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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:53 UTC
HMDB IDHMDB0000510
Secondary Accession Numbers
  • HMDB00510
Metabolite Identification
Common NameAminoadipic acid
DescriptionAminoadipic acid (CAS: 542-32-5), also known as 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. It antagonizes neuroexcitatory activity modulated by the glutamate receptor N-methyl-D-aspartate (NMDA). Aminoadipic acid has also been shown to inhibit the production of kynurenic acid, a broad spectrum excitatory amino acid receptor antagonist, in brain tissue slices (PMID: 8566117 ). 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 human 2-aminoadipic aciduria and 2-oxoadipic aciduria via impaired decarboxylation of 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 form 2-aminoadipic acid in human 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 three branched-chain amino acids: leucine, valine, and isoleucine) 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 can also lead to elevated levels of aminoadipate which is thought 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 ). Therefore, depending on the circumstances aminoadipic acid can act as an acidogen, a diabetogen, an atherogen, and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A diabetogen is a compound that can lead to type 2 diabetes. An atherogen is a compound that leads to atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of aminoadipic acid are associated with at least two inborn errors of metabolism including 2-aminoadipic aciduria and 2-oxoadipic aciduria. Aminoadipic acid is an organic acid and abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. As a diabetogen, serum aminoadipic levels appear to regulate glucose homeostasis and have been highly predictive of individuals who later develop diabetes (PMID: 24091325 ). In particular, aminoadipic acid lowers fasting plasma glucose levels and enhances insulin secretion from human islets. As an atherogen, aminoadipic acid has been found to be produced at high levels via protein lysine oxidation in atherosclerotic plaques (PMID: 28069522 ).
Structure
Data?1676999693
Synonyms
ValueSource
(S)-2-Aminohexanedioic acidChEBI
L-2-AminoadipateChEBI
L-2-AminohexanedioateChEBI
L-alpha-AminoadipateChEBI
L-alpha-Aminoadipic acidChEBI
L-2-Aminoadipic acidKegg
(S)-2-AminohexanedioateGenerator
L-2-Aminohexanedioic acidGenerator
L-a-AminoadipateGenerator
L-a-Aminoadipic acidGenerator
L-Α-aminoadipateGenerator
L-Α-aminoadipic acidGenerator
AminoadipateGenerator
(2S)-2-Aminohexanedioic acidHMDB
(2S)-2-Azaniumyl-6-hydroxy-6-oxohexanoateHMDB
(S)-2-Aminoadipic acidHMDB
2-AminoadipateHMDB
2-Aminoadipic acidHMDB
2-Aminohexanedioic acidHMDB
L-Aminoadipic acidHMDB
alpha-Aminoadipic acidHMDB
Α-aminoadipic acidHMDB
Chemical FormulaC6H11NO4
Average Molecular Weight161.1558
Monoisotopic Molecular Weight161.068807845
IUPAC Name(2S)-2-aminohexanedioic acid
Traditional Nameaminoadipate
CAS Registry Number1118-90-7
SMILES
N[C@@H](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)/t4-/m0/s1
InChI KeyOYIFNHCXNCRBQI-BYPYZUCNSA-N
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
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point196 - 198 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.2 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+132.24830932474
DeepCCS[M-H]-128.42130932474
DeepCCS[M-2H]-166.07930932474
DeepCCS[M+Na]+141.61830932474
AllCCS[M+H]+136.432859911
AllCCS[M+H-H2O]+132.532859911
AllCCS[M+NH4]+140.032859911
AllCCS[M+Na]+141.132859911
AllCCS[M-H]-131.032859911
AllCCS[M+Na-2H]-132.832859911
AllCCS[M+HCOO]-134.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Aminoadipic acidN[C@@H](CCCC(O)=O)C(O)=O2314.5Standard polar33892256
Aminoadipic acidN[C@@H](CCCC(O)=O)C(O)=O1346.5Standard non polar33892256
Aminoadipic acidN[C@@H](CCCC(O)=O)C(O)=O1771.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aminoadipic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC[C@H](N)C(=O)O1613.1Semi standard non polar33892256
Aminoadipic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CCCC(=O)O1567.0Semi standard non polar33892256
Aminoadipic acid,1TMS,isomer #3C[Si](C)(C)N[C@@H](CCCC(=O)O)C(=O)O1630.7Semi standard non polar33892256
Aminoadipic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC[C@H](N)C(=O)O[Si](C)(C)C1619.8Semi standard non polar33892256
Aminoadipic acid,2TMS,isomer #2C[Si](C)(C)N[C@@H](CCCC(=O)O[Si](C)(C)C)C(=O)O1706.9Semi standard non polar33892256
Aminoadipic acid,2TMS,isomer #3C[Si](C)(C)N[C@@H](CCCC(=O)O)C(=O)O[Si](C)(C)C1676.2Semi standard non polar33892256
