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Record Information
Version4.0
Creation Date2013-07-09 16:05:56 UTC
Update Date2017-09-27 08:43:56 UTC
HMDB IDHMDB0060897
Secondary Accession Numbers
  • HMDB60897
Metabolite Identification
Common NameDiphenhydramine N-glucuronide
DescriptionDiphenhydramine N-glucuronide is a metabolite of diphenhydramine. Diphenhydramine hydrochloride is a first-generation antihistamine possessing anticholinergic, antitussive, antiemetic, and sedative properties which is mainly used to treat allergies. Like most other first-generation antihistamines, the drug also has a powerful hypnotic effect, and for this reason is often used as a non-prescription sleep aid; especially in the form of diphenhydramine citrate. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H30NO7
Average Molecular Weight432.4868
Monoisotopic Molecular Weight432.202227319
IUPAC Name(3R,4S,5S,6S)-6-carboxy-N-[2-(diphenylmethoxy)ethyl]-3,4,5-trihydroxy-N,N-dimethyloxan-2-aminium
Traditional Name(3R,4S,5S,6S)-6-carboxy-N-[2-(diphenylmethoxy)ethyl]-3,4,5-trihydroxy-N,N-dimethyloxan-2-aminium
CAS Registry NumberNot Available
SMILES
C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C23H29NO7/c1-24(2,22-19(27)17(25)18(26)21(31-22)23(28)29)13-14-30-20(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17-22,25-27H,13-14H2,1-2H3/p+1/t17-,18-,19+,21-,22?/m0/s1
InChI KeyOAIGZXXQYIJBLR-VAUIJEFBSA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentN-glucuronides
Alternative Parents
Substituents
  • N-glucuronide
  • 1-n-glucuronide
  • Diphenylmethane
  • Glycosyl compound
  • N-glycosyl compound
  • Benzylether
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Oxane
  • Pyran
  • Benzenoid
  • Tetraalkylammonium salt
  • Secondary alcohol
  • Hemiaminal
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic salt
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
logP1.47ALOGPS
logP-2.6ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity123.37 m³·mol⁻¹ChemAxon
Polarizability45.04 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lei-6892100000-012c4e647e33583d8304View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f89-3894034000-ae320ceef91cf17db073View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0090800000-59446547e3397a43adb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2190000000-1c30de8d6f82b8d8791aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-7960000000-a7216de64e21182b177bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00087
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB 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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available