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Showing metabocard for Aminoadipic acid (BMDB0000510)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:31:53 UTC
Update Date2020-06-04 20:23:43 UTC
MCDB ID BMDB0000510
Secondary Accession Numbers
  • BMDB00510
Metabolite Identification
Common NameAminoadipic acid
DescriptionAminoadipic acid, also known as aminoadipic acid or Aminoadipic acid, 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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Aminoadipic acid exists in all eukaryotes, ranging from yeast to humans. Aminoadipic acid participates in a number of enzymatic reactions, within cattle. In particular, Aminoadipic acid can be biosynthesized from allysine through the action of the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In addition, Aminoadipic acid and oxoglutaric acid can be converted into oxoadipic acid and L-glutamic acid through its interaction with the enzyme kynurenine/alphaminoadipic acid aminotransferase, mitochondrial. In cattle, aminoadipic acid is involved in the metabolic pathway called the lysine degradation pathway. Aminoadipic acid is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point196 - 198 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.2 mg/mLNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02di-0950000000-ec4fd991a53a8b6bc6ae2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02di-0950000000-ec4fd991a53a8b6bc6ae2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r6-9300000000-9ef33042820e032c1af32017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ri-9620000000-052fe671da5a647876572017-10-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03xv-2900000000-58b4f0b3e06cbb7abb902012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4j-9000000000-cc9c0c03f7c3890b531c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-7b74167f01c922da9ef72012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-9400000000-71832a0d1e49341749a72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-014l-2900000000-08df6df87d0bea6dce312020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0006-0900000000-99e7d8729f7099c6e9ea2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-03di-0900000000-f542aa2756da9aa3ecb62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-03di-0900000000-3133117467ce925161cb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-03di-0900000000-9e5f27d91fd799c059d62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-03xu-0900000000-b801b3a34049e54a29152020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-014i-1900000000-2ef33d8640c4e57886182020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-014i-1900000000-281e4277990becc848322020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-014i-2900000000-a56c711aeb57c767fed82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0006-0900000000-862ae5fa10820c14bdf12020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-006t-9400000000-e007d0e2c3cec7f1a02c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0002-9000000000-4755db14192225e1eebf2020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kg-2900000000-3e45ac769d3b229221a32015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-9600000000-c51318834cc371625d462015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-edbc970f12ea186bcf062015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-0f7002659f604cc693952015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-4900000000-bf42ddc971a2a05516a22015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-1979c27463bab7d33d582015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-7913a597d0c94eebe02d2021-10-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-9100000000-523aa25ee55f888299e12021-10-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-0dcf3a7ca5d4e20885ee2021-10-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected and Quantified195 - 427 uM details
Detected and Quantified4.3 +/- 0.1 uM details
Detected and Quantified6.1 +/- 0.1 uM details
Detected and Quantified5.4 +/- 0.1 uM details
Detected and Quantified5.0 +/- 0.1 uM details
HMDB IDHMDB0302754
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007648
KNApSAcK IDC00007393
Chemspider ID456
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlpha-Aminoadipic_acid
METLIN IDNot Available
PubChem Compound469
PDB IDNot Available
ChEBI ID37024
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. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  3. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  4. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  5. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.