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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:15:18 UTC
Update Date2021-09-14 15:46:31 UTC
HMDB IDHMDB0061052
Secondary Accession Numbers
  • HMDB61052
Metabolite Identification
Common Name4-hydroxytriazolam
Description4-hydroxytriazolam is a metabolite of triazolam. Triazolam (marketed in English-speaking countries under the brand names Apo-Triazo, Halcion, Hypam, and Trilam) is a benzodiazepine drug. It possesses pharmacological properties similar to that of other benzodiazepines, but it is generally only used as a sedative to treat severe insomnia. In addition to the hypnotic properties triazolam possesses, amnesic, anxiolytic, sedative, anticonvulsant and muscle relaxant properties are also present. (Wikipedia)
Structure
Data?1563866140
SynonymsNot Available
Chemical FormulaC17H12Cl2N4O
Average Molecular Weight359.209
Monoisotopic Molecular Weight358.03881644
IUPAC Name12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-7-ol
Traditional Name12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-7-ol
CAS Registry NumberNot Available
SMILES
CC1=NN=C2C(O)N=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N12
InChI Identifier
InChI=1S/C17H12Cl2N4O/c1-9-21-22-16-17(24)20-15(11-4-2-3-5-13(11)19)12-8-10(18)6-7-14(12)23(9)16/h2-8,17,24H,1H3
InChI KeyYUQRFPYHTPARRM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,2,4-triazolo[4,3-a][1,4]benzodiazepines
Alternative Parents
Substituents
  • 1,2,4-triazolo[4,3-a][1,4]benzodiazepine
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Ketimine
  • Alkanolamine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxygen compound
  • Imine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • 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 Solubility0.044 g/LALOGPS
logP2.91ALOGPS
logP2.63ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)10.97ChemAxon
pKa (Strongest Basic)1.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity104.88 m³·mol⁻¹ChemAxon
Polarizability34.67 ųChemAxon
Number of Rings4ChemAxon
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-2H]-209.52930932474
DeepCCS[M+Na]+184.75630932474
AllCCS[M+H]+179.032859911
AllCCS[M+H-H2O]+175.732859911
AllCCS[M+NH4]+182.032859911
AllCCS[M+Na]+182.832859911
AllCCS[M-H]-176.332859911
AllCCS[M+Na-2H]-175.432859911
AllCCS[M+HCOO]-174.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-hydroxytriazolamCC1=NN=C2C(O)N=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N124256.5Standard polar33892256
4-hydroxytriazolamCC1=NN=C2C(O)N=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N123166.6Standard non polar33892256
4-hydroxytriazolamCC1=NN=C2C(O)N=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N123066.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-hydroxytriazolam,1TMS,isomer #1CC1=NN=C2C(O[Si](C)(C)C)N=C(C3=CC=CC=C3Cl)C3=CC(Cl)=CC=C3N123150.7Semi standard non polar33892256
4-hydroxytriazolam,1TBDMS,isomer #1CC1=NN=C2C(O[Si](C)(C)C(C)(C)C)N=C(C3=CC=CC=C3Cl)C3=CC(Cl)=CC=C3N123292.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxytriazolam GC-MS (Non-derivatized) - 70eV, Positivesplash10-009x-8297000000-7c97e6bdc5e8946ef42e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxytriazolam GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9003100000-8e0bdab92e374a08b6ac2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxytriazolam 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 - 4-hydroxytriazolam 10V, Positive-QTOFsplash10-0a4i-0019000000-bee6db338dffd4d2ba3b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 20V, Positive-QTOFsplash10-0a4i-0019000000-a05a3d532edc73495bee2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 40V, Positive-QTOFsplash10-01ow-2982000000-13b4fb69473773f3fdc72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 10V, Negative-QTOFsplash10-0a4i-0009000000-db58ab63a0e0101f62e82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 20V, Negative-QTOFsplash10-0a4i-0009000000-d686e2cd2f48f9d2f3802017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 40V, Negative-QTOFsplash10-0uyi-9465000000-00e756404d0dd8500add2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 10V, Positive-QTOFsplash10-0a4i-0009000000-d882a48b67f97fd7c3342021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 20V, Positive-QTOFsplash10-0a4i-0009000000-9bc6f5815d45774414892021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 40V, Positive-QTOFsplash10-0ufr-1139000000-36f160ddef620fe7109b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 10V, Negative-QTOFsplash10-0a4i-0009000000-2e74e59b074ab7ed5b282021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 20V, Negative-QTOFsplash10-05ai-6009000000-40992ed9fe59fa77de8c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxytriazolam 40V, Negative-QTOFsplash10-001i-9126000000-66d233fb3bd060ccc6cb2021-09-25Wishart 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 Compound128260
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