| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-05 21:50:47 UTC |
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| Updated at | 2022-09-05 21:50:47 UTC |
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| NP-MRD ID | NP0220513 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1r)-1-[(1s,12s,13s,14r)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8,15-pentaen-15-yl]ethanol |
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| Description | (1R)-1-[(1S,12S,13S,14R)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4,6,8,15-pentaen-15-yl]ethan-1-ol 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. (1r)-1-[(1s,12s,13s,14r)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8,15-pentaen-15-yl]ethanol is found in Alstonia angustifolia. Based on a literature review very few articles have been published on (1R)-1-[(1S,12S,13S,14R)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4,6,8,15-pentaen-15-yl]ethan-1-ol. |
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| Structure | C[C@@H](O)C1=CN2[C@H]3CC4=C([C@@H]2C[C@@H]1[C@@H]3CO)N(C)C1=CC=CC=C41 InChI=1S/C20H24N2O2/c1-11(24)15-9-22-18-8-14-12-5-3-4-6-17(12)21(2)20(14)19(22)7-13(15)16(18)10-23/h3-6,9,11,13,16,18-19,23-24H,7-8,10H2,1-2H3/t11-,13+,16+,18+,19+/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C20H24N2O2 |
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| Average Mass | 324.4240 Da |
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| Monoisotopic Mass | 324.18378 Da |
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| IUPAC Name | (1R)-1-[(1S,12S,13S,14R)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8,15-pentaen-15-yl]ethan-1-ol |
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| Traditional Name | (1R)-1-[(1S,12S,13S,14R)-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8,15-pentaen-15-yl]ethanol |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@@H](O)C1=CN2[C@H]3CC4=C([C@@H]2C[C@@H]1[C@@H]3CO)N(C)C1=CC=CC=C41 |
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| InChI Identifier | InChI=1S/C20H24N2O2/c1-11(24)15-9-22-18-8-14-12-5-3-4-6-17(12)21(2)20(14)19(22)7-13(15)16(18)10-23/h3-6,9,11,13,16,18-19,23-24H,7-8,10H2,1-2H3/t11-,13+,16+,18+,19+/m1/s1 |
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| InChI Key | LWSDVTSJDOUAFK-UCIANULWSA-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 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
- Vobasan skeleton
- Beta-carboline
- Pyridoindole
- N-alkylindole
- 3-alkylindole
- Indole
- Indole or derivatives
- Tetrahydropyridine
- Aralkylamine
- N-methylpyrrole
- Piperidine
- Substituted pyrrole
- Benzenoid
- Heteroaromatic compound
- 1,3-aminoalcohol
- Pyrrole
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Organoheterocyclic compound
- Azacycle
- Enamine
- Allylamine
- Organonitrogen compound
- Amine
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Alcohol
- Primary alcohol
- Hydrocarbon derivative
- 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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