Record Information
Version1.0
Creation date2011-04-11 17:01:42 UTC
Update date2019-11-26 03:20:54 UTC
Primary IDFDB021812
Secondary Accession Numbers
  • FDB006672
  • FDB006066
  • FDB007648
Chemical Information
FooDB NameAminoadipic acid
DescriptionAminoadipic acid, also known as a-aminoadipate or Aad, 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). Aminoadipic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Aminoadipic acid exists in all eukaryotes, ranging from yeast to humans. Aminoadipic acid is found, on average, in the highest concentration within a few different foods, such as wheats, milk (cow), and ryes and in a lower concentration in romaine lettuces, carrots, and potato. Aminoadipic acid has also been detected, but not quantified in, several different foods, such as barley, cow milks, cow milks, cow milks, and cow milks. This could make aminoadipic acid a potential biomarker for the consumption of these foods. Aminoadipic acid is a potentially toxic compound. Aminoadipic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, eosinophilic esophagitis, and metastatic melanoma; aminoadipic acid has also been linked to several inborn metabolic disorders including 2-ketoadipic acidemia and alpha-aminoadipic aciduria.
CAS Number542-32-5
Structure
Thumb
Synonyms
SynonymSource
(+/-)-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-AminoadipateHMDB
2-Aminoadipic acidHMDB
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 Aminoadipic acidHMDB
Acid, 2-aminohexanedioicHMDB
Acid, 2 aminoadipicHMDB
alpha Aminoadipic acidHMDB
2 Aminohexanedioic acidHMDB
Aminoadipic acid, 2HMDB
Acid, alpha-aminoadipicHMDB
Acid, 2-aminoadipicHMDB
2-Aminohexanedioic acidHMDB
alpha-amino-Adipic acidHMDB
DL-α-aminoadipateGenerator
DL-α-aminoadipic acidGenerator
α-aminoadipateGenerator
α-aminoadipic acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H11NO4
IUPAC name2-aminohexanedioic acid
InChI IdentifierInChI=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
Isomeric SMILESNC(CCCC(O)=O)C(O)=O
Average Molecular Weight161.1558
Monoisotopic Molecular Weight161.068807845
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2-Aminoadipic acid, non-derivatized, GC-MS Spectrumsplash10-02di-0950000000-ec4fd991a53a8b6bc6aeSpectrum
GC-MS2-Aminoadipic acid, non-derivatized, GC-MS Spectrumsplash10-02di-0950000000-ec4fd991a53a8b6bc6aeSpectrum
Predicted GC-MS2-Aminoadipic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00r6-9300000000-9ef33042820e032c1af3Spectrum
Predicted GC-MS2-Aminoadipic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ri-9620000000-052fe671da5a64787657Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03xv-2900000000-58b4f0b3e06cbb7abb90Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4j-9000000000-cc9c0c03f7c3890b531cSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-7b74167f01c922da9ef7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-9400000000-71832a0d1e49341749a7Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-014l-2900000000-08df6df87d0bea6dce31Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0006-0900000000-99e7d8729f7099c6e9eaSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-03di-0900000000-f542aa2756da9aa3ecb6Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-03di-0900000000-3133117467ce925161cbSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-03di-0900000000-9e5f27d91fd799c059d6Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-03xu-0900000000-b801b3a34049e54a2915Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-014i-1900000000-2ef33d8640c4e5788618Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-014i-1900000000-281e4277990becc84832Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-014i-2900000000-a56c711aeb57c767fed8Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0006-0900000000-862ae5fa10820c14bdf1Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-006t-9400000000-e007d0e2c3cec7f1a02cSpectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0002-9000000000-4755db14192225e1eebfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kg-2900000000-3e45ac769d3b229221a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-9600000000-c51318834cc371625d46Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-edbc970f12ea186bcf06Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-0f7002659f604cc69395Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-4900000000-bf42ddc971a2a05516a2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-1979c27463bab7d33d58Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID456
ChEMBL IDCHEMBL433238
KEGG Compound IDC00956
Pubchem Compound ID469
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00510
CRC / DFC (Dictionary of Food Compounds) IDHCF22-R:HCF22-R
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1485280
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialAADATQ8N5Z0
Acyl-CoA synthetase family member 4AASDHQ4L235
L-aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferaseAASDHPPTQ9NRN7
Pathways
NameSMPDB LinkKEGG Link
Lysine DegradationSMP00037 map00310
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference