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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:38 UTC
Update Date2021-09-14 15:00:47 UTC
HMDB IDHMDB0013970
Secondary Accession Numbers
  • HMDB13970
Metabolite Identification
Common NameDehydroxyzyleuton
DescriptionDehydroxyzyleuton is only found in individuals that have used or taken Zileuton. Dehydroxyzyleuton is a metabolite of Zileuton. Dehydroxyzyleuton belongs to the family of Benzothiophenes. These are organic compounds containing a benzene fused to a thiepine ring (a five-member ring with six carbon atoms and one sulfur atom).
Structure
Data?1582753158
Synonyms
ValueSource
Abbott 66193HMDB
Abbott-66193HMDB
N-(1-Benzo(b)thien-2-ylethyl)ureaHMDB
N-DehydroxyzileutonHMDB
N-[1-(1-Benzothiophen-2-yl)ethyl]carbamimidateHMDB
Chemical FormulaC11H12N2OS
Average Molecular Weight220.291
Monoisotopic Molecular Weight220.067033706
IUPAC Name[1-(1-benzothiophen-2-yl)ethyl]urea
Traditional Name1-(1-benzothiophen-2-yl)ethylurea
CAS Registry NumberNot Available
SMILES
CC(NC(N)=O)C1=CC2=CC=CC=C2S1
InChI Identifier
InChI=1S/C11H12N2OS/c1-7(13-11(12)14)10-6-8-4-2-3-5-9(8)15-10/h2-7H,1H3,(H3,12,13,14)
InChI KeyCKVDCQYUEYONIA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiophenes
Sub Class1-benzothiophenes
Direct Parent1-benzothiophenes
Alternative Parents
Substituents
  • 1-benzothiophene
  • 2,3,5-trisubstituted thiophene
  • Benzenoid
  • Thiophene
  • Heteroaromatic compound
  • Carbonic acid derivative
  • Urea
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

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
Water Solubility0.042 g/LALOGPS
logP10(2.24) g/LALOGPS
logP10(2.01) g/LChemAxon
logS10(-3.7) g/LALOGPS
pKa (Strongest Acidic)15.18ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.19 m³·mol⁻¹ChemAxon
Polarizability23.42 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
DarkChem[M+H]+150.30731661259
DarkChem[M-H]-145.13631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DehydroxyzyleutonCC(NC(N)=O)C1=CC2=CC=CC=C2S13393.4Standard polar33892256
DehydroxyzyleutonCC(NC(N)=O)C1=CC2=CC=CC=C2S11948.5Standard non polar33892256
DehydroxyzyleutonCC(NC(N)=O)C1=CC2=CC=CC=C2S12192.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dehydroxyzyleuton,1TMS,isomer #1CC(NC(=O)N[Si](C)(C)C)C1=CC2=CC=CC=C2S12227.7Semi standard non polar33892256
Dehydroxyzyleuton,1TMS,isomer #1CC(NC(=O)N[Si](C)(C)C)C1=CC2=CC=CC=C2S12118.2Standard non polar33892256
Dehydroxyzyleuton,1TMS,isomer #1CC(NC(=O)N[Si](C)(C)C)C1=CC2=CC=CC=C2S13083.2Standard polar33892256
Dehydroxyzyleuton,1TMS,isomer #2CC(C1=CC2=CC=CC=C2S1)N(C(N)=O)[Si](C)(C)C2122.9Semi standard non polar33892256
Dehydroxyzyleuton,1TMS,isomer #2CC(C1=CC2=CC=CC=C2S1)N(C(N)=O)[Si](C)(C)C2163.3Standard non polar33892256
Dehydroxyzyleuton,1TMS,isomer #2CC(C1=CC2=CC=CC=C2S1)N(C(N)=O)[Si](C)(C)C3093.8Standard polar33892256
Dehydroxyzyleuton,2TMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N[Si](C)(C)C)[Si](C)(C)C2166.9Semi standard non polar33892256
Dehydroxyzyleuton,2TMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N[Si](C)(C)C)[Si](C)(C)C2208.2Standard non polar33892256
Dehydroxyzyleuton,2TMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N[Si](C)(C)C)[Si](C)(C)C2726.5Standard polar33892256
Dehydroxyzyleuton,2TMS,isomer #2CC(NC(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC2=CC=CC=C2S12219.7Semi standard non polar33892256
Dehydroxyzyleuton,2TMS,isomer #2CC(NC(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC2=CC=CC=C2S12234.6Standard non polar33892256
Dehydroxyzyleuton,2TMS,isomer #2CC(NC(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC2=CC=CC=C2S12863.6Standard polar33892256
Dehydroxyzyleuton,3TMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2218.7Semi standard non polar33892256
Dehydroxyzyleuton,3TMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2368.9Standard non polar33892256
