Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 16:18:44 UTC |
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Update Date | 2022-09-22 17:44:26 UTC |
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HMDB ID | HMDB0256055 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | p-Phenylenediamine |
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Description | p-Phenylenediamine, also known as 1,4-phenylenediamine, PPD or 1,4-diaminobenzene, belongs to the class of organic compounds known as anilines and substituted anilines. These are organic compounds containing an aminobenzene moiety. PPD exists as a white solid, but samples can darken due to air oxidation. Because of its ability to oxidize readily, derivatives of PPD are often used as antiozonants in the production of rubber products. PPD is mainly used as a component of engineering polymers and plastic composites such as kevlar. PPD is also the main ingredient in permanent hair dye formulations (PMID: 24628345 ). When applied to hair, it undergoes oxidation and turns hair into a dark colour which doesn't fade over time. In the USA, one in every three women use PPD containing hair dyes and the chemical is present in more than 1000 hair dye formulations marketed across the globe. PPD is also occasionally used as a substitute for henna for temporary tattoos. Its usage as a tattoo dye can lead to severe contact dermatitis. The CDC lists PPD as being a contact allergen. It can cause reactions ranging from mild skin irritation to more severe allergic contact dermatitis (PMID: 28176912 ). Some sensitive individuals may also experience skin inflammation and eczema and in severe cases, there may also be marked reddening and swelling on the scalp and face (PMID: 24628345 ). Exposure routes are through inhalation, skin absorption, ingestion, and skin and/or eye contact. Symptoms of exposure to PPD include throat irritation (pharynx and larynx), bronchial asthma, and sensitization dermatitis. PPD is also used as a histological stain for phospholipids (PMID: 27770109 ). PPD has been identified in human blood as reported by (PMID: 31557052 ). PPD is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically, PPD is part of the human exposome (PMID: 16103423 ). The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | InChI=1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2 |
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Synonyms | Value | Source |
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1,4-Benzenediamine | ChEBI | 1,4-Diaminobenzene | ChEBI | 4-Aminoaniline | ChEBI | 4-Phenylenediamine | ChEBI | p-Diaminobenzene | ChEBI | p-Phenylenediamine | ChEBI | p-Phenylenediamine base | ChEBI | Para-phenylenediamine | ChEBI | Paraphenylene-diamine | ChEBI | PPD | ChEBI | PPDA | ChEBI | 1,4-Phenyldiamine | MeSH | 1,4-Phenylenediamine | MeSH | 4-Phenylenediamine bromide, ion(1+) | MeSH | 4-Phenylenediamine dihydrochloride | MeSH | 4-Phenylenediamine diperchlorate | MeSH | 4-Phenylenediamine ion (1+) | MeSH | 4-Phenylenediamine monohydrobromide | MeSH | 4-Phenylenediamine monohydrochloride | MeSH | 4-Phenylenediamine monohydroiodide | MeSH | 4-Phenylenediamine monooxalate | MeSH | 4-Phenylenediamine monoperchlorate | MeSH | 4-Phenylenediamine monosulfate | MeSH | 4-Phenylenediamine sulfate | MeSH | Ursol-D | MeSH | Black henna | MeSH | Paraphenylenediamine | MeSH |
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Chemical Formula | C6H8N2 |
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Average Molecular Weight | 108.144 |
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Monoisotopic Molecular Weight | 108.068748266 |
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IUPAC Name | benzene-1,4-diamine |
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Traditional Name | p-phenylenediamine |
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CAS Registry Number | Not Available |
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SMILES | NC1=CC=C(N)C=C1 |
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InChI Identifier | InChI=1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2 |
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InChI Key | CBCKQZAAMUWICA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Aniline and substituted anilines |
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Direct Parent | Aniline and substituted anilines |
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Alternative Parents | |
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Substituents | - Aniline or substituted anilines
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | |
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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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p-Phenylenediamine,1TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(N)C=C1 | 1545.3 | Semi standard non polar | 33892256 | p-Phenylenediamine,1TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(N)C=C1 | 1518.5 | Standard non polar | 33892256 | p-Phenylenediamine,1TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(N)C=C1 | 2000.7 | Standard polar | 33892256 | p-Phenylenediamine,2TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(N[Si](C)(C)C)C=C1 | 1711.7 | Semi standard non polar | 33892256 | p-Phenylenediamine,2TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(N[Si](C)(C)C)C=C1 | 1708.6 | Standard non polar | 33892256 | p-Phenylenediamine,2TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(N[Si](C)(C)C)C=C1 | 1695.0 | Standard polar | 33892256 | p-Phenylenediamine,2TMS,isomer #2 | C[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C | 1635.7 | Semi standard non polar | 33892256 | p-Phenylenediamine,2TMS,isomer #2 | C[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C | 1653.6 | Standard non polar | 33892256 | p-Phenylenediamine,2TMS,isomer #2 | C[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C | 1930.3 | Standard polar | 33892256 | p-Phenylenediamine,3TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1 | 1725.4 | Semi standard non polar | 33892256 | p-Phenylenediamine,3TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1 | 1735.3 | Standard non polar | 33892256 | p-Phenylenediamine,3TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1 | 1684.4 | Standard polar | 33892256 | p-Phenylenediamine,4TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C | 1828.9 | Semi standard non polar | 33892256 | p-Phenylenediamine,4TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C | 1848.3 | Standard non polar | 33892256 | p-Phenylenediamine,4TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C | 1600.0 | Standard polar | 33892256 | p-Phenylenediamine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(N)C=C1 | 1727.4 | Semi standard non polar | 33892256 | p-Phenylenediamine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(N)C=C1 | 1698.7 | Standard non polar | 33892256 | p-Phenylenediamine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(N)C=C1 | 2115.9 | Standard polar | 33892256 | p-Phenylenediamine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1 | 2188.6 | Semi standard non polar | 33892256 | p-Phenylenediamine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1 | 2070.6 | Standard non polar | 33892256 | p-Phenylenediamine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1 | 1951.5 | Standard polar | 33892256 | p-Phenylenediamine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C(C)(C)C | 2044.8 | Semi standard non polar | 33892256 | p-Phenylenediamine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C(C)(C)C | 2069.0 | Standard non polar | 33892256 | p-Phenylenediamine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C(C)(C)C | 2054.4 | Standard polar | 33892256 | p-Phenylenediamine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1 | 2467.1 | Semi standard non polar | 33892256 | p-Phenylenediamine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1 | 2338.6 | Standard non polar | 33892256 | p-Phenylenediamine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1 | 2051.2 | Standard polar | 33892256 | p-Phenylenediamine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 2712.1 | Semi standard non polar | 33892256 | p-Phenylenediamine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 2625.2 | Standard non polar | 33892256 | p-Phenylenediamine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 2073.3 | 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 - p-Phenylenediamine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-3900000000-61081929d919d712e335 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - p-Phenylenediamine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-9800000000-e3b4bf12745fc30aecd9 | 2014-10-20 | Not Available | 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 - p-Phenylenediamine 45V, Positive-QTOF | splash10-0006-9000000000-34661e2d00632dd3d051 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 60V, Positive-QTOF | splash10-0a4i-2900000000-ac88e1845d9bf63df052 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 105V, Positive-QTOF | splash10-052f-9300000000-507544e80b10aab33534 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 120V, Positive-QTOF | splash10-05mo-9300000000-21ac15e6aeee18f1222c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 150V, Positive-QTOF | splash10-014l-9200000000-a703ee189bc526ca921d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 180V, Positive-QTOF | splash10-014i-9100000000-06e266af4900a62680ef | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 25V, Positive-QTOF | splash10-052f-9400000000-7219f4ee8ca59ed3ecc9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 35V, Positive-QTOF | splash10-0006-9000000000-1d60caf090423cc1094f | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 90V, Positive-QTOF | splash10-052f-9600000000-12dcc6e2ac4da25c3ebf | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 75V, Positive-QTOF | splash10-0a4l-6900000000-b333335a7099f9a8b5f3 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 30V, Positive-QTOF | splash10-0a4i-0900000000-2c9680b8af4e12a2acfa | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 45V, Positive-QTOF | splash10-0a4i-0900000000-e44a8b42a4a6fca2f034 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 65V, Positive-QTOF | splash10-0006-9000000000-772244a291b18534be3c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - p-Phenylenediamine 55V, Positive-QTOF | splash10-0006-9000000000-4fc045d75a788d609c72 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - p-Phenylenediamine 10V, Positive-QTOF | splash10-0a4i-0900000000-c85293167c3205295bd9 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - p-Phenylenediamine 20V, Positive-QTOF | splash10-0a4i-0900000000-a313caa7a5892d95b415 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - p-Phenylenediamine 40V, Positive-QTOF | splash10-0f89-9000000000-b84951cb869463c57c01 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - p-Phenylenediamine 10V, Negative-QTOF | splash10-0a4i-0900000000-7f020be8fb005e0dfc4c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - p-Phenylenediamine 20V, Negative-QTOF | splash10-0a4i-0900000000-7f020be8fb005e0dfc4c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - p-Phenylenediamine 40V, Negative-QTOF | splash10-0a4i-3900000000-2d74ca8488bb9547e780 | 2016-08-03 | 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) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum |
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