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Identification
YMDB IDYMDB00999
NameL-2-aminoadipate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-2-Aminoadipate is an intermediate in the metabolism of lysine and saccharopine.
Structure
Thumb
Synonyms
  • (+/-)-2-Aminoadipate
  • (+/-)-2-Aminoadipic acid
  • (S)-2-aminohexanedioic acid
  • 2-Aminoadipate
  • 2-Aminoadipic acid
  • 2-aminohexanedioic acid
  • a-Aminoadipate
  • a-Aminoadipic acid
  • alpha-Amino-adipic acid
  • alpha-Aminoadipate
  • alpha-Aminoadipic acid
  • Aminoadipate
  • AMINOADIPIC ACID, ALPHA
  • DL-2-Aminoadipate
  • DL-2-Aminoadipic acid
  • DL-2-Aminohexanedioate
  • DL-2-Aminohexanedioic acid
  • DL-a-Aminoadipate
  • DL-a-Aminoadipic acid
  • DL-alpha-Aminoadipate
  • DL-alpha-Aminoadipic acid
  • Hexanedioic acid, 2-amino-
  • L-2-Aminoadipate
  • l-2-aminoadipic acid
  • L-2-Aminohexanedioate
  • L-2-Aminohexanedioic acid
  • l-alpha-aminoadipate
  • l-alpha-aminoadipic acid
  • (S)-2-Aminohexanedioate
  • L-a-Aminoadipate
  • L-a-Aminoadipic acid
  • L-α-aminoadipate
  • L-α-aminoadipic acid
CAS number542-32-5
WeightAverage: 161.1558
Monoisotopic: 161.068807845
InChI KeyOYIFNHCXNCRBQI-BYPYZUCNSA-N
InChIInChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)/t4-/m0/s1
IUPAC Name(2S)-2-aminohexanedioic acid
Traditional IUPAC Nameaminoadipate
Chemical FormulaC6H11NO4
SMILESN[C@@H](CCCC(O)=O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point196-198 °C
Experimental Properties
PropertyValueReference
Water Solubility2.2 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility32.7 g/LALOGPS
logP-3.4ALOGPS
logP-2.8ChemAxon
logS-0.69ALOGPS
pKa (Strongest Acidic)2.01ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.89 m³·mol⁻¹ChemAxon
Polarizability15.53 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 PathwaysNot Available
KEGG Pathways
Lysine biosynthesisec00300 Map00300
Lysine degradationec00310 Map00310
SMPDB ReactionsNot Available
KEGG Reactions
L-Glutamic acid + Oxoadipic acidL-2-aminoadipate + Oxoglutaric acid
L-2-aminoadipate + NADH + Adenosine triphosphate + hydronAdenosine monophosphate + L-Allysine + Pyrophosphate + NAD
L-2-aminoadipate + Adenosine triphosphate + NADPH + hydronAdenosine monophosphate + L-Allysine + Pyrophosphate + NADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • 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
  • Matsuda, M., Ogur, M. (1969). "Separation and specificity of the yeast glutamate-alpha-ketoadipate transaminase." J Biol Chem 244:3352-3358.5792664
  • Urrestarazu, A., Vissers, S., Iraqui, I., Grenson, M. (1998). "Phenylalanine- and tyrosine-auxotrophic mutants of Saccharomyces cerevisiae impaired in transamination." Mol Gen Genet 257:230-237.9491082
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • 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 ID37023
HMDB IDHMDB00510
Pubchem Compound ID92136
Kegg IDC00956
ChemSpider ID83182
FOODB IDNot Available
WikipediaAlpha-Aminoadipic_acid
BioCyc IDCPD-468

Enzymes

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.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity. Also active with methionine, alpha-aminoadipate and leucine when phenylpyruvate is the amino acceptor
Gene Name:
ARO8
Uniprot ID:
P53090
Molecular weight:
56177.30078
Reactions
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
L-2-aminoadipate + 2-oxoglutarate → 2-oxoadipate + L-glutamate