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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:03:32 UTC
Update Date2019-07-23 07:15:13 UTC
HMDB IDHMDB0060853
Secondary Accession Numbers
  • HMDB60853
Metabolite Identification
Common NameN1-(2-Hydroxyethyl)flurazepam
DescriptionN1-(2-Hydroxyethyl)flurazepam is a metabolite of flurazepam. Flurazepam (marketed under the brand names Dalmane and Dalmadorm) is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It produces a metabolite with a very long half-life (40–250 hours), which may stay in the bloodstream for up to four days. http://www. non-benzodiazepines. org. uk/equivalents. html Flurazepam is therefore unsuitable as a sleeping medication for some individuals due to next day sedation. (Wikipedia)
Structure
Data?1563866113
SynonymsNot Available
Chemical FormulaC18H16ClFN2O2
Average Molecular Weight346.783
Monoisotopic Molecular Weight346.088433678
IUPAC Name7-chloro-5-(2-fluorophenyl)-1-(2-methoxyethyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Name7-chloro-5-(2-fluorophenyl)-1-(2-methoxyethyl)-3H-1,4-benzodiazepin-2-one
CAS Registry NumberNot Available
SMILES
COCCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F
InChI Identifier
InChI=1S/C18H16ClFN2O2/c1-24-9-8-22-16-7-6-12(19)10-14(16)18(21-11-17(22)23)13-4-2-3-5-15(13)20/h2-7,10H,8-9,11H2,1H3
InChI KeyUBKVMFUMOAWHGB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
Substituents
  • 1,4-benzodiazepine
  • Alpha-amino acid or derivatives
  • Fluorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Ketimine
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Imine
  • Organooxygen compound
  • Organonitrogen compound
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
Water Solubility0.011 g/LALOGPS
logP2.97ALOGPS
logP3.17ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)2.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area41.9 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.07 m³·mol⁻¹ChemAxon
Polarizability34.76 ųChemAxon
Number of Rings3ChemAxon
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]+181.38330932474
DeepCCS[M-H]-179.02530932474
DeepCCS[M-2H]-213.21530932474
DeepCCS[M+Na]+188.44130932474
AllCCS[M+H]+178.032859911
AllCCS[M+H-H2O]+174.832859911
AllCCS[M+NH4]+180.932859911
AllCCS[M+Na]+181.832859911
AllCCS[M-H]-180.132859911
AllCCS[M+Na-2H]-179.732859911
AllCCS[M+HCOO]-179.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N1-(2-Hydroxyethyl)flurazepamCOCCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F3839.8Standard polar33892256
N1-(2-Hydroxyethyl)flurazepamCOCCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F2609.8Standard non polar33892256
N1-(2-Hydroxyethyl)flurazepamCOCCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F2565.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N1-(2-Hydroxyethyl)flurazepam GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-4169000000-3fff84a5d465e87f2d312017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 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 - N1-(2-Hydroxyethyl)flurazepam 10V, Positive-QTOFsplash10-0002-0019000000-a1a3b37e77ef936d7ba42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 20V, Positive-QTOFsplash10-014j-1019000000-82f6b5937ad0907e6f3a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 40V, Positive-QTOFsplash10-0aor-3950000000-b5e3af279f5337542b3d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 10V, Negative-QTOFsplash10-0002-0009000000-a3b6ce437f5b95923d142017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 20V, Negative-QTOFsplash10-0002-0019000000-456bc1246ffc39c95fde2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 40V, Negative-QTOFsplash10-0a4l-6291000000-9333facf68fbb7f2aba32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 10V, Positive-QTOFsplash10-0002-0009000000-d21824eed85f58e55e742021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 20V, Positive-QTOFsplash10-0udi-0019000000-628b436e9f8d8a6280472021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 40V, Positive-QTOFsplash10-0frj-0193000000-2d11847b118d1cea33382021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 10V, Negative-QTOFsplash10-0f6t-0029000000-a0a4c76282c7be799e772021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 20V, Negative-QTOFsplash10-0udi-1059000000-5a8eaceaad18a924647c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N1-(2-Hydroxyethyl)flurazepam 40V, Negative-QTOFsplash10-00lj-2090000000-8dfe2e9dddc05551de512021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21498643
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 ReferencesNot Available