Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:51:47 UTC
Update Date2019-07-23 07:15:53 UTC
HMDB IDHMDB0061161
Secondary Accession Numbers
  • HMDB61161
Metabolite Identification
Common NameN-Desalkyl flurazepam
DescriptionN-Desalkyl 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?1563866153
Synonyms
ValueSource
NorflutoprazepamHMDB
NorflurazepamHMDB
N-Desalkyl-2-oxoquazepamMeSH
NorfludiazepamMeSH
Chemical FormulaC15H10ClFN2O
Average Molecular Weight288.704
Monoisotopic Molecular Weight288.046568864
IUPAC Name7-chloro-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Name7-chloro-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one
CAS Registry NumberNot Available
SMILES
FC1=CC=CC=C1C1=NCC(=O)NC2=C1C=C(Cl)C=C2
InChI Identifier
InChI=1S/C15H10ClFN2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)
InChI KeyUVCOILFBWYKHHB-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
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Ketimine
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organooxygen compound
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.019 g/LALOGPS
logP2.87ALOGPS
logP3.35ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.91 m³·mol⁻¹ChemAxon
Polarizability28.04 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]+162.58730932474
DeepCCS[M-H]-160.19230932474
DeepCCS[M-2H]-193.13130932474
DeepCCS[M+Na]+168.64330932474
AllCCS[M+H]+162.132859911
AllCCS[M+H-H2O]+158.332859911
AllCCS[M+NH4]+165.632859911
AllCCS[M+Na]+166.732859911
AllCCS[M-H]-161.132859911
AllCCS[M+Na-2H]-160.332859911
AllCCS[M+HCOO]-159.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Desalkyl flurazepamFC1=CC=CC=C1C1=NCC(=O)NC2=C1C=C(Cl)C=C23758.6Standard polar33892256
N-Desalkyl flurazepamFC1=CC=CC=C1C1=NCC(=O)NC2=C1C=C(Cl)C=C22443.2Standard non polar33892256
N-Desalkyl flurazepamFC1=CC=CC=C1C1=NCC(=O)NC2=C1C=C(Cl)C=C22431.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Desalkyl flurazepam,1TMS,isomer #1C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2F)C2=CC(Cl)=CC=C212315.8Semi standard non polar33892256
N-Desalkyl flurazepam,1TMS,isomer #1C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2F)C2=CC(Cl)=CC=C212383.1Standard non polar33892256
N-Desalkyl flurazepam,1TMS,isomer #1C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2F)C2=CC(Cl)=CC=C213257.8Standard polar33892256
N-Desalkyl flurazepam,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2F)C2=CC(Cl)=CC=C212508.5Semi standard non polar33892256
N-Desalkyl flurazepam,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2F)C2=CC(Cl)=CC=C212583.0Standard non polar33892256
N-Desalkyl flurazepam,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2F)C2=CC(Cl)=CC=C213322.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Desalkyl flurazepam GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ir1-1190000000-2bb7221cad85f7e5beff2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Desalkyl flurazepam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Desalkyl flurazepam 10V, Negative-QTOFsplash10-000i-0090000000-6e5d33d01214218f3bc62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Desalkyl flurazepam 20V, Negative-QTOFsplash10-014i-0090000000-2602ce3a9ac70ccb00092021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Desalkyl flurazepam 40V, Negative-QTOFsplash10-00ku-0090000000-9d25b7d826dad96c44482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Desalkyl flurazepam 50V, Positive-QTOFsplash10-004l-0970000000-16ed83c5bfe2a4b0b51a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Desalkyl flurazepam 20V, Positive-QTOFsplash10-000i-0090000000-ec89dc22e0e7044675692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Desalkyl flurazepam 10V, Positive-QTOFsplash10-000i-0090000000-32ad44a4b7594ceced392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Desalkyl flurazepam 40V, Positive-QTOFsplash10-002f-0890000000-55f51208eb5ca0534fa42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Desalkyl flurazepam 30V, Positive-QTOFsplash10-000f-0390000000-d28e70b0b03e1a841f242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Desalkyl flurazepam 30V, Negative-QTOFsplash10-014i-0090000000-ae1aae8048ed8e1e09192021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 10V, Positive-QTOFsplash10-000i-0190000000-fe2298ee3d5ee938899d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 20V, Positive-QTOFsplash10-000i-0190000000-10bde3feb50b9273efce2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 40V, Positive-QTOFsplash10-000i-3950000000-2d1d77b15c0e26446b5e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 10V, Negative-QTOFsplash10-000i-0090000000-0020aad0810fd76553342017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 20V, Negative-QTOFsplash10-000i-0090000000-6d9e7b5550ece2fc21c32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 40V, Negative-QTOFsplash10-0006-9230000000-5cbadb820772178729432017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 10V, Positive-QTOFsplash10-000i-0090000000-e086a7f0b9e989fd0bc52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 20V, Positive-QTOFsplash10-000i-0090000000-e086a7f0b9e989fd0bc52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 40V, Positive-QTOFsplash10-08i4-0190000000-4a802ba28f098fc3e7bb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 10V, Negative-QTOFsplash10-014i-0090000000-86f5ce249408a3d7fda82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 20V, Negative-QTOFsplash10-014i-1090000000-0caa29dc7556e36236d92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desalkyl flurazepam 40V, Negative-QTOFsplash10-000x-9010000000-890546e9ed19aaaac0502021-09-24Wishart 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 Compound4540
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