| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 16:51:02 UTC |
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| Updated at | 2022-04-28 16:51:02 UTC |
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| NP-MRD ID | NP0071468 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Machaerogenin |
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| Description | (1R,4S,5R,8R,10S,13R,14R,18S,20R,21S)-10-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-22-oxahexacyclo[19.2.1.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-16-en-23-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Machaerogenin is found in Machaerocereus eruca and Stenocereus eruca. Based on a literature review very few articles have been published on (1R,4S,5R,8R,10S,13R,14R,18S,20R,21S)-10-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-22-oxahexacyclo[19.2.1.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-16-en-23-one. |
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| Structure | C[C@]1(CO)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]22C[C@@H]1OC2=O InChI=1S/C30H46O4/c1-25(2)20-9-12-29(6)21(27(20,4)11-10-22(25)32)8-7-18-19-15-26(3,17-31)23-16-30(19,24(33)34-23)14-13-28(18,29)5/h7,19-23,31-32H,8-17H2,1-6H3/t19-,20-,21+,22-,23-,26+,27-,28+,29+,30+/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C30H46O4 |
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| Average Mass | 470.6940 Da |
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| Monoisotopic Mass | 470.33961 Da |
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| IUPAC Name | (1R,4S,5R,8R,10S,13R,14R,18S,20R,21S)-10-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-22-oxahexacyclo[19.2.1.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-16-en-23-one |
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| Traditional Name | (1R,4S,5R,8R,10S,13R,14R,18S,20R,21S)-10-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-22-oxahexacyclo[19.2.1.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-16-en-23-one |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@]1(CO)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]22C[C@@H]1OC2=O |
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| InChI Identifier | InChI=1S/C30H46O4/c1-25(2)20-9-12-29(6)21(27(20,4)11-10-22(25)32)8-7-18-19-15-26(3,17-31)23-16-30(19,24(33)34-23)14-13-28(18,29)5/h7,19-23,31-32H,8-17H2,1-6H3/t19-,20-,21+,22-,23-,26+,27-,28+,29+,30+/m0/s1 |
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| InChI Key | CHTCCKSXBYVSBJ-VXJFNEKYSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
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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 | Triterpenoids |
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| Direct Parent | Triterpenoids |
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| Alternative Parents | |
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| Substituents | - Triterpenoid
- Caprolactone
- Oxepane
- Gamma butyrolactone
- Tetrahydrofuran
- Cyclic alcohol
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic 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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