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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-21 17:47:02 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
Synonyms
ValueSource
(+-)-2-Hydroxy-2-methylsuccinic acidChEBI
2-Hydroxy-2-methylbutanedioic acidChEBI
2-Hydroxy-2-methylsuccinic acidChEBI
2-Methylmalic acidChEBI
alpha-Hydroxypyrotartaric acidChEBI
Citramalic acidsChEBI
(+-)-2-Hydroxy-2-methylsuccinateGenerator
CitramalateGenerator
2-Hydroxy-2-methylbutanedioateGenerator
2-Hydroxy-2-methylsuccinateGenerator
2-MethylmalateGenerator
a-HydroxypyrotartarateGenerator
a-Hydroxypyrotartaric acidGenerator
alpha-HydroxypyrotartarateGenerator
α-hydroxypyrotartarateGenerator
α-hydroxypyrotartaric acidGenerator
(b)-2-MethylmalateHMDB
(b)-2-Methylmalic acidHMDB
(b)-CitramalateHMDB
(b)-Citramalic acidHMDB
(R,S)-(b)-CitramalateHMDB
(R,S)-(b)-Citramalic acidHMDB
(R,S)-b-MethylmalateHMDB
(R,S)-b-Methylmalic acidHMDB
(R,S)-beta-MethylmalateHMDB
(R,S)-beta-Methylmalic acidHMDB
2-Deoxy-3-C-methyltetrarateHMDB
2-Deoxy-3-C-methyltetraric acidHMDB
2-Hydroxy-2-methyl-(b)-butanedioateHMDB
2-Hydroxy-2-methyl-(b)-butanedioic acidHMDB
2-Hydroxy-2-methyl-butanedioateHMDB
2-Hydroxy-2-methyl-butanedioic acidHMDB
2-Methyl-(b)-malateHMDB
2-Methyl-(b)-malic acidHMDB
DL-CitramalateHMDB
DL-Citramalic acidHMDB
Citramalate, (+-)-isomerMeSH
Citramalate, (R)-isomerMeSH
Citramalate, (S)-isomerMeSH
alpha-MethylmalateMeSH
Chemical FormulaC5H8O5
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
IUPAC Name2-hydroxy-2-methylbutanedioic acid
Traditional Namecitramalate, (+-)-
CAS Registry Number597-44-4
SMILES
CC(O)(CC(O)=O)C(O)=O
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
DescriptionThis compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107 - 111 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility297.0 mg/mLALOGPS
logP-0.91ALOGPS
logP-0.68ChemAxon
logS0.3ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.59 m3·mol-1ChemAxon
Polarizability12.69 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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
    NuGOwiki LinkHMDB0000426
    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 ReferencesNot Available