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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 14:59:34 UTC
HMDB IDHMDB0014396
Secondary Accession Numbers
  • HMDB14396
Metabolite Identification
Common NameTerconazole
DescriptionTerconazole is only found in individuals that have used or taken this drug. It is an anti-fungal medication, primarily used to treat vaginal fungal infections. [Wikipedia ]Terconazole may exert its antifungal activity by disrupting normal fungal cell membrane permeability. Terconazole and other triazole antifungal agents inhibit cytochrome P450 14-alpha-demethylase in susceptible fungi, which leads to the accumulation of lanosterol and other methylated sterols and a decrease in ergosterol concentration. Depletion of ergosterol in the membrane disrupts the structure and function of the fungal cell leading to a decrease or inhibition of fungal growth.
Structure
Data?1582753174
Synonyms
ValueSource
Terazol 3Kegg
TriaconazoleHMDB
1-(4-((2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(1-methylethyl)piperazineHMDB
Cilag brand OF terconazoleHMDB
Janssen brand OF terconazoleHMDB
FungistatHMDB
Ortho brand OF terconazoleHMDB
Gyno-terazolHMDB
TerazolHMDB
TerconazoleMeSH
Chemical FormulaC26H31Cl2N5O3
Average Molecular Weight532.462
Monoisotopic Molecular Weight531.180395297
IUPAC Name1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propan-2-yl)piperazine
Traditional Nameterconazole
CAS Registry Number67915-31-5
SMILES
CC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1
InChI Identifier
InChI=1S/C26H31Cl2N5O3/c1-19(2)31-9-11-32(12-10-31)21-4-6-22(7-5-21)34-14-23-15-35-26(36-23,16-33-18-29-17-30-33)24-8-3-20(27)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/m0/s1
InChI KeyBLSQLHNBWJLIBQ-OZXSUGGESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • Phenylpiperazine
  • N-arylpiperazine
  • Aminophenyl ether
  • 1,3-dichlorobenzene
  • Phenoxy compound
  • Phenol ether
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Ketal
  • N-alkylpiperazine
  • Benzenoid
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Azole
  • Meta-dioxolane
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Acetal
  • Azacycle
  • Oxacycle
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
  • 1-(4-\{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy\}phenyl)-4-isopropylpiperazine (CHEBI:82980 )
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point126.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP4.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP10(4.58) g/LALOGPS
logP10(5.37) g/LChemAxon
logS10(-4.7) g/LALOGPS
pKa (Strongest Basic)8.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area64.88 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity153.19 m³·mol⁻¹ChemAxon
Polarizability56.15 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TerconazoleCC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C15032.4Standard polar33892256
TerconazoleCC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C13671.6Standard non polar33892256
TerconazoleCC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C14286.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Terconazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-9443500000-9564806da5509b6101352017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Terconazole , positive-QTOFsplash10-00o0-3971230000-dd66741ee49b1efec5ef2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 10V, Positive-QTOFsplash10-001i-1031290000-ae9cf158d06c702d67792016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 20V, Positive-QTOFsplash10-006y-2030900000-107157b00d324c679eaf2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 40V, Positive-QTOFsplash10-00di-9650000000-20fe5c34ac5ea92694b02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 10V, Negative-QTOFsplash10-014i-9040020000-0b48b94660b9f3ef6e8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 20V, Negative-QTOFsplash10-014i-9020000000-63022b7fa681bfa058322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 40V, Negative-QTOFsplash10-014i-9430000000-2d5aaa4b68e19d7bf8e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 10V, Positive-QTOFsplash10-001i-0000290000-f3aef95a41e4260dde022021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 20V, Positive-QTOFsplash10-001i-0001590000-49599976d635f6aacd4b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 40V, Positive-QTOFsplash10-0c0r-5589830000-780cdd0e0d8417618e232021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 10V, Negative-QTOFsplash10-001i-2000090000-c74ac4cbd2cd12fcbaeb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 20V, Negative-QTOFsplash10-00lr-6190360000-c1e756aeed62c31370902021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terconazole 40V, Negative-QTOFsplash10-00o0-3920210000-06b53e2e06769acd7c3c2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00251 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00251 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00251
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390122
KEGG Compound IDC08080
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTerconazole
METLIN IDNot Available
PubChem Compound441383
PDB IDNot Available
ChEBI ID82980
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