Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 19:03:41 UTC |
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Updated at | 2022-04-28 19:03:41 UTC |
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NP-MRD ID | NP0073838 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (-)-Bacobitacin D |
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Description | (3E,6R)-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-9,13-dihydroxy-4-{[(2S,3R,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. (-)-Bacobitacin D is found in Bacopa monnieri . It was first documented in 2022 (PMID: 35489815). Based on a literature review a significant number of articles have been published on (3E,6R)-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-9,13-dihydroxy-4-{[(2S,3R,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate (PMID: 35489814) (PMID: 35489813) (PMID: 35489812) (PMID: 35489811). |
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Structure | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](CO)O[C@H]2O[C@H]2CO[C@@H](OC3=C[C@@H]4C(=C[C@@H](O)[C@H]5[C@]6(C)C[C@@H](O)[C@H]([C@@](C)(O)C(=O)\C=C\C(C)(C)OC(C)=O)[C@@]6(C)CC(=O)[C@@]45C)C(C)(C)C3=O)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C54H80O25/c1-20-32(61)36(65)38(67)45(72-20)77-40-35(64)29(76-48-41(34(63)28(18-55)75-48)78-46-39(68)37(66)33(62)21(2)73-46)19-71-47(40)74-27-15-24-23(50(6,7)44(27)69)14-25(57)42-51(8)16-26(58)43(52(51,9)17-31(60)53(24,42)10)54(11,70)30(59)12-13-49(4,5)79-22(3)56/h12-15,20-21,24-26,28-29,32-43,45-48,55,57-58,61-68,70H,16-19H2,1-11H3/b13-12+/t20-,21-,24+,25+,26+,28-,29-,32-,33-,34-,35-,36+,37+,38+,39+,40+,41+,42-,43-,45-,46-,47-,48-,51-,52+,53+,54-/m0/s1 |
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Synonyms | Value | Source |
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(3E,6R)-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-9,13-Dihydroxy-4-{[(2S,3R,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0,.0,]heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetic acid | Generator |
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Chemical Formula | C54H80O25 |
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Average Mass | 1129.2090 Da |
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Monoisotopic Mass | 1128.49887 Da |
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IUPAC Name | (3E,6R)-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-9,13-dihydroxy-4-{[(2S,3R,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate |
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Traditional Name | (3E,6R)-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-9,13-dihydroxy-4-{[(2S,3R,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](CO)O[C@H]2O[C@H]2CO[C@@H](OC3=C[C@@H]4C(=C[C@@H](O)[C@H]5[C@]6(C)C[C@@H](O)[C@H]([C@@](C)(O)C(=O)\C=C\C(C)(C)OC(C)=O)[C@@]6(C)CC(=O)[C@@]45C)C(C)(C)C3=O)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C54H80O25/c1-20-32(61)36(65)38(67)45(72-20)77-40-35(64)29(76-48-41(34(63)28(18-55)75-48)78-46-39(68)37(66)33(62)21(2)73-46)19-71-47(40)74-27-15-24-23(50(6,7)44(27)69)14-25(57)42-51(8)16-26(58)43(52(51,9)17-31(60)53(24,42)10)54(11,70)30(59)12-13-49(4,5)79-22(3)56/h12-15,20-21,24-26,28-29,32-43,45-48,55,57-58,61-68,70H,16-19H2,1-11H3/b13-12+/t20-,21-,24+,25+,26+,28-,29-,32-,33-,34-,35-,36+,37+,38+,39+,40+,41+,42-,43-,45-,46-,47-,48-,51-,52+,53+,54-/m0/s1 |
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InChI Key | IFGSTKBYVZGKSH-JARDLGJNSA-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 cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. |
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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 | Steroidal glycosides |
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Direct Parent | Cucurbitacin glycosides |
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Alternative Parents | |
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Substituents | - Cucurbitacin glycoside skeleton
- Triterpenoid
- Cucurbitacin skeleton
- Oligosaccharide
- 22-oxosteroid
- 21-oxosteroid
- Steroid ester
- 20-hydroxysteroid
- 14-alpha-methylsteroid
- 7-hydroxysteroid
- 16-hydroxysteroid
- 16-alpha-hydroxysteroid
- Oxosteroid
- 11-oxosteroid
- Hydroxysteroid
- 3-oxosteroid
- 3-oxo-delta-1-steroid
- Delta-1-steroid
- O-glycosyl compound
- Glycosyl compound
- Cyclohexenone
- Oxane
- Acyloin
- Alpha,beta-unsaturated ketone
- Tetrahydrofuran
- Tertiary alcohol
- Enone
- Cyclic alcohol
- Alpha-hydroxy ketone
- Acryloyl-group
- Cyclic ketone
- Secondary alcohol
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Acetal
- 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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