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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:02 UTC
HMDB IDHMDB0015599
Secondary Accession Numbers
  • HMDB15599
Metabolite Identification
Common NameEnoximone
DescriptionEnoximone, also known as perfan, belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. Enoximone is a drug which is used for the treatment of congestive heart failure. Based on a literature review a significant number of articles have been published on Enoximone.
Structure
Data?1582753315
Synonyms
ValueSource
PerfanKegg
Aventis brand OF enoximoneHMDB
Enoximone aventis brandHMDB
FenoximoneHMDB
Enoximone myogen brandHMDB
Myogen brand OF enoximoneHMDB
Carinopharm brand OF enoximoneHMDB
Enoximone carinopharm brandHMDB
Chemical FormulaC12H12N2O2S
Average Molecular Weight248.301
Monoisotopic Molecular Weight248.061948328
IUPAC Name4-methyl-5-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1H-imidazol-2-one
Traditional Nameenoximone
CAS Registry Number77671-31-9
SMILES
CSC1=CC=C(C=C1)C(=O)C1=C(C)NC(=O)N1
InChI Identifier
InChI=1S/C12H12N2O2S/c1-7-10(14-12(16)13-7)11(15)8-3-5-9(17-2)6-4-8/h3-6H,1-2H3,(H2,13,14,16)
InChI KeyZJKNESGOIKRXQY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • Aryl thioether
  • Benzoyl
  • Thiophenol ether
  • Imidazole-4-carbonyl group
  • Alkylarylthioether
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Vinylogous amide
  • Urea
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Thioether
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point256 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.068 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP1.97ALOGPS
logP1.84ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity70.04 m³·mol⁻¹ChemAxon
Polarizability25.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.55131661259
DarkChem[M-H]-159.36731661259
DeepCCS[M+H]+160.20630932474
DeepCCS[M-H]-157.84830932474
DeepCCS[M-2H]-190.73430932474
DeepCCS[M+Na]+166.29930932474
AllCCS[M+H]+153.932859911
AllCCS[M+H-H2O]+149.932859911
AllCCS[M+NH4]+157.532859911
AllCCS[M+Na]+158.632859911
AllCCS[M-H]-157.232859911
AllCCS[M+Na-2H]-157.032859911
AllCCS[M+HCOO]-156.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EnoximoneCSC1=CC=C(C=C1)C(=O)C1=C(C)NC(=O)N13403.9Standard polar33892256
EnoximoneCSC1=CC=C(C=C1)C(=O)C1=C(C)NC(=O)N12376.1Standard non polar33892256
EnoximoneCSC1=CC=C(C=C1)C(=O)C1=C(C)NC(=O)N12707.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Enoximone,1TMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C)C(=O)[NH]2)C=C12518.7Semi standard non polar33892256
Enoximone,1TMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C)C(=O)[NH]2)C=C12310.2Standard non polar33892256
Enoximone,1TMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C)C(=O)[NH]2)C=C12886.6Standard polar33892256
Enoximone,1TMS,isomer #2CSC1=CC=C(C(=O)C2=C(C)[NH]C(=O)N2[Si](C)(C)C)C=C12499.2Semi standard non polar33892256
Enoximone,1TMS,isomer #2CSC1=CC=C(C(=O)C2=C(C)[NH]C(=O)N2[Si](C)(C)C)C=C12235.9Standard non polar33892256
Enoximone,1TMS,isomer #2CSC1=CC=C(C(=O)C2=C(C)[NH]C(=O)N2[Si](C)(C)C)C=C12828.3Standard polar33892256
Enoximone,2TMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=C12569.3Semi standard non polar33892256
Enoximone,2TMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=C12352.2Standard non polar33892256
Enoximone,2TMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=C12658.9Standard polar33892256
Enoximone,1TBDMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)C=C12712.1Semi standard non polar33892256
Enoximone,1TBDMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)C=C12552.3Standard non polar33892256
Enoximone,1TBDMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)C=C12949.7Standard polar33892256
Enoximone,1TBDMS,isomer #2CSC1=CC=C(C(=O)C2=C(C)[NH]C(=O)N2[Si](C)(C)C(C)(C)C)C=C12681.6Semi standard non polar33892256
Enoximone,1TBDMS,isomer #2CSC1=CC=C(C(=O)C2=C(C)[NH]C(=O)N2[Si](C)(C)C(C)(C)C)C=C12444.1Standard non polar33892256
Enoximone,1TBDMS,isomer #2CSC1=CC=C(C(=O)C2=C(C)[NH]C(=O)N2[Si](C)(C)C(C)(C)C)C=C12898.9Standard polar33892256