Dehydroxyzyleuton,3TMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2507.4Standard polar33892256
Dehydroxyzyleuton,1TBDMS,isomer #1CC(NC(=O)N[Si](C)(C)C(C)(C)C)C1=CC2=CC=CC=C2S12460.3Semi standard non polar33892256
Dehydroxyzyleuton,1TBDMS,isomer #1CC(NC(=O)N[Si](C)(C)C(C)(C)C)C1=CC2=CC=CC=C2S12330.6Standard non polar33892256
Dehydroxyzyleuton,1TBDMS,isomer #1CC(NC(=O)N[Si](C)(C)C(C)(C)C)C1=CC2=CC=CC=C2S13035.2Standard polar33892256
Dehydroxyzyleuton,1TBDMS,isomer #2CC(C1=CC2=CC=CC=C2S1)N(C(N)=O)[Si](C)(C)C(C)(C)C2380.0Semi standard non polar33892256
Dehydroxyzyleuton,1TBDMS,isomer #2CC(C1=CC2=CC=CC=C2S1)N(C(N)=O)[Si](C)(C)C(C)(C)C2356.3Standard non polar33892256
Dehydroxyzyleuton,1TBDMS,isomer #2CC(C1=CC2=CC=CC=C2S1)N(C(N)=O)[Si](C)(C)C(C)(C)C3139.3Standard polar33892256
Dehydroxyzyleuton,2TBDMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2648.9Semi standard non polar33892256
Dehydroxyzyleuton,2TBDMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2620.2Standard non polar33892256
Dehydroxyzyleuton,2TBDMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2853.1Standard polar33892256
Dehydroxyzyleuton,2TBDMS,isomer #2CC(NC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC2=CC=CC=C2S12666.1Semi standard non polar33892256
Dehydroxyzyleuton,2TBDMS,isomer #2CC(NC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC2=CC=CC=C2S12628.8Standard non polar33892256
Dehydroxyzyleuton,2TBDMS,isomer #2CC(NC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC2=CC=CC=C2S12887.5Standard polar33892256
Dehydroxyzyleuton,3TBDMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2895.5Semi standard non polar33892256
Dehydroxyzyleuton,3TBDMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2907.9Standard non polar33892256
Dehydroxyzyleuton,3TBDMS,isomer #1CC(C1=CC2=CC=CC=C2S1)N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2792.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroxyzyleuton GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-7920000000-93d33a30235fe8df1f8d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroxyzyleuton GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroxyzyleuton 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 - Dehydroxyzyleuton 10V, Positive-QTOFsplash10-00di-1490000000-e81394c9ee08e33711022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 20V, Positive-QTOFsplash10-01t9-4940000000-f9320ec4e9051fdf67482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 40V, Positive-QTOFsplash10-03du-5900000000-5b6cc21ce141df2f0e112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 10V, Negative-QTOFsplash10-004l-4930000000-1a95c48bc0eeaf0858892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 20V, Negative-QTOFsplash10-004l-4900000000-30b5b71a1982ec335bc92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 40V, Negative-QTOFsplash10-0006-9400000000-188d2b05419327e114172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 10V, Negative-QTOFsplash10-014i-2490000000-2f0c19c421f70873bcbb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 20V, Negative-QTOFsplash10-001l-3900000000-ab79160211b09d5adc532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 40V, Negative-QTOFsplash10-001i-0900000000-bdcd601869c6ef1ce5c32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 10V, Positive-QTOFsplash10-03k9-0940000000-81bf9d2b9ec5e24c15f12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 20V, Positive-QTOFsplash10-03di-0900000000-aff31a9a33ea23cdb6312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxyzyleuton 40V, Positive-QTOFsplash10-0bt9-1900000000-545b087e657909b8004b2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry 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 ID8280407
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10104880
PDB IDNot Available
ChEBI ID192798
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