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Record Information
Version4.0
Creation Date2013-07-09 16:18:10 UTC
Update Date2017-10-23 19:15:52 UTC
HMDB IDHMDB0061099
Secondary Accession Numbers
  • HMDB61099
Metabolite Identification
Common Name5-hydroxy saxagliptin
Description5-hydroxy saxagliptin is a metabolite of saxagliptin. Saxagliptin, previously identified as BMS-477118, is a new oral hypoglycemic of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. Early development was solely by Bristol-Myers Squibb; in 2007 AstraZeneca joined with Bristol-Myers Squibb to co-develop the final compound and collaborate on the marketing of the drug. A New Drug Application for saxagliptin in the treatment of type 2 diabetes was submitted to the FDA in June 2008. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H25N3O3
Average Molecular Weight331.4094
Monoisotopic Molecular Weight331.189591681
IUPAC Name(1R,3R,5R)-2-[(2S)-2-amino-2-(3,5-dihydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Traditional Name(1R,3R,5R)-2-[(2S)-2-amino-2-(3,5-dihydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
CAS Registry NumberNot Available
SMILES
[H]C12CC3(O)CC(O)(C1)CC(C2)(C3)[C@H](N)C(=O)N1[C@@H]2C[C@@H]2C[C@@H]1C#N
InChI Identifier
InChI=1S/C18H25N3O3/c19-6-12-1-11-2-13(11)21(12)15(22)14(20)16-3-10-4-17(23,7-16)9-18(24,5-10)8-16/h10-14,23-24H,1-5,7-9,20H2/t10?,11-,12+,13+,14+,16?,17?,18?/m0/s1
InChI KeyGAWUJFVQGSLSSZ-HREDRMPBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • N-acyl-piperidine
  • N-acylpyrrolidine
  • Piperidine
  • Cyclic alcohol
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Tertiary alcohol
  • Carboxamide group
  • Carbonitrile
  • Nitrile
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.4 g/LALOGPS
logP-0.23ALOGPS
logP-1.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)14.36ChemAxon
pKa (Strongest Basic)7.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area110.58 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.63 m³·mol⁻¹ChemAxon
Polarizability34.62 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0faa-6900000000-fa9bd810e62ae76bfc89View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f7c-9404000000-71aeb1ba2e89719be3afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-0229000000-687ba63be8245c7dfe7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-1912000000-cab6d4388d5d533a9957View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2900000000-2d4121387d4254ed68a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-e0048abf0d034075981fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-0916000000-4a3299d49b29b83d3acfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-7900000000-4b6960eb8f8304978ff0View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00459
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available