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 19:36:23 UTC |
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Update Date | 2021-10-01 23:09:13 UTC |
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HMDB ID | HMDB0258272 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Shikimate-3-phosphate |
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Description | 4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Based on a literature review very few articles have been published on 4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Shikimate-3-phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Shikimate-3-phosphate is part of the human exposome. 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 | OC1CC(=CC(OP(O)(O)=O)C1O)C(O)=O InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14) |
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Synonyms | Value | Source |
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4,5-Dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylate | Generator | Shikimate-3-phosphate | MeSH, Generator | Shikimic acid-3-phosphoric acid | Generator |
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Chemical Formula | C7H11O8P |
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Average Molecular Weight | 254.1312 |
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Monoisotopic Molecular Weight | 254.01915384 |
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IUPAC Name | 4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid |
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Traditional Name | shikimate 3-phosphate |
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CAS Registry Number | Not Available |
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SMILES | OC1CC(=CC(OP(O)(O)=O)C1O)C(O)=O |
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InChI Identifier | InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14) |
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InChI Key | QYOJSKGCWNAKGW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic phosphoric acids and derivatives |
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Sub Class | Phosphate esters |
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Direct Parent | Monoalkyl phosphates |
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Alternative Parents | |
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Substituents | - Monoalkyl phosphate
- Cyclitol or derivatives
- Secondary alcohol
- 1,2-diol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic 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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Shikimate-3-phosphate,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1 | 2301.7 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1 | 2258.9 | Standard non polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1 | 2655.8 | Standard polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #2 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1 | 2293.4 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #2 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1 | 2335.5 | Standard non polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #2 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1 | 2766.2 | Standard polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #3 | C[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C1O[Si](C)(C)C | 2365.7 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #3 | C[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C1O[Si](C)(C)C | 2315.6 | Standard non polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #3 | C[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C1O[Si](C)(C)C | 2646.6 | Standard polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #4 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1 | 2329.7 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #4 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1 | 2316.5 | Standard non polar | 33892256 | Shikimate-3-phosphate,4TMS,isomer #4 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1 | 2636.5 | Standard polar | 33892256 | Shikimate-3-phosphate,5TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1 | 2318.5 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,5TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1 | 2353.9 | Standard non polar | 33892256 | Shikimate-3-phosphate,5TMS,isomer #1 | C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1 | 2481.8 | Standard polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1 | 3130.9 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1 | 2978.4 | Standard non polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1 | 2988.5 | Standard polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1 | 3119.1 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1 | 3029.5 | Standard non polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1 | 3094.1 | Standard polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 3207.6 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 3036.3 | Standard non polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 2995.4 | Standard polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1 | 3168.2 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1 | 2998.4 | Standard non polar | 33892256 | Shikimate-3-phosphate,4TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1 | 2975.5 | Standard polar | 33892256 | Shikimate-3-phosphate,5TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1 | 3292.0 | Semi standard non polar | 33892256 | Shikimate-3-phosphate,5TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1 | 3165.0 | Standard non polar | 33892256 | Shikimate-3-phosphate,5TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1 | 2937.7 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Shikimate-3-phosphate GC-MS (5 TMS) | splash10-0w34-2982100000-7a121ca2be86ffd45cae | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9430000000-6f27ce1e9eabc07dd402 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_7) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_5) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_6) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_7) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
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