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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:39 UTC
HMDB IDHMDB00426
Secondary Accession NumbersNone
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-methylsuccinic acidChEBI
2-Methylmalic acidChEBI
alpha-Hydroxypyrotartaric acidChEBI
Citramalic acidsChEBI
(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-Hydroxy-2-methylbutanedioateHMDB
2-Methyl-(b)-malateHMDB
2-Methyl-(b)-malic acidHMDB
2-MethylmalateHMDB
CitramalateHMDB
DL-CitramalateHMDB
DL-Citramalic acidHMDB
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 KeyInChIKey=XFTRTWQBIOMVPK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Branched fatty acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
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
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
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.4 (1.0-4.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
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 LinkHMDB00426
Metagene LinkHMDB00426
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