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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:31:45 UTC
Update Date2019-07-23 06:28:44 UTC
HMDB IDHMDB0039160
Secondary Accession Numbers
  • HMDB39160
Metabolite Identification
Common NameL-Gizzerosine
DescriptionL-Gizzerosine 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). L-Gizzerosine is a very strong basic compound (based on its pKa). Causes gizzard erosion ("black vomit") in chicks. L-Gizzerosine is isolated from mackerel meal. Isolated from mackerel meal.
Structure
Data?1563863324
Synonyms
ValueSource
2-Amino-9-(4-imidazolyl)-7-azanonanoic acidHMDB
GizzerosineHMDB
N6-(2-(1H-Imidazol-4-yl)ethyl)-L-lysineHMDB
2-Amino-6-{[2-(1H-imidazol-5-yl)ethyl]amino}hexanoateGenerator
Chemical FormulaC11H20N4O2
Average Molecular Weight240.3021
Monoisotopic Molecular Weight240.158625904
IUPAC Name2-amino-6-{[2-(1H-imidazol-5-yl)ethyl]amino}hexanoic acid
Traditional Name2-amino-6-{[2-(3H-imidazol-4-yl)ethyl]amino}hexanoic acid
CAS Registry Number89238-78-8
SMILES
NC(CCCCNCCC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C11H20N4O2/c12-10(11(16)17)3-1-2-5-13-6-4-9-7-14-8-15-9/h7-8,10,13H,1-6,12H2,(H,14,15)(H,16,17)
InChI KeyLFNFNJYYTXESHV-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
  • Imidazolyl carboxylic acid derivative
  • Medium-chain fatty acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Aralkylamine
  • Fatty acyl
  • Fatty acid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organoheterocyclic compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point251 - 252 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.08 g/LALOGPS
logP-2.2ALOGPS
logP-3.3ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.68ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area104.03 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity64.89 m³·mol⁻¹ChemAxon
Polarizability26.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-008d-9500000000-006ba1f557b7a3656e2aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-4900000000-a37fb3537f0b9595a115Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006w-2980000000-16c895e55be26c5cb917Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-8910000000-8a4cdcda3c906353ed23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9100000000-f2e4e0bd3c9b26b0ac21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-a6cfe2c0b6ce8b6ad9dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ds-4980000000-7a0670266de9906a0a5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fft-9300000000-9f6e0f1cb9f001421484Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018684
KNApSAcK IDNot Available
Chemspider ID8552449
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10377006
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .