameVildagliptin
DescriptionVildagliptin, previously identified as LAF237, is a new oral anti-hyperglycemic agent (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. Vildagliptin inhibits the inactivation of GLP-1 and GIP by DPP-4, allowing GLP-1 and GIP to potentiate the secretion of insulin in the beta cells and suppress glucaon release by the alpha cells of the islets of Langerhans in the pancreas. It is currently in clinical trials in the U.S. and has been shown to reduce hyperglycemia in type 2 diabetes mellitus. While the drug is still not approved for use in the US, it was approved in Feb 2008 by European Medicines Agency for use within the EU and is listed on the Australian PBS with certain restrictions.
Structure
Data?1582753314
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 Weight303.3993
Monoisotopic Molecular Weight303.194677059
IUPAC Name(2S)-1-{2-[(3-hydroxyadamantan-1-yl)amino]acetyl}pyrrolidine-2-carbonitrile
Traditional NameEQUA
CAS Registry Number274901-16-5
SMILES
OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.75 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.39331661259
DarkChem[M-H]-168.56731661259
DeepCCS[M-2H]-204.96430932474
DeepCCS[M+Na]+180.19130932474
AllCCS[M+H]+172.532859911
AllCCS[M+H-H2O]+169.732859911
AllCCS[M+NH4]+175.232859911
AllCCS[M+Na]+176.032859911
AllCCS[M-H]-176.432859911
AllCCS[M+Na-2H]-175.932859911
AllCCS[M+HCOO]-175.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VildagliptinOC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N2608.3Standard polar33892256
VildagliptinOC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N2586.4Standard non polar33892256
VildagliptinOC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N2845.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vildagliptin,1TMS,isomer #1C[Si](C)(C)OC12CC3CC(CC(NCC(=O)N4CCC[C@H]4C#N)(C3)C1)C22607.7Semi standard non polar33892256
Vildagliptin,1TMS,isomer #2C[Si](C)(C)N(CC(=O)N1CCC[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C22690.6Semi standard non polar33892256
Vildagliptin,2TMS,isomer #1C[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C)(C3)C22650.0Semi standard non polar33892256
Vildagliptin,2TMS,isomer #1C[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C)(C3)C22728.8Standard non polar33892256
Vildagliptin,2TMS,isomer #1C[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C)(C3)C23722.5Standard polar33892256
Vildagliptin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC12CC3CC(CC(NCC(=O)N4CCC[C@H]4C#N)(C3)C1)C22840.7Semi standard non polar33892256
Vildagliptin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC(=O)N1CCC[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C22908.9Semi standard non polar33892256
Vildagliptin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C(C)(C)C)(C3)C23099.4Semi standard non polar33892256
Vildagliptin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C(C)(C)C)(C3)C23159.9Standard non polar33892256
Vildagliptin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C(C)(C)C)(C3)C23793.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vildagliptin GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9640000000-8d45705b266a6c8e72b72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vildagliptin GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-8924000000-5ae92687d7574a0713162017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vildagliptin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-qTof , Positive-QTOFsplash10-0002-0049000000-467b8774aceed12b4d582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOFsplash10-0udi-0109000000-f6f13525e0841cb9a0ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOFsplash10-0udi-0902000000-39449b9fce86086b9f422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOFsplash10-0udi-0900000000-e42a57f8c41f08f0fe2b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOFsplash10-0udi-0900000000-bdf96b3bb5758ccb2ee22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOFsplash10-0ue9-0900000000-813cd0c1f6616a3aac1a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOFsplash10-0udi-0309000000-4cc7261ec4a8a5eb3c502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOFsplash10-0udi-0901000000-2828160e08a3064679982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOFsplash10-0udi-5900000000-797e5126c08d2be98d022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOFsplash10-0f6t-9600000000-55a58d88d2018c5adff82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOFsplash10-0002-9200000000-b511fd9b2243cdaf69cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOFsplash10-0005-9100000000-5c5cb1119f70d68525722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin , positive-QTOFsplash10-0udi-1709000000-d62dc38a0bb019fd4bed2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin 20V, Positive-QTOFsplash10-0udi-0902000000-fb003533761fa4eb101c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin 10V, Positive-QTOFsplash10-0udi-0109000000-9e22f780279800f79e8c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin 30V, Positive-QTOFsplash10-0udi-0900000000-70a44e1224e6ccd6e6cf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin 40V, Positive-QTOFsplash10-0udi-0900000000-8aee1e33231f7ccb116e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin 50V, Positive-QTOFsplash10-0ue9-0900000000-813cd0c1f6616a3aac1a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vildagliptin 10V, Positive-QTOFsplash10-0udi-0109000000-245ea3783939a252f52c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vildagliptin 10V, Positive-QTOFsplash10-0f79-1975000000-6db3cd2ad45cf37d3b432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vildagliptin 20V, Positive-QTOFsplash10-01q9-1930000000-3e7f36dc245475385bfa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vildagliptin 40V, Positive-QTOFsplash10-0il0-4900000000-1ce29a450de87e7c1bec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vildagliptin 10V, Negative-QTOFsplash10-0udi-0119000000-033d575b95152dc083ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vildagliptin 20V, Negative-QTOFsplash10-0udj-9768000000-d519b4fc4f6961772f762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vildagliptin 40V, Negative-QTOFsplash10-00tg-9310000000-fa47fa8e44cd03fddfb22016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04876 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04876 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04876
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5293734
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVildagliptin
METLIN IDNot Available
PubChem Compound6918537
PDB IDNot Available
ChEBI ID334541
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:17244786 ]

Enzymes

General function:
Involved in serine-type endopeptidase 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 regulates lymphocyte-epithelial cell adhesion. In association with FAP is involved in the pericellular proteolysis of the extracellular matrix (ECM), the migration and invasion of endothelial cells into the ECM. May be involved in the promotion of lymphatic endothelial cells adhesion, migration and tube formation. When overexpressed, enhanced cell proliferation, a process inhibited by GPC3. Acts also as a serine exopeptidase with a dipeptidyl peptidase activity that regulates various physiological processes by cleaving peptides in the circulation, including many chemokines, mitogenic growth factors, neuropeptides and peptide hormones. Removes N-terminal dipeptides sequentially from polypeptides having unsubstituted N-termini provided that the penultimate residue is proline
Gene Name:
DPP4
Uniprot ID:
P27487
Molecular weight:
88277.9
References
  1. Ahren B, Gomis R, Standl E, Mills D, Schweizer A: Twelve- and 52-week efficacy of the dipeptidyl peptidase IV inhibitor LAF237 in metformin-treated patients with type 2 diabetes. Diabetes Care. 2004 Dec;27(12):2874-80. [PubMed:15562200 ]
  2. Mentlein R, Gallwitz B, Schmidt WE: Dipeptidyl-peptidase IV hydrolyses gastric inhibitory polypeptide, glucagon-like peptide-1(7-36)amide, peptide histidine methionine and is responsible for their degradation in human serum. Eur J Biochem. 1993 Jun 15;214(3):829-35. [PubMed:8100523 ]
  3. Gupta R, Walunj SS, Tokala RK, Parsa KV, Singh SK, Pal M: Emerging drug candidates of dipeptidyl peptidase IV (DPP IV) inhibitor class for the treatment of Type 2 Diabetes. Curr Drug Targets. 2009 Jan;10(1):71-87. [PubMed:19149538 ]