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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:00:37 UTC
Update Date2019-07-23 07:15:07 UTC
HMDB IDHMDB0060805
Secondary Accession Numbers
  • HMDB60805
Metabolite Identification
Common Name9-Carboxymethoxymethylguanine
Description9-Carboxymethoxymethylguanine, also known as CMMG, belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 9-Carboxymethoxymethylguanine (CMMG) is a compound which is known as the principal metabolite of the antiviral drug acyclovir (and its prodrug valacyclovir), and has been suggested as the causative agent in the neuropsychiatric side effects sometimes associated with these drugs. 9-Carboxymethoxymethylguanine is a strong basic compound (based on its pKa). These are mainly suffered by patients with renal failure or otherwise decreased kidney function, and can include psychotic reactions, hallucinations, and rarely more complex disorders such as Cotard delusion. Patients suffering these symptoms following acyclovir treatment were found to have much higher levels of CMMG than normal, and since this is the first time Cotard delusion has been linked to a drug as a side effect, this discovery may be useful in the study of Cotard delusion and its treatment.
Structure
Data?1563866107
Synonyms
ValueSource
9-[(Carboxymethoxy)methyl]-guanineHMDB
CMMGHMDB
Chemical FormulaC8H9N5O4
Average Molecular Weight239.1882
Monoisotopic Molecular Weight239.065453801
IUPAC Name2-[(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)methoxy]acetic acid
Traditional Name[(6-hydroxy-2-imino-3H-purin-9-yl)methoxy]acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)COCN1C=NC2=C1NC(=N)N=C2O
InChI Identifier
InChI=1S/C8H9N5O4/c9-8-11-6-5(7(16)12-8)10-2-13(6)3-17-1-4(14)15/h2H,1,3H2,(H,14,15)(H3,9,11,12,16)
InChI KeyMICNQLKUSOVNNG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Aminopyrimidine
  • Pyrimidone
  • Pyrimidine
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Azacycle
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.97 g/LALOGPS
logP-1.2ALOGPS
logP-2.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.1ChemAxon
pKa (Strongest Basic)4.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.44 m³·mol⁻¹ChemAxon
Polarizability21.49 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3900000000-8bfd7054ec6d4595c253Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9254000000-fa30ca38ef25ba85e0ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0950000000-ade2ffbcd940262b4bf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-f519bbb15269bc72c2b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-115i-0900000000-5e6a40251a60e6673140Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0490000000-f7f7bddf2fed308da37bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0930000000-906e1ee8e512fd7ee793Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-52a4890e8072d394880dSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FooDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia Link9-Carboxymethoxymethylguanine
      METLIN IDNot Available
      PubChem Compound133521
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available