Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:29:58 UTC |
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Update Date | 2022-03-07 02:52:08 UTC |
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HMDB ID | HMDB0029363 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Glaucamine |
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Description | Glaucamine, also known as alkaloid R-L, belongs to the class of organic compounds known as rhoeadine alkaloids. These are alkaloids with a structure based on rhoeadine. They usually contain a benzazepine system fused with a six-membered hemiacetal or acetal. Glaucamine is a very strong basic compound (based on its pKa). Alkaloid from Papaver rhoeas (corn poppy). |
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Structure | COC1=C(OC)C=C2C3OC(O)C4=C(C=CC5=C4OCO5)C3N(C)CCC2=C1 InChI=1S/C21H23NO6/c1-22-7-6-11-8-15(24-2)16(25-3)9-13(11)19-18(22)12-4-5-14-20(27-10-26-14)17(12)21(23)28-19/h4-5,8-9,18-19,21,23H,6-7,10H2,1-3H3 |
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Synonyms | Value | Source |
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2,3-Dimethoxy-16-methyl-10,11-[methylenebis(oxy)]rheadan-8-ol, 9ci | HMDB | Alkaloid R-L | HMDB |
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Chemical Formula | C21H23NO6 |
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Average Molecular Weight | 385.4104 |
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Monoisotopic Molecular Weight | 385.152537473 |
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IUPAC Name | 16,17-dimethoxy-22-methyl-6,8,12-trioxa-22-azapentacyclo[11.9.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]docosa-2(10),3,5(9),14,16,18-hexaen-11-ol |
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Traditional Name | 16,17-dimethoxy-22-methyl-6,8,12-trioxa-22-azapentacyclo[11.9.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]docosa-2(10),3,5(9),14,16,18-hexaen-11-ol |
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CAS Registry Number | 2255-44-9 |
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SMILES | COC1=C(OC)C=C2C3OC(O)C4=C(C=CC5=C4OCO5)C3N(C)CCC2=C1 |
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InChI Identifier | InChI=1S/C21H23NO6/c1-22-7-6-11-8-15(24-2)16(25-3)9-13(11)19-18(22)12-4-5-14-20(27-10-26-14)17(12)21(23)28-19/h4-5,8-9,18-19,21,23H,6-7,10H2,1-3H3 |
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InChI Key | XYWRZQQANNOTTD-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as rhoeadine alkaloids. These are alkaloids with a structure based on rhoeadine. They usually contain a benzazepine system fused with a six-membered hemiacetal or acetal. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Rhoeadine alkaloids |
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Sub Class | Not Available |
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Direct Parent | Rhoeadine alkaloids |
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Alternative Parents | |
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Substituents | - Rhoeadine-skeleton
- Benzazepine
- Benzopyran
- Isochromane
- 2-benzopyran
- Benzodioxole
- Anisole
- Alkyl aryl ether
- Azepine
- Aralkylamine
- Benzenoid
- Tertiary aliphatic amine
- Tertiary amine
- Hemiacetal
- Acetal
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Ether
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Amine
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen 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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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 222 - 223 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Glaucamine GC-MS (Non-derivatized) - 70eV, Positive | splash10-01b9-0559000000-802715b9fcccb968736c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Glaucamine GC-MS (1 TMS) - 70eV, Positive | splash10-00dl-5191600000-88fa6b8362955bfde44d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Glaucamine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 10V, Positive-QTOF | splash10-000i-0009000000-40014e1f5003722efb59 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 20V, Positive-QTOF | splash10-00kr-0009000000-44a31b88174997a4d2a6 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 40V, Positive-QTOF | splash10-02t9-3913000000-a6170b5635af08f40d1f | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 10V, Negative-QTOF | splash10-001i-0019000000-b66e981e8f2def415272 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 20V, Negative-QTOF | splash10-00li-0009000000-4162ef55fb63fa69eff4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 40V, Negative-QTOF | splash10-00di-3249000000-8fa542ab239c907d0345 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 10V, Negative-QTOF | splash10-001i-0009000000-fdb0793046af4f02e8be | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 20V, Negative-QTOF | splash10-001i-0009000000-d02d908dcee467031edb | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 40V, Negative-QTOF | splash10-001i-0019000000-9c6eadc24a42af4ca7d0 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 10V, Positive-QTOF | splash10-000i-0009000000-45bdbbe16c03fff37fee | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 20V, Positive-QTOF | splash10-000i-0009000000-28e8e53401cfc3678585 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glaucamine 40V, Positive-QTOF | splash10-00el-0197000000-f55becc8008551ecccba | 2021-09-24 | Wishart Lab | View Spectrum |
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