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Showing metabocard for Lorazepam glucuronide (HMDB0041917)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:47:52 UTC
Update Date2019-07-23 06:35:14 UTC
HMDB IDHMDB0041917
Secondary Accession Numbers
  • HMDB41917
Metabolite Identification
Common NameLorazepam glucuronide
DescriptionLorazepam glucuronide belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. Lorazepam glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). These are compounds containing a glucuronic acid moeity (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
Structure
Data?1563863714
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-6-{[7-chloro-5-(2-chlorophenyl)-2-hydroxy-3H-1,4-benzodiazepin-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Lorazepam glucuronideMeSH
Chemical FormulaC21H18Cl2N2O8
Average Molecular Weight497.282
Monoisotopic Molecular Weight496.044020976
IUPAC Name(2S,3S,4S,5R,6S)-6-{[7-chloro-5-(2-chlorophenyl)-2-hydroxy-3H-1,4-benzodiazepin-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{[7-chloro-5-(2-chlorophenyl)-2-hydroxy-3H-1,4-benzodiazepin-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number32781-79-6
SMILES
O[C@@H]1[C@@H](O)[C@H](OC2N=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N=C2O)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C21H18Cl2N2O8/c22-8-5-6-12-10(7-8)13(9-3-1-2-4-11(9)23)25-19(18(29)24-12)33-21-16(28)14(26)15(27)17(32-21)20(30)31/h1-7,14-17,19,21,26-28H,(H,24,29)(H,30,31)/t14-,15-,16+,17-,19?,21-/m0/s1
InChI KeyIWOJSSFCRQKNKN-IFBJMGMISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • O-glucuronide
  • 1-o-glucuronide
  • Hexose monosaccharide
  • O-glycosyl compound
  • Benzodiazepine
  • 1,4-benzodiazepine
  • Glycosyl compound
  • Alpha-amino acid or derivatives
  • Beta-hydroxy acid
  • Halobenzene
  • Chlorobenzene
  • Aryl chloride
  • Hydroxy acid
  • Pyran
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Aryl halide
  • Monocyclic benzene moiety
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Ketimine
  • Lactam
  • Polyol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organochloride
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organohalogen compound
  • Carbonyl group
  • Alcohol
  • Organic nitrogen compound
  • Imine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.076 g/LALOGPS
logP2.06ALOGPS
logP2.8ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.43ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity115.74 m³·mol⁻¹ChemAxon
Polarizability46.01 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9510300000-16b3846fccaf60501474Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fb9-4490114000-0132930a912b4ab57b34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0092-0004900000-cacce09b0b75b4bb5897Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0219100000-0492d763d141fe60a515Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4549000000-5a2a0dd7cdf6e564262eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6w-4804900000-49d70a30f9cc5117cfb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugi-6907700000-cf867aaaec1e37518dbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000g-9641000000-f4eaacea70909c73f3e7Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 ID56677
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62966
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available