Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-12 02:12:49 UTC |
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Update Date | 2022-03-07 02:56:40 UTC |
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HMDB ID | HMDB0040651 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Gibberellin A91 |
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Description | Gibberellin A91 (GA91) belongs to the class of organic compounds known as C19-gibberellin 6-carboxylic acids. These are C19-gibberellins with a carboxyl group at the 6-position. Gibberellin A91 is found in cereals and cereal products. Gibberellin A91 is a constituent of Triticum aestivum (wheat). |
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Structure | [H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@@]3(C)C[C@@H](O)[C@@H](O)[C@@]21OC3=O InChI=1S/C19H24O7/c1-8-5-17-7-18(8,25)4-3-10(17)19-12(11(17)14(22)23)16(2,15(24)26-19)6-9(20)13(19)21/h9-13,20-21,25H,1,3-7H2,2H3,(H,22,23)/t9-,10-,11-,12-,13-,16-,17+,18+,19-/m1/s1 |
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Synonyms | Value | Source |
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GA91 | HMDB | Gibberellin A91 | HMDB |
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Chemical Formula | C19H24O7 |
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Average Molecular Weight | 364.394 |
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Monoisotopic Molecular Weight | 364.152203113 |
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IUPAC Name | (1R,2R,5S,8S,9S,10R,11R,13R,14R)-5,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid |
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Traditional Name | (1R,2R,5S,8S,9S,10R,11R,13R,14R)-5,13,14-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadecane-9-carboxylic acid |
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CAS Registry Number | 160965-01-5 |
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SMILES | [H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@@]3(C)C[C@@H](O)[C@@H](O)[C@@]21OC3=O |
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InChI Identifier | InChI=1S/C19H24O7/c1-8-5-17-7-18(8,25)4-3-10(17)19-12(11(17)14(22)23)16(2,15(24)26-19)6-9(20)13(19)21/h9-13,20-21,25H,1,3-7H2,2H3,(H,22,23)/t9-,10-,11-,12-,13-,16-,17+,18+,19-/m1/s1 |
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InChI Key | VDQMXBWLDLPSSR-VAIUBWJFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as c19-gibberellin 6-carboxylic acids. These are c19-gibberellins with a carboxyl group at the 6-position. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | C19-gibberellin 6-carboxylic acids |
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Alternative Parents | |
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Substituents | - 20-norgibberellane-6-carboxylic acid
- 2-hydroxy,20-norgibberellane
- Diterpene lactone
- Caprolactone
- Oxepane
- Dicarboxylic acid or derivatives
- Gamma butyrolactone
- Cyclic alcohol
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Secondary alcohol
- Lactone
- Carboxylic acid derivative
- Carboxylic acid
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- Alcohol
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | |
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Role | |
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Physical Properties |
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State | Solid |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Gibberellin A91,1TMS,isomer #1 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O)[C@H]2[C@@H]3C(=O)O | 2826.6 | Semi standard non polar | 33892256 | Gibberellin A91,1TMS,isomer #2 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C | 2764.5 | Semi standard non polar | 33892256 | Gibberellin A91,1TMS,isomer #3 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C)[C@H]1O)[C@H]2[C@@H]3C(=O)O | 2766.5 | Semi standard non polar | 33892256 | Gibberellin A91,1TMS,isomer #4 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O[Si](C)(C)C)[C@H]2[C@@H]3C(=O)O | 2795.4 | Semi standard non polar | 33892256 | Gibberellin A91,2TMS,isomer #1 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C)[C@H]1O)[C@H]2[C@@H]3C(=O)O | 2803.1 | Semi standard non polar | 33892256 | Gibberellin A91,2TMS,isomer #2 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O[Si](C)(C)C)[C@H]2[C@@H]3C(=O)O | 2826.2 | Semi standard non polar | 33892256 | Gibberellin A91,2TMS,isomer #3 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C | 2793.2 | Semi standard non polar | 33892256 | Gibberellin A91,2TMS,isomer #4 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C)[C@H]1O)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C | 2756.0 | Semi standard non polar | 33892256 | Gibberellin A91,2TMS,isomer #5 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O[Si](C)(C)C)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C | 2783.7 | Semi standard non polar | 33892256 | Gibberellin A91,2TMS,isomer #6 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)[C@H]2[C@@H]3C(=O)O | 2782.0 | Semi standard non polar | 33892256 | Gibberellin A91,3TMS,isomer #1 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)[C@H]2[C@@H]3C(=O)O | 2817.5 | Semi standard non polar | 33892256 | Gibberellin A91,3TMS,isomer #2 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C)[C@H]1O)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C | 2795.8 | Semi standard non polar | 33892256 | Gibberellin A91,3TMS,isomer #3 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O[Si](C)(C)C)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C | 2809.8 | Semi standard non polar | 33892256 | Gibberellin A91,3TMS,isomer #4 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C | 2794.6 | Semi standard non polar | 33892256 | Gibberellin A91,4TMS,isomer #1 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C | 2824.9 | Semi standard non polar | 33892256 | Gibberellin A91,1TBDMS,isomer #1 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O)[C@H]2[C@@H]3C(=O)O | 3044.2 | Semi standard non polar | 33892256 | Gibberellin A91,1TBDMS,isomer #2 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C | 2995.9 | Semi standard non polar | 33892256 | Gibberellin A91,1TBDMS,isomer #3 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)[C@H]2[C@@H]3C(=O)O | 2988.2 | Semi standard non polar | 33892256 | Gibberellin A91,1TBDMS,isomer #4 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C(=O)O | 3007.4 | Semi standard non polar | 33892256 | Gibberellin A91,2TBDMS,isomer #1 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)[C@H]2[C@@H]3C(=O)O | 3244.2 | Semi standard non polar | 33892256 | Gibberellin A91,2TBDMS,isomer #2 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C(=O)O | 3252.3 | Semi standard non polar | 33892256 | Gibberellin A91,2TBDMS,isomer #3 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C | 3241.4 | Semi standard non polar | 33892256 | Gibberellin A91,2TBDMS,isomer #4 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C | 3206.3 | Semi standard non polar | 33892256 | Gibberellin A91,2TBDMS,isomer #5 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C | 3222.2 | Semi standard non polar | 33892256 | Gibberellin A91,2TBDMS,isomer #6 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C(=O)O | 3208.1 | Semi standard non polar | 33892256 | Gibberellin A91,3TBDMS,isomer #1 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C(=O)O | 3454.7 | Semi standard non polar | 33892256 | Gibberellin A91,3TBDMS,isomer #2 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C | 3458.7 | Semi standard non polar | 33892256 | Gibberellin A91,3TBDMS,isomer #3 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C | 3467.1 | Semi standard non polar | 33892256 | Gibberellin A91,3TBDMS,isomer #4 | C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C | 3431.0 | Semi standard non polar | 33892256 | Gibberellin A91,4TBDMS,isomer #1 | C=C1C[C@]23C[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@]12OC(=O)[C@](C)(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C(=O)O[Si](C)(C)C(C)(C)C | 3659.1 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Gibberellin A91 GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gibberellin A91 10V, Negative-QTOF | splash10-03di-0009000000-cbbc9df830dd6d6ce0ea | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gibberellin A91 20V, Negative-QTOF | splash10-03di-0009000000-4cd6ef2b14d8b47b4d97 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gibberellin A91 40V, Negative-QTOF | splash10-0ik9-1009000000-ad00732289cb064c46e3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gibberellin A91 10V, Positive-QTOF | splash10-014i-0009000000-a4d1f65d0f9e29074439 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gibberellin A91 20V, Positive-QTOF | splash10-014i-0019000000-aed6a8b4015431bb6e8f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Gibberellin A91 40V, Positive-QTOF | splash10-00n3-0179000000-840037649ad7a8248465 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB020446 |
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KNApSAcK ID | C00000216 |
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Chemspider ID | 103884037 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 101675590 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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