You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00346
NameAllysine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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 a very strong basic compound (based on its pKa). Allysine exists in all eukaryotes, ranging from yeast to humans. allysine and L-glutamic acid can be converted into saccharopine; which is mediated by the enzyme saccharopine dehydrogenase [nadp(+), L-glutamate-forming]. In yeast, allysine is involved in the metabolic pathway called the lysine metabolism pathway. Allysine is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (2S)-2-amino-6-oxohexanoate
  • (2S)-2-amino-6-oxohexanoic acid
  • 2-Amino-5-formylvalerate
  • 2-Amino-5-formylvaleric acid
  • 2-amino-hexanedioate
  • 2-amino-hexanedioic acid
  • 2-amino-hexanedioic acid semialdhyde
  • 2-aminoadipate 6-semialdehyde
  • 2-aminoadipate semialdehyde
  • 2-aminoadipate-6-semialdehyde
  • 5-formyl-Norvaline
  • 6-oxo-L-norleucine
  • 6-oxo-Norleucine
  • Allysine
  • alpha-Aminoadipic acid delta-semialdehyde
  • alpha-Aminoadipic delta-semialdehyde
  • alpha-Aminoadipic semialdehyde
  • L-2-Aminoadipate 6-semialdehyde
  • L-6-oxonorleucine
  • L-Allysine
  • 6-Oxonorleucine
  • HCO-[CH2]3-CH(NH2)-COOH
  • 2-Aminoadipic acid 6-semialdehyde
  • a-Aminoadipate delta-semialdehyde
  • a-Aminoadipic acid delta-semialdehyde
  • alpha-Aminoadipate delta-semialdehyde
  • Α-aminoadipate δ-semialdehyde
  • Α-aminoadipic acid δ-semialdehyde
  • a-Aminoadipic delta-semialdehyde
  • Α-aminoadipic δ-semialdehyde
  • a-Aminoadipate δ-semialdehyde
  • a-Aminoadipic acid δ-semialdehyde
  • a-Aminoadipic δ-semialdehyde
  • 2-Aminoadipic semialdehyde
  • alpha-AASA
  • alpha-Aminoadipate semialdehyde
CAS number1962-83-0
WeightAverage: 145.1564
Monoisotopic: 145.073893223
InChI KeyGFXYTQPNNXGICT-UHFFFAOYSA-N
InChIInChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)
IUPAC Name2-amino-6-oxohexanoic acid
Traditional IUPAC Nameallysine
Chemical FormulaC6H11NO3
SMILES[H]OC(=O)C([H])(N([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])=O
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
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility49.4 g/LALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
lysine metabolismPW002420 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
hydron + NADPH + L-2-aminoadipyl-[LYS2 peptidyl-carrier-protein] → NADP + holo-[LYS2 peptidyl-carrier-protein] + Allysine
Allysine + NADPH + L-Glutamic acid + hydronwater + NADP + Saccharopine
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-e7c5c166681ba0316b25JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8910000000-8fb215d3dd09e5553352JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-2900000000-cc3c3ade4cefc6b57880JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9700000000-1f5f0f3378ed80283ec8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-dd87ab890dceec9e01cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-5623b839bf292d641b92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-4900000000-7473bdea5b2f626515f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-12c42805d877e4f712b6JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17027
HMDB IDHMDB01263
Pubchem Compound ID207
Kegg IDC01475
ChemSpider ID202
FOODB IDFDB010644
WikipediaAllysine
BioCyc IDALLYSINE

Enzymes

General function:
Involved in binding
Specific function:
N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NADP(+) + H(2)O = L-glutamate + L-2-aminoadipate 6-semialdehyde + NADPH
Gene Name:
LYS9
Uniprot ID:
P38999
Molecular weight:
48917.30078
Reactions
N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NADP(+) + H(2)O → L-glutamate + L-2-aminoadipate 6-semialdehyde + NADPH.
General function:
Involved in ligase activity
Specific function:
Catalyzes the activation of alpha-aminoadipate by ATP- dependent adenylation and the reduction of activated alpha- aminoadipate by NADPH
Gene Name:
LYS2
Uniprot ID:
P07702
Molecular weight:
155344.0
Reactions
L-2-aminoadipate 6-semialdehyde + NAD(P)(+) + H(2)O → L-2-aminoadipate + NAD(P)H.