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Record Information
Version3.6
Creation Date2007-05-22 21:17:54 UTC
Update Date2016-02-11 01:07:27 UTC
HMDB IDHMDB06284
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-2,4-diaminobutyric acid
DescriptionL-3-Amino-isobutanoic acid is a component of branched-chain amino acid biosynthesis and metabolism. It can also be used in pyrimidine metabolism. L-3-Amino-isobutanoic acid is produced from S-methylmalonate semialdehyde by the enzyme 4-aminobutyrate aminotransferase.
Structure
Thumb
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
(2S)-2,4-DiaminobutanoateGenerator
a,g-DiaminobutyrateGenerator
a,g-Diaminobutyric acidGenerator
alpha,gamma-Diaminobutyric acidGenerator
α,γ-diaminobutyrateGenerator
α,γ-diaminobutyric acidGenerator
L-2,4-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
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 KeyInChIKey=OGNSCSPNOLGXSM-VKHMYHEASA-N
Chemical Taxonomy
DescriptionThis compound 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 acyl
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
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 Solubility270.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.56 m3·mol-1ChemAxon
Polarizability11.89 Å3ChemAxon
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-MS (3 TMS)splash10-0udi-0910000000-c063d8231376ede53de2View in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0fe0-2910000000-db971ca13fbd6bdfb5f2View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fki-1930000000-f3933f38127537d9d178View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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. [17031479 ]
Associated OMIM IDs
DrugBank IDDB03817
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012588
KNApSAcK IDC00034868
Chemspider ID118548
KEGG Compound IDC03283
BioCyc IDNot Available
BiGG ID41559
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06284
Metagene LinkHMDB06284
METLIN IDNot Available
PubChem Compound134490
PDB IDDAB
ChEBI 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