Nateglinide (CHEM017581)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:28:31 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017581
Identification
Common NameNateglinide
ClassSmall Molecule
DescriptionNateglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to β cells of the pancreas to stimulate insulin release. Nateglinide is an amino acid derivative that induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those naïve to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Nateglinide is extensively metabolized in the liver and excreted in urine (83%) and feces (10%). The major metabolites possess less activity than the parent compound. One minor metabolite, the isoprene, has the same potency as its parent compound.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-N-(trans-4-Isopropylcyclohexanecarbonyl)-D-phenylalanineChEBI
a 4166ChEBI
a-4166ChEBI
AY 4166ChEBI
AY-4166ChEBI
AY4166ChEBI
FasticChEBI
NateglinidaChEBI
NateglinidumChEBI
StarlixChEBI
StarsisChEBI
trans-N-{[4-(1-methylethyl)cyclohexyl]carbonyl}-D-phenylalanineChEBI
Chemical FormulaC19H27NO3
Average Molecular Mass317.429 g/mol
Monoisotopic Mass317.199 g/mol
CAS Registry Number105816-04-4
IUPAC Name(2R)-2-({hydroxy[(1r,4r)-4-(propan-2-yl)cyclohexyl]methylidene}amino)-3-phenylpropanoic acid
Traditional Namenateglinide
SMILES[H][C@](CC1=CC=CC=C1)(N=C(O)[C@@]1([H])CC[C@@]([H])(CC1)C(C)C)C(O)=O
InChI IdentifierInChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1
InChI KeyOELFLUMRDSZNSF-BRWVUGGUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Aromatic monoterpenoid
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP3.82ALOGPS
logP4.85ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)1.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.98 m³·mol⁻¹ChemAxon
Polarizability35.76 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9741000000-0cb56489bd73919de692Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-0593000000-1fed07ad435ca0bd7249Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0902000000-a4601550406e75607d7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0009000000-6d3ecfcb5cad6574fb53Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-2906000000-611e57a755195a18f161Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0297-4900000000-249affd02e2091b02c4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00kg-6900000000-75cf7590825f0daed817Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-006y-9800000000-9ae37acdd6880d2b5b15Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00dl-9500000000-04e4a14180f9ecbf261cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0903000000-ae545cd52cf21d62bac5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01di-4900000000-3e4bea96ab1e4494a977Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01b9-9600000000-3422b818749cdac92bc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01b9-9400000000-9a807ba353a9d85f21a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01b9-9400000000-05e5ef5df3d0b69272caSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01b9-9500000000-8ae951e802da41dc6224Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0901000000-44ac1cd2a68ec0f4bdfcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0902000000-a4601550406e75607d7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3449000000-50b24d9b3ac051164f7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-4931000000-d475a1738fae856ab419Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-2c0c4efc63c909e7557dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0259000000-7e7280ea8842be0f9884Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01di-1983000000-b31e6d0fa00dc39b50caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-7900000000-064b989d9bbdfcb88a70Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00731
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNateglinide
Chemspider IDNot Available
ChEBI ID31897
PubChem Compound IDNot Available
Kegg Compound IDC12508
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10820657
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11585005
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11724096
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12652357
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12918894
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=14748619
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16178991
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17253883
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=17573070
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18200800
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19337530
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21801074
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23229379
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23675267
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23867985
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23872227
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23935065
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24563597