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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-22 21:17:54 UTC
Update Date2020-02-26 21:26:19 UTC
HMDB IDHMDB0006284
Secondary Accession Numbers
  • HMDB06284
Metabolite Identification
Common NameL-2,4-diaminobutyric acid
DescriptionL-2,4-diaminobutyric acid, also known as Dbu or alpha,gamma-diaminobutyrate, 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. L-2,4-diaminobutyric acid is a very strong basic compound (based on its pKa). Outside of the human body, L-2,4-diaminobutyric acid has been detected, but not quantified in, several different foods, such as black cabbages, millets, fenugreeks, dates, and sweet oranges. This could make L-2,4-diaminobutyric acid a potential biomarker for the consumption of these foods.
Structure
Data?1582752379
Synonyms
ValueSource
(S)-2,4-Diaminobutanoic acidChEBI
alpha,gamma-DiaminobutyrateChEBI
DbuChEBI
L-2,4-DiaminobutanoateChEBI
L-2,4-Diaminobutanoic acidChEBI
L-2,4-DiaminobutyrateChEBI
L-DbuChEBI
L-Diaminobutyric acidChEBI
(S)-2,4-DiaminobutanoateGenerator
a,g-DiaminobutyrateGenerator
a,g-Diaminobutyric acidGenerator
alpha,gamma-Diaminobutyric acidGenerator
Α,γ-diaminobutyrateGenerator
Α,γ-diaminobutyric acidGenerator
L-DiaminobutyrateGenerator
(S)-2,4-Diamino-butanoateHMDB
(S)-2,4-Diamino-butanoic acidHMDB
(S)-2,4-Diaminobutyric acidHMDB
L-2,4-Diamino-butyric acidHMDB
L-2,4-Diamino-N-butyric acidHMDB
L-alpha,gamma-Diaminobutyric acidHMDB
L-DABAHMDB
2,4-Diaminobutyric acid dihydrochloride, (+-)-isomerHMDB
2,4-Diaminobutyric acid monohydrochloride, (+-)-isomerHMDB
2,4-Diaminobutyric acid, (+)-isomerHMDB
2,4-Diaminobutyric acid, (+-)-isomerHMDB
2,4-Diaminobutyric acid, (R)-isomerHMDB
2,4-Diaminobutyric acid, (S)-isomerHMDB
2,4-Diaminobutyric acid dihydrochloride, (S)-isomerHMDB
2,4-Diaminobutyric acidHMDB
2,4-Diaminobutyric acid monohydrochloride, (S)-isomerHMDB
Chemical FormulaC4H10N2O2
Average Molecular Weight118.1344
Monoisotopic Molecular Weight118.074227574
IUPAC Name(2S)-2,4-diaminobutanoic acid
Traditional Name2,4-diaminobutyric acid
CAS Registry Number1758-80-1
SMILES
NCC[C@H](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)/t3-/m0/s1
InChI KeyOGNSCSPNOLGXSM-VKHMYHEASA-N
Chemical Taxonomy
Description 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 acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability11.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-0910000000-c063d8231376ede53de2Spectrum
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0fe0-2910000000-db971ca13fbd6bdfb5f2Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fki-1930000000-f3933f38127537d9d178Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0910000000-c063d8231376ede53de2Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fe0-2910000000-db971ca13fbd6bdfb5f2Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fki-1930000000-f3933f38127537d9d178Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0089-9000000000-0ff95cc18b5212b1c153Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-8900000000-25af6f5f252b501941e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uxr-1900000000-499115725bc286b22b97Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-9800000000-2846e6524438703ab54dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-9000000000-d101f60f5f0933b1cc22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4l-9000000000-b4fce69a41761f7bd63eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-235022305b68ba272d34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-106r-9700000000-6ecfd43a641703f25d64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9100000000-b709fbaf63ddc2f4c0dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-76fb37fe98b182da1a5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-3208832c46b361f3099eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-8900000000-2ec3d4f8ca96f4005562Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-045583f642e304aeaaf7Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified116.35 +/- 10.0 uMAdult (>18 years old)BothAlzheimer's disease details
UrineDetected and Quantified36.0 +/- 5.0 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease 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. [PubMed:17031479 ]
Associated OMIM IDs
DrugBank IDDB03817
Phenol Explorer Compound IDNot Available
FooDB IDFDB030953
KNApSAcK IDC00001353
Chemspider ID118548
KEGG Compound IDC03283
BioCyc IDCPD-470
BiGG ID41559
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound134490
PDB IDDAB
ChEBI ID48950
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular weight:
56438.405