Record Information |
---|
Version | 1.0 |
---|
Creation date | 2015-05-07 21:13:00 UTC |
---|
Update date | 2019-11-26 03:22:10 UTC |
---|
Primary ID | FDB031172 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | shikimate |
---|
Description | Shikimic acid, also known as shikimate or 3,4,5-trihydroxy-1-cyclohexenecarboxylic acid, is a member of the class of compounds known as shikimic acids and derivatves. Shikimic acids and derivatves are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. Shikimic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Shikimic acid can be found in a number of food items such as date, rocket salad, redcurrant, and poppy, which makes shikimic acid a potential biomarker for the consumption of these food products. Shikimic acid can be found primarily in blood and urine. Shikimic acid exists in all living species, ranging from bacteria to humans. Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum), from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later . |
---|
CAS Number | 138-59-0 |
---|
Structure | |
---|
Synonyms | |
---|
Predicted Properties | |
---|
Chemical Formula | C7H10O5 |
---|
IUPAC name | (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid |
---|
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 |
---|
InChI Key | JXOHGGNKMLTUBP-HSUXUTPPSA-N |
---|
Isomeric SMILES | O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O |
---|
Average Molecular Weight | 174.1513 |
---|
Monoisotopic Molecular Weight | 174.05282343 |
---|
Classification |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Alcohols and polyols |
---|
Direct Parent | Shikimic acids and derivatves |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aliphatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Physico-Chemical Properties |
---|
Physico-Chemical Properties - Experimental | |
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
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 |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
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 |
|
---|
NMR | Type | Description | | View |
---|
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 |
|
---|
External Links |
---|
ChemSpider ID | Not Available |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | Not Available |
---|
Pubchem Compound ID | Not Available |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | Not Available |
---|
CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | Not Available |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Not Available |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | |
---|