Record Information |
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Version | 2.0 |
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Created at | 2021-06-21 00:44:13 UTC |
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Updated at | 2021-06-30 00:18:53 UTC |
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NP-MRD ID | NP0043285 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate |
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Provided By | JEOL Database |
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Description | 3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-tetradecahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position. (3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate is found in Aletris farinosa. It was first documented in 2013 (Challinor, V. L., et al.). Based on a literature review very few articles have been published on 3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-tetradecahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid. |
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Structure | [H]OC(=O)C([H])([H])C(=O)O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])C(=C(\[H])C(=O)OC([H])([H])[H])\C([H])([H])[H])[C@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]23[H])C1(C([H])([H])[H])C([H])([H])[H] InChI=1S/C29H46O7/c1-18(16-24(32)35-7)8-9-21-28(5)13-10-19-26(2,3)22(36-25(33)17-23(30)31)12-14-27(19,4)20(28)11-15-29(21,6)34/h16,19-22,34H,8-15,17H2,1-7H3,(H,30,31)/b18-16-/t19-,20+,21-,22+,27-,28+,29-/m0/s1 |
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Synonyms | Value | Source |
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3-{[(2R,4ar,4BR,7S,8S,8ar,10ar)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-tetradecahydrophenanthren-2-yl]oxy}-3-oxopropanoate | Generator |
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Chemical Formula | C29H46O7 |
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Average Mass | 506.6800 Da |
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Monoisotopic Mass | 506.32435 Da |
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IUPAC Name | 3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-tetradecahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid |
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Traditional Name | 3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-decahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]OC(=O)C([H])([H])C(=O)O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])C(=C(\[H])C(=O)OC([H])([H])[H])\C([H])([H])[H])[C@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]23[H])C1(C([H])([H])[H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C29H46O7/c1-18(16-24(32)35-7)8-9-21-28(5)13-10-19-26(2,3)22(36-25(33)17-23(30)31)12-14-27(19,4)20(28)11-15-29(21,6)34/h16,19-22,34H,8-15,17H2,1-7H3,(H,30,31)/b18-16-/t19-,20+,21-,22+,27-,28+,29-/m0/s1 |
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InChI Key | WZPRGXSKTPRFRQ-WSQSCVPOSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Species Name | Source | Reference |
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Aletris farinosa | JEOL database | - Challinor, V. L., et al, J. Nat. Prod. 76, 485 (2013)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-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 | Sesterterpenoids |
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Direct Parent | Cheilanthane sesterterpenoids |
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Alternative Parents | |
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Substituents | - Cheilanthane sesterterpenoid
- 13-hydroxysteroid
- Hydroxysteroid
- Steroid
- Hydrophenanthrene
- Phenanthrene
- Tricarboxylic acid or derivatives
- Fatty acid ester
- Fatty acyl
- 1,3-dicarbonyl compound
- Cyclic alcohol
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Methyl ester
- Tertiary alcohol
- Carboxylic acid ester
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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