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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:34 UTC
HMDB IDHMDB0000379
Secondary Accession Numbers
  • HMDB0003610
  • HMDB00379
  • HMDB03610
Metabolite Identification
Common Name2-Methylcitric acid
Description2-Methylcitric acid, also known as 2-methylcitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-Methylcitric acid exists in all living organisms, ranging from bacteria to humans. 2-Methylcitric acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make 2-methylcitric acid a potential biomarker for the consumption of these foods. 2-Methylcitric acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2-Methylcitric acid, with regard to humans, has been found to be associated with the diseases such as crohn's disease; 2-methylcitric acid has also been linked to several inborn metabolic disorders including propionic acidemia, isovaleric acidemia, vitamin B12 deficiency, and biotinidase deficiency. Based on a literature review a significant number of articles have been published on 2-Methylcitric acid.
Structure
Data?1582752127
Synonyms
ValueSource
2-Hydroxy-1,2,3-butanetricarboxylic acidChEBI
2-Hydroxy-1,2,3-butanetricarboxylateGenerator
2-MethylcitrateGenerator
(2S,3S)-2-MethylcitrateHMDB
2-Hydroxybutane-1,2,3-tricarboxylateHMDB
2-Hydroxybutane-1,2,3-tricarboxylic acidHMDB
2-Methylcitric acid, 3H-labeledHMDB
3-Carboxy-3-hydroxy-2-methylpentanedioic acidHMDB
Methylcitric acidHMDB
Chemical FormulaC7H10O7
Average Molecular Weight206.1501
Monoisotopic Molecular Weight206.042652674
IUPAC Name2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid
Traditional Namemethylcitric acid
CAS Registry Number6061-96-7
SMILES
CC(C(O)=O)C(O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)
InChI KeyYNOXCRMFGMSKIJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility175 g/LALOGPS
logP-0.89ALOGPS
logP-0.78ChemAxon
logS-0.07ALOGPS
pKa (Strongest Acidic)3.18ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.2 m³·mol⁻¹ChemAxon
Polarizability17.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.40731661259
DarkChem[M-H]-139.72531661259
AllCCS[M+H]+144.3732859911
AllCCS[M-H]-137.90632859911
DeepCCS[M+H]+133.63430932474
DeepCCS[M-H]-130.62930932474
DeepCCS[M-2H]-167.14930932474
DeepCCS[M+Na]+142.68730932474
AllCCS[M+H]+144.432859911
AllCCS[M+H-H2O]+140.732859911
AllCCS[M+NH4]+147.732859911
AllCCS[M+Na]+148.732859911
AllCCS[M-H]-137.932859911
AllCCS[M+Na-2H]-138.932859911
AllCCS[M+HCOO]-140.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methylcitric acidCC(C(O)=O)C(O)(CC(O)=O)C(O)=O2881.4Standard polar33892256
2-Methylcitric acidCC(C(O)=O)C(O)(CC(O)=O)C(O)=O1239.5Standard non polar33892256
2-Methylcitric acidCC(C(O)=O)C(O)(CC(O)=O)C(O)=O1733.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methylcitric acid,1TMS,isomer #1CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O1738.0Semi standard non polar33892256
2-Methylcitric acid,1TMS,isomer #2CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O1768.2Semi standard non polar33892256
2-Methylcitric acid,1TMS,isomer #3CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O1741.3Semi standard non polar33892256
2-Methylcitric acid,1TMS,isomer #4CC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C1707.6Semi standard non polar33892256
2-Methylcitric acid,2TMS,isomer #1CC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O1787.3Semi standard non polar33892256
2-Methylcitric acid,2TMS,isomer #2CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O1773.3Semi standard non polar33892256
2-Methylcitric acid,2TMS,isomer #3CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C1749.9Semi standard non polar33892256
2-Methylcitric acid,2TMS,isomer #4CC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O1789.1Semi standard non polar33892256
2-Methylcitric acid,2TMS,isomer #5CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1776.1Semi standard non polar33892256
2-Methylcitric acid,2TMS,isomer #6CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1743.7Semi standard non polar33892256
2-Methylcitric acid,3TMS,isomer #1CC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O1797.7Semi standard non polar33892256
2-Methylcitric acid,3TMS,isomer #2CC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1815.1Semi standard non polar33892256
2-Methylcitric acid,3TMS,isomer #3CC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1796.4Semi standard non polar33892256
2-Methylcitric acid,3TMS,isomer #4CC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1809.1Semi standard non polar33892256
2-Methylcitric acid,4TMS,isomer #1CC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1884.7Semi standard non polar33892256
2-Methylcitric acid,1TBDMS,isomer #1CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O)C(=O)O1979.3Semi standard non polar33892256
2-Methylcitric acid,1TBDMS,isomer #2CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O1987.8Semi standard non polar33892256
