| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:02:41 UTC |
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| Update Date | 2020-05-05 18:40:24 UTC |
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| BMDB ID | BMDB0003070 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common 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. Shikimic acid exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Shikimic acid. |
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| Structure | |
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| Synonyms | | Value | 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 |
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| Chemical Formula | C7H10O5 |
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| Average Molecular Weight | 174.1513 |
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| Monoisotopic Molecular Weight | 174.05282343 |
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| IUPAC Name | (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid |
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| Traditional Name | (-)-shikimate |
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| CAS Registry Number | 138-59-0 |
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| SMILES | O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O |
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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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| Chemical Taxonomy |
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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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| Status | Detected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 186 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 150 mg/mL at 21 °C | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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