Pregabalin (CHEM018660)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:25:33 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018660
Identification
Common NamePregabalin
ClassSmall Molecule
DescriptionA gamma-amino acid that is gamma-aminobutyric acid (GABA) carrying an isobutyl substitutent at the beta-position (the S-enantiomer). Binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-3-Isobutyl gabaChEBI
3-Isobutyl gabaChEBI
LyricaChEBI
3-(Aminomethyl)-5-methylhexanoic acidHMDB
(S+)-3-isobutyl gabaHMDB
3 Isobutyl gabaHMDB
(R-)-3-Isobutyl gabaHMDB
(S)-3-(Aminomethyl)-5-methylhexanoic acidHMDB
GABA, 3-isobutylHMDB
Chemical FormulaC8H17NO2
Average Molecular Mass159.226 g/mol
Monoisotopic Mass159.126 g/mol
CAS Registry Number148553-50-8
IUPAC Name(3S)-3-(aminomethyl)-5-methylhexanoic acid
Traditional Namepregabalin
SMILESCC(C)C[C@H](CN)CC(O)=O
InChI IdentifierInChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
InChI KeyAYXYPKUFHZROOJ-ZETCQYMHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Medium-chain fatty acid
  • Amino fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility11.3 g/LALOGPS
logP-1.4ALOGPS
logP-1.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.8ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity43.68 m³·mol⁻¹ChemAxon
Polarizability18.08 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9100000000-ff23b21ef03ce99e7cceSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9100000000-99ad7be9a2ea5e94fae2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-555454e7e8e11dab591dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-1a52554257d7f4b1c62eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-d48cd6eeef012787cc04Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-4b11df5208caa2e97dd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-605dc241ffd3a07a9220Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ox-0900000000-fb081cde39dde2ce89f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-3d95bb5278c7866658a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-96cebf4a3610cbf02059Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-8900000000-385584fca9e88b90a95bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9800000000-a1c6718b087b06101b8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-9200000000-5f291c943a1d1ae214adSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-9100000000-5283d02d98611a8c2c38Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-9000000000-8797f8d2776fcdb4b6d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-9000000000-a9ddfcf2032ffc9f53adSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0900000000-f61d6c12dadd60399296Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0a4i-9000000000-37e1f57223b0ba6b95f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4i-9100000000-ea797f17647a8718608dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-0900000000-96cebf4a3610cbf02059Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0900000000-142ab34d1881e6e3e247Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1900000000-0d022bd7f0e9af9f06f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ed-9800000000-fe82df47c3ac7c9c39e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5a-9000000000-20b509ce412ff8d7fe8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0900000000-d07b85e7e0d11beb1781Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-1900000000-6351cf9406ff25f78268Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9300000000-8f1f021c89d9316d47a0Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDDB00230
HMDB IDHMDB0014375
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPregabalin
Chemspider ID4589156
ChEBI ID64356
PubChem Compound ID5486971
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22339078
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22345870
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22362672
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22366121
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22404404
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22413436
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22415534
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22415535
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22424859
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22431439
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22448469
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22449111
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22459341
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22468635
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22470326
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22473300
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22473872
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22476240
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22480279
20. Su TZ, Feng MR, Weber ML: Mediation of highly concentrative uptake of pregabalin by L-type amino acid transport in Chinese hamster ovary and Caco-2 cells. J Pharmacol Exp Ther. 2005 Jun;313(3):1406-15. Epub 2005 Mar 15.
21. Authors unspecified: Schedules of controlled substances: placement of pregabalin into schedule V. Final rule. Fed Regist. 2005 Jul 28;70(144):43633-5.
22. Li Z, Taylor CP, Weber M, Piechan J, Prior F, Bian F, Cui M, Hoffman D, Donevan S: Pregabalin is a potent and selective ligand for alpha(2)delta-1 and alpha(2)delta-2 calcium channel subunits. Eur J Pharmacol. 2011 Sep 30;667(1-3):80-90. doi: 10.1016/j.ejphar.2011.05.054. Epub 2011 Jun 1.