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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 10:05:28 UTC
Update Date2021-09-26 23:04:41 UTC
HMDB IDHMDB0252240
Secondary Accession NumbersNone
Metabolite Identification
Common NameFexinidazole
DescriptionFexinidazole belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group. Based on a literature review very few articles have been published on Fexinidazole. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fexinidazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fexinidazole 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
HOE 239MeSH
Chemical FormulaC12H13N3O3S
Average Molecular Weight279.31
Monoisotopic Molecular Weight279.067762465
IUPAC Name1-methyl-2-{[4-(methylsulfanyl)phenoxy]methyl}-5-nitro-1H-imidazole
Traditional Namefexinidazole
CAS Registry NumberNot Available
SMILES
CSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C1
InChI Identifier
InChI=1S/C12H13N3O3S/c1-14-11(13-7-12(14)15(16)17)8-18-9-3-5-10(19-2)6-4-9/h3-7H,8H2,1-2H3
InChI KeyMIWWSGDADVMLTG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentNitroimidazoles
Alternative Parents
Substituents
  • 1,2,5-trisubstituted-imidazole
  • Phenoxy compound
  • Aryl thioether
  • Nitroaromatic compound
  • Nitroimidazole
  • Phenol ether
  • Trisubstituted imidazole
  • Thiophenol ether
  • Alkyl aryl ether
  • Alkylarylthioether
  • Monocyclic benzene moiety
  • N-substituted imidazole
  • Benzenoid
  • Heteroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Ether
  • Azacycle
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Thioether
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP2.28ALOGPS
logP2.38ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)1.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area70.19 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity72.64 m³·mol⁻¹ChemAxon
Polarizability28.53 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+160.81830932474
DeepCCS[M-H]-158.17930932474
DeepCCS[M-2H]-191.94430932474
DeepCCS[M+Na]+168.31630932474
AllCCS[M+H]+162.232859911
AllCCS[M+H-H2O]+158.732859911
AllCCS[M+NH4]+165.532859911
AllCCS[M+Na]+166.432859911
AllCCS[M-H]-162.532859911
AllCCS[M+Na-2H]-162.232859911
AllCCS[M+HCOO]-162.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FexinidazoleCSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C13146.7Standard polar33892256
FexinidazoleCSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C12388.6Standard non polar33892256
FexinidazoleCSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C12490.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fexinidazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-5960000000-1a2afbed3cec3c85a0612017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fexinidazole 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 - Fexinidazole 10V, Positive-QTOFsplash10-001i-0090000000-35015bda73a438e024322017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fexinidazole 20V, Positive-QTOFsplash10-05gi-0090000000-f1594a195f812dea81922017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fexinidazole 40V, Positive-QTOFsplash10-0kmr-9620000000-abb060105242ead34e622017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fexinidazole 10V, Negative-QTOFsplash10-004j-6090000000-faa54d094d8b356bff5c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fexinidazole 20V, Negative-QTOFsplash10-0092-9370000000-bf91049664b340197a4f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fexinidazole 40V, Negative-QTOFsplash10-0002-9000000000-cf335fbd1993d36336722017-07-26Wishart 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 IDDB12265
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID62032
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFexinidazole
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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 ]