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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2023-02-21 17:16:22 UTC
HMDB IDHMDB0002362
Secondary Accession Numbers
  • HMDB02362
Metabolite Identification
Common Name2,4-Diaminobutyric acid
Description2,4-Diaminobutyric acid, also known as 2,4-diaminobutanoate or Dbu, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 2,4-Diaminobutyric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2,4-Diaminobutyric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2,4-Diaminobutyric acid has been detected, but not quantified in cow milk. This could make 2,4-diaminobutyric acid a potential biomarker for the consumption of these foods. 2,4-Diaminobutyric acid is a non-physiological, cationic amino acid analogue that is transported into cells by System A with potent antitumoral activity in vitro against human glioma cells, the result of the pronounced concentrated uptake of DAB in glioma cells to the extent that a cellular lysis could occur due to osmotic reasons.
Structure
Thumb
Synonyms
Chemical FormulaC4H10N2O2
Average Molecular Weight118.1344
Monoisotopic Molecular Weight118.074227574
IUPAC Name2,4-diaminobutanoic acid
Traditional Name2,4-diaminobutanoic acid
CAS Registry Number305-62-4
SMILES
NCCC(N)C(O)=O
InChI Identifier
InChI=1S/C4H10N2O2/c5-2-1-3(6)4(7)8/h3H,1-2,5-6H2,(H,7,8)
InChI KeyOGNSCSPNOLGXSM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.64HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
UrineDetected and Quantified0.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022978
KNApSAcK IDC00034868
Chemspider ID457
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound470
PDB IDNot Available
ChEBI ID64307
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceTalbot, Guy; Gaudry, Roger; Berlinguet, Louis. Synthesis of 4-aminobutyric acid and 2,4-diaminobutyric acid from butyrolactone. Canadian Journal of Chemistry (1958), 36 593-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ronquist G, Hugosson R, Sjolander U, Ungerstedt U: Treatment of malignant glioma by a new therapeutic principle. Acta Neurochir (Wien). 1992;114(1-2):8-11. [PubMed:1561943 ]