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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-06-10 21:21:47 UTC
HMDB IDHMDB00452
Secondary Accession Numbers
  • HMDB00581
  • HMDB05815
Metabolite Identification
Common NameL-Alpha-aminobutyric acid
DescriptionA-Aminobutyric acid is an isomer of the amino acid aminobutyric acid. It is a key intermediate in the biosynthesis of ophthalmic acid or ophthalmate.
Structure
Thumb
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
L-a-AminobutyrateGenerator
L-a-Aminobutyric acidGenerator
L-alpha-AminobutyrateGenerator
L-α-aminobutyrateGenerator
L-α-aminobutyric acidGenerator
(2S)-2-AminobutyrateGenerator
(S)-2-AminobutyrateGenerator
(+)-2-AminobutanoateHMDB
(+)-2-Aminobutanoic acidHMDB
(+)-2-Aminobutyric acidHMDB
(+)-alpha-Aminobutyric acidHMDB
(2S)-2-AminobutanoateHMDB
(2S)-2-Aminobutanoic acidHMDB
(S)-(+)-alpha-Aminobutyric acidHMDB
(S)-2-amino-ButanoateHMDB
(S)-2-amino-Butanoic acidHMDB
2-AminobutanoateHMDB
2-Aminobutanoic acidHMDB
2-AminobutyrateHMDB
2S-amino-ButanoateHMDB
2S-amino-Butanoic acidHMDB
alpha-Aminobutyric acidHMDB
L-2-amino-N-Butyric acidHMDB
L-EthylglycineHMDB
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 KeyInChIKey=QWCKQJZIFLGMSD-VKHMYHEASA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis, waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point291 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.17HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility358.0 mg/mLALOGPS
logP-2.5ALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.02 m3·mol-1ChemAxon
Polarizability10.34 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-001i-0900000000-5659d6d78898cfc7e3e1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-0900000000-c8849b7c3a366e6c4cb8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-0790000000-70b33ceb8fc59cf98fc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9100000000-ee8abbcaf7c2b98fbbf2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9000000000-1345dd328d7b79523e9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9100000000-338f85ef5403099a76c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-01184422112c4f45d2c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-771c55fe95bc80e67d59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-1900000000-ddc187aaa752f4b10f2bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-3bdaa058b45a133c3bbdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-5900000000-116db8b71549d033ab56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4i-9000000000-4ce723a5a5c9873c57ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9000000000-7cce1c626271fbc1ff33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-052f-9000000000-d7ee22bb360494f5a6edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-e3892ebe321e35491da7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-9200000000-c71bee21cc5879ab61bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-02624b93137883b214adView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 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 ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
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
    • Mordechai, Hien, ...
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 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 but not QuantifiedNot ApplicableAdult (>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
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>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
UrineDetected and Quantified7.404 +/- 7.874 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothColorectal cancer details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified1.27 +/- 2.4 umol/mmol creatinineAdult (>18 years old)BothBone metastases 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. [17031479 ]
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. [19075476 ]
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. [16087168 ]
Associated OMIM IDs
DrugBank IDDB04454
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012537
KNApSAcK IDNot Available
Chemspider ID72524
KEGG Compound IDC02356
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkABA
NuGOwiki LinkHMDB00452
Metagene LinkHMDB00452
METLIN ID12
PubChem Compound80283
PDB IDABA
ChEBI ID35619
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. [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. [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. [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. [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. [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. [9866128 ]

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. [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. [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. [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. [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. [10592235 ]