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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015284
Secondary Accession Numbers
  • HMDB15284
Metabolite Identification
Common NameSertaconazole
DescriptionSertaconazole is only found in individuals that have used or taken this drug. Sertaconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athlete's foot. [Wikipedia]Sertaconazole interacts with 14-alpha demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Sertaconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
Structure
Data?1582753279
Synonyms
ValueSource
DermofixMeSH
DermosepticMeSH
GinedermofixMeSH
MykosertMeSH
ZalainMeSH
Sertaconazole mononitrateMeSH
Sertaconazole nitrateMeSH
DemofixChEMBL, HMDB
ErtaczoChEMBL, HMDB
SertaconazoleMeSH
Chemical FormulaC20H15Cl3N2OS
Average Molecular Weight437.77
Monoisotopic Molecular Weight435.997066923
IUPAC Name1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
Traditional Namesertaconazole
CAS Registry Number99592-32-2
SMILES
ClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl
InChI Identifier
InChI=1S/C20H15Cl3N2OS/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22/h1-8,11-12,19H,9-10H2
InChI KeyJLGKQTAYUIMGRK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiophenes
Sub Class1-benzothiophenes
Direct Parent1-benzothiophenes
Alternative Parents
Substituents
  • 1-benzothiophene
  • Benzylether
  • 1,3-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Thiophene
  • Imidazole
  • Azacycle
  • Dialkyl ether
  • Ether
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0064 g/LNot Available
LogP6.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0064 g/LALOGPS
logP5.74ALOGPS
logP6.23ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.05 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity111.6 m³·mol⁻¹ChemAxon
Polarizability42.93 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+183.44930932474
DeepCCS[M-H]-181.09130932474
DeepCCS[M-2H]-215.20130932474
DeepCCS[M+Na]+190.65130932474
AllCCS[M+H]+192.932859911
AllCCS[M+H-H2O]+190.532859911
AllCCS[M+NH4]+195.132859911
AllCCS[M+Na]+195.732859911
AllCCS[M-H]-174.132859911
AllCCS[M+Na-2H]-173.132859911
AllCCS[M+HCOO]-172.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SertaconazoleClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl4700.3Standard polar33892256
SertaconazoleClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl3324.6Standard non polar33892256
SertaconazoleClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl3443.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sertaconazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-8921000000-652bd3da9533b5e7b49c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sertaconazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sertaconazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sertaconazole 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 - Sertaconazole 10V, Positive-QTOFsplash10-000i-0010900000-e80248766f0207aed7472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 20V, Positive-QTOFsplash10-00kr-7172900000-fb816c23af8617fb0dfb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 40V, Positive-QTOFsplash10-014i-9230000000-a5524f8d3df959952f872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 10V, Negative-QTOFsplash10-001i-1000900000-8d6b59997574a7df6e252016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 20V, Negative-QTOFsplash10-014i-9000100000-00203eccb064d3b384622016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 40V, Negative-QTOFsplash10-014l-9210000000-31fa2b0a7600382a9cf42016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 10V, Positive-QTOFsplash10-0019-0920800000-325d5bb8842de14747ea2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 20V, Positive-QTOFsplash10-001r-1902200000-221501bc20a8a810369b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 40V, Positive-QTOFsplash10-00ls-4900000000-0394fe97ab0550a97abd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 10V, Negative-QTOFsplash10-000i-2390400000-66e76245f92d693d9a992021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 20V, Negative-QTOFsplash10-001i-9300000000-64f716aeb89d151ae51f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sertaconazole 40V, Negative-QTOFsplash10-014i-9100000000-6151c3cb1b71a9e4e4ca2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01153 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01153 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID59273
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65863
PDB IDNot Available
ChEBI ID83682
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

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular weight:
57277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]