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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 20:50:29 UTC
Update Date2021-09-26 22:50:43 UTC
HMDB IDHMDB0243587
Secondary Accession NumbersNone
Metabolite Identification
Common Name(2S,4S)-Ketoconazole
Description1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine 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 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2s,4s)-ketoconazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2S,4S)-Ketoconazole is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
Janssen brand OF ketoconazoleMeSH
Ketoconazole janssen brandMeSH
NizoralMeSH
Chemical FormulaC26H28Cl2N4O4
Average Molecular Weight531.431
Monoisotopic Molecular Weight530.148760818
IUPAC Name1-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
Traditional Nameketoconazole
CAS Registry NumberNot Available
SMILES
CC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(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
InChI KeyXMAYWYJOQHXEEK-UHFFFAOYSA-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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability54.83 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+214.75530932474
DeepCCS[M-H]-212.35930932474
DeepCCS[M-2H]-245.24330932474
DeepCCS[M+Na]+221.01630932474
AllCCS[M+H]+219.732859911
AllCCS[M+H-H2O]+218.132859911
AllCCS[M+NH4]+221.132859911
AllCCS[M+Na]+221.532859911
AllCCS[M-H]-211.032859911
AllCCS[M+Na-2H]-211.932859911
AllCCS[M+HCOO]-213.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(2S,4S)-KetoconazoleCC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C15224.1Standard polar33892256
(2S,4S)-KetoconazoleCC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C13837.4Standard non polar33892256
(2S,4S)-KetoconazoleCC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C14744.5Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 10V, Positive-QTOFsplash10-001i-0031490000-58a475e5974da2dfdc182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 20V, Positive-QTOFsplash10-0ik9-5395740000-08c010ea5c947e1a62f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 40V, Positive-QTOFsplash10-014i-9520100000-76672a88c60da8324f812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 10V, Negative-QTOFsplash10-00or-2090150000-e4d86d7a4af3843992542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 20V, Negative-QTOFsplash10-014i-9240000000-92849351dd004ec262392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 40V, Negative-QTOFsplash10-00or-5940000000-e2a0f55e6d356bbc9c0e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 10V, Positive-QTOFsplash10-001i-0000090000-081787cba0594aced9012021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 20V, Positive-QTOFsplash10-001i-0011980000-f9fa0eaf2d1b6889e0982021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 40V, Positive-QTOFsplash10-066v-3140900000-ae27808322ff5c503bcf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 10V, Negative-QTOFsplash10-004i-0010390000-0eb582e7b11176ec640c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 20V, Negative-QTOFsplash10-014i-9030210000-9ea18251d96dd5cc657e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2S,4S)-Ketoconazole 40V, Negative-QTOFsplash10-00o0-4930100000-6819285e7904a4b66c662021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3691
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID48339
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]