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 02:52:00 UTC |
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HMDB ID | HMDB0015494 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Alizapride |
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Description | Alizapride is only found in individuals that have used or taken this drug. It is a dopamine antagonist with prokinetic and antiemetic effects used in the treatment of nausea and vomiting, including postoperative nausea and vomiting.The anti-emetic action of Alizapride is due to its antagonist activity at D2 receptors in the chemoreceptor trigger zone (CTZ) in the central nervous system (CNS)—this action prevents nausea and vomiting triggered by most stimuli. Structurally similar to metoclopramide and, therefore, shares similar other atributres related to emesis and prokinetics. |
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Structure | COC1=CC2=NNN=C2C=C1C(=O)NCC1CCCN1CC=C InChI=1S/C16H21N5O2/c1-3-6-21-7-4-5-11(21)10-17-16(22)12-8-13-14(19-20-18-13)9-15(12)23-2/h3,8-9,11H,1,4-7,10H2,2H3,(H,17,22)(H,18,19,20) |
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Synonyms | Value | Source |
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Plitican | Kegg | N-((1-Allyl-2-pyrrolidinyl)methyl)-6-methoxy-1H-benzotriazole-5-carboxamide | HMDB | Litican | HMDB | N-((Allyl-1-pyrrolidinyl-2)-methyl)methoxy-2-azimido-4,5-benzamide | HMDB | Vergentan | HMDB | Alizapride hydrochloride | HMDB | N-(1-Allyl-2-pyrrolidinylmethyl)-6-methoxy-1H-benzotriazole-5-carboxamide hydrochloride | HMDB |
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Chemical Formula | C16H21N5O2 |
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Average Molecular Weight | 315.3702 |
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Monoisotopic Molecular Weight | 315.169524941 |
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IUPAC Name | 6-methoxy-N-{[1-(prop-2-en-1-yl)pyrrolidin-2-yl]methyl}-2H-1,2,3-benzotriazole-5-carboxamide |
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Traditional Name | alizapride |
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CAS Registry Number | 59338-93-1 |
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SMILES | COC1=CC2=NNN=C2C=C1C(=O)NCC1CCCN1CC=C |
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InChI Identifier | InChI=1S/C16H21N5O2/c1-3-6-21-7-4-5-11(21)10-17-16(22)12-8-13-14(19-20-18-13)9-15(12)23-2/h3,8-9,11H,1,4-7,10H2,2H3,(H,17,22)(H,18,19,20) |
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InChI Key | KSEYRUGYKHXGFW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzotriazoles. These are organic compounds containing a benzene fused to a triazole ring (a five-membered ring with two carbon atoms and three nitrogen atoms). |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzotriazoles |
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Sub Class | Not Available |
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Direct Parent | Benzotriazoles |
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Alternative Parents | |
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Substituents | - Benzotriazole
- Anisole
- Alkyl aryl ether
- N-alkylpyrrolidine
- Benzenoid
- Azole
- Pyrrolidine
- Triazole
- 1,2,3-triazole
- Heteroaromatic compound
- Amino acid or derivatives
- Tertiary aliphatic amine
- Tertiary amine
- Secondary carboxylic acid amide
- Carboxamide group
- Azacycle
- Carboxylic acid derivative
- Ether
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Organic oxide
- Organic oxygen compound
- Organic nitrogen compound
- Amine
- 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 | 139 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.5 g/L | Not Available | LogP | 1.79 | MANNHOLD,R ET AL. (1990) |
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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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Alizapride,1TMS,isomer #1 | C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC | 2968.7 | Semi standard non polar | 33892256 | Alizapride,1TMS,isomer #1 | C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC | 2803.1 | Standard non polar | 33892256 | Alizapride,1TMS,isomer #1 | C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC | 4232.7 | Standard polar | 33892256 | Alizapride,1TMS,isomer #2 | C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C | 2895.7 | Semi standard non polar | 33892256 | Alizapride,1TMS,isomer #2 | C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C | 2898.8 | Standard non polar | 33892256 | Alizapride,1TMS,isomer #2 | C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C | 4048.8 | Standard polar | 33892256 | Alizapride,2TMS,isomer #1 | C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC)[Si](C)(C)C | 2943.4 | Semi standard non polar | 33892256 | Alizapride,2TMS,isomer #1 | C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC)[Si](C)(C)C | 2813.1 | Standard non polar | 33892256 | Alizapride,2TMS,isomer #1 | C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC)[Si](C)(C)C | 3921.3 | Standard polar | 33892256 | Alizapride,1TBDMS,isomer #1 | C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC | 3125.6 | Semi standard non polar | 33892256 | Alizapride,1TBDMS,isomer #1 | C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC | 3022.8 | Standard non polar | 33892256 | Alizapride,1TBDMS,isomer #1 | C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC | 4182.0 | Standard polar | 33892256 | Alizapride,1TBDMS,isomer #2 | C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C(C)(C)C | 3112.7 | Semi standard non polar | 33892256 | Alizapride,1TBDMS,isomer #2 | C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C(C)(C)C | 3115.6 | Standard non polar | 33892256 | Alizapride,1TBDMS,isomer #2 | C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C(C)(C)C | 4106.2 | Standard polar | 33892256 | Alizapride,2TBDMS,isomer #1 | C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC)[Si](C)(C)C(C)(C)C | 3313.6 | Semi standard non polar | 33892256 | Alizapride,2TBDMS,isomer #1 | C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC)[Si](C)(C)C(C)(C)C | 3229.0 | Standard non polar | 33892256 | Alizapride,2TBDMS,isomer #1 | C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC)[Si](C)(C)C(C)(C)C | 3889.1 | 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 - Alizapride GC-MS (Non-derivatized) - 70eV, Positive | splash10-01rl-7981000000-7be855eb3fbb5813cbe6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Alizapride GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Alizapride 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 - Alizapride 10V, Positive-QTOF | splash10-014i-1938000000-1a8af33956ed83ccdece | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 20V, Positive-QTOF | splash10-00fu-4910000000-aab60443fb8b77f05e64 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 40V, Positive-QTOF | splash10-0006-9200000000-8ff3b2c5e6b60b7692c7 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 10V, Negative-QTOF | splash10-03di-0219000000-52729b51e26559af4d4f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 20V, Negative-QTOF | splash10-01wv-0491000000-3e6ef639690f6aafb33f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 40V, Negative-QTOF | splash10-0037-4920000000-327c228d69462d85a4df | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 10V, Positive-QTOF | splash10-014i-3209000000-58fb28ddbca5a2bd7806 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 20V, Positive-QTOF | splash10-01di-9764000000-219629153c84cf4e816c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 40V, Positive-QTOF | splash10-05o1-9300000000-f5d279616c5960f4e596 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 10V, Negative-QTOF | splash10-03di-0009000000-da585dbe03591bbbac5d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 20V, Negative-QTOF | splash10-01r5-2942000000-c37a4ccd7bec058b80cf | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alizapride 40V, Negative-QTOF | splash10-01u9-3910000000-0acbb871a78aa32d1c73 | 2021-10-11 | Wishart Lab | View Spectrum |
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