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 16:18:10 UTC |
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Update Date | 2019-07-23 07:15:46 UTC |
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HMDB ID | HMDB0061099 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5-hydroxy saxagliptin |
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Description | 5-hydroxy saxagliptin is a metabolite of saxagliptin. Saxagliptin, previously identified as BMS-477118, is a new oral hypoglycemic of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. Early development was solely by Bristol-Myers Squibb; in 2007 AstraZeneca joined with Bristol-Myers Squibb to co-develop the final compound and collaborate on the marketing of the drug. A New Drug Application for saxagliptin in the treatment of type 2 diabetes was submitted to the FDA in June 2008. (Wikipedia) |
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Structure | [H]C12CC3(O)CC(O)(C1)CC(C2)(C3)[C@H](N)C(=O)N1[C@@H]2C[C@@H]2C[C@@H]1C#N InChI=1S/C18H25N3O3/c19-6-12-1-11-2-13(11)21(12)15(22)14(20)16-3-10-4-17(23,7-16)9-18(24,5-10)8-16/h10-14,23-24H,1-5,7-9,20H2/t10?,11-,12+,13+,14+,16?,17?,18?/m0/s1 |
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Synonyms | Value | Source |
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5-Hydroxysaxagliptin | MeSH |
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Chemical Formula | C18H25N3O3 |
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Average Molecular Weight | 331.4094 |
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Monoisotopic Molecular Weight | 331.189591681 |
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IUPAC Name | (1R,3R,5R)-2-[(2S)-2-amino-2-(3,5-dihydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile |
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Traditional Name | (1R,3R,5R)-2-[(2S)-2-amino-2-(3,5-dihydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile |
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CAS Registry Number | Not Available |
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SMILES | [H]C12CC3(O)CC(O)(C1)CC(C2)(C3)[C@H](N)C(=O)N1[C@@H]2C[C@@H]2C[C@@H]1C#N |
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InChI Identifier | InChI=1S/C18H25N3O3/c19-6-12-1-11-2-13(11)21(12)15(22)14(20)16-3-10-4-17(23,7-16)9-18(24,5-10)8-16/h10-14,23-24H,1-5,7-9,20H2/t10?,11-,12+,13+,14+,16?,17?,18?/m0/s1 |
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InChI Key | GAWUJFVQGSLSSZ-HREDRMPBSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. |
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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 | Alpha amino acid amides |
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Alternative Parents | |
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Substituents | - Alpha-amino acid amide
- N-acyl-piperidine
- N-acylpyrrolidine
- Piperidine
- Cyclic alcohol
- Pyrrolidine
- Tertiary carboxylic acid amide
- Tertiary alcohol
- Carboxamide group
- Carbonitrile
- Nitrile
- Azacycle
- Organoheterocyclic compound
- Organonitrogen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Primary aliphatic amine
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Organic nitrogen compound
- Primary amine
- Amine
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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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5-hydroxy saxagliptin,1TMS,isomer #1 | C[Si](C)(C)OC12CC3CC(O)(C1)CC([C@H](N)C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)(C3)C2 | 2727.8 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,1TMS,isomer #2 | C[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O)(CC(O)(C3)C1)C2 | 2839.9 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,2TMS,isomer #1 | C[Si](C)(C)OC12CC3CC(O[Si](C)(C)C)(C1)CC([C@H](N)C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)(C3)C2 | 2701.1 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,2TMS,isomer #2 | C[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O)(CC(O[Si](C)(C)C)(C3)C1)C2 | 2716.4 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,2TMS,isomer #3 | C[Si](C)(C)N([C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O)(CC(O)(C3)C1)C2)[Si](C)(C)C | 2962.6 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,3TMS,isomer #1 | C[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O[Si](C)(C)C)(CC(O[Si](C)(C)C)(C3)C1)C2 | 2700.6 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,3TMS,isomer #1 | C[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O[Si](C)(C)C)(CC(O[Si](C)(C)C)(C3)C1)C2 | 2905.2 | Standard non polar | 33892256 | 5-hydroxy saxagliptin,3TMS,isomer #1 | C[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O[Si](C)(C)C)(CC(O[Si](C)(C)C)(C3)C1)C2 | 3899.4 | Standard polar | 33892256 | 5-hydroxy saxagliptin,3TMS,isomer #2 | C[Si](C)(C)OC12CC3CC(O)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2 | 2867.6 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,3TMS,isomer #2 | C[Si](C)(C)OC12CC3CC(O)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2 | 3024.5 | Standard non polar | 33892256 | 5-hydroxy