Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 12:58:42 UTC |
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Update Date | 2023-02-21 17:16:56 UTC |
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HMDB ID | HMDB0004145 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | BOX B |
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Description | BOX B is produced by bilirubin oxidation, a heme-derived compound. BOXes are produced as a mixture of isomers, and may be involved in cerebral vasospasm. BOXes are subject of interest in the neurosurgical and neurological fields because of their correlation with and/or role in subarachnoid hemorrhage induced cerebral vasospasm. Subarachnoid hemorrhage (SAH) induces cerebral vasospasm that can lead to ischemic injury or death and is a common complication of SAH. BOX B can be found in cerebrospinal fluid in SAH. (PMID: 17981669 ). |
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Structure | CC1=C(C=C)C(=O)N\C1=C/C(N)=O InChI=1S/C9H10N2O2/c1-3-6-5(2)7(4-8(10)12)11-9(6)13/h3-4H,1H2,2H3,(H2,10,12)(H,11,13)/b7-4- |
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Synonyms | Value | Source |
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2-(4-Ethenyl-1,5-dihydro-3-methyl-5-oxo-2H-pyrrol-2-ylidene)-acetamide | HMDB | 3-Methyl-5-oxo-4-vinyl- (1,5-dihydropyrrol-2-ylidene)acetamide | HMDB | 2-[(2Z)-4-Ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]ethanimidate | Generator, HMDB |
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Chemical Formula | C9H10N2O2 |
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Average Molecular Weight | 178.1879 |
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Monoisotopic Molecular Weight | 178.074227574 |
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IUPAC Name | 2-[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]acetamide |
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Traditional Name | 2-[(2Z)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]acetamide |
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CAS Registry Number | 329314-75-2 |
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SMILES | CC1=C(C=C)C(=O)N\C1=C/C(N)=O |
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InChI Identifier | InChI=1S/C9H10N2O2/c1-3-6-5(2)7(4-8(10)12)11-9(6)13/h3-4H,1H2,2H3,(H2,10,12)(H,11,13)/b7-4- |
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InChI Key | JJDLLVZMTMEVBY-DAXSKMNVSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyrrolines |
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Sub Class | Not Available |
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Direct Parent | Pyrrolines |
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Alternative Parents | |
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Substituents | - Pyrroline
- Vinylogous amide
- Carboxamide group
- Lactam
- Primary carboxylic acid amide
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Azacycle
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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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BOX B,1TMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C)NC1=O | 2088.8 | Semi standard non polar | 33892256 | BOX B,1TMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C)NC1=O | 2019.7 | Standard non polar | 33892256 | BOX B,1TMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C)NC1=O | 3040.9 | Standard polar | 33892256 | BOX B,1TMS,isomer #2 | C=CC1=C(C)/C(=C/C(N)=O)N([Si](C)(C)C)C1=O | 2036.4 | Semi standard non polar | 33892256 | BOX B,1TMS,isomer #2 | C=CC1=C(C)/C(=C/C(N)=O)N([Si](C)(C)C)C1=O | 1762.4 | Standard non polar | 33892256 | BOX B,1TMS,isomer #2 | C=CC1=C(C)/C(=C/C(N)=O)N([Si](C)(C)C)C1=O | 2860.2 | Standard polar | 33892256 | BOX B,2TMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C)[Si](C)(C)C)NC1=O | 2219.9 | Semi standard non polar | 33892256 | BOX B,2TMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C)[Si](C)(C)C)NC1=O | 2139.7 | Standard non polar | 33892256 | BOX B,2TMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C)[Si](C)(C)C)NC1=O | 2916.2 | Standard polar | 33892256 | BOX B,2TMS,isomer #2 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C)N([Si](C)(C)C)C1=O | 2075.0 | Semi standard non polar | 33892256 | BOX B,2TMS,isomer #2 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C)N([Si](C)(C)C)C1=O | 1945.2 | Standard non polar | 33892256 | BOX B,2TMS,isomer #2 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C)N([Si](C)(C)C)C1=O | 2424.9 | Standard polar | 33892256 | BOX B,3TMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C1=O | 2119.8 | Semi standard non polar | 33892256 | BOX B,3TMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C1=O | 2020.8 | Standard non polar | 33892256 | BOX B,3TMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C1=O | 2304.9 | Standard polar | 33892256 | BOX B,1TBDMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C(C)(C)C)NC1=O | 2321.4 | Semi standard non polar | 33892256 | BOX B,1TBDMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C(C)(C)C)NC1=O | 2260.1 | Standard non polar | 33892256 | BOX B,1TBDMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C(C)(C)C)NC1=O | 3045.3 | Standard polar | 33892256 | BOX B,1TBDMS,isomer #2 | C=CC1=C(C)/C(=C/C(N)=O)N([Si](C)(C)C(C)(C)C)C1=O | 2298.3 | Semi standard non polar | 33892256 | BOX B,1TBDMS,isomer #2 | C=CC1=C(C)/C(=C/C(N)=O)N([Si](C)(C)C(C)(C)C)C1=O | 1962.4 | Standard non polar | 33892256 | BOX B,1TBDMS,isomer #2 | C=CC1=C(C)/C(=C/C(N)=O)N([Si](C)(C)C(C)(C)C)C1=O | 2883.6 | Standard polar | 33892256 | BOX B,2TBDMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=O | 2618.9 | Semi standard non polar | 33892256 | BOX B,2TBDMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=O | 2526.5 | Standard non polar | 33892256 | BOX B,2TBDMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=O | 2957.7 | Standard polar | 33892256 | BOX B,2TBDMS,isomer #2 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O | 2517.6 | Semi standard non polar | 33892256 | BOX B,2TBDMS,isomer #2 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O | 2316.9 | Standard non polar | 33892256 | BOX B,2TBDMS,isomer #2 | C=CC1=C(C)/C(=C/C(=O)N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O | 2513.9 | Standard polar | 33892256 | BOX B,3TBDMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O | 2761.5 | Semi standard non polar | 33892256 | BOX B,3TBDMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O | 2576.9 | Standard non polar | 33892256 | BOX B,3TBDMS,isomer #1 | C=CC1=C(C)/C(=C/C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O | 2536.4 | 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 - BOX B GC-MS (Non-derivatized) - 70eV, Positive | splash10-0400-4900000000-c1366f5209cffc053b5e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - BOX B 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 - BOX B 10V, Positive-QTOF | splash10-03fr-0900000000-85fad0e47305eb3c531a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 20V, Positive-QTOF | splash10-03di-1900000000-2659cd347d73cc48d1d8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 40V, Positive-QTOF | splash10-014i-9100000000-7cb6476a27b464ddba9b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 10V, Negative-QTOF | splash10-004i-0900000000-3609e056fe28b3ba21c5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 20V, Negative-QTOF | splash10-002f-5900000000-227f05e5a598f7b90260 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 40V, Negative-QTOF | splash10-0006-9000000000-8a484129caa93e901d50 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 10V, Positive-QTOF | splash10-01u0-0900000000-daa225a0c0291b0f07c8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 20V, Positive-QTOF | splash10-03e9-3900000000-a4ba9f03bc7ddd85235e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 40V, Positive-QTOF | splash10-00kf-9200000000-01df55e78f84a12e9246 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 10V, Negative-QTOF | splash10-001i-0900000000-bfdf4900a6655ee50219 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 20V, Negative-QTOF | splash10-005c-4900000000-52986e9c0ff2d8a70ed3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - BOX B 40V, Negative-QTOF | splash10-0006-9000000000-b1c13bace664aa7ddc69 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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