L-Allysine (YMDB00721)

Identification
YMDB IDYMDB00721
NameL-Allysine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(S)-2-amino-6-oxohexanoate, also known as allysine or L-2-aminoadipate 6-semialdehyde, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom (S)-2-amino-6-oxohexanoate is a very strong basic compound (based on its pKa) (S)-2-amino-6-oxohexanoate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2S)-2-amino-6-oxohexanoate
  • (2S)-2-amino-6-oxohexanoic acid
  • (S)-2-Amino-6-oxohexanoate
  • (S)-2-aminoadipate 6-semialdehyde
  • 2-Amino-5-formylvalerate
  • 2-Amino-5-formylvaleric acid
  • 2-AMINO-6-OXO-HEXANOIC 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-aminoadipate 6-semialdehyde
  • alpha-Aminoadipic acid delta-semialdehyde
  • alpha-Aminoadipic delta-semialdehyde
  • alpha-Aminoadipic semialdehyde
  • L-2-Aminoadipate 6-semialdehyde
  • L-6-oxonorleucine
  • L-Allysine
  • 2-AMINO-6-oxo-hexanoate
  • L-2-Aminoadipic acid 6-semialdehyde
  • 2-Aminoadipic acid 6-semialdehyde
  • (S)-2-Amino-6-oxohexanoic acid
  • alpha-AASA
  • alpha-Aminoadipate semialdehyde
  • 2-Aminoadipic semialdehyde
  • 2-Amino-6-oxohexanoate
  • 6-Oxonorleucine
  • L-Homoglutamic semialdehyde
  • α-Aminoadipic acid δ-semialdehyde
  • α-Aminoadipic δ-semialdehyde
CAS number1962-83-0
WeightAverage: 145.1564
Monoisotopic: 145.073893223
InChI KeyGFXYTQPNNXGICT-YFKPBYRVSA-N
InChIInChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)/t5-/m0/s1
IUPAC Name(2S)-2-amino-6-oxohexanoic acid
Traditional IUPAC Name2-amino-6-oxo-hexanoic acid
Chemical FormulaC6H11NO3
SMILES[H]C(=O)CCC[C@H](N)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-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
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • 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
Polarizability14.58 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
lysine metabolismPW002420 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Lysine biosynthesisec00300 Map00300
Lysine degradationec00310 Map00310
SMPDB ReactionsNot Available
KEGG Reactions
L-2-aminoadipate + NADH + Adenosine triphosphate + hydron → Adenosine monophosphate + L-Allysine + Pyrophosphate + NAD
L-2-aminoadipate + Adenosine triphosphate + NADPH + hydron → Adenosine monophosphate + L-Allysine + Pyrophosphate + NADP
L-Allysine + L-Glutamic acid + NADPH + hydron ↔ NADP + water + Saccharopine
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, Positivesplash10-0udi-7900000000-a87d074458b671b94f65JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-6900000000-d34f08b905440e7d7964JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-684e25a1d77f85cbfa55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-96069f1c2588457b97ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-0900000000-06ca102489283c43f7e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-054o-2900000000-46f0e454239e803a8554JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3fc953bdebc8fddb25d1JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Ramos, F., Dubois, E., Pierard, A. (1988). "Control of enzyme synthesis in the lysine biosynthetic pathway of Saccharomyces cerevisiae. Evidence for a regulatory role of gene LYS14." Eur J Biochem 171:171-176.3123231
  • Bhattacharjee, J. K. (1985). "alpha-Aminoadipate pathway for the biosynthesis of lysine in lower eukaryotes." Crit Rev Microbiol 12:131-151.3928261
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17917
HMDB IDHMDB01263
Pubchem Compound ID36688062
Kegg IDC04076
ChemSpider ID141126
FOODB IDFDB010644
WikipediaAllysine
BioCyc IDALLYSINE

Enzymes

Protein Details
1. Saccharopine dehydrogenase [NADP+, L-glutamate-forming]
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.
Protein Details
2. L-aminoadipate-semialdehyde dehydrogenase
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.