Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-09 16:05:56 UTC |
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Update Date | 2021-09-14 15:41:59 UTC |
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HMDB ID | HMDB0060897 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Diphenhydramine N-glucuronide |
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Description | Diphenhydramine 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) |
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Structure | 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=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 |
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Synonyms | Not Available |
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Chemical Formula | C23H30NO7 |
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Average Molecular Weight | 432.4868 |
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Monoisotopic Molecular Weight | 432.202227319 |
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IUPAC Name | (3R,4S,5S,6S)-6-carboxy-N-[2-(diphenylmethoxy)ethyl]-3,4,5-trihydroxy-N,N-dimethyloxan-2-aminium |
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Traditional Name | (3R,4S,5S,6S)-6-carboxy-N-[2-(diphenylmethoxy)ethyl]-3,4,5-trihydroxy-N,N-dimethyloxan-2-aminium |
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CAS Registry Number | Not Available |
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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 |
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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 |
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InChI Key | OAIGZXXQYIJBLR-VAUIJEFBSA-O |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | N-carbamoyl-alpha amino acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Diphenhydramine N-glucuronide,1TMS,isomer #1 | C[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 | 3235.1 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,1TMS,isomer #2 | C[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 | 3198.0 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,1TMS,isomer #3 | C[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)C | 3253.1 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,1TMS,isomer #4 | C[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 | 3215.8 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TMS,isomer #1 | C[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 | 3197.7 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TMS,isomer #2 | C[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 | 3169.1 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TMS,isomer #3 | C[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)C | 3191.9 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TMS,isomer #4 | C[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 | 3158.8 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TMS,isomer #5 | C[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)C | 3185.3 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TMS,isomer #6 | C[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)C | 3180.8 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,3TMS,isomer #1 | C[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 | 3184.3 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,3TMS,isomer #2 | C[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)C | 3180.2 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,3TMS,isomer #3 | C[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)C | 3189.6 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,3TMS,isomer #4 | C[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)C | 3176.0 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,4TMS,isomer #1 | C[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)C | 3224.3 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,1TBDMS,isomer #1 | CC(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 | 3424.5 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,1TBDMS,isomer #2 | CC(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]1O | 3413.3 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,1TBDMS,isomer #3 | CC(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]1O | 3464.4 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,1TBDMS,isomer #4 | CC(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 | 3449.0 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TBDMS,isomer #1 | CC(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)C | 3587.1 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TBDMS,isomer #2 | CC(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]1O | 3569.9 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TBDMS,isomer #3 | CC(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)C | 3538.4 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TBDMS,isomer #4 | CC(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 | 3563.1 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TBDMS,isomer #5 | CC(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 | 3565.2 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,2TBDMS,isomer #6 | CC(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 | 3598.3 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,3TBDMS,isomer #1 | CC(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)C | 3724.6 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,3TBDMS,isomer #2 | CC(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)C | 3717.9 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,3TBDMS,isomer #3 | CC(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)C | 3713.5 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,3TBDMS,isomer #4 | CC(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 | 3722.8 | Semi standard non polar | 33892256 | Diphenhydramine N-glucuronide,4TBDMS,isomer #1 | CC(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)C | 3875.7 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Diphenhydramine N-glucuronide GC-MS (Non-derivatized) - 70eV, Positive | splash10-0lei-6892100000-012c4e647e33583d8304 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diphenhydramine N-glucuronide GC-MS (3 TMS) - 70eV, Positive | splash10-0f89-3894034000-ae320ceef91cf17db073 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diphenhydramine N-glucuronide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diphenhydramine N-glucuronide 10V, Positive-QTOF | splash10-0a59-0090800000-59446547e3397a43adb1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diphenhydramine N-glucuronide 20V, Positive-QTOF | splash10-0a4i-2190000000-1c30de8d6f82b8d8791a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diphenhydramine N-glucuronide 40V, Positive-QTOF | splash10-0600-7960000000-a7216de64e21182b177b | 2017-10-06 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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