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Record Information
Version1.0
Creation Date2016-07-13 19:43:51 UTC
Update Date2021-04-30 20:57:41 UTC
LmdbLMDB00168
Secondary Accession NumbersNone
Metabolite Identification
Common NameAminoadipic acid
DescriptionAminoadipic acid (2-aminoadipate) is a metabolite in the principal biochemical pathway of lysine. It is an intermediate in the metabolism (i.e. breakdown or degradation) of lysine and saccharopine.(Wikipedia). It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-methyl-D-aspartate; (NMDA). Aminoadipic has also been shown to inhibit the production of kynurenic acid in brain tissue slices (PMID: 8566117 ). Kynurenic acid is a broad spectrum excitatory amino acid receptor antagonist. Recent studies have shown that aminoadipic acid is elevated in prostate biopsy tissues from prostate cancer patients (PMID: 23737455 ). Mutations in DHTKD1 (dehydrogenase E1 and transketolase domain-containing protein 1) have been shown to cause animal 2-aminoadipic and 2-oxoadipic aciduria via impaired turnover of decarboxylation 2-oxoadipate to glutaryl-CoA, which is the last step in the lysine degradation pathway (PMID: 23141293 ). Aging, diabetes, sepsis and renal failure are known to catalyze the oxidation of lysyl residues to 2-aminoadipic acid in animal skin collagen and potentially other tissues (PMID: 18448817 ). Proteolytic breakdown of these tissues can lead to the release of free 2-aminoadipic acid. Studies in rats indicate that aminoadipic acid (along with the 3 branched chain amino acid ñ Leu, Val and Ile) levels are elevated in the pre-diabetic phase and so aminoadipic acid may serve as a predictive biomarker for the development of diabetes. (PMID: 15389298 ). Long-term hyperglycemia of endothelial cells leads to elevated levels of aminoadipate which is though to be a sign of lysine breakdown through oxidative stress and reactive oxygen species (ROS) (PMID: 21961526 ). 2-aminoadipate is a potential small-molecule marker of oxidative stress (PMID: 21647514 )
Structure
Thumb
Synonyms
ValueSource
(+/-)-2-aminoadipic acidChEBI
AadChEBI
alpha-Aminoadipic acidChEBI
DL-2-Aminoadipic acidChEBI
DL-2-Aminohexanedioic acidChEBI
DL-alpha-Aminoadipic acidChEBI
(+/-)-2-aminoadipateGenerator
a-AminoadipateGenerator
a-Aminoadipic acidGenerator
alpha-AminoadipateGenerator
Α-aminoadipateGenerator
Α-aminoadipic acidGenerator
DL-2-AminoadipateGenerator
DL-2-AminohexanedioateGenerator
DL-a-AminoadipateGenerator
DL-a-Aminoadipic acidGenerator
DL-alpha-AminoadipateGenerator
DL-Α-aminoadipateGenerator
DL-Α-aminoadipic acidGenerator
AminoadipateGenerator
2 Aminoadipic acidMeSH
2 Aminohexanedioic acidMeSH
2-Aminoadipic acidMeSH
Acid, 2 aminoadipicMeSH
Acid, 2-aminoadipicMeSH
Acid, 2-aminohexanedioicMeSH
Acid, alpha-aminoadipicMeSH
Aminoadipic acid, 2MeSH
alpha Aminoadipic acidMeSH
2-AminoadipateHMDB
alpha-amino-Adipic acidHMDB
L-2-AminoadipateHMDB
L-2-Aminoadipic acidHMDB
L-2-AminohexanedioateHMDB
L-2-Aminohexanedioic acidHMDB
L-alpha-AminoadipateHMDB
L-alpha-Aminoadipic acidHMDB
2-Aminohexanedioic acidMeSH, HMDB
Chemical FormulaC6H11NO4
Average Molecular Weight161.1558
Monoisotopic Molecular Weight161.068807845
IUPAC Name2-aminohexanedioic acid
Traditional Nameaminoadipic acid
CAS Registry Number542-32-5
SMILES
NC(CCCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)
InChI KeyOYIFNHCXNCRBQI-UHFFFAOYSA-N
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
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02di-0950000000-ec4fd991a53a8b6bc6aeSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02di-0950000000-ec4fd991a53a8b6bc6aeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r6-9300000000-9ef33042820e032c1af3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ri-9620000000-052fe671da5a64787657Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03xv-2900000000-58b4f0b3e06cbb7abb90Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4j-9000000000-cc9c0c03f7c3890b531cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-7b74167f01c922da9ef7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-9400000000-71832a0d1e49341749a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-014l-2900000000-08df6df87d0bea6dce31Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0006-0900000000-99e7d8729f7099c6e9eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-03di-0900000000-f542aa2756da9aa3ecb6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-03di-0900000000-3133117467ce925161cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-03di-0900000000-9e5f27d91fd799c059d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-03xu-0900000000-b801b3a34049e54a2915Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-014i-1900000000-2ef33d8640c4e5788618Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-014i-1900000000-281e4277990becc84832Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-014i-2900000000-a56c711aeb57c767fed8Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