You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2013-07-04 19:00:37 UTC
Update Date2016-02-11 08:13:12 UTC
HMDB IDHMDB60805
Secondary Accession NumbersNone
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
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 KeyInChIKey=MICNQLKUSOVNNG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Hydroxypyrimidine
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.44 m3·mol-1ChemAxon
Polarizability21.49 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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 LinkNot Available
NuGOwiki LinkHMDB60805
Metagene LinkHMDB60805
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