You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:16:51 UTC
HMDB IDHMDB0000422
Secondary Accession Numbers
  • HMDB00422
Metabolite Identification
Common Name2-Methylglutaric acid
Description2-Methylglutaric acid is an organic acid normally found in human urine, in healthy adults and children. 2-Methylglutaric acid is a metabolite of succinic acid, a citric acid cycle intermediate. (PMID: 2925825 , 8087979 , 16379391 , 1688138 ).
Structure
Thumb
Synonyms
ValueSource
alpha-Methylglutaric acidChEBI
a-MethylglutarateGenerator
a-Methylglutaric acidGenerator
alpha-MethylglutarateGenerator
α-methylglutarateGenerator
α-methylglutaric acidGenerator
2-MethylglutarateGenerator
(+-)-2-Methylglutaric acidHMDB
2-MethylpentanedioateHMDB
2-Methylpentanedioic acidHMDB
2-Methyleneglutaric acidMeSH
2-MethyleneglutarateMeSH
alpha-Methylene glutarateMeSH
alpha-Methylene glutarate, ion(2-)MeSH
2-Methylene glutarateMeSH
Chemical FormulaC6H10O4
Average Molecular Weight146.1412
Monoisotopic Molecular Weight146.057908808
IUPAC Name2-methylpentanedioic acid
Traditional Nameα-methylglutaric acid
CAS Registry Number617-62-9
SMILES
CC(CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)
InChI KeyAQYCMVICBNBXNA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility908 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility40.6 g/LALOGPS
logP0.33ALOGPS
logP0.59ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.71 m³·mol⁻¹ChemAxon
Polarizability13.96 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0920000000-058119efdad0e6068deaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00ai-3940000000-8782dc79a05f39a17f8dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-058119efdad0e6068deaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ai-3940000000-8782dc79a05f39a17f8dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-0bd8441fd4009432274cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufu-9400000000-1e9201c037b72e9c87edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9330000000-52eec5e35a4ce98c0c8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0lds-2900000000-123aaa34af2e8d52e51dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0040-9200000000-faea3a69ade74a66ca8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udj-0900000000-fa03e7ba7f633b68fc46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udj-0900000000-fa03e7ba7f633b68fc46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-2900000000-53f4bf9bd33ce331bf8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi9-9700000000-138f9359c8b2e1649fe9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8b29b71e8ebeb8a47d58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-a2cb03ab6a83bf49c1c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfs-5900000000-9cad4067f18ca4925fe1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-319d179b79e3ded5f35cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.1 (0.1-0.1) umol/mmol creatinineAdolescent (13-18 years old)Both
    Normal
    details
    UrineDetected and Quantified3.409 +/- 5.482 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified0.1 (0.1-0.1) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
    UrineDetected and Quantified0.1 (0.1-2.6) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified0.1 (0.1-1.0) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified0.8 (0.3-1.7) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified3.282 +/- 1.466 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    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 IDFDB022036
    KNApSAcK IDNot Available
    Chemspider ID11549
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5411
    PubChem Compound12046
    PDB IDNot Available
    ChEBI ID68567
    References
    Synthesis ReferenceIgnaczak, M.; Deka, M. Synthesis of 2-methylglutaric acid by oxidation of 3-methyl-1,2-cyclopentanedione by anode-generated Ce(IV). Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya (1994), 37(7-9), 63-6.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. 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 ]
    2. Isidorov VA, Kotowska U, Vinogorova VT: GC identification of organic compounds based on partition coefficients of their TMS derivatives in a hexane-acetonitrile system and retention indices. Anal Sci. 2005 Dec;21(12):1483-9. [PubMed:16379391 ]
    3. Lefevere MF, Verhaeghe BJ, Declerck DH, Van Bocxlaer JF, De Leenheer AP, De Sagher RM: Metabolic profiling of urinary organic acids by single and multicolumn capillary gas chromatography. J Chromatogr Sci. 1989 Jan;27(1):23-9. [PubMed:2925825 ]
    4. Waddell TG, Miller TJ: Chemical evolution of the citric acid cycle: sunlight photolysis of the amino acids glutamate and aspartate. Orig Life Evol Biosph. 1991-1992;21(4):219-23. [PubMed:1688138 ]