Record Information |
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Version | 2.0 |
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Created at | 2022-04-28 19:03:30 UTC |
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Updated at | 2022-04-28 19:03:30 UTC |
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NP-MRD ID | NP0073835 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (-)-Bacobitacin A |
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Description | (3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. (-)-Bacobitacin A is found in Bacopa monnieri . Based on a literature review very few articles have been published on (3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate. |
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Structure | CC(=O)OC(C)(C)\C=C\C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3[C@H](O)C=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C InChI=1S/C32H44O9/c1-16(33)41-27(2,3)11-10-22(37)32(9,40)25-21(36)14-29(6)24-19(34)12-17-18(13-20(35)26(39)28(17,4)5)31(24,8)23(38)15-30(25,29)7/h10-13,18-19,21,24-25,34-36,40H,14-15H2,1-9H3/b11-10+/t18-,19-,21-,24+,25+,29+,30-,31-,32+/m1/s1 |
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Synonyms | Value | Source |
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(3E,6R)-6-Hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0,.0,]heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetic acid | Generator |
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Chemical Formula | C32H44O9 |
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Average Mass | 572.6950 Da |
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Monoisotopic Mass | 572.29853 Da |
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IUPAC Name | (3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate |
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Traditional Name | (3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)OC(C)(C)\C=C\C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3[C@H](O)C=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C |
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InChI Identifier | InChI=1S/C32H44O9/c1-16(33)41-27(2,3)11-10-22(37)32(9,40)25-21(36)14-29(6)24-19(34)12-17-18(13-20(35)26(39)28(17,4)5)31(24,8)23(38)15-30(25,29)7/h10-13,18-19,21,24-25,34-36,40H,14-15H2,1-9H3/b11-10+/t18-,19-,21-,24+,25+,29+,30-,31-,32+/m1/s1 |
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InChI Key | SGUCHYFOTGXDTG-DOFUNFASSA-N |
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Experimental Spectra |
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| Not Available |
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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 |
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Chemical Shift Submissions |
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| Not Available |
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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 cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Cucurbitacins |
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Direct Parent | Cucurbitacins |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Cucurbitacin skeleton
- 22-oxosteroid
- 21-oxosteroid
- Steroid ester
- 20-hydroxysteroid
- 14-alpha-methylsteroid
- 7-hydroxysteroid
- 16-hydroxysteroid
- 16-alpha-hydroxysteroid
- Oxosteroid
- 11-oxosteroid
- Hydroxysteroid
- 2-hydroxysteroid
- 3-oxosteroid
- 3-oxo-delta-1-steroid
- Delta-1-steroid
- Cyclohexenone
- Acyloin
- Alpha,beta-unsaturated ketone
- Tertiary alcohol
- Enone
- Cyclic alcohol
- Alpha-hydroxy ketone
- Acryloyl-group
- Cyclic ketone
- Secondary alcohol
- Ketone
- Carboxylic acid ester
- Polyol
- Monocarboxylic acid or derivatives
- Enol
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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