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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:57:59 UTC
NP-MRD IDNP0000260
Secondary Accession NumbersNone
Natural Product Identification
Common NameOxoadipic acid
Description2-Oxoadipic acid is produced from lysine in the cytosol of cells via the saccharopine and the pipecolic acid pathways. Catabolites of hydroxylysine and tryptophan enter these pathways as 2-aminoadipic- -semialdehyde and 2-oxoadipate, respectively. In the matrix of mitochondria, 2-oxoadipate is decarboxylated to glutaryl-CoA by the 2-oxoadipate dehydrogenase complex and then converted to acetyl-CoA. 2-Oxoadipic aciduria is an in-born error of metabolism of lysine, tryptophan, and hydroxylysine, in which abnormal quantities of 2-aminoadipic acid are found in body fluids along with 2-oxoadipic acid. Patients with 2-Oxoadipic acidemias are mentally retarded with hypotonia or seizures. 2-Oxoadipic aciduria can occur in patients with Kearns-Sayre Syndrome, a progressive disorder with onset prior to 20 years of age in which multiple organ systems are affected, including progressive external ophthalmoplegia, retinopathy, and the age of onset, and these are associated classically with abnormalities in cardiac conduction, cerebellar signs, and elevated cerebrospinal fluid protein (PMID: 10655159 , 16183823 , 11083877 ). Oxoadipic acid is found to be associated with alpha-aminoadipic aciduria, which is an inborn error of metabolism.
Structure
Thumb
Synonyms
ValueSource
2-Ketoadipic acidChEBI
2-oxo-Hexanedioic acidChEBI
alpha-Ketoadipic acidChEBI
alpha-Oxoadipic acidChEBI
2-Oxoadipic acidKegg
2-KetoadipateGenerator
2-oxo-HexanedioateGenerator
a-KetoadipateGenerator
a-Ketoadipic acidGenerator
alpha-KetoadipateGenerator
Α-ketoadipateGenerator
Α-ketoadipic acidGenerator
a-OxoadipateGenerator
a-Oxoadipic acidGenerator
alpha-OxoadipateGenerator
Α-oxoadipateGenerator
Α-oxoadipic acidGenerator
2-OxoadipateGenerator
OxoadipateGenerator
2-Keto-adipateHMDB
2-OxohexanedioateHMDB
2-Oxohexanedioic acidHMDB
2-Oxohexanedionic acidHMDB
Chemical FormulaC6H8O5
Average Mass160.1247 Da
Monoisotopic Mass160.03717 Da
IUPAC Name2-oxohexanedioic acid
Traditional Nameoxoadipate
CAS Registry Number3184-35-8
SMILES
OC(=O)CCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)
InChI KeyFGSBNBBHOZHUBO-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • Plantae
  • Fungo
  • Species Where Detected
    Species NameSourceReference
    Methanococcus voltaeKNApSAcK Database
    Pseudomonas putidaKNApSAcK Database
    Sphingomonas paucimobilisKNApSAcK Database
    Chemical Taxonomy
    Description Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
    KingdomOrganic compounds
    Super ClassOrganic acids and derivatives
    ClassKeto acids and derivatives
    Sub ClassMedium-chain keto acids and derivatives
    Direct ParentMedium-chain keto acids and derivatives
    Alternative ParentsNot Available
    SubstituentsNot Available
    Molecular FrameworkAliphatic acyclic compounds
    External DescriptorsNot Available
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point127 °CNot Available
    Boiling Point364.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
    Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
    LogP-1.220 (est)The Good Scents Company Information System
    Predicted Properties
    PropertyValueSource
    Water Solubility23.4 g/LALOGPS
    logP-0.37ALOGPS
    logP0.34ChemAxon
    logS-0.83ALOGPS
    pKa (Strongest Acidic)2.84ChemAxon
    pKa (Strongest Basic)-9.7ChemAxon
    Physiological Charge-2ChemAxon
    Hydrogen Acceptor Count5ChemAxon
    Hydrogen Donor Count2ChemAxon
    Polar Surface Area91.67 ŲChemAxon
    Rotatable Bond Count5ChemAxon
    Refractivity33.48 m³·mol⁻¹ChemAxon
    Polarizability14.16 ųChemAxon
    Number of Rings0ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    External Links
    HMDB IDHMDB0000225
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB003362
    KNApSAcK IDC00000770
    Chemspider ID70
    KEGG Compound IDC00322
    BioCyc ID2K-ADIPATE
    BiGG ID1485244
    Wikipedia LinkAlpha-Ketoadipic_acid
    METLIN ID5234
    PubChem Compound71
    PDB IDNot Available
    ChEBI ID15753
    Good Scents IDrw1180191
    References
    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. Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
    3. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
    4. Barshop BA, Nyhan WL, Naviaux RK, McGowan KA, Friedlander M, Haas RH: Kearns-Sayre syndrome presenting as 2-oxoadipic aciduria. Mol Genet Metab. 2000 Jan;69(1):64-8. [PubMed:10655159 ]
    5. Schulze-Bergkamen A, Okun JG, Spiekerkotter U, Lindner M, Haas D, Kohlmuller D, Mayatepek E, Schulze-Bergkamen H, Greenberg CR, Zschocke J, Hoffmann GF, Kolker S: Quantitative acylcarnitine profiling in peripheral blood mononuclear cells using in vitro loading with palmitic and 2-oxoadipic acids: biochemical confirmation of fatty acid oxidation and organic acid disorders. Pediatr Res. 2005 Nov;58(5):873-80. Epub 2005 Sep 23. [PubMed:16183823 ]