Record Information |
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Version | 1.0 |
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Created at | 2021-06-19 17:34:09 UTC |
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Updated at | 2021-06-29 23:50:24 UTC |
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NP-MRD ID | NP0025442 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Mersinine A |
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Provided By | JEOL Database |
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Description | 11,12,16-Trimethyl (1R,12R,13R,16R,23R)-12-hydroxy-6,8-dioxa-11,20-diazahexacyclo[14.6.1.0¹,¹³.0²,¹⁰.0⁵,⁹.0²⁰,²³]Tricosa-2(10),3,5(9),17-tetraene-11,12,16-tricarboxylate belongs to the class of organic compounds known as melodinus alkaloids. These are alkaloids with a structure that is based on the melodinus skeleton. This backbone is a pentacyclic structure that contains a tetrahydroquinoline and an indolizine joined to each other through a cyclopentane. Mersinine A is found in Kopsia. It was first documented in 2001 (Kam, T.-S., et al.). Based on a literature review very few articles have been published on 11,12,16-trimethyl (1R,12R,13R,16R,23R)-12-hydroxy-6,8-dioxa-11,20-diazahexacyclo[14.6.1.0¹,¹³.0²,¹⁰.0⁵,⁹.0²⁰,²³]Tricosa-2(10),3,5(9),17-tetraene-11,12,16-tricarboxylate. |
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Structure | [H]O[C@@]1(N(C(=O)OC([H])([H])[H])C2=C3OC([H])([H])OC3=C([H])C([H])=C2[C@@]23C([H])([H])C([H])([H])N4C([H])([H])C([H])=C([H])[C@](C(=O)OC([H])([H])[H])(C([H])([H])C([H])([H])[C@@]12[H])[C@@]34[H])C(=O)OC([H])([H])[H] InChI=1S/C25H28N2O9/c1-32-20(28)23-8-4-11-26-12-10-24(19(23)26)14-5-6-15-18(36-13-35-15)17(14)27(22(30)34-3)25(31,21(29)33-2)16(24)7-9-23/h4-6,8,16,19,31H,7,9-13H2,1-3H3/t16-,19+,23+,24+,25-/m1/s1 |
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Synonyms | Value | Source |
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11,12,16-Trimethyl (1R,12R,13R,16R,23R)-12-hydroxy-6,8-dioxa-11,20-diazahexacyclo[14.6.1.0,.0,.0,.0,]tricosa-2(10),3,5(9),17-tetraene-11,12,16-tricarboxylic acid | Generator |
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Chemical Formula | C25H28N2O9 |
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Average Mass | 500.5040 Da |
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Monoisotopic Mass | 500.17948 Da |
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IUPAC Name | 11,12,16-trimethyl (1R,12R,13R,16R,23R)-12-hydroxy-6,8-dioxa-11,20-diazahexacyclo[14.6.1.0^{1,13}.0^{2,10}.0^{5,9}.0^{20,23}]tricosa-2,4,9,17-tetraene-11,12,16-tricarboxylate |
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Traditional Name | 11,12,16-trimethyl (1R,12R,13R,16R,23R)-12-hydroxy-6,8-dioxa-11,20-diazahexacyclo[14.6.1.0^{1,13}.0^{2,10}.0^{5,9}.0^{20,23}]tricosa-2,4,9,17-tetraene-11,12,16-tricarboxylate |
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CAS Registry Number | Not Available |
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SMILES | [H]O[C@@]1(N(C(=O)OC([H])([H])[H])C2=C3OC([H])([H])OC3=C([H])C([H])=C2[C@@]23C([H])([H])C([H])([H])N4C([H])([H])C([H])=C([H])[C@](C(=O)OC([H])([H])[H])(C([H])([H])C([H])([H])[C@@]12[H])[C@@]34[H])C(=O)OC([H])([H])[H] |
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InChI Identifier | InChI=1S/C25H28N2O9/c1-32-20(28)23-8-4-11-26-12-10-24(19(23)26)14-5-6-15-18(36-13-35-15)17(14)27(22(30)34-3)25(31,21(29)33-2)16(24)7-9-23/h4-6,8,16,19,31H,7,9-13H2,1-3H3/t16-,19+,23+,24+,25-/m1/s1 |
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InChI Key | WTHKQEVBLOSRDI-QYJDRXKLSA-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, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, 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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Kopsia | JEOL database | - Kam, T.-S., et al, Tetrahedron Letts. 42, 5977 (2001)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as melodinus alkaloids. These are alkaloids with a structure that is based on the melodinus skeleton. This backbone is a pentacyclic structure that contains a tetrahydroquinoline and an indolizine joined to each other through a cyclopentane. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Melodinus alkaloids |
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Sub Class | Not Available |
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Direct Parent | Melodinus alkaloids |
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Alternative Parents | |
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Substituents | - Melodinus skeleton
- 1,8-phenanthroline
- Phenanthridine
- Benzoquinoline
- Alpha-amino acid ester
- Quinoline
- Tetrahydroquinoline
- Alpha-amino acid or derivatives
- Indole or derivatives
- Benzodioxole
- Aralkylamine
- Benzenoid
- N-alkylpyrrolidine
- Dicarboxylic acid or derivatives
- Methyl ester
- Carbamic acid ester
- Pyrrolidine
- Tertiary aliphatic amine
- Tertiary amine
- Carbonic acid derivative
- Carboxylic acid ester
- Amino acid or derivatives
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Alkanolamine
- Acetal
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- 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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