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Record Information
Version4.0
Creation Date2013-07-04 19:00:37 UTC
Update Date2017-09-27 08:43:55 UTC
HMDB IDHMDB0060805
Secondary Accession Numbers
  • HMDB60805
Metabolite Identification
Common Name9-Carboxymethoxymethylguanine
Description9-Carboxymethoxymethylguanine is a metabolite of aciclovir. Aciclovir or acyclovir, chemical name acycloguanosine, abbreviated as ACV, is a guanosine analogue antiviral drug, marketed under trade names such as Cyclovir, Herpex, Acivir, Acivirax, Zovirax, and Xovir. One of the most commonly used antiviral drugs, it is primarily used for the treatment of herpes simplex virus infections, as well as in the treatment of varicella zoster (chickenpox) and herpes zoster (shingles). (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
9-[(Carboxymethoxy)methyl]-guanineChEMBL
CMMGMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as hypoxanthines. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Aminopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

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
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, Positivesplash10-03di-3900000000-8bfd7054ec6d4595c253View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9254000000-fa30ca38ef25ba85e0ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0950000000-ade2ffbcd940262b4bf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-f519bbb15269bc72c2b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-115i-0900000000-5e6a40251a60e6673140View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0490000000-f7f7bddf2fed308da37bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0930000000-906e1ee8e512fd7ee793View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-52a4890e8072d394880dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
      DrugBank Metabolite IDDBMET00782
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB 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
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available