Hmdb loader
Survey
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
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:08:02 UTC
Update Date2019-07-23 07:15:24 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
Data?1563866124
Synonyms
ValueSource
Citrate, sildenafilHMDB
Desmethyl sildenafilHMDB
Sildenafil lactateHMDB
1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citrateHMDB
Lactate, sildenafilHMDB
NCX-911HMDB
Nitrate, sildenafilHMDB
RevatioHMDB
ViagraHMDB
AcetildenafilHMDB
Sildenafil citrateHMDB
Sildenafil, desmethylHMDB
HydroxyhomosildenafilHMDB
NCX 911HMDB
HomosildenafilHMDB
SildenafilHMDB
Sildenafil nitrateHMDB
5-[2-Ethoxy-5-(piperazine-1-sulphonyl)phenyl]-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-D]pyrimidin-7-oneGenerator
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
Description Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.39 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity134.15 m³·mol⁻¹ChemAxon
Polarizability48.96 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+205.06531661259
DarkChem[M-H]-202.63231661259
DeepCCS[M+H]+205.79230932474
DeepCCS[M-H]-203.39630932474
DeepCCS[M-2H]-236.49730932474
DeepCCS[M+Na]+211.79430932474
AllCCS[M+H]+205.932859911
AllCCS[M+H-H2O]+203.832859911
AllCCS[M+NH4]+207.932859911
AllCCS[M+Na]+208.532859911
AllCCS[M-H]-201.332859911
AllCCS[M+Na-2H]-202.132859911
AllCCS[M+HCOO]-203.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Desmethyl sildenafil (UK-103,320)CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC14911.4Standard polar33892256
N-Desmethyl sildenafil (UK-103,320)CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC13798.9Standard non polar33892256
N-Desmethyl sildenafil (UK-103,320)CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC14209.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O3810.6Semi standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O3842.0Standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O5788.9Standard polar33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #2CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O4007.4Semi standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #2CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O3940.5Standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #2CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O5666.6Standard polar33892256
N-Desmethyl sildenafil (UK-103,320),2TMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O3994.3Semi standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),2TMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O4063.9Standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),2TMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O5282.9Standard polar33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O3930.5Semi standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O4112.9Standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O5655.7Standard polar33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #2CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O4178.3Semi standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #2CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O4178.3Standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #2CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O5709.4Standard polar33892256
N-Desmethyl sildenafil (UK-103,320),2TBDMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O4276.6Semi standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),2TBDMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O4550.5Standard non polar33892256
N-Desmethyl sildenafil (UK-103,320),2TBDMS,isomer #1CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O5266.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl sildenafil (UK-103,320) GC-MS (Non-derivatized) - 70eV, Positivesplash10-06su-9003200000-8c16e5a5f7c9fd1beeec2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl sildenafil (UK-103,320) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl sildenafil (UK-103,320) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 10V, Positive-QTOFsplash10-03di-0002900000-f0e3e78187afd93a48412017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 20V, Positive-QTOFsplash10-03dr-3235900000-dd447bbc8e39fc99d1232017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 40V, Positive-QTOFsplash10-014u-5092100000-0b6e7602ec4d55ff9d632017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 10V, Negative-QTOFsplash10-0a4i-0000900000-f84c25238b265817528b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 20V, Negative-QTOFsplash10-053s-0303900000-1fb03e95cc836e9368b42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 40V, Negative-QTOFsplash10-0002-9716200000-b08598b77f5c8dcf3abf2017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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 LinkNot Available
METLIN IDNot Available
PubChem Compound6426858
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available