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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:14:52 UTC
HMDB IDHMDB0000650
Secondary Accession Numbers
  • HMDB00650
Metabolite Identification
Common NameD-alpha-Aminobutyric acid
DescriptionD-alpha-Aminobutyric acid is the D-isomer of alpha-aminobutyric acid. The L-form of this amino acid is used in the biosynthesis of ophthalmic acid (a tripeptide analogue of glutathione in which the cysteine group is replaced by L-2-aminobutyrate, which was first discovered and isolated from calf lens). The D-form of this amino acid is a substrate for D-amino acid oxidase. There is little evidence that the D-form of this amino acid is found in human biofluids or tissues. What little does exist is likely of bacterial origin.
Structure
Data?1547234092
Synonyms
ValueSource
(2R)-2-Aminobutyric acidChEBI
(R)-2-Aminobutanoic acidChEBI
(R)-2-Aminobutyric acidChEBI
alpha-Aminobutyric acidChEBI
D-(-)-2-Aminobutyric acidChEBI
D-2-Aminobutanoic acidChEBI
D-2-AminobuttersaeureChEBI
D-2-AminobutyrateChEBI
D-2-Aminobutyric acidChEBI
(2R)-2-AminobutyrateGenerator
D-a-AminobutyrateGenerator
D-a-Aminobutyric acidGenerator
D-alpha-AminobutyrateGenerator
D-α-aminobutyrateGenerator
D-α-aminobutyric acidGenerator
(R)-2-AminobutanoateGenerator
(R)-2-AminobutyrateGenerator
a-AminobutyrateGenerator
a-Aminobutyric acidGenerator
alpha-AminobutyrateGenerator
α-aminobutyrateGenerator
α-aminobutyric acidGenerator
D-(-)-2-AminobutyrateGenerator
D-2-AminobutanoateGenerator
(2R)-2-AminobutanoateHMDB
(2R)-2-Aminobutanoic acidHMDB
(R)-2-amino-ButanoateHMDB
(R)-2-amino-Butanoic acidHMDB
delta-(-)-2-Aminobutyric acidHMDB
delta-2-AminobutanoateHMDB
delta-2-Aminobutanoic acidHMDB
delta-2-AminobuttersaeureHMDB
delta-2-AminobutyrateHMDB
delta-2-Aminobutyric acidHMDB
delta-alpha-Aminobutyric acidHMDB
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name(2R)-2-aminobutanoic acid
Traditional NameD-2-aminobutyric acid
CAS Registry Number2623-91-8
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-/m1/s1
InChI KeyQWCKQJZIFLGMSD-GSVOUGTGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility278 mg/mLNot Available
LogPNot AvailableNot Available
Predicted 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
Polarizability10.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-231d9b85dacdfc8cfa1aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9100000000-33d5541d982bdb08b1ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9100000000-0daee71ea831f7bbc7d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9000000000-bfbde6993a601589833aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9000000000-2758c754fa3d1a866313View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-80692ccd320ae9397188View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-0c48c0d7bd360678818dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-3f73f991c6b16f4243deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-30bd7a490cb370274562View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-0900000000-4643b2987ca1e5d6835dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-b00f3c9d8e1430fd47d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-4900000000-4f8fca780d8148405257View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-0e57b77365acd0b22fb6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-aa6a0c5e4a3ee00a68adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-fade3973755c5e8311cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-0900000000-4b7a0e5c50e7e0b22d32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-4900000000-8ff7d03a0770e04e7c91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4i-9100000000-ba75c4a0743928ae4796View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9000000000-ce841184a0d4a39e10cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4l-9000000000-da87cbb3df36c3786e14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-915c65b6ad120179d86eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-9300000000-bf6d819e5329e5129707View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-75c44b202b0cf165ca64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-48f42fa88ffd58848a44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-19ddd8258055e0c777c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-9800000000-e086424e89a725ee4f8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-b493c61a56938d3b47d5View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)FemaleNormal details
    SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified0.30 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    SalivaDetected but not Quantified Adult (>18 years old)BothOral cancer details
    SalivaDetected but not Quantified Adult (>18 years old)FemaleBreast cancer details
    SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedPancreatic cancer details
    SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedPeriodontal diseases details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
    Perillyl alcohol administration for cancer treatment
    1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
    Pancreatic cancer
    1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
    Periodontal disease
    1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
    Associated OMIM IDs
    DrugBank IDDB04454
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB012680
    KNApSAcK IDNot Available
    Chemspider ID388757
    KEGG Compound IDC02261
    BioCyc IDCPD0-1952
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound439691
    PDB IDDBB
    ChEBI ID28797
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
    2. Ketting D, Wadman SK, Spaapen LJ, Van der Meer SB, Duran M: Gas chromatography method for the separation of amino acids enantiomers in plasma and urine. Application in a case of short bowel syndrome. Clin Chim Acta. 1991 Dec 31;204(1-3):79-86. [PubMed:1819475 ]
    3. Lange R, Hui Bon Hoa G, Douzou P, Yagi K: Kinetics of primary interaction of D-amino acid oxidase with its substrate. Biochem Int. 1983 May;6(5):693-8. [PubMed:6148943 ]