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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:05:56 UTC
Update Date2021-09-14 15:41:59 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
Data?1563866119
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
Description Belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids and derivatives. N-carbamoyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an carbamoyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-carbamoyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • Valine or derivatives
  • N-carbamoyl-alpha-amino acid or derivatives
  • Alpha-amino acid amide
  • Amphetamine or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Carbamic acid ester
  • Thiazole
  • Carboxamide group
  • Urea
  • Carbonic acid derivative
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Azacycle
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.059 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+196.85331661259
DarkChem[M-H]-184.36331661259
DeepCCS[M+H]+188.76730932474
DeepCCS[M-H]-186.37230932474
DeepCCS[M-2H]-219.31330932474
DeepCCS[M+Na]+195.67530932474
AllCCS[M+H]+205.132859911
AllCCS[M+H-H2O]+202.832859911
AllCCS[M+NH4]+207.232859911
AllCCS[M+Na]+207.832859911
AllCCS[M-H]-202.332859911
AllCCS[M+Na-2H]-203.432859911
AllCCS[M+HCOO]-204.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Diphenhydramine N-glucuronideC[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)=O4043.0Standard polar33892256
Diphenhydramine N-glucuronideC[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)=O3132.3Standard non polar33892256
Diphenhydramine N-glucuronideC[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)=O3456.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diphenhydramine N-glucuronide,1TMS,isomer #1C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O3235.1Semi standard non polar33892256
Diphenhydramine N-glucuronide,1TMS,isomer #2C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O3198.0Semi standard non polar33892256
Diphenhydramine N-glucuronide,1TMS,isomer #3C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C3253.1Semi standard non polar33892256
Diphenhydramine N-glucuronide,1TMS,isomer #4C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O3215.8Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TMS,isomer #1C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O3197.7Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TMS,isomer #2C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O3169.1Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TMS,isomer #3C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C3191.9Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TMS,isomer #4C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O3158.8Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TMS,isomer #5C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C3185.3Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TMS,isomer #6C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C3180.8Semi standard non polar33892256
Diphenhydramine N-glucuronide,3TMS,isomer #1C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O3184.3Semi standard non polar33892256
Diphenhydramine N-glucuronide,3TMS,isomer #2C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C3180.2Semi standard non polar33892256
Diphenhydramine N-glucuronide,3TMS,isomer #3C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C3189.6Semi standard non polar33892256
Diphenhydramine N-glucuronide,3TMS,isomer #4C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C3176.0Semi standard non polar33892256
Diphenhydramine N-glucuronide,4TMS,isomer #1C[N+](C)(CCOC(C1=CC=CC=C1)C1=CC=CC=C1)C1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C3224.3Semi standard non polar33892256
Diphenhydramine N-glucuronide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O)[C@H]1O3424.5Semi standard non polar33892256
Diphenhydramine N-glucuronide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)C([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)O[C@H](C(=O)O)[C@H]1O3413.3Semi standard non polar33892256
Diphenhydramine N-glucuronide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1C([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)O[C@H](C(=O)O)[C@@H](O)[C@@H]1O3464.4Semi standard non polar33892256
Diphenhydramine N-glucuronide,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H]1OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O3449.0Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H]1OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3587.1Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O3569.9Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C3538.4Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)O[C@H](C(=O)O)[C@H]1O3563.1Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@H]1OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3565.2Semi standard non polar33892256
Diphenhydramine N-glucuronide,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)[C@H]1OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O3598.3Semi standard non polar33892256
Diphenhydramine N-glucuronide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H]1OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3724.6Semi standard non polar33892256
Diphenhydramine N-glucuronide,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H]1OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3717.9Semi standard non polar33892256
Diphenhydramine N-glucuronide,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)O[C@H](C(=O)O)[C@H]1O[Si](C)(C)C(C)(C)C3713.5Semi standard non polar33892256
Diphenhydramine N-glucuronide,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H]1OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3722.8Semi standard non polar33892256
Diphenhydramine N-glucuronide,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H]1OC([N+](C)(C)CCOC(C2=CC=CC=C2)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3875.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Diphenhydramine N-glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lei-6892100000-012c4e647e33583d83042017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diphenhydramine N-glucuronide GC-MS (3 TMS) - 70eV, Positivesplash10-0f89-3894034000-ae320ceef91cf17db0732017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diphenhydramine N-glucuronide 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 - Diphenhydramine N-glucuronide 10V, Positive-QTOFsplash10-0a59-0090800000-59446547e3397a43adb12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenhydramine N-glucuronide 20V, Positive-QTOFsplash10-0a4i-2190000000-1c30de8d6f82b8d8791a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenhydramine N-glucuronide 40V, Positive-QTOFsplash10-0600-7960000000-a7216de64e21182b177b2017-10-06Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769988
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