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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:50:58 UTC
HMDB IDHMDB0000858
Secondary Accession Numbers
  • HMDB00858
Metabolite Identification
Common NameMonomethyl glutaric acid
DescriptionMonomethyl glutaric acid is a metabolitelism of dibasic esters(DBEs) by nasal respiratory and olfactory mucosae in vitro demonstrated that hydrolysis of DBEs yields mainly the monomethyl esters (monomethyl adipate, monomethyl. glutarate, and monomethyl succinate). PMCID: 1568341.
Structure
Thumb
Synonyms
ValueSource
4-(Methoxycarbonyl)butyric acidChEBI
4-Methoxycarbonylbutanoic acidChEBI
Monomethyl glutarateChEBI
4-(Methoxycarbonyl)butyrateGenerator
4-MethoxycarbonylbutanoateGenerator
2-MethyleneglutarateHMDB
4-CarboxybutanoateHMDB
4-Carboxybutanoic acidHMDB
4-Carboxybutanoic acid methyl esterHMDB
5-Methoxy-5-oxopentanoateHMDB
5-Methoxy-5-oxopentanoic acidHMDB
Glutaric acid methyl esterHMDB
Glutaric acid methyl half esterHMDB
Glutaric acid monomethyl esterHMDB
Glutaric acid monomethylesterHMDB
Methyl glutarateHMDB
Methyl glutarate,monoHMDB
Methyl hydrogen glutarateHMDB
mono-Methyl glutarateHMDB
Monomethyl ester OF glutarateHMDB
Monomethyl ester OF glutaric acidHMDB
PentanedioateHMDB
Pentanedioic acidHMDB
Pentanedioic acid monomethyl esterHMDB
Chemical FormulaC6H10O4
Average Molecular Weight146.1412
Monoisotopic Molecular Weight146.057908808
IUPAC Name5-methoxy-5-oxopentanoic acid
Traditional Nameglutaric acid monomethyl ester
CAS Registry Number1501-27-5
SMILES
COC(=O)CCCC(O)=O
InChI Identifier
InChI=1S/C6H10O4/c1-10-6(9)4-2-3-5(7)8/h2-4H2,1H3,(H,7,8)
InChI KeyIBMRTYCHDPMBFN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as fatty acid methyl esters. These are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentFatty acid methyl esters
Alternative Parents
Substituents
  • Fatty acid methyl ester
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Carboxylic acid ester
  • 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:

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 Point150 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility57.6 g/LALOGPS
logP0.19ALOGPS
logP0.19ChemAxon
logS-0.4ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity32.91 m³·mol⁻¹ChemAxon
Polarizability14.31 ųChemAxon
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-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-02t9-9500000000-e5caac5ace69543e05e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9000000000-a3583f0b1b836865929fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9000000000-7367386631dcd87166f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0f6t-0900000000-ef965d7cd6e886deba24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1900000000-a524a85a4054ac2b0efbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fvs-9800000000-7819f1be449b417d63b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9000000000-c1c7555cc2a29713bf98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-802b6c932cf976c61882View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-5900000000-491b5fc13867ce9f0277View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-499af4f9df33e46ff879View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified2.3 (0.6-4.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified5.165 +/- 1.821 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified13.382 +/- 11.399 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 IDFDB022284
KNApSAcK IDNot Available
Chemspider ID66550
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5821
PubChem Compound73917
PDB IDNot Available
ChEBI ID1007322
References
Synthesis ReferenceYajima, Tatsuhiko; Suzuki, Takamasa. Oxidation reaction of liquid dimethyl glutarate exposed to low-temperature oxygen plasma. Journal of Photopolymer Science and Technology (2005), 18(2), 233-236.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hardeman D, Beyer C, Backer ET: Abrupt changes in the concentrations of five prostatic tumor-associated markers in serum after acute myocardial infarction. Clin Chem. 1992 Apr;38(4):605-7. [PubMed:1568341 ]