Enoximone,2TBDMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)C=C12930.4Semi standard non polar33892256
Enoximone,2TBDMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)C=C12768.8Standard non polar33892256
Enoximone,2TBDMS,isomer #1CSC1=CC=C(C(=O)C2=C(C)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)C=C12854.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Enoximone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4940000000-2c3d1d1ddd2652a0e57c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enoximone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoximone LC-ESI-qTof , Positive-QTOFsplash10-004i-3910100000-ff2ed6a9d4b5b25301852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoximone , positive-QTOFsplash10-004i-3910100000-ff2ed6a9d4b5b25301852017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 10V, Positive-QTOFsplash10-0002-0090000000-0e4975ce7aaf5ff4fc282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 20V, Positive-QTOFsplash10-0002-1190000000-df4edb235b0c4a91505e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 40V, Positive-QTOFsplash10-0f7y-9640000000-920c05b460908f7874652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 10V, Negative-QTOFsplash10-0002-4390000000-c4adff3885f495ea4c8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 20V, Negative-QTOFsplash10-0002-3970000000-c39dc81cb11ea90992ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 40V, Negative-QTOFsplash10-0005-9000000000-495a6052f4f3d6d213982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 10V, Positive-QTOFsplash10-0002-0090000000-8bd98f7a7fc6db23ff0f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 20V, Positive-QTOFsplash10-001i-0690000000-1303c6a9cc10a41205742021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 40V, Positive-QTOFsplash10-0ukc-6900000000-b391e964d41a1cc1220a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 10V, Negative-QTOFsplash10-0002-0090000000-409760192e17bc5104c62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 20V, Negative-QTOFsplash10-0f6t-9830000000-c2debf31c8846a740a402021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoximone 40V, Negative-QTOFsplash10-0006-9600000000-a31795b584b0ae92bcff2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04880 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04880 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04880
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID48492
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEnoximone
METLIN IDNot Available
PubChem Compound53708
PDB IDNot Available
ChEBI ID521520
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 References
  1. Boldt J, Suttner S: Combined use of ultra-short acting beta-blocker esmolol and intravenous phosphodiesterase 3 inhibitor enoximone. Expert Opin Pharmacother. 2007 Sep;8(13):2135-47. [PubMed:17714066 ]
  2. Sandroni C, Cavallaro F, Caricato A, Scapigliati A, Fenici P, Antonelli M: Enoximone in cardiac arrest caused by propranolol: two case reports. Acta Anaesthesiol Scand. 2006 Jul;50(6):759-61. [PubMed:16987374 ]
  3. van der Maaten JM, de Vries AJ, Rietman GW, Gallandat Huet RC, De Hert SG: Effects of preemptive enoximone on left ventricular diastolic function after valve replacement for aortic stenosis. J Cardiothorac Vasc Anesth. 2007 Jun;21(3):357-66. Epub 2006 May 4. [PubMed:17544886 ]
  4. Schauvliege S, Van den Eede A, Duchateau L, Gasthuys F: Cardiovascular effects of enoximone in isoflurane anaesthetized ponies. Vet Anaesth Analg. 2007 Nov;34(6):416-30. Epub 2007 Aug 13. [PubMed:17696974 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes (By similarity).
Gene Name:
PDE3A
Uniprot ID:
Q14432
Molecular weight:
124978.06
References
  1. Boldt J, Suttner S: Combined use of ultra-short acting beta-blocker esmolol and intravenous phosphodiesterase 3 inhibitor enoximone. Expert Opin Pharmacother. 2007 Sep;8(13):2135-47. [PubMed:17714066 ]
  2. Sandroni C, Cavallaro F, Caricato A, Scapigliati A, Fenici P, Antonelli M: Enoximone in cardiac arrest caused by propranolol: two case reports. Acta Anaesthesiol Scand. 2006 Jul;50(6):759-61. [PubMed:16987374 ]