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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2023-02-21 17:18:09 UTC

HMDB ID

HMDB0014375

Secondary Accession Numbers

HMDB14375

Metabolite Identification

Common Name

Pregabalin

Description

Pregabalin 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0014375
HETATM    1  C1  UNL     1       2.624   0.357  -1.013  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.675  -0.279  -0.011  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.219  -0.043   1.339  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.308   0.195  -0.307  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.801  -0.274   0.519  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.997  -1.771   0.518  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.265  -2.233  -0.815  1.00  0.00           N  
HETATM    8  C7  UNL     1      -2.106   0.334   0.034  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.030   1.834   0.122  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.072   2.344   1.262  1.00  0.00           O  
HETATM   11  O2  UNL     1      -1.917   2.623  -1.003  1.00  0.00           O  
HETATM   12  H1  UNL     1       2.559  -0.201  -1.946  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.649   0.459  -0.604  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.237   1.404  -1.189  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.716  -1.386  -0.223  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.536  -0.222   2.182  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.096  -0.709   1.493  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.608   0.992   1.442  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.337   1.329  -0.230  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.093   0.027  -1.376  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.757   0.007   1.595  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.057  -2.204   0.935  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.865  -2.034   1.182  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.219  -2.606  -0.864  1.00  0.00           H  
HETATM   25  H14 UNL     1      -1.112  -1.538  -1.541  1.00  0.00           H  
HETATM   26  H15 UNL     1      -2.968  -0.014   0.624  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.227   0.057  -1.030  1.00  0.00           H  
HETATM   28  H17 UNL     1      -2.263   3.550  -1.095  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   19   20
CONECT    5    6    8   21
CONECT    6    7   22   23
CONECT    7   24   25
CONECT    8    9   26   27
CONECT    9   10   10   11
CONECT   11   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-3-Isobutyl gaba	ChEBI
3-Isobutyl gaba	ChEBI
Lyrica	ChEBI
3-(Aminomethyl)-5-methylhexanoic acid	HMDB
(S+)-3-isobutyl gaba	HMDB
3 Isobutyl gaba	HMDB
(R-)-3-Isobutyl gaba	HMDB
(S)-3-(Aminomethyl)-5-methylhexanoic acid	HMDB
GABA, 3-isobutyl	HMDB

Chemical Formula

C₈H₁₇NO₂

Average Molecular Weight

159.2261

Monoisotopic Molecular Weight

159.125928793

IUPAC Name

(3S)-3-(aminomethyl)-5-methylhexanoic acid

Traditional Name

pregabalin

CAS Registry Number

148553-50-8

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 Key

AYXYPKUFHZROOJ-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma 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 Framework

Aliphatic acyclic compounds

External Descriptors

gamma-amino acid (CHEBI:64356 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014375)

