Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 18:29:37 UTC |
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Update Date | 2022-03-07 02:53:50 UTC |
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HMDB ID | HMDB0033734 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | DIBOA-Glc |
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Description | DIBOA-Glc belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. DIBOA-Glc has been detected, but not quantified in, several different foods, such as fats and oils, corns (Zea mays), cereals and cereal products, breakfast cereal, and ryes (Secale cereale). This could make diboa-GLC a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on DIBOA-Glc. |
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Structure | OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O)C1O InChI=1S/C14H17NO9/c16-5-8-9(17)10(18)11(19)13(23-8)24-14-12(20)15(21)6-3-1-2-4-7(6)22-14/h1-4,8-11,13-14,16-19,21H,5H2 |
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Synonyms | Value | Source |
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2-(2,4-Dihydroxy-1,4-benzoxazin-3-one)-beta-D-glucopyranose | HMDB | Diboa-glucoside | HMDB | GDIMBOA | HMDB | (2R)-2-O-beta-D-Glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one | MeSH, HMDB | DIBOA-GLC | MeSH |
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Chemical Formula | C14H17NO9 |
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Average Molecular Weight | 343.2861 |
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Monoisotopic Molecular Weight | 343.090331147 |
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IUPAC Name | 4-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1,4-benzoxazin-3-one |
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Traditional Name | 4-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-1,4-benzoxazin-3-one |
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CAS Registry Number | 155835-54-4 |
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SMILES | OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O)C1O |
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InChI Identifier | InChI=1S/C14H17NO9/c16-5-8-9(17)10(18)11(19)13(23-8)24-14-12(20)15(21)6-3-1-2-4-7(6)22-14/h1-4,8-11,13-14,16-19,21H,5H2 |
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InChI Key | OUSLYTBGQGKTME-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | O-glycosyl compounds |
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Alternative Parents | |
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Substituents | - Hexose monosaccharide
- Benzoxazinone
- O-glycosyl compound
- Benzomorpholine
- Benzoxazine
- Monosaccharide
- Benzenoid
- Oxane
- Oxazinane
- Hydroxamic acid
- Secondary alcohol
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- Organic nitrogen compound
- Organopnictogen compound
- Organonitrogen compound
- Primary alcohol
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 186.5 - 187 °C | 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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DIBOA-Glc,1TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O)C1O | 3021.0 | Semi standard non polar | 33892256 | DIBOA-Glc,1TMS,isomer #2 | C[Si](C)(C)OC1C(OC2OC3=CC=CC=C3N(O)C2=O)OC(CO)C(O)C1O | 2997.4 | Semi standard non polar | 33892256 | DIBOA-Glc,1TMS,isomer #3 | C[Si](C)(C)OC1C(O)C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C1O | 2974.0 | Semi standard non polar | 33892256 | DIBOA-Glc,1TMS,isomer #4 | C[Si](C)(C)OC1C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C1O | 2988.3 | Semi standard non polar | 33892256 | DIBOA-Glc,2TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C)C(O)C1O | 2947.3 | Semi standard non polar | 33892256 | DIBOA-Glc,2TMS,isomer #2 | C[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O[Si](C)(C)C)C1O | 2953.1 | Semi standard non polar | 33892256 | DIBOA-Glc,2TMS,isomer #3 | C[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O)C1O[Si](C)(C)C | 2949.4 | Semi standard non polar | 33892256 | DIBOA-Glc,2TMS,isomer #4 | C[Si](C)(C)OC1C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C)C1O | 2946.7 | Semi standard non polar | 33892256 | DIBOA-Glc,2TMS,isomer #5 | C[Si](C)(C)OC1C(OC2OC3=CC=CC=C3N(O)C2=O)OC(CO)C(O)C1O[Si](C)(C)C | 2940.8 | Semi standard non polar | 33892256 | DIBOA-Glc,2TMS,isomer #6 | C[Si](C)(C)OC1C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C1O[Si](C)(C)C | 2940.6 | Semi standard non polar | 33892256 | DIBOA-Glc,3TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O | 