Aminoadipic acid,2TMS,isomer #4C[Si](C)(C)N([C@@H](CCCC(=O)O)C(=O)O)[Si](C)(C)C1829.2Semi standard non polar33892256
Aminoadipic acid,3TMS,isomer #1C[Si](C)(C)N[C@@H](CCCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1723.0Semi standard non polar33892256
Aminoadipic acid,3TMS,isomer #1C[Si](C)(C)N[C@@H](CCCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1763.3Standard non polar33892256
Aminoadipic acid,3TMS,isomer #1C[Si](C)(C)N[C@@H](CCCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1896.1Standard polar33892256
Aminoadipic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1874.8Semi standard non polar33892256
Aminoadipic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1807.8Standard non polar33892256
Aminoadipic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2057.4Standard polar33892256
Aminoadipic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CCCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C1861.9Semi standard non polar33892256
Aminoadipic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CCCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C1800.2Standard non polar33892256
Aminoadipic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CCCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C2049.0Standard polar33892256
Aminoadipic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1903.7Semi standard non polar33892256
Aminoadipic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1865.6Standard non polar33892256
Aminoadipic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1822.6Standard polar33892256
Aminoadipic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](N)C(=O)O1867.3Semi standard non polar33892256
Aminoadipic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCC(=O)O1833.1Semi standard non polar33892256
Aminoadipic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CCCC(=O)O)C(=O)O1904.3Semi standard non polar33892256
Aminoadipic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2076.3Semi standard non polar33892256
Aminoadipic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2204.0Semi standard non polar33892256
Aminoadipic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CCCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2135.3Semi standard non polar33892256
Aminoadipic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CCCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C2280.7Semi standard non polar33892256
Aminoadipic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2381.4Semi standard non polar33892256
Aminoadipic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2343.2Standard non polar33892256
Aminoadipic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2272.6Standard polar33892256
Aminoadipic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2549.6Semi standard non polar33892256
Aminoadipic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2399.4Standard non polar33892256
Aminoadipic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2342.7Standard polar33892256
Aminoadipic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2526.9Semi standard non polar33892256
Aminoadipic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2370.5Standard non polar33892256
Aminoadipic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2341.2Standard polar33892256
Aminoadipic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2774.1Semi standard non polar33892256
Aminoadipic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2607.9Standard non polar33892256
Aminoadipic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2313.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Aminoadipic acid GC-MS (3 TMS)splash10-02vi-1890000000-cb81ff688a4a1d2ee9262014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-9200000000-2a666aa0f9c15fd2295b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminoadipic acid GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 10V, Positive-QTOFsplash10-0002-9600000000-77ab58046847c3ea82f02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 20V, Positive-QTOFsplash10-0a4j-9000000000-fced5385ac147b0fd6a02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-3f7c5858ac3e97d89e6e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 30V, Positive-QTOFsplash10-0a4i-9000000000-af6e2d829df2d68bd2622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-3664a98748e89e99cd2d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 10V, Positive-QTOFsplash10-0002-9700000000-e1040cea3fd3c274b4682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 20V, Positive-QTOFsplash10-052b-9000000000-c9da617e7f36084d02762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 10V, Positive-QTOFsplash10-00kb-9800000000-2738b9d8b78b33fed9f72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 