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 17:35:16 UTC |
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Update Date | 2022-03-07 02:52:27 UTC |
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HMDB ID | HMDB0030174 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Isotetrandrine |
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Description | Isotetrandrine, also known as isosinomenine a or NSC 97338, belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Isotetrandrine is a very strong basic compound (based on its pKa). Outside of the human body, isotetrandrine has been detected, but not quantified in, herbs and spices. This could make isotetrandrine a potential biomarker for the consumption of these foods. |
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Structure | COC1=CC=C2CC3N(C)CCC4=C3C(OC3=CC5=C(CCN(C)C5CC5=CC=C(OC1=C2)C=C5)C=C3OC)=C(OC)C(OC)=C4 InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3 |
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Synonyms | Value | Source |
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(+)-Isotetrandrine | HMDB | 1-Isotetrandrine | HMDB | 6,6',7,12-Tetramethoxy-2,2'-dimethyl-berbaman | HMDB | Isosinomenine a | HMDB | NSC 97338 | HMDB | O,O'-dimethylobamegine | HMDB | O,O'-dimethylstepholine | HMDB | O,O-Dimethylobamegine | HMDB | O,O-Dimethylstepholine | HMDB | O-Methylberbamine | HMDB | 6,6',7,12-Tetramethoxy-2,2'-dimethyl-1 beta-berbaman | MeSH | D-Tetrandrine | MeSH | Hanjisong | MeSH | Isotetrandrine dihydrochloride | MeSH | Tetradrine | MeSH | Tetrandrine, (1'beta)-isomer | MeSH | Tetrandrine | MeSH | Tetrandrine dihydrochloride, (1beta)-isomer | MeSH |
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Chemical Formula | C38H42N2O6 |
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Average Molecular Weight | 622.7499 |
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Monoisotopic Molecular Weight | 622.304287086 |
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IUPAC Name | 9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24(32),25,27(31),35-dodecaene |
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Traditional Name | 9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24(32),25,27(31),35-dodecaene |
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CAS Registry Number | 477-57-6 |
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SMILES | COC1=CC=C2CC3N(C)CCC4=C3C(OC3=CC5=C(CCN(C)C5CC5=CC=C(OC1=C2)C=C5)C=C3OC)=C(OC)C(OC)=C4 |
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InChI Identifier | InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3 |
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InChI Key | WVTKBKWTSCPRNU-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Not Available |
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Sub Class | Not Available |
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Direct Parent | Lignans, neolignans and related compounds |
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Alternative Parents | |
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Substituents | - Oxyneolignan skeleton
- Diaryl ether
- Tetrahydroisoquinoline
- Anisole
- Alkyl aryl ether
- Aralkylamine
- Benzenoid
- Tertiary amine
- Tertiary aliphatic amine
- Ether
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Amine
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | 182 - 183 °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 IndicesUnderivatized |
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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 - Isotetrandrine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a6r-0000094000-16e7e9ec7c849aa8fbde | 2017-09-01 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Isotetrandrine 6V, Positive-QTOF | splash10-00di-0000009000-544f8625c973d44a9517 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Isotetrandrine 6V, Positive-QTOF | splash10-00di-0000009000-7cd87556e84cce573231 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 10V, Positive-QTOF | splash10-00di-0000039000-76a7f64bf880d385153d | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 20V, Positive-QTOF | splash10-006x-0000093000-34a3976b989b8ead2206 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 40V, Positive-QTOF | splash10-03gi-0000090000-fa6d47c3b396f5190241 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 10V, Negative-QTOF | splash10-00di-0000009000-f6f0adfcee090fea8e0a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 20V, Negative-QTOF | splash10-05fr-0000049000-5571f5eae59c0fe4abd0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 40V, Negative-QTOF | splash10-00os-0000090000-c489b8ee8fa69f3ed5f5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 10V, Positive-QTOF | splash10-00di-0000009000-2e1e1758bf77504b12f8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 20V, Positive-QTOF | splash10-00dl-0000089000-896c1e5c16b5e3465ae5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 40V, Positive-QTOF | splash10-00al-1000091000-6979ac568989952592b8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 10V, Negative-QTOF | splash10-00di-0000009000-4e8191be91182248f3a2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 20V, Negative-QTOF | splash10-00dr-0000089000-b77b4f80f79c3c02f292 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isotetrandrine 40V, Negative-QTOF | splash10-00pi-0000091000-62acbe5b9bef88e45717 | 2021-09-24 | Wishart Lab | View Spectrum |
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