Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2018-10-12 16:05:50 UTC |
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Update Date | 2022-03-07 03:18:15 UTC |
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HMDB ID | HMDB0240294 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 2-O-Methylascorbic acid |
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Description | 2-O-Methylascorbic acid (2-O-MA) is a derivative of vitamin C (ascorbic acid). The enzyme catechol-O-methyltransferase catalyzes the methylation of L-ascorbic acid into 2-O-methylascorbic acid (PMID: 7129800 ). 2-O-Methylascorbic acid belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 2-O-Methylascorbic acid has been identified in urine and was found to be higher in older women than in younger women (PMID: 28813537 ). |
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Structure | [H][C@@]1(OC(=O)C(OC)=C1O)[C@@H](O)CO InChI=1S/C7H10O6/c1-12-6-4(10)5(3(9)2-8)13-7(6)11/h3,5,8-10H,2H2,1H3/t3-,5+/m0/s1 |
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Synonyms | Value | Source |
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2-O-Methylascorbate | Generator | 2-O-Methyl-L-ascorbic acid | HMDB | 2-Methyl-L-ascorbic acid | HMDB | 2-Methylascorbic acid | HMDB | 2-O-MA | HMDB | 2-O-Methylascorbic acid | HMDB |
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Chemical Formula | C7H10O6 |
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Average Molecular Weight | 190.151 |
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Monoisotopic Molecular Weight | 190.047738042 |
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IUPAC Name | (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-3-methoxy-2,5-dihydrofuran-2-one |
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Traditional Name | (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-3-methoxy-5H-furan-2-one |
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CAS Registry Number | 17860-87-6 |
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SMILES | [H][C@@]1(OC(=O)C(OC)=C1O)[C@@H](O)CO |
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InChI Identifier | InChI=1S/C7H10O6/c1-12-6-4(10)5(3(9)2-8)13-7(6)11/h3,5,8-10H,2H2,1H3/t3-,5+/m0/s1 |
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InChI Key | JBXPKMHATRSERD-WVZVXSGGSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Dihydrofurans |
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Sub Class | Furanones |
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Direct Parent | Butenolides |
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Alternative Parents | |
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Substituents | - 2-furanone
- Vinylogous acid
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- 1,2-diol
- Secondary alcohol
- Carboxylic acid ester
- Lactone
- Carboxylic acid derivative
- Oxacycle
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Organooxygen compound
- Primary alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic 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 SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 142.756 | 30932474 | DeepCCS | [M-H]- | 140.586 | 30932474 | DeepCCS | [M-2H]- | 174.109 | 30932474 | DeepCCS | [M+Na]+ | 148.668 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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2-O-Methylascorbic acid,1TMS,isomer #1 | COC1=C(O[Si](C)(C)C)[C@@H]([C@@H](O)CO)OC1=O | 1637.3 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,1TMS,isomer #2 | COC1=C(O)[C@@H]([C@H](CO)O[Si](C)(C)C)OC1=O | 1641.9 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,1TMS,isomer #3 | COC1=C(O)[C@@H]([C@@H](O)CO[Si](C)(C)C)OC1=O | 1616.0 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,2TMS,isomer #1 | COC1=C(O[Si](C)(C)C)[C@@H]([C@H](CO)O[Si](C)(C)C)OC1=O | 1757.5 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,2TMS,isomer #2 | COC1=C(O[Si](C)(C)C)[C@@H]([C@@H](O)CO[Si](C)(C)C)OC1=O | 1738.1 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,2TMS,isomer #3 | COC1=C(O)[C@@H]([C@H](CO[Si](C)(C)C)O[Si](C)(C)C)OC1=O | 1700.7 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,3TMS,isomer #1 | COC1=C(O[Si](C)(C)C)[C@@H]([C@H](CO[Si](C)(C)C)O[Si](C)(C)C)OC1=O | 1852.2 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,1TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)[C@@H]([C@@H](O)CO)OC1=O | 1891.5 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,1TBDMS,isomer #2 | COC1=C(O)[C@@H]([C@H](CO)O[Si](C)(C)C(C)(C)C)OC1=O | 1883.6 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,1TBDMS,isomer #3 | COC1=C(O)[C@@H]([C@@H](O)CO[Si](C)(C)C(C)(C)C)OC1=O | 1870.6 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,2TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)[C@@H]([C@H](CO)O[Si](C)(C)C(C)(C)C)OC1=O | 2213.5 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,2TBDMS,isomer #2 | COC1=C(O[Si](C)(C)C(C)(C)C)[C@@H]([C@@H](O)CO[Si](C)(C)C(C)(C)C)OC1=O | 2199.6 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,2TBDMS,isomer #3 | COC1=C(O)[C@@H]([C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC1=O | 2160.7 | Semi standard non polar | 33892256 | 2-O-Methylascorbic acid,3TBDMS,isomer #1 | COC1=C(O[Si](C)(C)C(C)(C)C)[C@@H]([C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC1=O | 2503.9 | Semi standard non polar | 33892256 |
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Spectra |
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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 - 2-O-Methylascorbic acid 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 - 2-O-Methylascorbic acid 10V, Positive-QTOF | splash10-006x-1900000000-5d8fc1cafdc45c3e80b6 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 20V, Positive-QTOF | splash10-06xx-6900000000-95e8dc3e4e0cfe00ab96 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 40V, Positive-QTOF | splash10-0a4i-9000000000-3a4affc68cde303d900b | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 10V, Negative-QTOF | splash10-052r-2900000000-0be23e09dcae5ca23f80 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 20V, Negative-QTOF | splash10-0bti-5900000000-dab16c5297ce5d715361 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 40V, Negative-QTOF | splash10-06r6-9200000000-9a7a210afc02b6a045f4 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 10V, Negative-QTOF | splash10-002r-1900000000-3163b171e9011ac159e2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 20V, Negative-QTOF | splash10-0a4i-9000000000-2051e8e9a090b7531c16 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 40V, Negative-QTOF | splash10-0006-9000000000-9cfd9352b7342a5822f9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 10V, Positive-QTOF | splash10-006x-4900000000-f97828be1a706909a163 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 20V, Positive-QTOF | splash10-0006-9500000000-0fa2bb5d689b3e40c2da | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-O-Methylascorbic acid 40V, Positive-QTOF | splash10-006w-9200000000-1855698902d2d4faed12 | 2021-09-22 | 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) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 24688154 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 54726398 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Bowers-Komro DM, McCormick DB, King GA, Sweeny JG, Iacobucci GA: Confirmation of 2-O-methyl ascorbic acid as the product from the enzymatic methylation of L-ascorbic acid by catechol-O-methyltransferase. Int J Vitam Nutr Res. 1982;52(2):186-93. [PubMed:7129800 ]
- Rist MJ, Roth A, Frommherz L, Weinert CH, Kruger R, Merz B, Bunzel D, Mack C, Egert B, Bub A, Gorling B, Tzvetkova P, Luy B, Hoffmann I, Kulling SE, Watzl B: Metabolite patterns predicting sex and age in participants of the Karlsruhe Metabolomics and Nutrition (KarMeN) study. PLoS One. 2017 Aug 16;12(8):e0183228. doi: 10.1371/journal.pone.0183228. eCollection 2017. [PubMed:28813537 ]
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