Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-24 04:20:45 UTC |
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Update Date | 2021-09-24 04:20:45 UTC |
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HMDB ID | HMDB0303749 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 7-Epi-12-hydroxyjasmonic acid |
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Description | 7-epi-12-hydroxyjasmonic acid, also known as (+)-12-hydroxy-7-isojasmonate, is a member of the class of compounds known as jasmonic acids. Jasmonic acids are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. Thus, 7-epi-12-hydroxyjasmonic acid is considered to be an octadecanoid lipid molecule. 7-epi-12-hydroxyjasmonic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 7-epi-12-hydroxyjasmonic acid can be synthesized from (+)-7-isojasmonic acid. 7-epi-12-hydroxyjasmonic acid can also be synthesized into N-[(+)-12-hydroxy-7-isojasmonyl]-L-isoleucine and methyl tuberonate. 7-epi-12-hydroxyjasmonic acid can be found in potato, which makes 7-epi-12-hydroxyjasmonic acid a potential biomarker for the consumption of this food product. |
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Structure | OCC\C=C/C[C@H]1[C@@H](CC(O)=O)CCC1=O InChI=1S/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10+/m1/s1 |
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Synonyms | Value | Source |
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(+)-12-Hydroxy-7-isojasmonic acid | ChEBI | (1R,2S)-3-oxo-2-(5'-Hydroxy-2'z-pentenyl)-cyclopentaneacetic acid | ChEBI | 12-Hydroxy-epi-jasmonic acid | ChEBI | (+)-12-Hydroxy-7-isojasmonate | Generator | (1R,2S)-3-oxo-2-(5'-Hydroxy-2'z-pentenyl)-cyclopentaneacetate | Generator | 12-Hydroxy-epi-jasmonate | Generator | Tuberonate | Generator | 7-Epi-12-hydroxyjasmonate | Generator |
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Chemical Formula | C12H18O4 |
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Average Molecular Weight | 226.2689 |
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Monoisotopic Molecular Weight | 226.120509064 |
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IUPAC Name | 2-[(1R,2S)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid |
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Traditional Name | tuberonic acid |
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CAS Registry Number | Not Available |
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SMILES | OCC\C=C/C[C@H]1[C@@H](CC(O)=O)CCC1=O |
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InChI Identifier | InChI=1S/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10+/m1/s1 |
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InChI Key | RZGFUGXQKMEMOO-SZXTZRQCSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Lineolic acids and derivatives |
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Direct Parent | Jasmonic acids |
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Alternative Parents | |
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Substituents | - Jasmonic acid
- Fatty alcohol
- Cyclic ketone
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #1 | C[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C | 2116.7 | Semi standard non polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #1 | C[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C | 2191.6 | Standard non polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #1 | C[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C | 2213.9 | Standard polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #2 | C[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C | 2104.1 | Semi standard non polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #2 | C[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C | 2190.4 | Standard non polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #2 | C[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C | 2262.1 | Standard polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C | 2832.8 | Semi standard non polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C | 2739.0 | Standard non polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C | 2538.2 | Standard polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C | 2797.6 | Semi standard non polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C | 2590.8 | Standard non polar | 33892256 | 7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C | 2537.4 | Standard polar | 33892256 |
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