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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:29 UTC
Update Date2020-02-26 21:23:39 UTC
HMDB IDHMDB0001959
Secondary Accession Numbers
  • HMDB01959
Metabolite Identification
Common Namegamma-Aminobutyryllysine
Descriptiongamma-Aminobutyryllysine, also known as N2-(4-amino-1-oxobutyl)-lysine, belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. gamma-Aminobutyryllysine is a very strong basic compound (based on its pKa). gamma-Aminobutyryllysine is a dipeptide present in the human brain. This dipeptide occurs in much higher concentrations in the human brain than in the brains of lower mammals (PMID: 5559257 ). Adult brain and cerebrospinal fluid gamma-aminobutyryllysine levels and adult brain homocarnosine levels are higher than those found in children (PMID: 5031796 ).
Structure
Data?1582752219
Synonyms
ValueSource
N2-(4-Amino-1-oxobutyl)-L-lysineHMDB
Nalpha-(gamma-Aminobutyryl)-L-lysineHMDB
Nalpha-(gamma-Aminobutyryl)lysineHMDB
Nα-(γ-Aminobutyryl)-L-lysineHMDB
Nα-(γ-Aminobutyryl)lysineHMDB
alpha-(gamma-Aminobutyryl)-lysineHMDB
gamma-Aminobutyryl-lysineHMDB
gamma-AminobutyryllysineHMDB
α-(γ-Aminobutyryl)-lysineHMDB
γ-Aminobutyryl-lysineHMDB
γ-AminobutyryllysineHMDB
Chemical FormulaC10H21N3O3
Average Molecular Weight231.296
Monoisotopic Molecular Weight231.158291548
IUPAC Name(2S)-6-amino-2-(4-aminobutanamido)hexanoic acid
Traditional Namegamma-aminobutyryl-lysine
CAS Registry Number22468-02-6
SMILES
NCCCC[C@H](NC(=O)CCCN)C(O)=O
InChI Identifier
InChI=1S/C10H21N3O3/c11-6-2-1-4-8(10(15)16)13-9(14)5-3-7-12/h8H,1-7,11-12H2,(H,13,14)(H,15,16)/t8-/m0/s1
InChI KeyOCBQYJFUZHJRIU-QMMMGPOBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Gamma amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

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 Solubility12.9 g/LALOGPS
logP-3.3ALOGPS
logP-3.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.91ChemAxon
pKa (Strongest Basic)10.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.44 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity60.07 m³·mol⁻¹ChemAxon
Polarizability25.27 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
Tissue Locations
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.32 (0.1-1.1) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022766
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20849140
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Perry TL, Berry K, Hansen S, Diamond S, Mok C: Regional distribution of amino acids in human brain obtained at autopsy. J Neurochem. 1971 Mar;18(3):513-9. [PubMed:5559257 ]
  2. Van Regemorter N, Mardens Y, Lowenthal A, Van Sande M, Lavinha F: [Distribution of two peptides of -aminobutyric acid in human brain and CSF]. Clin Chim Acta. 1972 Apr;38(1):59-65. [PubMed:5031796 ]