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Identification
YMDB IDYMDB00999
NameL-2-aminoadipate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAminoadipic acid, also known as L-2-aminoadipate, 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. Aminoadipic acid is a very strong basic compound (based on its pKa). Aminoadipic acid exists in both E. coli (prokaryote) and yeast (eukaryote). In yeast, aminoadipic acid is involved in the metabolic pathway called the lysine metabolism pathway.
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
  • (2S)-2-Aminohexanedioic acid
  • (2S)-2-Azaniumyl-6-hydroxy-6-oxohexanoate
  • (S)-2-Aminoadipic acid
  • L-Aminoadipic acid
  • 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
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
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • 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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-02vi-1890000000-cb81ff688a4a1d2ee926JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-9200000000-2a666aa0f9c15fd2295bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kg-2900000000-3e45ac769d3b229221a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-9600000000-c51318834cc371625d46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-edbc970f12ea186bcf06JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-0f7002659f604cc69395JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-4900000000-bf42ddc971a2a05516a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-1979c27463bab7d33d58JSpectraViewer
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 IDFDB021812
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