Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:09 UTC
HMDB IDHMDB0014375
Secondary Accession Numbers
  • HMDB14375
Metabolite Identification
Common NamePregabalin
DescriptionPregabalin is an anticonvulsant drug used for neuropathic pain, as an adjunct therapy for partial seizures, and in generalized anxiety disorder. It was designed as a more potent successor to gabapentin. Pregabalin is marketed by Pfizer under the trade name Lyrica. It is considered to have a dependence liability if misused, and is classified as a Schedule V drug in the U.S. [Wikipedia ]
Structure
Data?1676999889
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 Weight159.2261
Monoisotopic Molecular Weight159.125928793
IUPAC Name(3S)-3-(aminomethyl)-5-methylhexanoic acid
Traditional Namepregabalin
CAS Registry Number148553-50-8
SMILES
CC(C)C[C@H](CN)CC(O)=O
InChI Identifier
InChI=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
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 Solubility11.3 g/LNot Available
LogP1.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.0131661259
DarkChem[M-H]-131.85931661259
DeepCCS[M+H]+135.92230932474
DeepCCS[M-H]-132.09230932474
DeepCCS[M-2H]-169.33430932474
DeepCCS[M+Na]+144.87430932474
AllCCS[M+H]+137.732859911
AllCCS[M+H-H2O]+133.832859911
AllCCS[M+NH4]+141.432859911
AllCCS[M+Na]+142.432859911
AllCCS[M-H]-137.632859911
AllCCS[M+Na-2H]-139.732859911
AllCCS[M+HCOO]-142.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PregabalinCC(C)C[C@H](CN)CC(O)=O2164.2Standard polar33892256
PregabalinCC(C)C[C@H](CN)CC(O)=O1353.7Standard non polar33892256
PregabalinCC(C)C[C@H](CN)CC(O)=O1360.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pregabalin,1TMS,isomer #1CC(C)C[C@H](CN)CC(=O)O[Si](C)(C)C1393.5Semi standard non polar33892256
Pregabalin,1TMS,isomer #2CC(C)C[C@H](CN[Si](C)(C)C)CC(=O)O1484.6Semi standard non polar33892256
Pregabalin,2TMS,isomer #1CC(C)C[C@H](CN[Si](C)(C)C)CC(=O)O[Si](C)(C)C1519.6Semi standard non polar33892256
Pregabalin,2TMS,isomer #1CC(C)C[C@H](CN[Si](C)(C)C)CC(=O)O[Si](C)(C)C1585.3Standard non polar33892256
Pregabalin,2TMS,isomer #1CC(C)C[C@H](CN[Si](C)(C)C)CC(=O)O[Si](C)(C)C1633.0Standard polar33892256
Pregabalin,2TMS,isomer #2CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C)[Si](C)(C)C1674.2Semi standard non polar33892256
Pregabalin,2TMS,isomer #2CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C)[Si](C)(C)C1621.2Standard non polar33892256
Pregabalin,2TMS,isomer #2CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C)[Si](C)(C)C1772.4Standard polar33892256
Pregabalin,3TMS,isomer #1CC(C)C[C@@H](CC(=O)O[Si](C)(C)C)CN([Si](C)(C)C)[Si](C)(C)C1718.4Semi standard non polar33892256
Pregabalin,3TMS,isomer #1CC(C)C[C@@H](CC(=O)O[Si](C)(C)C)CN([Si](C)(C)C)[Si](C)(C)C1726.3Standard non polar33892256
Pregabalin,3TMS,isomer #1CC(C)C[C@@H](CC(=O)O[Si](C)(C)C)CN([Si](C)(C)C)[Si](C)(C)C1618.0Standard polar33892256
Pregabalin,1TBDMS,isomer #1CC(C)C[C@H](CN)CC(=O)O[Si](C)(C)C(C)(C)C1624.7Semi standard non polar33892256
Pregabalin,1TBDMS,isomer #2CC(C)C[C@H](CN[Si](C)(C)C(C)(C)C)CC(=O)O1699.0Semi standard non polar33892256
Pregabalin,2TBDMS,isomer #1CC(C)C[C@H](CN[Si](C)(C)C(C)(C)C)CC(=O)O[Si](C)(C)C(C)(C)C1974.2Semi standard non polar33892256
Pregabalin,2TBDMS,isomer #1CC(C)C[C@H](CN[Si](C)(C)C(C)(C)C)CC(=O)O[Si](C)(C)C(C)(C)C1956.5Standard non polar33892256
Pregabalin,2TBDMS,isomer #1CC(C)C[C@H](CN[Si](C)(C)C(C)(C)C)CC(=O)O[Si](C)(C)C(C)(C)C1911.0Standard polar33892256
Pregabalin,2TBDMS,isomer #2CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2068.3Semi standard non polar33892256
Pregabalin,2TBDMS,isomer #2CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1987.2Standard non polar33892256
Pregabalin,2TBDMS,isomer #2CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1978.1Standard polar33892256
Pregabalin,3TBDMS,isomer #1CC(C)C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2376.6Semi standard non polar33892256
Pregabalin,3TBDMS,isomer #1CC(C)C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2276.7Standard non polar33892256
Pregabalin,3TBDMS,isomer #1CC(C)C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2012.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pregabalin GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9100000000-ff23b21ef03ce99e7cce2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pregabalin GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9100000000-99ad7be9a2ea5e94fae22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pregabalin 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 - Pregabalin LC-ESI-QFT , negative-QTOFsplash10-0a4i-0900000000-555454e7e8e11dab591d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , negative-QTOFsplash10-0a4i-0900000000-1a52554257d7f4b1c62e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , negative-QTOFsplash10-0a4i-0900000000-d48cd6eeef012787cc042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , negative-QTOFsplash10-0a4i-0900000000-4b11df5208caa2e97dd22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , negative-QTOFsplash10-0a4i-0900000000-605dc241ffd3a07a92202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QTOF , positive-QTOFsplash10-01ox-0900000000-fb081cde39dde2ce89f82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-3d95bb5278c7866658a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-96cebf4a3610cbf020592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOFsplash10-0006-8900000000-385584fca9e88b90a95b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOFsplash10-0006-9800000000-a1c6718b087b06101b8d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOFsplash10-0a4i-9200000000-5f291c943a1d1ae214ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOFsplash10-0a4i-9100000000-5283d02d98611a8c2c382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOFsplash10-0a4i-9000000000-8797f8d2776fcdb4b6d52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOFsplash10-0a4i-9000000000-a9ddfcf2032ffc9f53ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin 10V, Positive-QTOFsplash10-01ox-0900000000-f61d6c12dadd603992962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin 75V, Positive-QTOFsplash10-0a4i-9000000000-37e1f57223b0ba6b95f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin 60V, Positive-QTOFsplash10-0a4i-9100000000-ea797f17647a8718608d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin 30V, Positive-QTOFsplash10-0006-0900000000-96cebf4a3610cbf020592021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pregabalin 10V, Positive-QTOFsplash10-01ox-0900000000-142ab34d1881e6e3e2472021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregabalin 10V, Positive-QTOFsplash10-01ox-1900000000-0d022bd7f0e9af9f06f82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregabalin 20V, Positive-QTOFsplash10-03ed-9800000000-fe82df47c3ac7c9c39e32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregabalin 40V, Positive-QTOFsplash10-0a5a-9000000000-20b509ce412ff8d7fe8c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregabalin 10V, Negative-QTOFsplash10-0bt9-0900000000-d07b85e7e0d11beb17812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregabalin 20V, Negative-QTOFsplash10-0bt9-1900000000-6351cf9406ff25f782682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregabalin 40V, Negative-QTOFsplash10-0a4m-9300000000-8f1f021c89d9316d47a02016-08-03Wishart 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00230 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00230 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00230
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4589156
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPregabalin
METLIN IDNot Available
PubChem Compound5486971
PDB IDNot Available
ChEBI ID64356
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. 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. [PubMed:15769862 ]
  2. Authors unspecified: Schedules of controlled substances: placement of pregabalin into schedule V. Final rule. Fed Regist. 2005 Jul 28;70(144):43633-5. [PubMed:16050051 ]
  3. 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. [PubMed:21651903 ]

Enzymes

General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1A gives rise to P and/or Q-type calcium currents. P/Q-type calcium channels belong to the 'high-voltage activated' (HVA) group and are blocked by the funnel toxin (Ftx) and by the omega-agatoxin- IVA (omega-Aga-IVA). They are however insensitive to dihydropyridines (DHP), and omega-conotoxin-GVIA (omega-CTx-GVIA)
Gene Name:
CACNA1A
Uniprot ID:
O00555
Molecular weight:
282362.4
References
  1. Gazulla J, Tintore M: The P/Q-type voltage-dependent calcium channel: a therapeutic target in spinocerebellar ataxia type 6. Acta Neurol Scand. 2007 May;115(5):356-63. [PubMed:17489948 ]
  2. Gazulla J, Tintore MA: The P/Q-type voltage-dependent calcium channel as pharmacological target in spinocerebellar ataxia type 6: gabapentin and pregabalin may be of therapeutic benefit. Med Hypotheses. 2007;68(1):131-6. Epub 2006 Aug 8. [PubMed:16899342 ]
  3. Jacquy J, Lossignol D, Sternon J: [Pregabalin (Lyrica) and neuropathic pain syndromes]. Rev Med Brux. 2006 Sep-Oct;27(5):445-50. [PubMed:17144644 ]
  4. Taylor CP, Angelotti T, Fauman E: Pharmacology and mechanism of action of pregabalin: the calcium channel alpha2-delta (alpha2-delta) subunit as a target for antiepileptic drug discovery. Epilepsy Res. 2007 Feb;73(2):137-50. Epub 2006 Nov 28. [PubMed:17126531 ]
  5. Field MJ, Cox PJ, Stott E, Melrose H, Offord J, Su TZ, Bramwell S, Corradini L, England S, Winks J, Kinloch RA, Hendrich J, Dolphin AC, Webb T, Williams D: Identification of the alpha2-delta-1 subunit of voltage-dependent calcium channels as a molecular target for pain mediating the analgesic actions of pregabalin. Proc Natl Acad Sci U S A. 2006 Nov 14;103(46):17537-42. Epub 2006 Nov 6. [PubMed:17088553 ]