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 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:48 UTC |
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HMDB ID | HMDB0014975 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Progabide |
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Description | Progabide, also known as halogabide or gabrene, belongs to the class of organic compounds known as o-quinomethanes. These are organic compounds containing a benzene ring conjugated to a methylidene group and a ketone at carbon atoms 1 and 2, respectively. Binding to GABAA results in an increased affinity of the GABA receptor for the amino acid, an augmented flux of chloride ions across the terminal membrane, and an increase in the amount of presynaptic inhibition. Progabide is a strong basic compound (based on its pKa). Progabide is an analog and prodrug of gamma-aminobutyric acid. Progabide is a potentially toxic compound. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease. It has agonistic activity for both the GABAA and GABAB receptors. Activation of the GABAB receptors retards the influx of calcium ions into the terminals, thereby reducing the evoked release of excitatory amino acids and possibly other transmitters. |
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Structure | NC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,21H,1-2,9H2,(H2,20,23)/b17-14+ |
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Synonyms | Value | Source |
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Halogabide | HMDB | Gabrene | HMDB | 4-{[(4-chlorophenyl)[(1E)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanimidate | Generator | Progabide | MeSH |
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Chemical Formula | C17H16ClFN2O2 |
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Average Molecular Weight | 334.773 |
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Monoisotopic Molecular Weight | 334.088433678 |
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IUPAC Name | 4-{[(4-chlorophenyl)[(1E)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanamide |
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Traditional Name | progabide |
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CAS Registry Number | 62666-20-0 |
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SMILES | NC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O |
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InChI Identifier | InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,21H,1-2,9H2,(H2,20,23)/b17-14+ |
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InChI Key | DWEQWXSKOHHBNT-SAPNQHFASA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as o-quinomethanes. These are organic compounds containing a benzene ring conjugated to a methylidene group and a ketone at carbon atoms 1 and 2, respectively. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | O-quinomethanes |
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Alternative Parents | |
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Substituents | - O-quinomethane
- Chlorobenzene
- Halobenzene
- Aryl chloride
- Aryl halide
- Monocyclic benzene moiety
- Benzenoid
- Vinylogous amide
- Carboximidic acid
- Carboximidic acid derivative
- Secondary aliphatic amine
- Enamine
- Fluoroalkene
- Haloalkene
- Secondary amine
- Vinyl fluoride
- Vinyl halide
- Organopnictogen compound
- Organic oxide
- Amine
- Organohalogen compound
- Organochloride
- Organofluoride
- Organonitrogen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | 133 - 135 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0044 g/L | Not Available | LogP | 2.6 | 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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Progabide,1TMS,isomer #1 | C[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3054.5 | Semi standard non polar | 33892256 | Progabide,1TMS,isomer #1 | C[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 2901.7 | Standard non polar | 33892256 | Progabide,1TMS,isomer #1 | C[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 4107.1 | Standard polar | 33892256 | Progabide,1TMS,isomer #2 | C[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3127.1 | Semi standard non polar | 33892256 | Progabide,1TMS,isomer #2 | C[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 2687.5 | Standard non polar | 33892256 | Progabide,1TMS,isomer #2 | C[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 4171.0 | Standard polar | 33892256 | Progabide,2TMS,isomer #1 | C[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C | 3137.9 | Semi standard non polar | 33892256 | Progabide,2TMS,isomer #1 | C[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C | 2929.5 | Standard non polar | 33892256 | Progabide,2TMS,isomer #1 | C[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C | 3995.7 | Standard polar | 33892256 | Progabide,2TMS,isomer #2 | C[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C | 3118.8 | Semi standard non polar | 33892256 | Progabide,2TMS,isomer #2 | C[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C | 2895.1 | Standard non polar | 33892256 | Progabide,2TMS,isomer #2 | C[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C | 3803.0 | Standard polar | 33892256 | Progabide,3TMS,isomer #1 | C[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3161.3 | Semi standard non polar | 33892256 | Progabide,3TMS,isomer #1 | C[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 2959.8 | Standard non polar | 33892256 | Progabide,3TMS,isomer #1 | C[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3654.5 | Standard polar | 33892256 | Progabide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3259.3 | Semi standard non polar | 33892256 | Progabide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3106.0 | Standard non polar | 33892256 | Progabide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 4118.6 | Standard polar | 33892256 | Progabide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3368.4 | Semi standard non polar | 33892256 | Progabide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 2890.9 | Standard non polar | 33892256 | Progabide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 4209.6 | Standard polar | 33892256 | Progabide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C | 3591.7 | Semi standard non polar | 33892256 | Progabide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C | 3317.7 | Standard non polar | 33892256 | Progabide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C | 3987.7 | Standard polar | 33892256 | Progabide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C | 3593.3 | Semi standard non polar | 33892256 | Progabide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C | 3273.2 | Standard non polar | 33892256 | Progabide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C | 3850.8 | Standard polar | 33892256 | Progabide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3843.3 | Semi standard non polar | 33892256 | Progabide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3514.5 | Standard non polar | 33892256 | Progabide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1 | 3749.2 | 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 - Progabide GC-MS (Non-derivatized) - 70eV, Positive | splash10-000x-5091000000-45493775f8e316fed345 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Progabide 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 - Progabide 10V, Positive-QTOF | splash10-00kr-1029000000-fc0da8ed87727a709a1f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 20V, Positive-QTOF | splash10-014i-5059000000-63dcad42741a847ae8ff | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 40V, Positive-QTOF | splash10-000f-9520000000-da113f6ba6c4a6d23a82 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 10V, Negative-QTOF | splash10-001i-0129000000-3de1ea119383317ba355 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 20V, Negative-QTOF | splash10-000y-6289000000-b086ccb10b99604720a8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 40V, Negative-QTOF | splash10-0006-9330000000-2be76f698dbbc120b6b1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 10V, Positive-QTOF | splash10-000i-0009000000-513fcdf8c10f3b29cd13 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 20V, Positive-QTOF | splash10-0f80-0094000000-8c5c8a6b47f57d482e91 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 40V, Positive-QTOF | splash10-01q9-0090000000-990d46a622dd2ff2264d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 10V, Negative-QTOF | splash10-001i-0029000000-8d3aa9ae2fda5750dbf2 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 20V, Negative-QTOF | splash10-000t-2196000000-d2a509d2c58ae1850d29 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Progabide 40V, Negative-QTOF | splash10-01qj-3490000000-5a245325ccd99decd7c9 | 2021-10-11 | Wishart Lab | View Spectrum |
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