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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:07 UTC
HMDB IDHMDB01263
Secondary Accession NumbersNone
Metabolite Identification
Common NameAllysine
DescriptionAllysine is a derivative of Lysine, used in the production of elastin and collagen. It is produced by the actions of the enzyme lysyl oxidase in the extracellular matrix and is essential in the crosslink formation that stabilizes collagen and elastin.
Structure
Thumb
Synonyms
ValueSource
2-amino-5-Formylvaleric acidChEBI
2-Aminoadipate 6-semialdehydeChEBI
6-OxonorleucineChEBI
alpha-Aminoadipic acid delta-semialdehydeChEBI
alpha-Aminoadipic delta-semialdehydeChEBI
hco-[CH2]3-CH(NH2)-COOHChEBI
2-amino-5-FormylvalerateGenerator
2-amino-6-OxohexanoateGenerator
2-Aminoadipic acid 6-semialdehydeGenerator
a-Aminoadipate delta-semialdehydeGenerator
a-Aminoadipic acid delta-semialdehydeGenerator
alpha-Aminoadipate delta-semialdehydeGenerator
α-aminoadipate δ-semialdehydeGenerator
α-aminoadipic acid δ-semialdehydeGenerator
a-Aminoadipic delta-semialdehydeGenerator
α-aminoadipic δ-semialdehydeGenerator
a-Aminoadipate δ-semialdehydeGenerator
a-Aminoadipic acid δ-semialdehydeGenerator
a-Aminoadipic δ-semialdehydeGenerator
(2S)-2-amino-6-OxohexanoateHMDB
(2S)-2-amino-6-Oxohexanoic acidHMDB
2-amino-HexanedioateHMDB
2-amino-Hexanedioic acidHMDB
2-amino-Hexanedioic acid semialdhydeHMDB
2-Aminoadipate semialdehydeHMDB
2-Aminoadipate-6-semialdehydeHMDB
5-Formyl-norvalineHMDB
6-oxo-L-NorleucineHMDB
6-oxo-NorleucineHMDB
alpha-Aminoadipic semialdehydeHMDB
L-2-Aminoadipate 6-semialdehydeHMDB
L-6-OxonorleucineHMDB
L-AllysineHMDB
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 KeyInChIKey=GFXYTQPNNXGICT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • 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 Solubility49.4 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.96 m3·mol-1ChemAxon
Polarizability14.59 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-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
2-aminoadipic 2-oxoadipic aciduriaSMP00719Not Available
Glutaric Aciduria Type ISMP00186Not Available
Hyperlysinemia I, FamilialSMP00527Not Available
Hyperlysinemia II or SaccharopinuriaSMP00528Not Available
Lysine DegradationSMP00037map00310
Pyridoxine dependency with seizuresSMP00571Not Available
Saccharopinuria/Hyperlysinemia IISMP00239Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022519
KNApSAcK IDNot Available
Chemspider ID202
KEGG Compound IDC01475
BioCyc IDALLYSINE
BiGG ID1445244
Wikipedia LinkAllysine
NuGOwiki LinkHMDB01263
Metagene LinkHMDB01263
METLIN ID6118
PubChem Compound207
PDB IDNot Available
ChEBI ID17027
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme that catalyzes the first two steps in lysine degradation. The N-terminal and the C-terminal contain lysine-ketoglutarate reductase and saccharopine dehydrogenase activity, respectively.
Gene Name:
AASS
Uniprot ID:
Q9UDR5
Molecular weight:
102130.895
General function:
Involved in acyl carrier activity
Specific function:
Acyl-CoA synthases catalyze the initial reaction in fatty acid metabolism, by forming a thioester with CoA
Gene Name:
AASDH
Uniprot ID:
Q4L235
Molecular weight:
122596.1