Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:05:14 UTC |
---|
Update date | 2020-02-24 19:10:25 UTC |
---|
Primary ID | FDB002116 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | Cinchonidine |
---|
Description | Cinchonidine, also known as a-quinidine or cinchovatine, 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 is a very strong basic compound (based on its pKa). Cinchonidine has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and olives. This could make cinchonidine a potential biomarker for the consumption of these foods. |
---|
CAS Number | 485-71-2 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
(-)-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 | HMDB | Cinchonidine sulfate(2:1) | HMDB | Cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isomer | HMDB | Cinchonidine hydrochloride | MeSH | 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 |
|
---|
Predicted Properties | |
---|
Chemical Formula | C19H22N2O |
---|
IUPAC name | {5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol |
---|
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 |
---|
InChI Key | KMPWYEUPVWOPIM-UHFFFAOYSA-N |
---|
Isomeric SMILES | OC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2 |
---|
Average Molecular Weight | 294.3908 |
---|
Monoisotopic Molecular Weight | 294.173213336 |
---|
Classification |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Alkaloids and derivatives |
---|
Class | Cinchona alkaloids |
---|
Sub Class | Not Available |
---|
Direct Parent | Cinchona alkaloids |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
|
Disposition | Route of exposure: Biological location: Source: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Not Available | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 77.52%; H 7.53%; N 9.52%; O 5.43% | DFC |
---|
Melting Point | Mp 210.5° (205°) | DFC |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | 0.2 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
---|
Experimental logP | 2.82 | SANGSTER (1994) |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | [a]D -110 (EtOH) | DFC |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a5i-2910000000-0f0ed0cb19d7fe7fadca | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00a9-9875000000-eaf01aacdc509130f140 | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0002-0960000000-6456c6c3bb2715a7fa00 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0002-0960000000-6456c6c3bb2715a7fa00 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004j-0090000000-ad4802f48f7823037200 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004r-0890000000-dfa80dddb949e8796af0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ac9-0910000000-23c8a136dc8bfb4979ca | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0190000000-49f8db7ac84bad0edd86 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002f-0290000000-9d17bd1a54e6ff3cde9b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-057r-1910000000-835c9a14cf1712dd341b | JSpectraViewer |
|
---|
External Links |
---|
ChemSpider ID | Not Available |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | C11379 |
---|
Pubchem Compound ID | 101744 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | Not Available |
---|
CRC / DFC (Dictionary of Food Compounds) ID | CFP80-X:CFP80-X |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | CINCHONIDINE |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00002147 |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Cinchonidine |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
---|
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 |
|
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
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).
|
---|