Record Information |
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Version | 2.0 |
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Created at | 2021-06-21 00:33:00 UTC |
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Updated at | 2021-06-30 00:18:29 UTC |
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NP-MRD ID | NP0043036 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | melosuavine D |
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Provided By | JEOL Database |
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Description | Methyl (1R,12S,13S,15R,16R,20R)-12-ethyl-16-[(1R,12R,19S)-12-ethyl-5-hydroxy-10-(methoxycarbonyl)-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2,4,6,9,13-pentaen-4-yl]-5-hydroxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2(7),3,5,9-tetraene-10-carboxylate belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. melosuavine D is found in Melodinus suaveolens. It was first documented in 2002 (PMID: 33651529). Based on a literature review very few articles have been published on methyl (1R,12S,13S,15R,16R,20R)-12-ethyl-16-[(1R,12R,19S)-12-ethyl-5-hydroxy-10-(methoxycarbonyl)-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2,4,6,9,13-pentaen-4-yl]-5-hydroxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2(7),3,5,9-tetraene-10-carboxylate (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454). |
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Structure | [H]OC1=C([H])C2=C(C([H])=C1[H])[C@]13C(N2[H])=C(C(=O)OC([H])([H])[H])C([H])([H])[C@]2(C([H])([H])C([H])([H])[H])[C@]4([H])O[C@]4([H])[C@]([H])(N(C([H])([H])C1([H])[H])[C@]32[H])C1=C(O[H])C([H])=C2N([H])C3=C(C(=O)OC([H])([H])[H])C([H])([H])[C@@]4(C([H])=C([H])C([H])([H])N5C([H])([H])C([H])([H])[C@@]3(C2=C1[H])[C@]45[H])C([H])([H])C([H])([H])[H] InChI=1S/C42H46N4O7/c1-5-39-10-7-13-45-14-11-42(37(39)45)26-17-22(29(48)18-28(26)44-32(42)23(19-39)35(49)51-3)30-31-34(53-31)40(6-2)20-24(36(50)52-4)33-41(12-15-46(30)38(40)41)25-9-8-21(47)16-27(25)43-33/h7-10,16-18,30-31,34,37-38,43-44,47-48H,5-6,11-15,19-20H2,1-4H3/t30-,31-,34-,37+,38+,39+,40-,41+,42+/m1/s1 |
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Synonyms | Value | Source |
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Methyl (1R,12S,13S,15R,16R,20R)-12-ethyl-16-[(1R,12R,19S)-12-ethyl-5-hydroxy-10-(methoxycarbonyl)-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2,4,6,9,13-pentaen-4-yl]-5-hydroxy-14-oxa-8,17-diazahexacyclo[10.7.1.0,.0,.0,.0,]icosa-2(7),3,5,9-tetraene-10-carboxylic acid | Generator |
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Chemical Formula | C42H46N4O7 |
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Average Mass | 718.8510 Da |
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Monoisotopic Mass | 718.33665 Da |
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IUPAC Name | methyl (1R,12S,13S,15R,16R,20R)-12-ethyl-16-[(1R,12R,19S)-12-ethyl-5-hydroxy-10-(methoxycarbonyl)-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9,13-pentaen-4-yl]-5-hydroxy-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2(7),3,5,9-tetraene-10-carboxylate |
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Traditional Name | methyl (1R,12S,13S,15R,16R,20R)-12-ethyl-16-[(1R,12R,19S)-12-ethyl-5-hydroxy-10-(methoxycarbonyl)-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9,13-pentaen-4-yl]-5-hydroxy-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2(7),3,5,9-tetraene-10-carboxylate |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C([H])C2=C(C([H])=C1[H])[C@]13C(N2[H])=C(C(=O)OC([H])([H])[H])C([H])([H])[C@]2(C([H])([H])C([H])([H])[H])[C@]4([H])O[C@]4([H])[C@]([H])(N(C([H])([H])C1([H])[H])[C@]32[H])C1=C(O[H])C([H])=C2N([H])C3=C(C(=O)OC([H])([H])[H])C([H])([H])[C@@]4(C([H])=C([H])C([H])([H])N5C([H])([H])C([H])([H])[C@@]3(C2=C1[H])[C@]45[H])C([H])([H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C42H46N4O7/c1-5-39-10-7-13-45-14-11-42(37(39)45)26-17-22(29(48)18-28(26)44-32(42)23(19-39)35(49)51-3)30-31-34(53-31)40(6-2)20-24(36(50)52-4)33-41(12-15-46(30)38(40)41)25-9-8-21(47)16-27(25)43-33/h7-10,16-18,30-31,34,37-38,43-44,47-48H,5-6,11-15,19-20H2,1-4H3/t30-,31-,34-,37+,38+,39+,40-,41+,42+/m1/s1 |
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InChI Key | LYIGHNVZRJJMOV-FTYDJIKKSA-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, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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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Melodinus suaveolens | JEOL database | - Liu, Y. -P., et al, J. Nat. Prod. 76, 2322 (2013)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Aspidospermatan-type alkaloids |
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Sub Class | Not Available |
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Direct Parent | Aspidospermatan-type alkaloids |
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Alternative Parents | |
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Substituents | - Aspidosperma alkaloid
- Plumeran-type alkaloid
- Carbazole
- Indole or derivatives
- Dihydroindole
- Indolizidine
- Para-oxazepine
- 1-hydroxy-2-unsubstituted benzenoid
- Epoxypiperidine
- Aralkylamine
- Phenol
- Secondary aliphatic/aromatic amine
- Dicarboxylic acid or derivatives
- Piperidine
- Benzenoid
- N-alkylpyrrolidine
- Methyl ester
- Vinylogous amide
- Alpha,beta-unsaturated carboxylic ester
- Pyrrolidine
- Enoate ester
- Carboxylic acid ester
- Tertiary aliphatic amine
- Tertiary amine
- Amino acid or derivatives
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Ether
- Carboxylic acid derivative
- Dialkyl ether
- Enamine
- Secondary amine
- Oxirane
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- 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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