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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:25:21 UTC
HMDB IDHMDB0000426
Secondary Accession Numbers
  • HMDB00426
Metabolite Identification
Common NameCitramalic acid
DescriptionCitramalic acid is an analog of malic acid. The structure is citramalic acid is similar to the structure of malic acid except it has an extra CH3 group on it. It can inhibit the production of malic acid.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC5H8O5
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number597-44-4
SMILESNot Available
InChI Identifier
InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)
InChI KeyXFTRTWQBIOMVPK-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107 - 111 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9200000000-d88cf81bb63b8badd74dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00gs-8492000000-d1c8fb9235f1de536d15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000j-7900000000-efbe2adf2c82decc64a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-052u-9000000000-3754186783f820cbff7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052o-9000000000-0656e8e194378442727fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-2900000000-be1cc6b0ea685f5d7ac2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-002r-8900000000-7dd192ed79cd2d306ea5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9500000000-c96a62314140c10f1245View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001a-5900000000-437d36fe16a8d6f79c68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9200000000-6aed3a8e654948bbd5e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-31c6a41b79f5b68fa431View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uds-4900000000-0d782e5134753ac75aebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-9800000000-79154974b5c30f915ea5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-16648250719da0016f96View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Infant (0-1 year old)Both
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified2.5-4.5 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified2.4 (1.0-4.8) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified2.5-3.4 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified3.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified14.0 (5.5-24.6) umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal details
    UrineDetected and Quantified11.8 (5.5-21.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
    UrineDetected and Quantified5.5 (4.2-8.9) umol/mmol creatinineChildren (1-13 years old)BothNormal details
    UrineDetected and Quantified4.7 (1.3-11.2) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB001372
    KNApSAcK IDNot Available
    Chemspider ID1051
    KEGG Compound IDC00815
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5415
    PubChem Compound1081
    PDB IDNot Available
    ChEBI ID15584
    References
    Synthesis ReferenceBarker, H. A. Chemical synthesis and resolution of (±)-citramalic acid. Biochemical Preparations (1962), 9 25-9.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. HULME AC: The oxidation of citramalic acid and beta-hydroxyglutaric acid to acetoacetic acid and the possible significance of citramalic acid in plant metabolism. Biochim Biophys Acta. 1954 May;14(1):44-51. [PubMed:13160012 ]
    2. Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666 ]
    3. Perlman S, Carr SA: Citramalic acid in cerebrospinal fluid of patients with bacterial meningitis. Clin Chem. 1984 Jul;30(7):1209-12. [PubMed:6145530 ]
    4. Greter J, Lindstedt S, Seeman H, Steen G: 2-hydroxy-2-methylsuccinic acid--a urinary metabolite in propionyl-CoA carboxylase deficiency. Clin Chim Acta. 1980 Sep 8;106(1):103-6. [PubMed:7408203 ]