2-Methylcitric acid,1TBDMS,isomer #3CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1994.3Semi standard non polar33892256
2-Methylcitric acid,1TBDMS,isomer #4CC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1977.2Semi standard non polar33892256
2-Methylcitric acid,2TBDMS,isomer #1CC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O2210.2Semi standard non polar33892256
2-Methylcitric acid,2TBDMS,isomer #2CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2227.3Semi standard non polar33892256
2-Methylcitric acid,2TBDMS,isomer #3CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2227.9Semi standard non polar33892256
2-Methylcitric acid,2TBDMS,isomer #4CC(C(=O)O)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O2214.4Semi standard non polar33892256
2-Methylcitric acid,2TBDMS,isomer #5CC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2211.9Semi standard non polar33892256
2-Methylcitric acid,2TBDMS,isomer #6CC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2236.0Semi standard non polar33892256
2-Methylcitric acid,3TBDMS,isomer #1CC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O2464.1Semi standard non polar33892256
2-Methylcitric acid,3TBDMS,isomer #2CC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2454.5Semi standard non polar33892256
2-Methylcitric acid,3TBDMS,isomer #3CC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2437.2Semi standard non polar33892256
2-Methylcitric acid,3TBDMS,isomer #4CC(C(=O)O)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2455.0Semi standard non polar33892256
2-Methylcitric acid,4TBDMS,isomer #1CC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2665.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0hhi-3900000000-c705fb286a4c575f98522017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (4 TMS) - 70eV, Positivesplash10-00b9-8029800000-dc9ef9d5a5a220f1ae9f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylcitric acid GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 10V, Positive-QTOFsplash10-000i-0900000000-be0da5c29220e9e503252015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 20V, Positive-QTOFsplash10-05i0-9600000000-2bead66ba2514df6497f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 40V, Positive-QTOFsplash10-1093-7900000000-e7a5530b8562d859e0322015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 10V, Negative-QTOFsplash10-0900-1910000000-0a84eb8e0df2e6eb450d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 20V, Negative-QTOFsplash10-07vi-4900000000-e89ea7de4d7e433cae1e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 40V, Negative-QTOFsplash10-0a4i-9300000000-c68ffdf8bf6f5380005e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 10V, Positive-QTOFsplash10-0ab9-9720000000-dfe31f5432e1eccb8ed32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 20V, Positive-QTOFsplash10-0a4i-9100000000-1cfd78c68dd469eef7442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 40V, Positive-QTOFsplash10-0a4i-9000000000-21ac8232326ad1ff9cb42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 10V, Negative-QTOFsplash10-0cdu-0920000000-84f91e237b14a40e1dd32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 20V, Negative-QTOFsplash10-014i-1900000000-6f38bc0fc7fc8a8246002021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylcitric acid 40V, Negative-QTOFsplash10-00ku-9400000000-2c55ccaee8c29d5510a82021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.1 (0.08-0.26) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.059 (0.021-0.097) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.323-1.07 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.50 (0.24-0.80) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.4-2.9 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified<15 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified6.7 (0.7-19.6) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified7.7 (3.3-28.6) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified3.4 (1.4-8.5) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified3.2 (2.0-8.1) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified2.6 (1.6-6.2) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified1.2-1.8 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified<6.09 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0.59 (0.05-1.15) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified1.37-16.3 uMNot SpecifiedNot Specifiedcobalamin deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIron deficiency details
UrineDetected and Quantified31 umol/mmol creatinineAdult (>18 years old)Not Specified
Propionic acidemia
details
UrineDetected and Quantified0.780-3.600 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
isovaleric acidemia
details
UrineDetected and Quantified1.470-1.560 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
isovaleric acidemia
details
UrineDetected and Quantified7.0 (2.0-12.0) umol/mmol creatinineAdult (>18 years old)BothBiotinidase deficiency
    • MetaGene: Metabol...
