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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-11-15 21:04:30 UTC
HMDB IDHMDB0000452
Secondary Accession Numbers
  • HMDB0000581
  • HMDB0005815
  • HMDB00452
  • HMDB00581
  • HMDB05815
Metabolite Identification
Common NameL-alpha-Aminobutyric acid
DescriptionL-alpha-Aminobutyric acid, also known as (S)-2-aminobutanoic acid, homoalanine, 2-AABA, or alpha-Aminobutyric acid, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-Amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alpha-Aminobutyric acid is a non-proteogenic amino acid that can be found in the human kidney, in liver tissues, and in most biofluids or excreta (e.g. feces, breast milk, urine, and blood). Within the cell, L-alpha-aminobutyric acid is primarily located in the cytoplasm. alpha-Aminobutyric acid is biosynthesized by transamination of oxobutyrate, a metabolite in isoleucine biosynthesis. As a non-proteogenic amino acid, alpha-aminobutyric acid can be used by nonribosomal peptide synthases. One example of a nonribosomal peptide containing alpha-aminobutyric acid is ophthalmic acid, which was first isolated from calf lens. alpha-Aminobutyric acid is a non-essential amino acid that is primarily derived from the catabolism of methionine, threonine, and serine. High protein diets can result in significantly higher alpha-aminobutyrate levels in plasma (PMID: 26227325 ). alpha-Aminobutyric acid is elevated in the plasma of children with Reye's syndrome, tyrosinemia, homocystinuria, nonketotic hyperglycinemia, and ornithine transcarbamylase deficiency (PMID: 420125 ). alpha-Aminobutyric acid is one of the three isomers of aminobutyric acid. The two others are the neurotransmitter gamma-aminobutyric acid (GABA) and beta-aminobutyric acid (BABA) which is known for inducing plant disease resistance.
Structure
Data?1582752132
Synonyms
ValueSource
(-)-2-Aminobutyric acidChEBI
(2S)-2-Aminobutyric acidChEBI
(S)-2-AminobutanoateChEBI
(S)-2-Aminobutanoic acidChEBI
(S)-2-Aminobutyric acidChEBI
L-(+)-2-Aminobutyric acidChEBI
L-2-AminobuttersaeureChEBI
L-2-Aminobutyric acidChEBI
L-alpha-Amino-N-butyric acidChEBI
L-ButyrineChEBI
S-ButyrineChEBI
(-)-2-AminobutyrateGenerator
(2S)-2-AminobutyrateGenerator
(S)-2-AminobutyrateGenerator
L-(+)-2-AminobutyrateGenerator
L-2-AminobutyrateGenerator
L-a-Amino-N-butyrateGenerator
L-a-Amino-N-butyric acidGenerator
L-alpha-Amino-N-butyrateGenerator
L-Α-amino-N-butyrateGenerator
L-Α-amino-N-butyric acidGenerator
L-a-AminobutyrateGenerator
L-a-Aminobutyric acidGenerator
L-alpha-AminobutyrateGenerator
L-Α-aminobutyrateGenerator
L-Α-aminobutyric acidGenerator
(+)-2-AminobutanoateHMDB
(+)-2-Aminobutanoic acidHMDB
(+)-2-Aminobutyric acidHMDB
(+)-alpha-Aminobutyric acidHMDB
(2S)-2-AminobutanoateHMDB
(2S)-2-Aminobutanoic acidHMDB, MeSH
(S)-(+)-alpha-Aminobutyric acidHMDB
(S)-2-amino-ButanoateHMDB
(S)-2-amino-Butanoic acidHMDB
2-AminobutanoateHMDB
2-Aminobutanoic acidHMDB, MeSH
2-AminobutyrateHMDB
2S-amino-ButanoateHMDB, Generator
2S-amino-Butanoic acidHMDB
alpha-Aminobutyric acidHMDB, MeSH
L-2-amino-N-Butyric acidHMDB
L-EthylglycineHMDB
Butyrine, (R)-isomerMeSH, HMDB
2-Aminobutyric acidMeSH, HMDB, Generator
alpha-Aminobutyric acid, (+-)-isomerMeSH, HMDB
ButyrineMeSH, HMDB
Butyrine, (S)-isomerMeSH, HMDB
L-HomoalanineMeSH, HMDB
alpha-Aminobutyric acid, (S)-isomerMeSH, HMDB
HomoalanineMeSH, HMDB
alpha-Aminobutyric acid, (R)-isomerMeSH, HMDB
Butyrine, (+-)-isomerMeSH, HMDB
L-2-AminobutanoateGenerator, HMDB
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name(2S)-2-aminobutanoic acid
Traditional Name(-)-2-aminobutyric acid
CAS Registry Number1492-24-6
SMILES
CC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyQWCKQJZIFLGMSD-VKHMYHEASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point291 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility143800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-3.17HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility358 g/LALOGPS
logP-2.6ALOGPS
logP-2.3ChemAxon
logS0.54ALOGPS
pKa (Strongest Acidic)2.62ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.02 m³·mol⁻¹ChemAxon
Polarizability10.34 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]+121.19131661259
DarkChem[M-H]-117.33631661259
