Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:06:02 UTC |
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Update date | 2020-09-17 15:40:48 UTC |
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Primary ID | FDB003991 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Shikimic acid |
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Description | Shikimic acid, also known as shikimate or acid, shikimic, belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). Shikimic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Shikimic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Shikimic acid has been detected, but not quantified in, several different foods, such as barley, macadamia nuts, nutmegs, winter squash, and borages. This could make shikimic acid a potential biomarker for the consumption of these foods. |
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CAS Number | 138-59-0 |
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Structure | |
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Synonyms | Synonym | Source |
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3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid | ChEBI | 3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acid | ChEBI | [3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid | ChEBI | L-Shikimic acid | ChEBI | Shikimate | ChEBI | 3,4,5-Trihydroxy-1-cyclohexenecarboxylate | Generator | 3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylate | Generator | 3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylic acid | Generator | 3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylate | Generator | 3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylate | Generator | 3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylic acid | Generator | [3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylate | Generator | [3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid | Generator | [3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylate | Generator | [3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate | Generator | [3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid | Generator | L-Shikimate | Generator | Acid, shikimic | MeSH | (-)-Shikimate | HMDB | (-)-Shikimic acid | HMDB | Skikimate | HMDB | Skikimic acid | HMDB | (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid | PhytoBank | (-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid | PhytoBank | Shikimic acid | PhytoBank | (3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-ene carboxylic acid | biospider | [3R-(3α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate | Generator | [3R-(3α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid | Generator | 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid | biospider | 3α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylate | Generator | 3α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylic acid | Generator |
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Predicted Properties | |
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Chemical Formula | C7H10O5 |
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IUPAC name | (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid |
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InChI Identifier | InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1 |
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InChI Key | JXOHGGNKMLTUBP-HSUXUTPPSA-N |
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Isomeric SMILES | O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O |
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Average Molecular Weight | 174.1513 |
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Monoisotopic Molecular Weight | 174.05282343 |
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Classification |
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Description | Belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. |
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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 | Alcohols and polyols |
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Direct Parent | Shikimic acids and derivatves |
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Alternative Parents | |
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Substituents | - Shikimic acid or derivatives
- Secondary alcohol
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | 186 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 150 mg/mL at 21 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Shikimic acid, 4 TMS, GC-MS Spectrum | splash10-0udj-0970000000-42465cd3f3e138b0bc12 | Spectrum | GC-MS | Shikimic acid, non-derivatized, GC-MS Spectrum | splash10-0udi-0790000000-1100443abb8605953f58 | Spectrum | GC-MS | Shikimic acid, 4 TMS, GC-MS Spectrum | splash10-00di-9450000000-e6ca954dc1a9c1cc4285 | Spectrum | GC-MS | Shikimic acid, 4 TMS, GC-MS Spectrum | splash10-0udi-0491000000-49993b9b18e12b9461fc | Spectrum | GC-MS | Shikimic acid, non-derivatized, GC-MS Spectrum | splash10-0udi-0391000000-ddb2c574233062a911fa | Spectrum | GC-MS | Shikimic acid, non-derivatized, GC-MS Spectrum | splash10-0udj-0970000000-42465cd3f3e138b0bc12 | Spectrum | GC-MS | Shikimic acid, non-derivatized, GC-MS Spectrum | splash10-0udi-0790000000-1100443abb8605953f58 | Spectrum | GC-MS | Shikimic acid, non-derivatized, GC-MS Spectrum | splash10-00di-9450000000-e6ca954dc1a9c1cc4285 | Spectrum | GC-MS | Shikimic acid, non-derivatized, GC-MS Spectrum | splash10-0udi-0491000000-49993b9b18e12b9461fc | Spectrum | Predicted GC-MS | Shikimic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-4900000000-817f1ed3feb4c763285f | Spectrum | Predicted GC-MS | Shikimic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0092-7119400000-67b0989b5019a72e1016 | Spectrum | Predicted GC-MS | Shikimic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-01b9-1900000000-fd80f5e7f51d927e8e15 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0a4i-9300000000-cf8a3148fd132540bf97 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0a4i-9000000000-ed28bc20ae43473043c9 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a4i-9000000000-65249fc24f2de4acf2c7 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4i-9000000000-26dfc876ae35c2cdb845 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-006x-9600000000-3a5ab91754d9d837d8b4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-01b9-1900000000-6cba5b9b7c4891522045 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9300000000-12d15a049b141a37f34e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-ed28bc20ae43473043c9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-9864f7359ffed65d6ef0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-26dfc876ae35c2cdb845 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-006x-9600000000-3a5ab91754d9d837d8b4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-00di-7900000000-d77a830354efe8731a42 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-01vx-9700000000-d2060c544171987e3dcd | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-01vx-9500000000-baa64c3938f3d039c6e4 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9000000000-d5821372fd8a830dc962 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00dl-9000000000-cb13aba83ba37150b931 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-01vo-9600000000-3433190ea61f16d92efd | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-022l-9600000000-60e85b9b59edb135e4c4 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-58e1775d1e013c416201 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-1f370d2806fd8245ebfb | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-01vx-9600000000-d502f575cada8c0b5aea | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-00dl-9400000000-d0ff38d5a290b8e8248d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0900000000-e6ca4ce5acb44dc23a74 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004r-9700000000-18afe769b0ef5ba3fbdb | 2012-07-25 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 8412 |
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ChEMBL ID | CHEMBL290345 |
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KEGG Compound ID | C00493 |
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Pubchem Compound ID | 8742 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16119 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB03070 |
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CRC / DFC (Dictionary of Food Compounds) ID | CTQ51-O:CTQ47-R |
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EAFUS ID | Not Available |
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Dr. Duke ID | SHIKIMIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001203 |
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HET ID | SKM |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Shikimic_acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti convulsant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti radicular | | | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | antitumor promoter | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | bruchifuge | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | carcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | ileorelaxant | | | DUKE | mutagenic | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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