Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:16 UTC |
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Update date | 2020-02-24 19:10:27 UTC |
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Primary ID | FDB002188 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (R)-Pronuciferine |
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Description | (R)-Pronuciferine, also known as milthanthine or N-methylstepharine, belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol (R)-Pronuciferine is a very strong basic compound (based on its pKa) (R)-Pronuciferine has been detected, but not quantified in, several different foods, such as cherimoya, coffee and coffee products, poppies, and sacred lotus. This could make (R)-pronuciferine a potential biomarker for the consumption of these foods. |
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CAS Number | 2128-60-1 |
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Structure | |
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Synonyms | Synonym | Source |
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(+)-Pronuciferine | HMDB | Milthanthine | HMDB | N,O-Dimethylcrotonosine | HMDB | N-Methylstepharine | HMDB | Pronuciferin | HMDB | Pronuciferine | HMDB | (+)-pronuciferine | biospider | N-methylstepharine | biospider | N,o-dimethylcrotonosine | biospider |
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Predicted Properties | |
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Chemical Formula | C19H21NO3 |
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IUPAC name | 10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one |
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InChI Identifier | InChI=1S/C19H21NO3/c1-20-9-6-12-10-15(22-2)18(23-3)17-16(12)14(20)11-19(17)7-4-13(21)5-8-19/h4-5,7-8,10,14H,6,9,11H2,1-3H3 |
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InChI Key | WUYQEGNOQLRQAQ-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=C(OC)C2=C3C(CC22C=CC(=O)C=C2)N(C)CCC3=C1 |
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Average Molecular Weight | 311.3749 |
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Monoisotopic Molecular Weight | 311.152143543 |
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Classification |
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Description | Belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Proaporphines |
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Sub Class | Not Available |
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Direct Parent | Proaporphines |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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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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Disposition | Route of exposure: Biological location: Source: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 73.29%; H 6.80%; N 4.50%; O 15.41% | DFC |
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Melting Point | Mp 127-129° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D +106 (c, 0.41 in EtOH) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | (R)-Pronuciferine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0002-0090000000-86334b4a99135535b468 | Spectrum | Predicted GC-MS | (R)-Pronuciferine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0059000000-24ed1e33f6d78af24232 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-0092000000-f4f2970614db51a81d97 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0v00-2090000000-14cc8227698e8328a57e | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0009000000-35a9eef82c86df85fa6e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0079000000-79ce4bd105b65de6f1df | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03kc-0090000000-86e72526e0832cd9e0b8 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0009000000-9f3b29c8dcdf015b99e9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0039000000-5009deaf9268e5c4f8a9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0909-1090000000-41fa0a4fc39efba03adc | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0009000000-9bf675b2e28db05b0d3b | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0009000000-7c0bcc885755bb30ace8 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-1049000000-bd5ec9bb499964d23c7e | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 545754 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C09611 |
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Pubchem Compound ID | 628376 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 42 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB30344 |
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CRC / DFC (Dictionary of Food Compounds) ID | CGQ83-M:CGQ84-N |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001905 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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