| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-02 14:44:30 UTC |
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| Updated at | 2022-09-02 14:44:30 UTC |
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| NP-MRD ID | NP0157370 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1r,10s,13r,14s,15s,16s,17s,18r)-18-(acetyloxy)-13-carboxy-14-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraene-8,15-diium-8,15-bis(olate) |
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| Description | (1R,10S,13R,14S,15S,16S,17S,18R)-18-(acetyloxy)-14-methyl-8,15-dioxo-8λ⁵,15λ⁵-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2,4,6,8-tetraene-13-carboxylic acid belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. (1r,10s,13r,14s,15s,16s,17s,18r)-18-(acetyloxy)-13-carboxy-14-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraene-8,15-diium-8,15-bis(olate) is found in Alstonia yunnanensis. Based on a literature review very few articles have been published on (1R,10S,13R,14S,15S,16S,17S,18R)-18-(acetyloxy)-14-methyl-8,15-dioxo-8λ⁵,15λ⁵-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2,4,6,8-tetraene-13-carboxylic acid. |
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| Structure | C[C@H]1[C@@H](C2C[C@H]3C4=[N+]([O-])C5=CC=CC=C5[C@]44C[C@@H]([C@H]2[C@H]4OC(C)=O)[N@@+]13[O-])C(O)=O InChI=1S/C21H22N2O6/c1-9-16(20(25)26)11-7-14-18-21(12-5-3-4-6-13(12)22(18)27)8-15(23(9,14)28)17(11)19(21)29-10(2)24/h3-6,9,11,14-17,19H,7-8H2,1-2H3,(H,25,26)/t9-,11?,14-,15-,16-,17-,19+,21+,23+/m0/s1 |
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| Synonyms | | Value | Source |
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| (1R,10S,13R,14S,15S,16S,17S,18R)-18-(Acetyloxy)-14-methyl-8,15-dioxo-8,15-diazahexacyclo[14.2.1.0,.0,.0,.0,]nonadeca-2,4,6,8-tetraene-13-carboxylate | Generator |
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| Chemical Formula | C21H22N2O6 |
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| Average Mass | 398.4150 Da |
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| Monoisotopic Mass | 398.14779 Da |
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| IUPAC Name | (1R,10S,13R,14S,15S,16S,17S,18R)-18-(acetyloxy)-13-carboxy-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraene-8,15-diium-8,15-bis(olate) |
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| Traditional Name | (1R,10S,13R,14S,15S,16S,17S,18R)-18-(acetyloxy)-13-carboxy-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraene-8,15-diium-8,15-bis(olate) |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@H]1[C@@H](C2C[C@H]3C4=[N+]([O-])C5=CC=CC=C5[C@]44C[C@@H]([C@H]2[C@H]4OC(C)=O)[N@@+]13[O-])C(O)=O |
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| InChI Identifier | InChI=1S/C21H22N2O6/c1-9-16(20(25)26)11-7-14-18-21(12-5-3-4-6-13(12)22(18)27)8-15(23(9,14)28)17(11)19(21)29-10(2)24/h3-6,9,11,14-17,19H,7-8H2,1-2H3,(H,25,26)/t9-,11?,14-,15-,16-,17-,19+,21+,23+/m0/s1 |
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| InChI Key | BZASEFCQVJQJFJ-OIVLKFHSSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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 ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Ajmaline-sarpagine alkaloids |
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| Sub Class | Not Available |
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| Direct Parent | Ajmaline-sarpagine alkaloids |
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| Alternative Parents | |
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| Substituents | - Sarpagine-skeleton
- 3-alkylindole
- Quinolizidine
- Piperidinecarboxylic acid
- Indole or derivatives
- Quinuclidine
- Azepane
- Benzenoid
- Piperidine
- Dicarboxylic acid or derivatives
- Trialkyl amine oxide
- Nitrone
- Carboxylic acid ester
- Azacycle
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Allyl-type 1,3-dipolar organic compound
- Trisubstituted n-oxide
- Carboxylic acid
- Carboxylic acid derivative
- N-oxide
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic zwitterion
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- 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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