details
UrineDetected and Quantified30.0 (10.0-50.0) umol/mmol creatinineChildren (1-13 years old)BothBiotinidase deficiency
    • MetaGene: Metabol...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Vitamin B12 deficiency
  1. Allen RH, Stabler SP, Savage DG, Lindenbaum J: Elevation of 2-methylcitric acid I and II levels in serum, urine, and cerebrospinal fluid of patients with cobalamin deficiency. Metabolism. 1993 Aug;42(8):978-88. [PubMed:8345822 ]
Crohn's disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Iron deficiency
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Biotinidase deficiency
  1. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Propionic acidemia
  1. Riemersma M, Hazebroek MR, Helderman-van den Enden ATJM, Salomons GS, Ferdinandusse S, Brouwers MCGJ, van der Ploeg L, Heymans S, Glatz JFC, van den Wijngaard A, Krapels IPC, Bierau J, Brunner HG: Propionic acidemia as a cause of adult-onset dilated cardiomyopathy. Eur J Hum Genet. 2017 Nov;25(11):1195-1201. doi: 10.1038/ejhg.2017.127. Epub 2017 Aug 30. [PubMed:28853722 ]
Isovaleric acidemia
  1. Loots DT: Abnormal tricarboxylic acid cycle metabolites in isovaleric acidaemia. J Inherit Metab Dis. 2009 Jun;32(3):403-11. doi: 10.1007/s10545-009-1071-6. Epub 2009 Apr 5. [PubMed:19343532 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021997
KNApSAcK IDNot Available
Chemspider ID500
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID39369
Wikipedia LinkNot Available
METLIN ID5368
PubChem Compound515
PDB IDNot Available
ChEBI ID30835
Food Biomarker OntologyNot Available
VMH ID2MCIT
MarkerDB IDMDB00000155
Good Scents IDNot Available
References
Synthesis ReferenceEwering, Christian; Braemer, Christian Oliver; Steinbuechel, Alexander. Production of 2-methylcitric acid by a recombinant Ralstonia eutropha strain. PCT Int. Appl. (2007), 30pp. CODEN: PIXXD2 WO 2007101866 A2 20070913 CAN 147:363646 AN 2007:1033111
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. Allen RH, Stabler SP, Savage DG, Lindenbaum J: Elevation of 2-methylcitric acid I and II levels in serum, urine, and cerebrospinal fluid of patients with cobalamin deficiency. Metabolism. 1993 Aug;42(8):978-88. [PubMed:8345822 ]
  3. Busch M, Stein G, Poppitz W, Hein G, Muller A: Validated capillary gas chromatographic-mass spectrometric assay to determine 2-methylcitric acid I and II levels in human serum by using a pulsed splitless injection procedure. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Aug 5;775(2):215-23. [PubMed:12113988 ]
  4. Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. [PubMed:7313494 ]
  5. Thompson GN, Chalmers RA: Increased urinary metabolite excretion during fasting in disorders of propionate metabolism. Pediatr Res. 1990 Apr;27(4 Pt 1):413-6. [PubMed:2342832 ]
  6. Krawczyk H, Gradowska W: 1H NMR spectra of methylcitric acid in urine. J Inherit Metab Dis. 2007 Apr;30(2):263. Epub 2007 Feb 14. [PubMed:17295121 ]
  7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]