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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 IDHMDB00422
Secondary Accession NumbersNone
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-MethylpentanedioateGenerator
(+-)-2-Methylglutaric acidHMDB
2-MethylglutarateHMDB
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 KeyInChIKey=AQYCMVICBNBXNA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.71 m3·mol-1ChemAxon
Polarizability13.96 Å3ChemAxon
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)splash10-0002-0920000000-058119efdad0e6068deaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00ai-3940000000-8782dc79a05f39a17f8dView 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
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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
NuGOwiki LinkHMDB00422
Metagene LinkHMDB00422
METLIN ID5411
PubChem Compound12046
PDB IDNot Available
ChEBI IDNot Available
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. [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. [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. [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. [1688138 ]