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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2021-09-14 15:45:10 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
Data?1582752245
Synonyms
ValueSource
2,4-Diaminobutanoic acidChEBI
alpha,gamma-Diaminobutanoic acidChEBI
alpha,gamma-Diaminobutyric acidChEBI
DbuChEBI
2,4-DiaminobutanoateGenerator
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
2,4-DiaminobutyrateGenerator
(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, HMDB
2,4-Diaminobutyric acid monohydrochloride, (S)-isomerMeSH, HMDB
2,4-Diaminobutyric acid, (+)-isomerMeSH, HMDB
2,4-Diaminobutyric acid, (+-)-isomerMeSH, HMDB
2,4-Diaminobutyric acid, (R)-isomerMeSH, HMDB
2,4-Diaminobutyric acid, (S)-isomerMeSH, HMDB
L-2,4-Diaminobutyric acidMeSH, HMDB
2,4-Diaminobutyric acid dihydrochloride, (S)-isomerMeSH, HMDB
2,4-Diaminobutyric acid monohydrochloride, (+-)-isomerMeSH, HMDB
2,4-Diamino-butyrateGenerator, HMDB
2,4-Diaminobutyric acidMeSH
Chemical FormulaC4H10N2O2
Average Molecular Weight118.1344
Monoisotopic Molecular Weight118.074227574
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number305-62-4
SMILESNot Available
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
Disposition

Biological location

Source

Route of exposure

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 Spectral PropertiesNot Available
Predicted Molecular PropertiesNot Available
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.98231661259
DarkChem[M-H]-117.96831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,4-Diaminobutyric acid,1TMS,#1C[Si](C)(C)OC(=O)C(N)CCN1285.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
2,4-Diaminobutyric acid,1TMS,#2C[Si](C)(C)NCCC(N)C(=O)O1432.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
2,4-Diaminobutyric acid,1TMS,#3C[Si](C)(C)NC(CCN)C(=O)O1396.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
2,4-Diaminobutyric acid,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)C(N)CCN1512.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
2,4-Diaminobutyric acid,1TBDMS,#2CC(C)(C)[Si](C)(C)NCCC(N)C(=O)O1683.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
2,4-Diaminobutyric acid,1TBDMS,#3CC(C)(C)[Si](C)(C)NC(CCN)C(=O)O1645.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0fk9-1920000000-4022550ff40c74b94da22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0uki-1910000000-34aec762a0d88f0ff2eb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0h00-0920000000-ed1d230736f0552926442017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0fe0-2900000000-011f7377726e8e3fba202017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0udi-0923000000-fcaabed9d8d79390c0792017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0fk9-1920000000-4022550ff40c74b94da22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0uki-1910000000-34aec762a0d88f0ff2eb2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0h00-0920000000-ed1d230736f0552926442018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0fe0-2900000000-011f7377726e8e3fba202018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Diaminobutyric acid GC-EI-TOF (Non-derivatized)splash10-0udi-0923000000-fcaabed9d8d79390c0792018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Diaminobutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0089-9000000000-0ff95cc18b5212b1c1532017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Diaminobutyric acid GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-8900000000-25af6f5f252b501941e02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Diaminobutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Diaminobutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,4-Diaminobutyric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0udi-5900000000-c2bc77978186654145152012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,4-Diaminobutyric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-86fc81ed1cba676fc6152012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,4-Diaminobutyric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-dbbf8294790c9cfa42472012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 10V, Positive-QTOFsplash10-0v4i-7900000000-ca2dc0489c4a710e50dd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 20V, Positive-QTOFsplash10-0ab9-9000000000-72113ca7f0d0dd46ad4f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 40V, Positive-QTOFsplash10-0a4i-9000000000-787cd47720f4158a02012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 10V, Negative-QTOFsplash10-014i-3900000000-fd55d2abd69c5f1c09cd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 20V, Negative-QTOFsplash10-01b9-8900000000-d0f5d2df75ce6b0023472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 40V, Negative-QTOFsplash10-006x-9000000000-da3e8260fa5485a69ab12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 10V, Positive-QTOFsplash10-00xr-9700000000-fdbd4f0e5bb81c5569f42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 20V, Positive-QTOFsplash10-0a4i-9000000000-880db7b265999a2be6b52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 40V, Positive-QTOFsplash10-0a4i-9000000000-b2689f286fc18087ebce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 10V, Negative-QTOFsplash10-014i-1900000000-de9219963e7858b4c55a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 20V, Negative-QTOFsplash10-014i-4900000000-2a4facf9f300cca661572021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diaminobutyric acid 40V, Negative-QTOFsplash10-001i-9000000000-d4591f1517185fa3d7192021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart 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 (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)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 ]