35V, Positive-QTOFsplash10-00ke-7900000000-461c76f7d777bbdee97e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-b096dea8b50a6e2c75c42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 10V, Positive-QTOFsplash10-00ke-7900000000-cfb9ae7bd0906a9393682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 20V, Positive-QTOFsplash10-0a4j-9000000000-7c27445e72a5da0c3bb62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 10V, Positive-QTOFsplash10-014j-6900000000-f349746a9f0635231c652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 0V, Positive-QTOFsplash10-03di-0900000000-1bc82027155d45c9a43d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 30V, Positive-QTOFsplash10-0a4i-9000000000-2749c34e547a235a0f782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 0V, Positive-QTOFsplash10-03di-0900000000-97545962897518937c042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 30V, Positive-QTOFsplash10-0a4i-9000000000-0e2bf30c88b4dafc0c5f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 10V, Positive-QTOFsplash10-0002-9500000000-83d347e56da993118fba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminoadipic acid 10V, Negative-QTOFsplash10-03xu-1900000000-db1ee9542c240bfe00b72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminoadipic acid 10V, Positive-QTOFsplash10-00kg-2900000000-3e45ac769d3b229221a32015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminoadipic acid 20V, Positive-QTOFsplash10-01ba-9600000000-c51318834cc371625d462015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminoadipic acid 40V, Positive-QTOFsplash10-05fu-9000000000-edbc970f12ea186bcf062015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminoadipic acid 10V, Negative-QTOFsplash10-03di-1900000000-0f7002659f604cc693952015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminoadipic acid 20V, Negative-QTOFsplash10-01ox-4900000000-bf42ddc971a2a05516a22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminoadipic acid 40V, Negative-QTOFsplash10-0abc-9100000000-1979c27463bab7d33d582015-09-15Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.0-5.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.30-3.40 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.14(0.81-9.66) uMChildren (1-13 uears old)Both
Normal
details
BloodDetected and Quantified0 uMChildren (1 - 13 years old)FemaleNormal details
BloodDetected and Quantified0.30-3.40 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified0.804 +/- 1.44 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.821 +/- 0.408 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.952 +/- 1.49 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.336 +/- 0.475 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified20.4023 +/- 11.4518 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified15.83 +/- 12.44 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified19.22 +/- 15.83 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified24.87 +/- 15.83 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified<9.50 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.7-4.2 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified4.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified40.736 +/- 34.234 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.23-15.5 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified8.52 +/- 4.45 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified6.09 +/- 3.36 umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified<8.60 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<5.32 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.9-4.3 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified1.13-31.1 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.633 +/- 1.0288 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal details
UrineDetected and Quantified7.3 (3.4-11.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.70-36.65 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified7.2 (2.5-16.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.13-15.27 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.0 (7.0-8.0) uMAdult (>18 years old)Bothalpha-Aminoadipic aciduria details
BloodDetected and Quantified1.07(0.70-3.17) uMChildren (1-13 uears old)Both
Environmental enteric dysfunction
details
BloodDetected and Quantified18.7 uMChildren (1-13 years old)Male
Alpha-aminoadipic and alpha-ketoadipic aciduria
details
BloodDetected and Quantified48.0 uMChildren (1-13 years old)Bothalpha-Aminoadipic aciduria
    • MetaGene: Metabol...
details
BloodDetected and Quantified55.0 (30.0-80.0) uMChildren (1-13 years old)Both2-Ketoadipic Acidemia
    • MetaGene: Metabol...
