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Record Information
Version1.0
Creation Date2016-09-30 22:43:16 UTC
Update Date2020-05-19 22:01:07 UTC
MCDB ID BMDB0001263
Secondary Accession Numbers
  • BMDB01263
Metabolite Identification
Common NameAllysine
DescriptionAllysine, also known as 6-oxonorleucine or alpha-aasa, 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). Allysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Allysine exists in all eukaryotes, ranging from yeast to humans. Allysine participates in a number of enzymatic reactions, within cattle. In particular, Allysine and L-glutamic acid can be biosynthesized from saccharopine through the action of the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In addition, Allysine can be converted into aminoadipic acid; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In cattle, allysine is involved in the metabolic pathway called the lysine degradation pathway. Allysine is a potentially toxic compound.
Structure
Thumb
Synonyms
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Name2-amino-6-oxohexanoic acid
Traditional Nameallysine
CAS Registry Number1962-83-0
SMILES
NC(CCCC=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)
InChI KeyGFXYTQPNNXGICT-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
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Alpha-hydrogen aldehyde
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.2ALOGPS
logP-2.9ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)2.25ChemAxon
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.96 m³·mol⁻¹ChemAxon
Polarizability14.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0303320
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022519
KNApSAcK IDC00051877
Chemspider ID202
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17027
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]