Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 12:42:09 UTC |
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Updated at | 2022-04-28 12:42:09 UTC |
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NP-MRD ID | NP0067861 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (19R)-19-Hydroxytabernaelegantine A |
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Description | Methyl (1R,15S,17R,18R)-5-[(1S,12R,14S,15R,18R)-15-ethyl-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]Octadeca-3(11),4,6,8-tetraen-12-yl]-17-[(1S)-1-hydroxyethyl]-6-methoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]Nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond. (19R)-19-Hydroxytabernaelegantine A is found in Tabernaemontana coffeoides Boj. Based on a literature review very few articles have been published on methyl (1R,15S,17R,18R)-5-[(1S,12R,14S,15R,18R)-15-ethyl-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]Octadeca-3(11),4,6,8-tetraen-12-yl]-17-[(1S)-1-hydroxyethyl]-6-methoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]Nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate. |
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Structure | CC[C@H]1CN(C)[C@H]2CC3=C(NC4=CC=CC=C34)[C@H](C[C@@H]1[C@H]2C(=O)OC)C1=C2NC3=C(CCN4C[C@H]5C[C@@H]([C@H](C)O)[C@@H]4[C@@]3(C5)C(=O)OC)C2=CC=C1OC InChI=1S/C43H54N4O6/c1-7-24-21-46(3)33-18-30-25-10-8-9-11-32(25)44-37(30)31(17-29(24)35(33)41(49)52-5)36-34(51-4)13-12-26-27-14-15-47-20-23-16-28(22(2)48)40(47)43(19-23,42(50)53-6)39(27)45-38(26)36/h8-13,22-24,28-29,31,33,35,40,44-45,48H,7,14-21H2,1-6H3/t22-,23-,24-,28-,29-,31+,33-,35+,40+,43-/m0/s1 |
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Synonyms | Value | Source |
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Methyl (1R,15S,17R,18R)-5-[(1S,12R,14S,15R,18R)-15-ethyl-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0,.0,]octadeca-3(11),4,6,8-tetraen-12-yl]-17-[(1S)-1-hydroxyethyl]-6-methoxy-3,13-diazapentacyclo[13.3.1.0,.0,.0,]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylic acid | Generator |
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Chemical Formula | C43H54N4O6 |
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Average Mass | 722.9270 Da |
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Monoisotopic Mass | 722.40434 Da |
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IUPAC Name | methyl (1R,15S,17R,18R)-5-[(1S,12R,14S,15R,18R)-15-ethyl-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-17-[(1S)-1-hydroxyethyl]-6-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate |
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Traditional Name | methyl (1R,15S,17R,18R)-5-[(1S,12R,14S,15R,18R)-15-ethyl-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-17-[(1S)-1-hydroxyethyl]-6-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate |
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CAS Registry Number | Not Available |
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SMILES | CC[C@H]1CN(C)[C@H]2CC3=C(NC4=CC=CC=C34)[C@H](C[C@@H]1[C@H]2C(=O)OC)C1=C2NC3=C(CCN4C[C@H]5C[C@@H]([C@H](C)O)[C@@H]4[C@@]3(C5)C(=O)OC)C2=CC=C1OC |
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InChI Identifier | InChI=1S/C43H54N4O6/c1-7-24-21-46(3)33-18-30-25-10-8-9-11-32(25)44-37(30)31(17-29(24)35(33)41(49)52-5)36-34(51-4)13-12-26-27-14-15-47-20-23-16-28(22(2)48)40(47)43(19-23,42(50)53-6)39(27)45-38(26)36/h8-13,22-24,28-29,31,33,35,40,44-45,48H,7,14-21H2,1-6H3/t22-,23-,24-,28-,29-,31+,33-,35+,40+,43-/m0/s1 |
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InChI Key | PYIDSJMLYRYDMC-XEXWFEGZSA-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 ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Ibogan-type alkaloids |
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Sub Class | Not Available |
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Direct Parent | Ibogan-type alkaloids |
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Alternative Parents | |
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Substituents | - Ibogan skeleton
- Vobasan skeleton
- Catharanthine skeleton
- 3-alkylindole
- Pyrroloazepine
- Piperidinecarboxylic acid
- Indole or derivatives
- Indole
- Anisole
- Aralkylamine
- Azepine
- Alkyl aryl ether
- Benzenoid
- Piperidine
- Dicarboxylic acid or derivatives
- Heteroaromatic compound
- Methyl ester
- Pyrrole
- 1,3-aminoalcohol
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Carboxylic acid ester
- Amino acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Ether
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Amine
- Alcohol
- 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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