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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2017-12-07 01:49:04 UTC
HMDB IDHMDB0002362
Secondary Accession Numbers
  • HMDB02362
Metabolite Identification
Common Name2,4-Diaminobutyric acid
Description2,4-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. (PMID: 1561943 ).
Structure
Thumb
Synonyms
ValueSource
2,4-Diaminobutanoic acidChEBI
alpha,gamma-Diaminobutanoic acidChEBI
alpha,gamma-Diaminobutyric acidChEBI
DbuChEBI
2,4-DiaminobutanoateGenerator
2,4-DiaminobutyrateGenerator
a,g-DiaminobutanoateGenerator
a,g-Diaminobutanoic acidGenerator
alpha,gamma-DiaminobutanoateGenerator
α,γ-diaminobutanoateGenerator
α,γ-diaminobutanoic acidGenerator
a,g-DiaminobutyrateGenerator
a,g-Diaminobutyric acidGenerator
alpha,gamma-DiaminobutyrateGenerator
α,γ-diaminobutyrateGenerator
α,γ-diaminobutyric acidGenerator
(RS)-2,4-Diaminobutyric acidHMDB
2,4-diamino-ButanoateHMDB
2,4-diamino-Butanoic acidHMDB
2,4-diamino-Butyric acidHMDB
2,4-diamino-N-Butyric acidHMDB
DL-2,4-diamino-N-Butyric acidHMDB
DL-2,4-DiaminobutanoateHMDB
DL-2,4-Diaminobutanoic acidHMDB
DL-2,4-Diaminobutyric acidHMDB
DL-alpha,gamma-Diaminobutyric acidHMDB
2,4-Diaminobutyric acid dihydrochloride, (+-)-isomerMeSH
2,4-Diaminobutyric acid monohydrochloride, (S)-isomerMeSH
2,4-Diaminobutyric acid, (+)-isomerMeSH
2,4-Diaminobutyric acid, (+-)-isomerMeSH
2,4-Diaminobutyric acid, (R)-isomerMeSH
2,4-Diaminobutyric acid, (S)-isomerMeSH
L-2,4-Diaminobutyric acidMeSH
2,4-Diaminobutyric acid dihydrochloride, (S)-isomerMeSH
2,4-Diaminobutyric acid monohydrochloride, (+-)-isomerMeSH
Chemical FormulaC4H10N2O2
Average Molecular Weight118.1344
Monoisotopic Molecular Weight118.074227574
IUPAC Name2,4-diaminobutanoic acid
Traditional Namel-2,4-diaminobutyric 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
DescriptionThis compound 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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.64HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility270 g/LALOGPS
logP-3.7ALOGPS
logP-4ChemAxon
logS0.36ALOGPS
pKa (Strongest Acidic)2.55ChemAxon
pKa (Strongest Basic)10.25ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.56 m³·mol⁻¹ChemAxon
Polarizability11.79 ųChemAxon
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 (Non-derivatized)splash10-0fk9-1920000000-4022550ff40c74b94da2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uki-1910000000-34aec762a0d88f0ff2ebView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0h00-0920000000-ed1d230736f055292644View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fe0-2900000000-011f7377726e8e3fba20View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0923000000-fcaabed9d8d79390c079View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0089-9000000000-0ff95cc18b5212b1c153View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-8900000000-25af6f5f252b501941e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-5900000000-c2bc7797818665414515View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-86fc81ed1cba676fc615View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-dbbf8294790c9cfa4247View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0v4i-7900000000-ca2dc0489c4a710e50ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-72113ca7f0d0dd46ad4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-787cd47720f4158a0201View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-fd55d2abd69c5f1c09cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-8900000000-d0f5d2df75ce6b002347View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-da3e8260fa5485a69ab1View 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)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Not 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
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022978
    KNApSAcK IDNot Available
    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
    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)Download (PDF)
    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 ]