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metastatic melanoma
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified14.3982 +/- 9.7148 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified14.0068 +/- 9.2776 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
UrineDetected and Quantified45.554 +/- 68.592 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified148 umol/mmol creatinineAdolescent (13-18 years old)Malealpha-Ketoadipic Aciduria details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
UrineDetected and Quantified42.612 umol/mmol creatinineChildren (1-13 years old)Male
Alpha-aminoadipic and alpha-ketoadipic aciduria
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
UrineDetected and Quantified13000 umol/mmol creatinineChildren (1-13 years old)Bothalpha-Aminoadipic aciduria
    • MetaGene: Metabol...
details
UrineDetected and Quantified240-1910 umol/mmol creatinineChildren (1-13 years old)Not Specifiedalpha-Aminoadipic aciduria details
UrineDetected and Quantified1243 umol/mmol creatinineInfant (0-1 year old)Not Specified
alpha-ketoadipic aciduria
details
UrineDetected and Quantified176 umol/mmol creatinineNewborn (0-30 days old)Not Specified
alpha-ketoadipic aciduria
details
Associated Disorders and Diseases
Disease References
Alpha-aminoadipic aciduria
  1. Vallat C, Rivier F, Bellet H, Magnan de Bornier B, Mion H, Echenne B: Treatment with vigabatrin may mimic alpha-aminoadipic aciduria. Epilepsia. 1996 Aug;37(8):803-5. [PubMed:8764822 ]
  2. Gray RG, O'Neill EM, Pollitt RJ: Alpha-aminoadipic aciduria: chemical and enzymatic studies. J Inherit Metab Dis. 1980;2(4):89-92. [PubMed:6796766 ]
  3. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
2-Ketoadipic acidemia
  1. Chalmers RA, Lawson AM, Watts RW, Tavill AS, Kamerling JP, Hey E, Ogilvie D: D-2-hydroxyglutaric aciduria: case report and biochemical studies. J Inherit Metab Dis. 1980;3(1):11-5. [PubMed:6774165 ]
  2. Peng H, Shinka T, Inoue Y, Mitsubuchi H, Ishimatsu J, Yoshino M, Kuhara T: Asymptomatic alpha-ketoadipic aciduria detected during a pilot study of neonatal urine screening. Acta Paediatr. 1999 Aug;88(8):911-4. [PubMed:10503694 ]
  3. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Alpha-aminoadipic and alpha-ketoadipic aciduria
  1. Takechi T, Okada T, Wakiguchi H, Morita H, Kurashige T, Sugahara K, Kodama H: Identification of N-acetyl-alpha-aminoadipic acid in the urine of a patient with alpha-aminoadipic and alpha-ketoadipic aciduria. J Inherit Metab Dis. 1993;16(1):119-26. [PubMed:8487492 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021812
KNApSAcK IDC00007393
Chemspider ID83182
KEGG Compound IDC00956
BioCyc IDCPD-468
BiGG IDNot Available
Wikipedia LinkAlpha-Aminoadipic_acid
METLIN IDNot Available
PubChem Compound92136
PDB IDNot Available
ChEBI ID37023
Food Biomarker OntologyNot Available
VMH IDL2AADP
MarkerDB IDMDB00000178
Good Scents IDNot Available
References
Synthesis ReferenceKhan, Naseem H.; Ali, Mohd.; Panda, H.; Rakhshinda. Synthesis of a-aminoadipic acid. Journal of the Indian Chemical Society (1982), 59(9), 1077-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Fiermonte G, Dolce V, Palmieri L, Ventura M, Runswick MJ, Palmieri F, Walker JE: Identification of the human mitochondrial oxodicarboxylate carrier. Bacterial expression, reconstitution, functional characterization, tissue distribution, and chromosomal location. J Biol Chem. 2001 Mar 16;276(11):8225-30. Epub 2000 Nov 16. [PubMed:11083877 ]
  2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. Brauner-Osborne H, Slok FA, Skjaerbaek N, Ebert B, Sekiyama N, Nakanishi S, Krogsgaard-Larsen P: A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid. J Med Chem. 1996 Aug 2;39(16):3188-94. [PubMed:8759641 ]
