Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:14 UTC |
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Update date | 2020-02-24 19:10:25 UTC |
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Primary ID | FDB002116 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Cinchonidine |
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Description | Cinchonidine belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety. Cinchonidine has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and olives (Olea europaea). This could make cinchonidine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cinchonidine. |
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CAS Number | 485-71-2 |
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Structure | |
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Synonyms | Synonym | Source |
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Cinchonine, hexaiodotl(-2) (1:1), (9S)-isomer | MeSH | Cinchonine, hydrochloride, (9S)-isomer | MeSH | Cinchonine, monohydrochloride, (9S)-isomer | MeSH | Cinchonine, sulfate (2:1), (9S)-isomer | MeSH | (-)-Cinchonidine | HMDB | (8a,9R)-Cinchonan-9-ol, 9ci | HMDB | (8alpha ,9R)-Cinchonan-9-ol | HMDB | (8S,9R)-Cinchonidine | HMDB | a-Quinidine | HMDB | alpha -Quinidine | HMDB | alpha-Quinidine | HMDB | Cinchovatine | HMDB | L-Cinchonidine | HMDB | Nchem.180-comp1b | HMDB | Cinchonidine monohydrochloride | MeSH, HMDB | Cinchonidine sulfate(2:1) | MeSH, HMDB | Cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isomer | MeSH, HMDB | Cinchonidine hydrochloride | MeSH, HMDB | Cinchonidine | MeSH | (-)-cinchonidine | biospider | (8α,9R)-Cinchonan-9-ol | biospider | (8a,9R)-Cinchonan-9-ol, 9CI | db_source | α-quinidine | biospider | Alpha-quinidine | biospider | Cinchonan-9-ol, (8α, 9R)- | biospider | Cinchonan-9-ol, (8α,9R)- | biospider | L-cinchonidine | biospider | nchem.180-comp1b | biospider |
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Predicted Properties | |
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Chemical Formula | C19H22N2O |
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IUPAC name | {5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol |
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InChI Identifier | InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2 |
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InChI Key | KMPWYEUPVWOPIM-UHFFFAOYSA-N |
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Isomeric SMILES | OC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2 |
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Average Molecular Weight | 294.3908 |
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Monoisotopic Molecular Weight | 294.173213336 |
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Classification |
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Description | Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Cinchona alkaloids |
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Sub Class | Not Available |
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Direct Parent | Cinchona alkaloids |
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Alternative Parents | |
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Substituents | - Cinchonan-skeleton
- 4-quinolinemethanol
- Quinoline
- Quinuclidine
- Aralkylamine
- Piperidine
- Pyridine
- Benzenoid
- Heteroaromatic compound
- 1,2-aminoalcohol
- Secondary alcohol
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Amine
- Alcohol
- Aromatic alcohol
- 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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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 77.52%; H 7.53%; N 9.52%; O 5.43% | DFC |
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Melting Point | Mp 210.5° (205°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.2 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 2.82 | SANGSTER (1994) |
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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 -110 (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 | Cinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a5i-2910000000-0f0ed0cb19d7fe7fadca | Spectrum | Predicted GC-MS | Cinchonidine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00a9-9875000000-eaf01aacdc509130f140 | Spectrum | Predicted GC-MS | Cinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cinchonidine, 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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MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0002-0960000000-6456c6c3bb2715a7fa00 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0002-0960000000-6456c6c3bb2715a7fa00 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0090000000-6187f815acdbbec47fb2 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00lu-2900000000-14f3c34cde5aa2a11079 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00nb-2940000000-eb3a248cf968cf941040 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-069v-0980000000-48c213347c975179636c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-0002-0090000000-0e970cbc2afa57a9654f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0190000000-858bee716ec1d75adc07 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0561-1940000000-26e7e3cbae5ea5fb610f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0090000000-b480b5a0b696f940452f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0190000000-f93b51b0818b008b49b7 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00lr-1900000000-603d73783b786d42fdc1 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0190000000-6595d19fdd23a9e3238b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0190000000-5a94ad8c559d5c375bdd | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0190000000-c81a1076dcd69ebccce3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0090000000-ae336d292aca65dcc174 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0090000000-166d01b77083c7e27751 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-001j-2950000000-88afa86bed375ec3a70c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0190000000-6abca9144bc157cadb34 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004j-0090000000-ad4802f48f7823037200 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004r-0890000000-dfa80dddb949e8796af0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ac9-0910000000-23c8a136dc8bfb4979ca | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0190000000-49f8db7ac84bad0edd86 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002f-0290000000-9d17bd1a54e6ff3cde9b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-057r-1910000000-835c9a14cf1712dd341b | 2016-08-03 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C11379 |
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Pubchem Compound ID | 101744 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | CFP80-X:CFP80-X |
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EAFUS ID | Not Available |
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Dr. Duke ID | CINCHONIDINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002147 |
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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 | Cinchonidine |
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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 | Descriptor | ID | Definition | Reference |
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anti flu | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti herpetic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti malarial | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti pyretic | 35493 | A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever. | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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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. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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