Record Information |
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Version | 2.0 |
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Created at | 2021-06-21 00:21:15 UTC |
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Updated at | 2021-06-30 00:18:04 UTC |
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NP-MRD ID | NP0042779 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | voacalgine C |
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Provided By | JEOL Database |
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Description | Voacalgine C belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. voacalgine C is found in Voacanga grandifolia. voacalgine C was first documented in 2013 (Hirasawa, Y., et al.). Based on a literature review very few articles have been published on Voacalgine C. |
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Structure | [H]O[C@@]1([H])C([H])([H])C([H])([H])C([H])([H])O[C@]11O[C@@]2(OC([H])([H])[C@@]3([H])[C@@]4([H])N(C([H])([H])[H])[C@]([H])(C5=C(C6=C(C([H])=C([H])C([H])=C6[H])N5C([H])([H])[H])C4([H])[H])C([H])([H])[C@@]3([H])[C@]2([H])C1([H])[H])C([H])([H])[H] InChI=1S/C26H34N2O4/c1-25-19(13-26(32-25)23(29)9-6-10-30-26)16-11-22-24-17(12-21(27(22)2)18(16)14-31-25)15-7-4-5-8-20(15)28(24)3/h4-5,7-8,16,18-19,21-23,29H,6,9-14H2,1-3H3/t16-,18-,19+,21+,22+,23+,25+,26-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C26H34N2O4 |
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Average Mass | 438.5680 Da |
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Monoisotopic Mass | 438.25186 Da |
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IUPAC Name | (1S,3'S,12S,13R,16S,18R,20S,21R)-3,16,23-trimethyl-15,17-dioxa-3,23-diazaspiro[hexacyclo[10.10.1.0^{2,10}.0^{4,9}.0^{13,21}.0^{16,20}]tricosane-18,2'-oxane]-2(10),4(9),5,7-tetraen-3'-ol |
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Traditional Name | (1S,3'S,12S,13R,16S,18R,20S,21R)-3,16,23-trimethyl-15,17-dioxa-3,23-diazaspiro[hexacyclo[10.10.1.0^{2,10}.0^{4,9}.0^{13,21}.0^{16,20}]tricosane-18,2'-oxane]-2(10),4(9),5,7-tetraen-3'-ol |
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CAS Registry Number | Not Available |
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SMILES | [H]O[C@@]1([H])C([H])([H])C([H])([H])C([H])([H])O[C@]11O[C@@]2(OC([H])([H])[C@@]3([H])[C@@]4([H])N(C([H])([H])[H])[C@]([H])(C5=C(C6=C(C([H])=C([H])C([H])=C6[H])N5C([H])([H])[H])C4([H])[H])C([H])([H])[C@@]3([H])[C@]2([H])C1([H])[H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C26H34N2O4/c1-25-19(13-26(32-25)23(29)9-6-10-30-26)16-11-22-24-17(12-21(27(22)2)18(16)14-31-25)15-7-4-5-8-20(15)28(24)3/h4-5,7-8,16,18-19,21-23,29H,6,9-14H2,1-3H3/t16-,18-,19+,21+,22+,23+,25+,26-/m1/s1 |
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InChI Key | VBDQTJIQJAGBJF-RLHFXQFGSA-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, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CD3OD, 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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Voacanga grandifolia | JEOL database | - Hirasawa, Y., et. al, Tetrahedron 69, 10869 (2013)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Macroline alkaloids |
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Sub Class | Not Available |
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Direct Parent | Macroline alkaloids |
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Alternative Parents | |
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Substituents | - Macroline skeleton
- Beta-carboline
- Pyridoindole
- 3-alkylindole
- N-alkylindole
- Furopyran
- Indole
- Indole or derivatives
- Ketal
- Aralkylamine
- Oxane
- Benzenoid
- Piperidine
- Substituted pyrrole
- Pyran
- N-methylpyrrole
- Heteroaromatic compound
- Furan
- Oxolane
- Pyrrole
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Acetal
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Alcohol
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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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