  4. Hori S: [Pathophysiology of intraocular neovascularization]. Nippon Ganka Gakkai Zasshi. 1990 Dec;94(12):1103-21. [PubMed:1707214 ]
  5. Ouwerkerk-Mahadevan S, Mulder GJ: Inhibition of glutathione conjugation in the rat in vivo by analogues of glutathione conjugates. Chem Biol Interact. 1998 Apr 24;111-112:163-76. [PubMed:9679552 ]
  6. Mechanic GL: The qualitative and quantitative crosslink chemistry of collagen matrices. Adv Exp Med Biol. 1977;86B:699-708. [PubMed:20755 ]
  7. Okuno E, Tsujimoto M, Nakamura M, Kido R: 2-Aminoadipate-2-oxoglutarate aminotransferase isoenzymes in human liver: a plausible physiological role in lysine and tryptophan metabolism. Enzyme Protein. 1993;47(3):136-48. [PubMed:8087205 ]
  8. Takechi T, Okada T, Wakiguchi H, Morita H, Kurashige T, Sugahara K, Kodama H: Identification of N-acetyl-alpha-aminoadipic acid in the urine of a patient with alpha-aminoadipic and alpha-ketoadipic aciduria. J Inherit Metab Dis. 1993;16(1):119-26. [PubMed:8487492 ]
  9. 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. [PubMed:8566117 ]
  10. 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. [PubMed:23737455 ]
  11. 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. [PubMed:23141293 ]
  12. Sell DR, Strauch CM, Shen W, Monnier VM: 2-aminoadipic acid is a marker of protein carbonyl oxidation in the aging human skin: effects of diabetes, renal failure and sepsis. Biochem J. 2007 Jun 1;404(2):269-77. [PubMed:17313367 ]
  13. 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. [PubMed:15389298 ]
  14. 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. [PubMed:21961526 ]
  15. 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. [PubMed:21647514 ]
  16. 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. [PubMed:18448817 ]
  17. Wang TJ, Ngo D, Psychogios N, Dejam A, Larson MG, Vasan RS, Ghorbani A, O'Sullivan J, Cheng S, Rhee EP, Sinha S, McCabe E, Fox CS, O'Donnell CJ, Ho JE, Florez JC, Magnusson M, Pierce KA, Souza AL, Yu Y, Carter C, Light PE, Melander O, Clish CB, Gerszten RE: 2-Aminoadipic acid is a biomarker for diabetes risk. J Clin Invest. 2013 Oct;123(10):4309-17. doi: 10.1172/JCI64801. Epub 2013 Sep 16. [PubMed:24091325 ]
  18. Lin H, Levison BS, Buffa JA, Huang Y, Fu X, Wang Z, Gogonea V, DiDonato JA, Hazen SL: Myeloperoxidase-mediated protein lysine oxidation generates 2-aminoadipic acid and lysine nitrile in vivo. Free Radic Biol Med. 2017 Mar;104:20-31. doi: 10.1016/j.freeradbiomed.2017.01.006. Epub 2017 Jan 6. [PubMed:28069522 ]
  19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
Allysine + NAD(P)(+) + Water → Aminoadipic acid + NAD(P)Hdetails
Aminoadipic acid + Adenosine triphosphate → L-2-Aminoadipate adenylate + Pyrophosphatedetails
Allysine + NAD + Water → Aminoadipic acid + NADH + Hydrogen Iondetails
Allysine + NADP + Water → Aminoadipic acid + NADPH + Hydrogen Iondetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro).
Gene Name:
AADAT
Uniprot ID:
Q8N5Z0
Molecular weight:
47351.17
Reactions
Aminoadipic acid + Oxoglutaric acid → Oxoadipic acid + L-Glutamic aciddetails
General function:
Transcription
Specific function:
Not Available
Gene Name:
AADAT
Uniprot ID:
Q4W5N8
Molecular weight:
47351.2
General function:
Involved in acyl carrier activity
Specific function:
Acyl-CoA synthases catalyze the initial reaction in fatty acid metabolism, by forming a thioester with CoA
Gene Name:
AASDH
Uniprot ID:
Q4L235
Molecular weight:
122596.1
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the post-translational modification of target proteins by phosphopantetheine. Can transfer the 4'-phosphopantetheine moiety from coenzyme A to a serine residue of a broad range of acceptors, such as the acyl carrier domain of FASN.
Gene Name:
AASDHPPT
Uniprot ID:
Q9NRN7
Molecular weight:
35775.64