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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2018-05-20 20:48:56 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
Thumb
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)piperazineMeSH
Cilag brand OF terconazoleMeSH
Janssen brand OF terconazoleMeSH
FungistatMeSH
ortho Brand OF terconazoleMeSH
gyno-TerazolMeSH
TerazolMeSH
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
DescriptionThis compound belongs to the class of organic compounds known as phenylpiperazines. These 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:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point126.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.58ALOGPS
logP5.37ChemAxon
logS-4.7ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-9443500000-9564806da5509b610135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00o0-3971230000-dd66741ee49b1efec5efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1031290000-ae9cf158d06c702d6779View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-2030900000-107157b00d324c679eafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9650000000-20fe5c34ac5ea92694b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9040020000-0b48b94660b9f3ef6e8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9020000000-63022b7fa681bfa05832View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9430000000-2d5aaa4b68e19d7bf8e6View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00251 details
UrineExpected but not Quantified Not 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
FoodDB 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available