0006-0900000000-862ae5fa10820c14bdf1Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-006t-9400000000-e007d0e2c3cec7f1a02cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0002-9000000000-4755db14192225e1eebfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kg-2900000000-3e45ac769d3b229221a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-9600000000-c51318834cc371625d46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-edbc970f12ea186bcf06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-0f7002659f604cc69395Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-4900000000-bf42ddc971a2a05516a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-1979c27463bab7d33d58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-7913a597d0c94eebe02dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-9100000000-523aa25ee55f888299e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-0dcf3a7ca5d4e20885eeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Follicular Fluid
  • Milk
  • Plasma
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Follicular FluidDetected and Quantified27 +/- 4-37+/-4 uMNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected and Quantified195-427 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected and Quantified44 +/- 2-37+/-4 uMNot AvailablePorcine details
PlasmaDetected and Quantified54 +/- 8-83+/-13 uMNot AvailablePorcine details
PlasmaDetected and Quantified55 +/- 7-75+/-15 uMNot AvailablePorcine details
SerumDetected and Quantified1.4316 +/- 0.4262 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.4892 +/- 0.5005 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified2.1757 +/- 0.7708 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.5796 +/- 0.4215 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.6284 +/- 0.4872 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.89 +/- 3.95 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified1.6636 +/- 0.6341 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.9958 +/- 0.7143 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified3 +/- 9 uMNot AvailablePorcine details
SerumDetected and Quantified1.6302 +/- 0.798 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified2.9 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified3.6 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified4.2 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified4.3 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified1.8689 +/- 0.6061 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.3136 +/- 0.5757 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.4315 +/- 0.4727 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified2.1748 +/- 0.6959 uM
Normal
Ovine
    • Goldansaz et al.,...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0302754
FooDB IDFDB007648
Phenol Explorer IDNot Available
KNApSAcK IDC00007393
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlpha-Aminoadipic_acid
Chemspider ID456
ChEBI ID37024
PubChem Compound ID469
Kegg Compound IDNot Available
YMDB IDYMDB00305
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wu HQ, Ungerstedt U, Schwarcz R: L-alpha-aminoadipic acid as a regulator of kynurenic acid production in the hippocampus: a microdialysis study in freely moving rats. Eur J Pharmacol. 1995 Jul 25;281(1):55-61. [8566117 ]
  2. Jung K, Reszka R, Kamlage B, Bethan B, Stephan C, Lein M, Kristiansen G: Tissue metabolite profiling identifies differentiating and prognostic biomarkers for prostate carcinoma. Int J Cancer. 2013 Dec 15;133(12):2914-24. doi: 10.1002/ijc.28303. Epub 2013 Jun 29. [23737455 ]
  3. Danhauser K, Sauer SW, Haack TB, Wieland T, Staufner C, Graf E, Zschocke J, Strom TM, Traub T, Okun JG, Meitinger T, Hoffmann GF, Prokisch H, Kolker S: DHTKD1 mutations cause 2-aminoadipic and 2-oxoadipic aciduria. Am J Hum Genet. 2012 Dec 7;91(6):1082-7. doi: 10.1016/j.ajhg.2012.10.006. Epub 2012 Nov 8. [23141293 ]
  4. Sell DR, Strauch CM, Shen W, Monnier VM: Aging, diabetes, and renal failure catalyze the oxidation of lysyl residues to 2-aminoadipic acid in human skin collagen: evidence for metal-catalyzed oxidation mediated by alpha-dicarbonyls. Ann N Y Acad Sci. 2008 Apr;1126:205-9. doi: 10.1196/annals.1433.065. [18448817 ]
  5. Wijekoon EP, Skinner C, Brosnan ME, Brosnan JT: Amino acid metabolism in the Zucker diabetic fatty rat: effects of insulin resistance and of type 2 diabetes. Can J Physiol Pharmacol. 2004 Jul;82(7):506-14. [15389298 ]
  6. Yuan W, Zhang J, Li S, Edwards JL: Amine metabolomics of hyperglycemic endothelial cells using capillary LC-MS with isobaric tagging. J Proteome Res. 2011 Nov 4;10(11):5242-50. doi: 10.1021/pr200815c. Epub 2011 Oct 17. [21961526 ]
  7. Zeitoun-Ghandour S, Leszczyszyn OI, Blindauer CA, Geier FM, Bundy JG, Sturzenbaum SR: C. elegans metallothioneins: response to and defence against ROS toxicity. Mol Biosyst. 2011 Aug;7(8):2397-406. doi: 10.1039/c1mb05114h. Epub 2011 Jun 7. [21647514 ]