AllCCS[M+H]+127.38732859911
AllCCS[M-H]-123.32532859911
DeepCCS[M+H]+121.50230932474
DeepCCS[M-H]-118.70230932474
DeepCCS[M-2H]-155.22330932474
DeepCCS[M+Na]+129.93830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-alpha-Aminobutyric acidCC[C@H](N)C(O)=O1783.7Standard polar33892256
L-alpha-Aminobutyric acidCC[C@H](N)C(O)=O971.1Standard non polar33892256
L-alpha-Aminobutyric acidCC[C@H](N)C(O)=O1416.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-alpha-Aminobutyric acid,1TMS,isomer #1CC[C@H](N)C(=O)O[Si](C)(C)C1033.7Semi standard non polar33892256
L-alpha-Aminobutyric acid,1TMS,isomer #2CC[C@H](N[Si](C)(C)C)C(=O)O1141.2Semi standard non polar33892256
L-alpha-Aminobutyric acid,2TMS,isomer #1CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1185.8Semi standard non polar33892256
L-alpha-Aminobutyric acid,2TMS,isomer #1CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1198.3Standard non polar33892256
L-alpha-Aminobutyric acid,2TMS,isomer #1CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1318.6Standard polar33892256
L-alpha-Aminobutyric acid,2TMS,isomer #2CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1357.8Semi standard non polar33892256
L-alpha-Aminobutyric acid,2TMS,isomer #2CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1241.7Standard non polar33892256
L-alpha-Aminobutyric acid,2TMS,isomer #2CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1478.6Standard polar33892256
L-alpha-Aminobutyric acid,3TMS,isomer #1CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1418.9Semi standard non polar33892256
L-alpha-Aminobutyric acid,3TMS,isomer #1CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1319.2Standard non polar33892256
L-alpha-Aminobutyric acid,3TMS,isomer #1CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1311.7Standard polar33892256
L-alpha-Aminobutyric acid,1TBDMS,isomer #1CC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C1253.8Semi standard non polar33892256
L-alpha-Aminobutyric acid,1TBDMS,isomer #2CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O1379.2Semi standard non polar33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #1CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1605.1Semi standard non polar33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #1CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1617.8Standard non polar33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #1CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1614.9Standard polar33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #2CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1780.1Semi standard non polar33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #2CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1682.0Standard non polar33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #2CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1685.8Standard polar33892256
L-alpha-Aminobutyric acid,3TBDMS,isomer #1CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2044.3Semi standard non polar33892256
L-alpha-Aminobutyric acid,3TBDMS,isomer #1CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1965.0Standard non polar33892256
L-alpha-Aminobutyric acid,3TBDMS,isomer #1CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1739.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-alpha-Aminobutyric acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0900000000-5659d6d78898cfc7e3e12014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (2 TMS)splash10-001i-0900000000-c8849b7c3a366e6c4cb82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (3 TMS)splash10-0udi-0790000000-70b33ceb8fc59cf98fc52014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-alpha-Aminobutyric acid GC-EI-TOF (Non-derivatized)splash10-001i-0900000000-5659d6d78898cfc7e3e12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (Non-derivatized)splash10-0udi-0790000000-70b33ceb8fc59cf98fc52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (Non-derivatized)splash10-001i-0900000000-c8849b7c3a366e6c4cb82017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-231d9b85dacdfc8cfa1a2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9500000000-47e250b31bdc60f6848c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-9100000000-ee8abbcaf7c2b98fbbf22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4l-9000000000-1345dd328d7b79523e9b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-052f-9100000000-338f85ef5403099a76c72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0udi-0900000000-01184422112c4f45d2c22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0udi-0900000000-771c55fe95bc80e67d592012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0udi-1900000000-ddc187aaa752f4b10f2b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0006-9000000000-3bdaa058b45a133c3bbd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0udi-5900000000-116db8b71549d033ab562012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0a4i-9000000000-4ce723a5a5c9873c57dd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0a4i-9000000000-7cce1c626271fbc1ff332012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-052f-9000000000-d7ee22bb360494f5a6ed2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-0006-9000000000-e3892ebe321e35491da72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0a4i-9200000000-c71bee21cc5879ab61bb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0udi-0900000000-02624b93137883b214ad2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , negative-QTOFsplash10-0udi-0900000000-01184422112c4f45d2c22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , negative-QTOFsplash10-0udi-0900000000-771c55fe95bc80e67d592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , negative-QTOFsplash10-0udi-1900000000-ddc187aaa752f4b10f2b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-3bdaa058b45a133c3bbd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QTOF , negative-QTOFsplash10-0udi-0900000000-02624b93137883b214ad2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-alpha-Aminobutyric acid 10V, Positive-QTOFsplash10-0pb9-9300000000-bf6d819e5329e51297072016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-alpha-Aminobutyric acid 20V, Positive-QTOFsplash10-0a4i-9000000000-75c44b202b0cf165ca642016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-alpha-Aminobutyric acid 40V, Positive-QTOFsplash10-0a4l-9000000000-48f42fa88ffd58848a442016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-alpha-Aminobutyric acid 10V, Negative-QTOFsplash10-0udi-2900000000-19ddd8258055e0c777c72016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-alpha-Aminobutyric acid 20V, Negative-QTOFsplash10-0udi-9800000000-e086424e89a725ee4f8e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-alpha-Aminobutyric acid 40V, Negative-QTOFsplash10-0a4l-9000000000-b493c61a56938d3b47d52016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified23.0 (15.0-31.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified21.0 +/- 5.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified24.0 +/- 6.0 uMChildren (1-13 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified25.0 +/- 5.0 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified21.0 +/- 7.0 uMAdult (>18 years old)FemaleNormal details
Breast MilkDetected and Quantified17.7 +/- 6.9 uMAdult (>18 years old)Female
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified4.3 +/- 1.4 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3.5 +/- 2.2 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3.33 (1.80-4.86) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.13 +/- 4.52 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified3.392 +/- 6.78 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified6.784 +/- 5.65 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified<3.39 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.46-1.1 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified1.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.97 +/- 1.828 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified<3.51 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<2.15 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.032 (0.0-0.065) umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.52-0.71 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified<7.13 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified1.37 +/- 1.05 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.2 (1.1-4.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<6.33 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.045 +/- 0.045 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<4.30 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