saxagliptin,3TMS,isomer #2 | C[Si](C)(C)OC12CC3CC(O)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2 | 3898.0 | Standard polar | 33892256 | 5-hydroxy saxagliptin,4TMS,isomer #1 | C[Si](C)(C)OC12CC3CC(O[Si](C)(C)C)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2 | 2868.6 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,4TMS,isomer #1 | C[Si](C)(C)OC12CC3CC(O[Si](C)(C)C)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2 | 2978.1 | Standard non polar | 33892256 | 5-hydroxy saxagliptin,4TMS,isomer #1 | C[Si](C)(C)OC12CC3CC(O[Si](C)(C)C)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2 | 3714.6 | Standard polar | 33892256 | 5-hydroxy saxagliptin,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC12CC3CC(O)(C1)CC([C@H](N)C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)(C3)C2 | 2963.3 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O)(CC(O)(C3)C1)C2 | 3074.7 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC12CC3CC(O[Si](C)(C)C(C)(C)C)(C1)CC([C@H](N)C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)(C3)C2 | 3171.0 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O)(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2 | 3181.7 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N([C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O)(CC(O)(C3)C1)C2)[Si](C)(C)C(C)(C)C | 3385.4 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O[Si](C)(C)C(C)(C)C)(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2 | 3381.9 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O[Si](C)(C)C(C)(C)C)(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2 | 3469.6 | Standard non polar | 33892256 | 5-hydroxy saxagliptin,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@@H](C#N)C[C@H]2C[C@H]21)C12CC3CC(O[Si](C)(C)C(C)(C)C)(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2 | 3983.4 | Standard polar | 33892256 | 5-hydroxy saxagliptin,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC12CC3CC(O)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2 | 3541.0 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC12CC3CC(O)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2 | 3591.0 | Standard non polar | 33892256 | 5-hydroxy saxagliptin,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC12CC3CC(O)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2 | 4023.8 | Standard polar | 33892256 | 5-hydroxy saxagliptin,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC12CC3CC(O[Si](C)(C)C(C)(C)C)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2 | 3787.9 | Semi standard non polar | 33892256 | 5-hydroxy saxagliptin,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC12CC3CC(O[Si](C)(C)C(C)(C)C)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2 | 3652.0 | Standard non polar | 33892256 | 5-hydroxy saxagliptin,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC12CC3CC(O[Si](C)(C)C(C)(C)C)(C1)CC([C@@H](C(=O)N1[C@@H](C#N)C[C@H]4C[C@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2 | 3825.3 | Standard 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 - 5-hydroxy saxagliptin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0faa-6900000000-fa9bd810e62ae76bfc89 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-hydroxy saxagliptin GC-MS (2 TMS) - 70eV, Positive | splash10-0f7c-9404000000-71aeb1ba2e89719be3af | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-hydroxy saxagliptin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-hydroxy saxagliptin 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 - 5-hydroxy saxagliptin 10V, Positive-QTOF | splash10-01qa-0229000000-687ba63be8245c7dfe7a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 20V, Positive-QTOF | splash10-004j-1912000000-cab6d4388d5d533a9957 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 40V, Positive-QTOF | splash10-004i-2900000000-2d4121387d4254ed68a9 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 10V, Negative-QTOF | splash10-001i-0009000000-e0048abf0d034075981f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 20V, Negative-QTOF | splash10-0bu0-0916000000-4a3299d49b29b83d3acf | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 40V, Negative-QTOF | splash10-0aou-7900000000-4b6960eb8f8304978ff0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 10V, Negative-QTOF | splash10-001i-0009000000-0c64c0293ac2bef0dff4 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 20V, Negative-QTOF | splash10-0bu0-0918000000-dbfbde2e7052b6c5c3d9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 40V, Negative-QTOF | splash10-0a4i-5954000000-870163506c4ad3fee304 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 10V, Positive-QTOF | splash10-001i-0309000000-bd3a7173d2981ce30c73 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 20V, Positive-QTOF | splash10-0fsi-0913000000-65c1e3bc92f468af0cc9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-hydroxy saxagliptin 40V, Positive-QTOF | splash10-0a5c-4900000000-9dbd3cbb79fa4af418b0 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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 | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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