Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 18:10:28 UTC |
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Update Date | 2022-03-07 02:53:42 UTC |
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HMDB ID | HMDB0033440 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Narcotoline |
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Description | Narcotoline is found in opium poppy. Narcotoline is an alkaloid from straw of Papaver somniferum (opium poppy) Narcotoline is an opiate alkaloid chemically related to noscapine. It binds to the same receptors in the brain as noscapine to act as an antitussive, and has also been used in tissue culture media. It can be obtained from the opium poppy Papaver somniferum. It is present at much higher levels in strains used for culinary purposes (poppyseed production) than in high-morphine strains used for opium production. |
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Structure | COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C12 InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3 |
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Synonyms | Not Available |
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Chemical Formula | C21H21NO7 |
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Average Molecular Weight | 399.3939 |
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Monoisotopic Molecular Weight | 399.131802031 |
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IUPAC Name | 3-{4-hydroxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one |
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Traditional Name | 3-{4-hydroxy-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-6,7-dimethoxy-3H-2-benzofuran-1-one |
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CAS Registry Number | 521-40-4 |
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SMILES | COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C12 |
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InChI Identifier | InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3 |
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InChI Key | LMGZCSKYOKDBES-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Phthalide isoquinolines |
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Sub Class | Not Available |
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Direct Parent | Phthalide isoquinolines |
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Alternative Parents | |
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Substituents | - Phthalide isoquinoline
- Phthalide
- Isobenzofuranone
- Benzofuranone
- Tetrahydroisoquinoline
- Benzodioxole
- Isocoumaran
- Anisole
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- Aralkylamine
- Benzenoid
- Amino acid or derivatives
- Tertiary aliphatic amine
- Carboxylic acid ester
- Tertiary amine
- Lactone
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Ether
- Azacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Amine
- Organic oxygen compound
- Organopnictogen compound
- Organonitrogen compound
- Organooxygen compound
- Organic oxide
- 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 | |
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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 | 202 °C | 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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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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 - Narcotoline GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-0090000000-8d36861fe0a3f59dbd49 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Narcotoline GC-MS (1 TMS) - 70eV, Positive | splash10-004i-0090000000-83da6a230540709d25ed | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Narcotoline 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 - Narcotoline 10V, Positive-QTOF | splash10-0udi-0012900000-eb91c9a66be98f3a0e6a | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 20V, Positive-QTOF | splash10-0zfr-0439500000-73d8dce5952ad6dabd42 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 40V, Positive-QTOF | splash10-004i-1913000000-f9a62eb623879958a12a | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 10V, Negative-QTOF | splash10-0002-0009000000-46306f2e15cf4d8ab386 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 20V, Negative-QTOF | splash10-000t-0009000000-4f29fdfaf4b68c9a4380 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 40V, Negative-QTOF | splash10-0f7a-4149000000-ae5a71e7bcc549404f18 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 10V, Negative-QTOF | splash10-0002-0009000000-493e5720e60337ba3deb | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 20V, Negative-QTOF | splash10-0002-0009000000-78f035578ab74eed99fa | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 40V, Negative-QTOF | splash10-0lxw-0529000000-1cb32954177b072022c8 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 10V, Positive-QTOF | splash10-0udi-0010900000-00307be5f0edf24e3e7d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 20V, Positive-QTOF | splash10-0udi-0021900000-5a924610ef954314a386 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Narcotoline 40V, Positive-QTOF | splash10-0690-0977000000-146ce1b694343cd559a7 | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB011478 |
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KNApSAcK ID | C00001892 |
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Chemspider ID | 2736756 |
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KEGG Compound ID | C09593 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Narcotoline |
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METLIN ID | Not Available |
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PubChem Compound | 3496496 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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