2887.1 | Semi standard non polar | 33892256 | DIBOA-Glc,3TMS,isomer #2 | C[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C | 2912.8 | Semi standard non polar | 33892256 | DIBOA-Glc,3TMS,isomer #3 | C[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2906.7 | Semi standard non polar | 33892256 | DIBOA-Glc,3TMS,isomer #4 | C[Si](C)(C)OC1C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2878.4 | Semi standard non polar | 33892256 | DIBOA-Glc,4TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 2848.2 | Semi standard non polar | 33892256 | DIBOA-Glc,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O)C1O | 3245.1 | Semi standard non polar | 33892256 | DIBOA-Glc,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1C(OC2OC3=CC=CC=C3N(O)C2=O)OC(CO)C(O)C1O | 3251.1 | Semi standard non polar | 33892256 | DIBOA-Glc,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1C(O)C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C1O | 3244.5 | Semi standard non polar | 33892256 | DIBOA-Glc,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C1O | 3243.0 | Semi standard non polar | 33892256 | DIBOA-Glc,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C(C)(C)C)C(O)C1O | 3425.9 | Semi standard non polar | 33892256 | DIBOA-Glc,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O[Si](C)(C)C(C)(C)C)C1O | 3428.9 | Semi standard non polar | 33892256 | DIBOA-Glc,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O)C1O[Si](C)(C)C(C)(C)C | 3427.5 | Semi standard non polar | 33892256 | DIBOA-Glc,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C(C)(C)C)C1O | 3427.9 | Semi standard non polar | 33892256 | DIBOA-Glc,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC1C(OC2OC3=CC=CC=C3N(O)C2=O)OC(CO)C(O)C1O[Si](C)(C)C(C)(C)C | 3435.7 | Semi standard non polar | 33892256 | DIBOA-Glc,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C1O[Si](C)(C)C(C)(C)C | 3432.4 | Semi standard non polar | 33892256 | DIBOA-Glc,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O | 3555.4 | Semi standard non polar | 33892256 | DIBOA-Glc,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C | 3578.0 | Semi standard non polar | 33892256 | DIBOA-Glc,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 3572.3 | Semi standard non polar | 33892256 | DIBOA-Glc,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 3537.5 | Semi standard non polar | 33892256 | DIBOA-Glc,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC2OC3=CC=CC=C3N(O)C2=O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 3689.5 | 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 - DIBOA-Glc GC-MS (Non-derivatized) - 70eV, Positive | splash10-01u0-6946000000-4db470e421d1976b04b3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - DIBOA-Glc GC-MS (4 TMS) - 70eV, Positive | splash10-014i-2311239000-e92109ed91edab73c0e9 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - DIBOA-Glc 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - DIBOA-Glc 6V, Negative-QTOF | splash10-001i-0901000000-0f053783b1fa72f42aa4 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 10V, Positive-QTOF | splash10-001i-0903000000-36cf1a8c33cdc2e98d21 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 20V, Positive-QTOF | splash10-01q9-2901000000-91283a704c6110ae6d10 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 40V, Positive-QTOF | splash10-005c-9400000000-d2500a036f2d1bf5d7c0 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 10V, Negative-QTOF | splash10-0ue9-0902000000-156c78001c48aba76c98 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 20V, Negative-QTOF | splash10-03l0-2901000000-3d4b1fc1238d21ceb03f | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 40V, Negative-QTOF | splash10-0a4i-9700000000-5d53d28c5ee389d7200b | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 10V, Positive-QTOF | splash10-0006-0009000000-c5b5835f594d6408a00e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 20V, Positive-QTOF | splash10-03e9-0900000000-9826151f81acc7c75a0c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 40V, Positive-QTOF | splash10-0ab9-3900000000-3cb0e5e4b0665aa0b2c7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 10V, Negative-QTOF | splash10-0006-0329000000-82ec45290ee4cadd56ec | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 20V, Negative-QTOF | splash10-03k9-1911000000-5c07f6fec42a9f01d34f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DIBOA-Glc 40V, Negative-QTOF | splash10-03k9-2900000000-606e5d0ad1b801e418a0 | 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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