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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 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:
  • 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.