Source

Exogenous

Exogenous (HMDB: HMDB0014375)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.3 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.3 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.8	ChemAxon
pKa (Strongest Basic)	10.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	43.68 m³·mol⁻¹	ChemAxon
Polarizability	18.08 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.01	31661259
DarkChem	[M-H]-	131.859	31661259
DeepCCS	[M+H]+	135.922	30932474
DeepCCS	[M-H]-	132.092	30932474
DeepCCS	[M-2H]-	169.334	30932474
DeepCCS	[M+Na]+	144.874	30932474
AllCCS	[M+H]+	137.7	32859911
AllCCS	[M+H-H2O]+	133.8	32859911
AllCCS	[M+NH4]+	141.4	32859911
AllCCS	[M+Na]+	142.4	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	139.7	32859911
AllCCS	[M+HCOO]-	142.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.11 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8474 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.5 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	234.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	782.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	99.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	300.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	298.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	412.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	666.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	246.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	859.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	462.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	377.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	208.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pregabalin	CC(C)C[C@H](CN)CC(O)=O	2164.2	Standard polar	33892256
Pregabalin	CC(C)C[C@H](CN)CC(O)=O	1353.7	Standard non polar	33892256
Pregabalin	CC(C)C[C@H](CN)CC(O)=O	1360.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pregabalin,1TMS,isomer #1	CC(C)C[C@H](CN)CC(=O)O[Si](C)(C)C	1393.5	Semi standard non polar	33892256
Pregabalin,1TMS,isomer #2	CC(C)C[C@H](CN[Si](C)(C)C)CC(=O)O	1484.6	Semi standard non polar	33892256
Pregabalin,2TMS,isomer #1	CC(C)C[C@H](CN[Si](C)(C)C)CC(=O)O[Si](C)(C)C	1519.6	Semi standard non polar	33892256
Pregabalin,2TMS,isomer #1	CC(C)C[C@H](CN[Si](C)(C)C)CC(=O)O[Si](C)(C)C	1585.3	Standard non polar	33892256
Pregabalin,2TMS,isomer #1	CC(C)C[C@H](CN[Si](C)(C)C)CC(=O)O[Si](C)(C)C	1633.0	Standard polar	33892256
Pregabalin,2TMS,isomer #2	CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C)[Si](C)(C)C	1674.2	Semi standard non polar	33892256
Pregabalin,2TMS,isomer #2	CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C)[Si](C)(C)C	1621.2	Standard non polar	33892256
Pregabalin,2TMS,isomer #2	CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C)[Si](C)(C)C	1772.4	Standard polar	33892256
Pregabalin,3TMS,isomer #1	CC(C)C[C@@H](CC(=O)O[Si](C)(C)C)CN([Si](C)(C)C)[Si](C)(C)C	1718.4	Semi standard non polar	33892256
Pregabalin,3TMS,isomer #1	CC(C)C[C@@H](CC(=O)O[Si](C)(C)C)CN([Si](C)(C)C)[Si](C)(C)C	1726.3	Standard non polar	33892256
Pregabalin,3TMS,isomer #1	CC(C)C[C@@H](CC(=O)O[Si](C)(C)C)CN([Si](C)(C)C)[Si](C)(C)C	1618.0	Standard polar	33892256
Pregabalin,1TBDMS,isomer #1	CC(C)C[C@H](CN)CC(=O)O[Si](C)(C)C(C)(C)C	1624.7	Semi standard non polar	33892256
Pregabalin,1TBDMS,isomer #2	CC(C)C[C@H](CN[Si](C)(C)C(C)(C)C)CC(=O)O	1699.0	Semi standard non polar	33892256
Pregabalin,2TBDMS,isomer #1	CC(C)C[C@H](CN[Si](C)(C)C(C)(C)C)CC(=O)O[Si](C)(C)C(C)(C)C	1974.2	Semi standard non polar	33892256
Pregabalin,2TBDMS,isomer #1	CC(C)C[C@H](CN[Si](C)(C)C(C)(C)C)CC(=O)O[Si](C)(C)C(C)(C)C	1956.5	Standard non polar	33892256
Pregabalin,2TBDMS,isomer #1	CC(C)C[C@H](CN[Si](C)(C)C(C)(C)C)CC(=O)O[Si](C)(C)C(C)(C)C	1911.0	Standard polar	33892256
Pregabalin,2TBDMS,isomer #2	CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2068.3	Semi standard non polar	33892256
Pregabalin,2TBDMS,isomer #2	CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1987.2	Standard non polar	33892256
Pregabalin,2TBDMS,isomer #2	CC(C)C[C@@H](CC(=O)O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1978.1	Standard polar	33892256
Pregabalin,3TBDMS,isomer #1	CC(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)C	2376.6	Semi standard non polar	33892256
Pregabalin,3TBDMS,isomer #1	CC(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)C	2276.7	Standard non polar	33892256
