Record Information |
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Version | 1.0 |
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Created at | 2020-12-09 01:46:37 UTC |
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Updated at | 2021-07-15 16:48:41 UTC |
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NP-MRD ID | NP0004258 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | α-ergocryptine |
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Provided By | NPAtlas |
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Description | α-ergocryptine is found in Claviceps, Claviceps zizaniae and Festuca rubra. It was first documented in 2002 (PMID: 12141870). Based on a literature review a significant number of articles have been published on alpha-ergocryptine (PMID: 34148344) (PMID: 33114663) (PMID: 31052444) (PMID: 30000365). |
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Structure | [H]O[C@@]12O[C@@](N([H])C(=O)[C@]3([H])C([H])=C4C5=C([H])C([H])=C([H])C6=C5C(=C([H])N6[H])C([H])([H])[C@@]4([H])N(C([H])([H])[H])C3([H])[H])(C(=O)N1[C@]([H])(C(=O)N1C([H])([H])C([H])([H])C([H])([H])[C@@]21[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H] InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)/t20-,24-,25+,26+,31-,32+/m1/s1 |
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Synonyms | Value | Source |
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12'-Hydroxy-2'-(1-methylethyl)-5'alpha-(2-methylpropyl)ergotaman-3',6',18-trione | ChEBI | 12'-Hydroxy-5'alpha-isobutyl-2'-isopropylergotaman-3',6',18-trione | ChEBI | 12'-Hydroxy-2'-(1-methylethyl)-5'a-(2-methylpropyl)ergotaman-3',6',18-trione | Generator | 12'-Hydroxy-2'-(1-methylethyl)-5'α-(2-methylpropyl)ergotaman-3',6',18-trione | Generator | 12'-Hydroxy-5'a-isobutyl-2'-isopropylergotaman-3',6',18-trione | Generator | 12'-Hydroxy-5'α-isobutyl-2'-isopropylergotaman-3',6',18-trione | Generator | a-Ergocryptine | Generator | Α-ergocryptine | Generator | Ergocryptine monomethanesulfonate, (5'alpha)-isomer | MeSH | Ergocryptine phosphate, (5'alpha)-isomer | MeSH | Ergocryptine citrate, (5'alpha)-isomer | MeSH | Ergocryptine sulfate, (1:1) salt, (5'alpha)-isomer | MeSH | Ergocryptine | MeSH | Ergocryptine mesylate | MeSH | Ergocryptine, (5'alpha,8alpha)-isomer | MeSH | Ergocryptine tartrate, (5'alpha)-isomer | MeSH | Ergocryptine, (5'alpha(S),8alpha)-isomer | MeSH | Ergokryptin | MeSH | Ergocryptine monomethanesulfonate, (5'alpha,8alpha)-isomer | MeSH |
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Chemical Formula | C32H41N5O5 |
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Average Mass | 575.7100 Da |
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Monoisotopic Mass | 575.31077 Da |
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IUPAC Name | (4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide |
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Traditional Name | (4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-isopropyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C[C@@H]1N2C(=O)[C@](NC(=O)[C@H]3CN(C)[C@@H]4CC5=CNC6=CC=CC(=C56)C4=C3)(O[C@@]2(O)[C@@H]2CCCN2C1=O)C(C)C |
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InChI Identifier | InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)/t20-,24-,25+,26+,31-,32+/m1/s1 |
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InChI Key | YDOTUXAWKBPQJW-NSLWYYNWSA-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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Species Where Detected | |
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Chemical Taxonomy |
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Classification | Not classified |
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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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General References | - Kantorova M, Kolinska R, Pazoutova S, Honzatko A, Havlicek V, Flieger M: Ergot alkaloids produced by submerged cultures of Claviceps zizaniae. J Nat Prod. 2002 Jul;65(7):1039-40. doi: 10.1021/np010639w. [PubMed:12141870 ]
- Uhlig S, Rangel-Huerta OD, Divon HH, Rolen E, Pauchon K, Sumarah MW, Vralstad T, Renaud JB: Unraveling the Ergot Alkaloid and Indole Diterpenoid Metabolome in the Claviceps purpurea Species Complex Using LC-HRMS/MS Diagnostic Fragmentation Filtering. J Agric Food Chem. 2021 Jun 30;69(25):7137-7148. doi: 10.1021/acs.jafc.1c01973. Epub 2021 Jun 20. [PubMed:34148344 ]
- Kodisch A, Oberforster M, Raditschnig A, Rodemann B, Tratwal A, Danielewicz J, Korbas M, Schmiedchen B, Eifler J, Gordillo A, Siekmann D, Fromme FJ, Wuppermann FN, Wieser F, Zechner E, Niewinska M, Miedaner T: Covariation of Ergot Severity and Alkaloid Content Measured by HPLC and One ELISA Method in Inoculated Winter Rye across Three Isolates and Three European Countries. Toxins (Basel). 2020 Oct 26;12(11). pii: toxins12110676. doi: 10.3390/toxins12110676. [PubMed:33114663 ]
- Debegnach F, Patriarca S, Brera C, Gregori E, Sonego E, Moracci G, De Santis B: Ergot Alkaloids in Wheat and Rye Derived Products in Italy. Foods. 2019 May 1;8(5). pii: foods8050150. doi: 10.3390/foods8050150. [PubMed:31052444 ]
- Authors unspecified: Bromocriptine. 2006. [PubMed:30000365 ]
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