Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:52:04 UTC |
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HMDB ID | HMDB0015669 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Drotaverine |
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Description | Drotaverine, also known as nospan or drotin, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Drotaverine is a drug which is used in the treatment of functional bowel disorders and alleviating pain in renal colic. Drotaverine is a very strong basic compound (based on its pKa). Drotaverine inhibits phosphodiesterases hydrolysing cAMP, thereby increasing cAMP concentration, decreasing Ca uptake of the cells and changing the distribution of calcium among the cells. |
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Structure | CCOC1=C(OCC)C=C(\C=C2/NCCC3=CC(OCC)=C(OCC)C=C23)C=C1 InChI=1S/C24H31NO4/c1-5-26-21-10-9-17(14-22(21)27-6-2)13-20-19-16-24(29-8-4)23(28-7-3)15-18(19)11-12-25-20/h9-10,13-16,25H,5-8,11-12H2,1-4H3/b20-13- |
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Synonyms | Value | Source |
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Drotin | Kegg | Drotaverin | HMDB | Nospan | HMDB | Isodihydroperparine | HMDB | NO-Shpa | HMDB | Dihydroisoperparine | HMDB | Drotaverin hydrochloride | HMDB | NO-Spa | HMDB | Nospanum | HMDB |
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Chemical Formula | C24H31NO4 |
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Average Molecular Weight | 397.5072 |
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Monoisotopic Molecular Weight | 397.225308485 |
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IUPAC Name | (1Z)-1-[(3,4-diethoxyphenyl)methylidene]-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline |
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Traditional Name | drotaverine |
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CAS Registry Number | 985-12-6 |
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SMILES | CCOC1=C(OCC)C=C(\C=C2/NCCC3=CC(OCC)=C(OCC)C=C23)C=C1 |
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InChI Identifier | InChI=1S/C24H31NO4/c1-5-26-21-10-9-17(14-22(21)27-6-2)13-20-19-16-24(29-8-4)23(28-7-3)15-18(19)11-12-25-20/h9-10,13-16,25H,5-8,11-12H2,1-4H3/b20-13- |
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InChI Key | OMFNSKIUKYOYRG-MOSHPQCFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Tetrahydroisoquinolines |
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Sub Class | Not Available |
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Direct Parent | Tetrahydroisoquinolines |
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Alternative Parents | |
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Substituents | - Tetrahydroisoquinoline
- Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Aralkylamine
- Monocyclic benzene moiety
- Benzenoid
- Secondary aliphatic amine
- Enamine
- Ether
- Secondary amine
- Azacycle
- Organonitrogen compound
- Amine
- Organooxygen compound
- Organopnictogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic nitrogen 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 | 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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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Drotaverine,1TMS,isomer #1 | CCOC1=CC=C(/C=C2/C3=CC(OCC)=C(OCC)C=C3CCN2[Si](C)(C)C)C=C1OCC | 3195.7 | Semi standard non polar | 33892256 | Drotaverine,1TMS,isomer #1 | CCOC1=CC=C(/C=C2/C3=CC(OCC)=C(OCC)C=C3CCN2[Si](C)(C)C)C=C1OCC | 3180.5 | Standard non polar | 33892256 | Drotaverine,1TMS,isomer #1 | CCOC1=CC=C(/C=C2/C3=CC(OCC)=C(OCC)C=C3CCN2[Si](C)(C)C)C=C1OCC | 3934.3 | Standard polar | 33892256 | Drotaverine,1TBDMS,isomer #1 | CCOC1=CC=C(/C=C2/C3=CC(OCC)=C(OCC)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1OCC | 3342.9 | Semi standard non polar | 33892256 | Drotaverine,1TBDMS,isomer #1 | CCOC1=CC=C(/C=C2/C3=CC(OCC)=C(OCC)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1OCC | 3356.3 | Standard non polar | 33892256 | Drotaverine,1TBDMS,isomer #1 | CCOC1=CC=C(/C=C2/C3=CC(OCC)=C(OCC)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1OCC | 4031.1 | Standard polar | 33892256 |
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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 - Drotaverine GC-MS (Non-derivatized) - 70eV, Positive | splash10-01b9-0029000000-cc21574b335ef828553c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Drotaverine 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 - Drotaverine 10V, Positive-QTOF | splash10-006t-0109000000-7cad269f41adee8417ce | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 20V, Positive-QTOF | splash10-00vm-0938000000-6d87baa6b9b9001f72b3 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 40V, Positive-QTOF | splash10-0fai-0903000000-32461a4dd8213a4ccaae | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 10V, Negative-QTOF | splash10-00kb-0009000000-ab1aeeb006841b3fa9c8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 20V, Negative-QTOF | splash10-01b9-0009000000-06822dcfe079230d41a9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 40V, Negative-QTOF | splash10-01pc-0019000000-acda050fb3e73672fc3e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 10V, Positive-QTOF | splash10-0002-0009000000-8c6d856694872eafbde7 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 20V, Positive-QTOF | splash10-006t-0009000000-753a599270e1789b1d24 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 40V, Positive-QTOF | splash10-006x-0169000000-2f0a9da1a5938c47a4e9 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 10V, Negative-QTOF | splash10-0002-0009000000-a71d93a03163a6601571 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 20V, Negative-QTOF | splash10-000i-0009000000-c70358ec5190b857e386 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drotaverine 40V, Negative-QTOF | splash10-00du-0019000000-7c1afa91b9c7710b0f53 | 2021-10-11 | Wishart Lab | View Spectrum |
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