Showing metabocard for Ketoconazole (BMDB0012242)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:34:49 UTC
Update Date2020-04-22 15:49:14 UTC
BMDB IDBMDB0012242
Secondary Accession Numbers
  • BMDB12242
Metabolite Identification
Common NameKetoconazole
DescriptionKetoconazole, also known as nizoral or xolegel, 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. Based on a literature review very few articles have been published on Ketoconazole.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,4R)-1-Acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazineChEBI
1-ACETYL-4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazineChEBI
NizoralKegg
XolegelKegg
ABBR KTCKegg
(+-)-cis-1-Acetyl-4-(P-((2-(2,4-dichlorophenyl)-2-(imidazol-1- ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazineHMDB
cis-1-Acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H- imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-ketoconazolHMDB
FungarestHMDB
FungoralHMDB
KetodermHMDB
KetoisdinHMDB
Orifungal mHMDB
PanfungolHMDB
PiperazineHMDB
Janssen brand OF ketoconazoleMeSH, HMDB
Ketoconazole janssen brandMeSH, HMDB
KetoconazoleMeSH
Chemical FormulaC26H28Cl2N4O4
Average Molecular Weight531.431
Monoisotopic Molecular Weight530.148760818
IUPAC Name1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
Traditional Namenizoral
CAS Registry Number65277-42-1
SMILES
CC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1
InChI Identifier
InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1
InChI KeyXMAYWYJOQHXEEK-ZEQKJWHPSA-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
  • Phenol ether
  • Tertiary aliphatic/aromatic amine
  • Phenoxy compound
  • Dialkylarylamine
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Ketal
  • Halobenzene
  • Chlorobenzene
  • Monocyclic benzene moiety
  • Aryl chloride
  • Aryl halide
  • N-substituted imidazole
  • Benzenoid
  • Meta-dioxolane
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Imidazole
  • Azole
  • Acetamide
  • Carboxamide group
  • Amino acid or derivatives
  • Tertiary amine
  • Acetal
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organonitrogen compound
  • Organochloride
  • Organopnictogen compound
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
  • cis-1-acetyl-4-(4-\{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy\}phenyl)piperazine (CHEBI:47518 )
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point146 °CPhysProp
Boiling PointNot AvailableNot Available
Water Solubility0.0866 mg/LNot Available
LogP4.35SANGSTER (1993)
Predicted Properties
PropertyValueSource
logP4.3ALOGPS
logP4.19ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.06 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity138.07 m³·mol⁻¹ChemAxon
Polarizability54.67 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-001i-9345700000-032f45d476928c144063View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-3530190000-a2b05a2498270bcd4a7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-3430090000-055d7bbaadb1e1716a8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0031490000-58a475e5974da2dfdc18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-5395740000-08c010ea5c947e1a62f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9520100000-76672a88c60da8324f81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-2090150000-e4d86d7a4af384399254View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9240000000-92849351dd004ec26239View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-5940000000-e2a0f55e6d356bbc9c0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0010390000-00106b8b890fdebbf036View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9030210000-22cee3cdcfef8b4b8068View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-4930100000-6819285e7904a4b66c66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-081787cba0594aced901View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0011980000-f9fa0eaf2d1b6889e098View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066v-3140900000-ae27808322ff5c503bcfView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012242
DrugBank IDDB05667
Phenol Explorer Compound IDNot Available
FooDB IDFDB028884
KNApSAcK IDNot Available
Chemspider ID43284
KEGG Compound IDNot Available
BioCyc IDCPD-4503
BiGG IDNot Available
Wikipedia LinkKetoconazole
METLIN IDNot Available
PubChem Compound47576
PDB IDKLN
ChEBI ID47518
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available