BloodDetected and Quantified24.0 +/- 3.0 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified19.79 +/- 2.17 uMAdult (>18 years old)BothAlzheimer's disease details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified7.404 +/- 7.874 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified1.27 +/- 2.4 umol/mmol creatinineAdult (>18 years old)BothBone metastases details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
Kidney disease
  1. Chuang CK, Lin SP, Chen HH, Chen YC, Wang TJ, Shieh WH, Wu CJ: Plasma free amino acids and their metabolites in Taiwanese patients on hemodialysis and continuous ambulatory peritoneal dialysis. Clin Chim Acta. 2006 Feb;364(1-2):209-16. Epub 2005 Aug 8. [PubMed:16087168 ]
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Cancer with metastatic bone disease
  1. Tsuruta Y, Matsumoto M, Inoue H, Munemura S, Yamano S, Iguchi H: Determination of N-ethylglycine in urine of cancer patients with metastatic bone disease by HPLC using 4-(5,6-dimethoxy-2-phthalimidinyl)-2-methoxyphenylsulfonyl chloride as a fluorescent labeling reagent. Anal Sci. 2008 Dec;24(12):1629-31. [PubMed:19075476 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Colorectal cancer
  1. Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28. [PubMed:22148915 ]
  2. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  3. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  4. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012537
KNApSAcK IDNot Available
Chemspider ID72524
KEGG Compound IDC02356
BioCyc IDCPD0-1942
BiGG IDNot Available
Wikipedia LinkAlpha-Aminobutyric acid
METLIN ID12
PubChem Compound80283
PDB IDNot Available
ChEBI ID35619
Food Biomarker OntologyNot Available
VMH IDC02356
MarkerDB IDNot Available
Good Scents IDrw1141141
References
Synthesis ReferenceFotheringham, I. G.; Grinter, N.; Pantaleone, D. P.; Senkpeil, R. F.; Taylor, P. P. Engineering of a novel biochemical pathway for the biosynthesis of l-2-aminobutyric acid in Escherichia coli K12. Bioorganic & Medicinal Chemistry (1999), 7(10), 2209-2213.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yang W, Roth KS: Defect in alpha-ketobutyrate metabolism: a new inborn error. Clin Chim Acta. 1985 Jan 30;145(2):173-82. [PubMed:3918815 ]
  2. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
  3. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
  4. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
  5. Le Boucher J, Charret C, Coudray-Lucas C, Giboudeau J, Cynober L: Amino acid determination in biological fluids by automated ion-exchange chromatography: performance of Hitachi L-8500A. Clin Chem. 1997 Aug;43(8 Pt 1):1421-8. [PubMed:9267323 ]
  6. Oishi M, Mochizuki Y, Sanuki E: [Regional cerebral blood flow and cerebrospinal fluid amino acid analysis in elderly dementia]. No To Shinkei. 1998 Nov;50(11):1018-21. [PubMed:9866128 ]
  7. Haschke-Becher E, Kainz A, Bachmann C: Reference values of amino acids and of common clinical chemistry in plasma of healthy infants aged 1 and 4 months. J Inherit Metab Dis. 2016 Jan;39(1):25-37. doi: 10.1007/s10545-015-9870-4. Epub 2015 Jul 31. [PubMed:26227325 ]
  8. Yudkoff M, Blazer-Yost B, Cohn R, Segal S: On the clinical significance of the plasma alpha-amino-n-butyric acid:leucine ratio. Am J Clin Nutr. 1979 Feb;32(2):282-5. [PubMed:420125 ]

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central nervous system development. May be involved in the response to heart failure by elevating local creatine synthesis.
Gene Name:
GATM
Uniprot ID:
P50440
Molecular weight:
48455.01
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in calcium ion binding
Specific function:
EGF stimulates the growth of various epidermal and epithelial tissues in vivo and in vitro and of some fibroblasts in cell culture. Magnesiotropic hormone that stimulates magnesium reabsorption in the renal distal convoluted tubule via engagement of EGFR and activation of the magnesium channel TRPM6
Gene Name:
EGF
Uniprot ID:
P01133
Molecular weight:
133993.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]