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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2018-05-20 20:49:29 UTC
HMDB IDHMDB0014444
Secondary Accession Numbers
  • HMDB14444
Metabolite Identification
Common NamePenciclovir
DescriptionPenciclovir is only found in individuals that have used or taken this drug. It is a guanine analogue antiviral drug used for the treatment of various herpesvirus infections. It is a nucleoside analogue which exhibits low toxicity and good selectivity. [Wikipedia]Penciclovir has in vitro activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). In cells infected with HSV-1 or HSV-2, viral thymidine kinase phosphorylates penciclovir to a monophosphate form. The monophosphate form of the drug is then converted to penciclovir triphosphate by cellular kinases. The intracellular triphosphate of penciclovir is retained in vitro inside HSV-infected cells for 10-20 hours, compared with 0.7-1 hour for acyclovir. in vitro studies show that penciclovir triphosphate selectively inhibits viral DNA polymerase by competing with deoxyguanosine triphosphate. Inhibition of DNA synthesis of virus-infected cells inhibits viral replication. In cells not infected with HSV, DNA synthesis is unaltered. Resistant mutants of HSV can occur from qualitative changes in viral thymidine kinase or DNA polymerase. The most commonly encountered acyclovir-resistant mutants that are deficient in viral thymidine kinase are also resistant to penciclovir.
Structure
Thumb
Synonyms
ValueSource
9-(4-Hydroxy-3-(hydroxymethyl)butyl)guanineChEBI
9-(4-Hydroxy-3-hydroxymethylbut-1-yl)-guanineChEBI
9-[2-Hydroxy-1-(hydroxymethyl)-ethoxymethyl]guanineChEBI
9-[4-Hydroxy-3-(hydroxymethyl)but-1-yl]guanineChEBI
PCVChEBI
PE2ChEBI
PenciclovirumChEBI
Novartis brand OF penciclovirMeSH
Penciclovir visfarmMeSH
SB-CH Brand OF penciclovirMeSH
9-(4-Hydroxy-3-hydroxymethylbut-1-yl)guanineMeSH
DenavirMeSH
VectavirMeSH
Visfarm brand OF penciclovirMeSH
Penciclovir, monosodium saltMeSH
Penciclovir, monosodium salt, monohydrateMeSH
Chemical FormulaC10H15N5O3
Average Molecular Weight253.2578
Monoisotopic Molecular Weight253.117489371
IUPAC Name2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6,9-dihydro-3H-purin-6-one
Traditional Namedenavir
CAS Registry Number39809-25-1
SMILES
NC1=NC(=O)C2=C(N1)N(CCC(CO)CO)C=N2
InChI Identifier
InChI=1S/C10H15N5O3/c11-10-13-8-7(9(18)14-10)12-5-15(8)2-1-6(3-16)4-17/h5-6,16-17H,1-4H2,(H3,11,13,14,18)
InChI KeyJNTOCHDNEULJHD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Aminopyrimidine
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point275 - 277 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.45 g/LNot Available
LogP-1.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.45 g/LALOGPS
logP-0.86ALOGPS
logP-1.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)2.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.59 m³·mol⁻¹ChemAxon
Polarizability25.11 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, Positivesplash10-024r-4890000000-ed3881f9b07a40fef086View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-4039000000-39d85efcb22394abeb78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0190000000-ed1701b795cb216e6d66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0790000000-212e25de28163f343cacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0910000000-3a8ca3a0b3701c27b51dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0kai-0900000000-36122e670b73f1113fffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-053r-1900000000-bceccffce9861527c0c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0api-3900000000-2322dab886ffdf508841View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0490000000-0e41d127a3f6d343b9d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0920000000-8e58b381a6b3d470746bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0900000000-d498bce256e98e4cf88cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0900000000-ae0beed2651e1125764fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0900000000-19ad8b8788d0275996b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udr-1900000000-5c4ec47a69c82954d428View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f79-0390000000-2bec5fbdf1e72aa84bdeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uei-1940000000-6e49677068b47b74940fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-3900000000-cc1f9ce4e3ed563ded5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0zfr-8900000000-326741cdbb592bb9d271View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f8c-7900000000-295551b253f3f85729c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0900000000-44a1abcea55a53906b2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0090000000-b771df12ed0fcbbee1caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-1980000000-be68269fbcfeb1eda4f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-4900000000-54f7176cadc1b67a66dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-b42cd4e9561cb4baa03aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0960000000-012e01c533768b510f86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-8dda187de53e2d7eb1fbView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00299 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00299 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00299
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4563
KEGG Compound IDC07417
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPenciclovir
METLIN IDNot Available
PubChem Compound4725
PDB IDPE2
ChEBI ID7956
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available