Pregabalin,3TBDMS,isomer #1	CC(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)C	2012.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pregabalin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9100000000-ff23b21ef03ce99e7cce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pregabalin GC-MS (1 TMS) - 70eV, Positive	splash10-001i-9100000000-99ad7be9a2ea5e94fae2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pregabalin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , negative-QTOF	splash10-0a4i-0900000000-555454e7e8e11dab591d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , negative-QTOF	splash10-0a4i-0900000000-1a52554257d7f4b1c62e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , negative-QTOF	splash10-0a4i-0900000000-d48cd6eeef012787cc04	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , negative-QTOF	splash10-0a4i-0900000000-4b11df5208caa2e97dd2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , negative-QTOF	splash10-0a4i-0900000000-605dc241ffd3a07a9220	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QTOF , positive-QTOF	splash10-01ox-0900000000-fb081cde39dde2ce89f8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QTOF , positive-QTOF	splash10-0006-0900000000-3d95bb5278c7866658a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QTOF , positive-QTOF	splash10-0006-0900000000-96cebf4a3610cbf02059	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOF	splash10-0006-8900000000-385584fca9e88b90a95b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOF	splash10-0006-9800000000-a1c6718b087b06101b8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOF	splash10-0a4i-9200000000-5f291c943a1d1ae214ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOF	splash10-0a4i-9100000000-5283d02d98611a8c2c38	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOF	splash10-0a4i-9000000000-8797f8d2776fcdb4b6d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin LC-ESI-QFT , positive-QTOF	splash10-0a4i-9000000000-a9ddfcf2032ffc9f53ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin 10V, Positive-QTOF	splash10-01ox-0900000000-f61d6c12dadd60399296	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin 75V, Positive-QTOF	splash10-0a4i-9000000000-37e1f57223b0ba6b95f6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin 60V, Positive-QTOF	splash10-0a4i-9100000000-ea797f17647a8718608d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin 30V, Positive-QTOF	splash10-0006-0900000000-96cebf4a3610cbf02059	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pregabalin 10V, Positive-QTOF	splash10-01ox-0900000000-142ab34d1881e6e3e247	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregabalin 10V, Positive-QTOF	splash10-01ox-1900000000-0d022bd7f0e9af9f06f8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregabalin 20V, Positive-QTOF	splash10-03ed-9800000000-fe82df47c3ac7c9c39e3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregabalin 40V, Positive-QTOF	splash10-0a5a-9000000000-20b509ce412ff8d7fe8c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregabalin 10V, Negative-QTOF	splash10-0bt9-0900000000-d07b85e7e0d11beb1781	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregabalin 20V, Negative-QTOF	splash10-0bt9-1900000000-6351cf9406ff25f78268	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pregabalin 40V, Negative-QTOF	splash10-0a4m-9300000000-8f1f021c89d9316d47a0	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00230	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00230	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00230

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4589156

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pregabalin

METLIN ID

Not Available

PubChem Compound

5486971

PDB ID

Not Available

ChEBI ID

64356

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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

Enzyme Details

1. Voltage-dependent P/Q-type calcium channel subunit alpha-1A

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

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 ]
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 ]
Jacquy J, Lossignol D, Sternon J: [Pregabalin (Lyrica) and neuropathic pain syndromes]. Rev Med Brux. 2006 Sep-Oct;27(5):445-50. [PubMed:17144644 ]
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 ]
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 ]

Showing metabocard for Pregabalin (HMDB0014375)

MOL for HMDB0014375 (Pregabalin)

3D MOL for HMDB0014375 (Pregabalin)

3D SDF for HMDB0014375 (Pregabalin)

3D-SDF for HMDB0014375 (Pregabalin)

PDB for HMDB0014375 (Pregabalin)

3D PDB for HMDB0014375 (Pregabalin)

SMILES for HMDB0014375 (Pregabalin)

INCHI for HMDB0014375 (Pregabalin)

Structure for HMDB0014375 (Pregabalin)

3D Structure for HMDB0014375 (Pregabalin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References