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Record Information
Version3.6
Creation Date2013-07-09 16:08:02 UTC
Update Date2017-08-18 12:53:36 UTC
HMDB IDHMDB0060932
Secondary Accession Numbers
  • HMDB60932
Metabolite Identification
Common NameN-Desmethyl sildenafil (UK-103,320)
DescriptionN-Desmethyl sildenafil (UK-103 320) is a metabolite of sildenafil. Sildenafil citrate, sold as Viagra, Revatio and under various other trade names, is a drug used to treat erectile dysfunction and pulmonary arterial hypertension (PAH). It was originally developed by British scientists and then brought to market by the US-based pharmaceutical company Pfizer. It acts by inhibiting cGMP-specific phosphodiesterase type 5, an enzyme that promotes degradation of cGMP, which regulates blood flow in the penis. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
Citrate, sildenafilMeSH
Desmethyl sildenafilMeSH
Sildenafil lactateMeSH
1-((3-(6,7-dihydro-1-Methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citrateMeSH
Lactate, sildenafilMeSH
NCX-911MeSH
Nitrate, sildenafilMeSH
RevatioMeSH
ViagraMeSH
AcetildenafilMeSH
Sildenafil citrateMeSH
Sildenafil, desmethylMeSH
HydroxyhomosildenafilMeSH
NCX 911MeSH
HomosildenafilMeSH
SildenafilMeSH
Sildenafil nitrateMeSH
Chemical FormulaC21H28N6O4S
Average Molecular Weight460.55
Monoisotopic Molecular Weight460.189274104
IUPAC Name5-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one
Traditional Name5-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-7-one
CAS Registry NumberNot Available
SMILES
CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC1
InChI Identifier
InChI=1S/C21H28N6O4S/c1-4-6-16-18-19(26(3)25-16)21(28)24-20(23-18)15-13-14(7-8-17(15)31-5-2)32(29,30)27-11-9-22-10-12-27/h7-8,13,22H,4-6,9-12H2,1-3H3,(H,23,24,28)
InChI KeyUZTKBZXHEOVDRL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Pyrazolopyrimidine
  • Benzenesulfonyl group
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Pyrimidone
  • Pyrimidine
  • 1,4-diazinane
  • Organosulfonic acid amide
  • Piperazine
  • Sulfonyl
  • Azole
  • Organosulfonic acid or derivatives
  • Vinylogous amide
  • Pyrazole
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Secondary aliphatic amine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxide
  • Organic nitrogen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • 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 Solubility0.39 mg/mLALOGPS
logP1.78ALOGPS
logP0.93ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.51ChemAxon
pKa (Strongest Basic)6.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.92 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity134.15 m3·mol-1ChemAxon
Polarizability48.96 Å3ChemAxon
Number of Rings4ChemAxon
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 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 IDDBMET00182
      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 LinkHMDB0060932
      METLIN IDNot Available
      PubChem Compound6426858
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available