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Homocarnosine (PC000144)

Record Information
Version1.0
Creation date2015-10-09 22:28:48 UTC
Update date2017-01-19 02:36:14 UTC
FoodComEx IDPC000144
FoodDB RecordFDB022217
Chemical Information
NameHomocarnosine
DescriptionHomocarnosine is a normal human metabolite, the brain-specific dipeptide of gamma-aminobutyric acid (GABA) and histidine. (PMID 1266573) Increased concentration of CSF homocarnosine has been found in familial spastic paraplegia. (PMID 842287) Homocarnosinosis (an inherited disorder, OMIM 236130) is characterized by an elevated level of the dipeptide homocarnosine (Hca) in the Cerebrospinal fluid (CSF) and the brain and by carnosinuria and serum carnosinase deficiency, and can co-exist with paraplegia, retinitis pigmentosa, and a progressive mental deficiency. (PMID 3736769) In glial tumors of human brain the content of homocarnosine has been found to be lower than in brain tissue (PMID 1032224), while an increase in content of homocarnosine was observed in brain tissue of animals under experimental trauma of cranium. (PMID 1025883) [HMDB]
CAS Number3650-73-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
g-Aminobutyryl histidineGenerator
g-Aminobutyryl-L-histidinehmdb
g-Aminobutyrylhistidinehmdb
gamma-Aminobutyryl histidineKegg
gamma-Aminobutyryl-L-histidinehmdb
gamma-Aminobutyrylhistidinehmdb
Homocarnosinehmdb
L-Homocarnosinehmdb
N-(4-amino-1-Oxobutyryl)histidineKegg
N-(4-aminobutyryl)-Histidinehmdb
N-(4-aminobutyryl)-L-Histidinehmdb
γ-aminobutyryl histidineGenerator
Chemical FormulaC10H16N4O3
IUPAC name(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid
InChI IdentifierInChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1
InChI KeyCCLQKVKJOGVQLU-QMMMGPOBSA-N
Isomeric SMILESNCCCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O
Average Molecular Weight240.259
Monoisotopic Molecular Weight240.122240398
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
  • Histidine or derivatives
  • 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
  • Imidazolyl carboxylic acid derivative
  • N-acyl-amine
  • Fatty amide
  • Fatty acyl
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Primary amine
  • Organooxygen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 5 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci X6647