Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:07:34 UTC |
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Update date | 2019-11-26 03:01:38 UTC |
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Primary ID | FDB007359 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Gentianine |
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Description | Gentianine, also known as 4-(2-hydroxyethyl)-5-vinylnicotinate g-lactone, is a member of the class of compounds known as pyranopyridines. Pyranopyridines are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring. Gentianine is soluble (in water) and a strong basic compound (based on its pKa). Gentianine is a bitter tasting compound found in fenugreek, which makes gentianine a potential biomarker for the consumption of this food product. |
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CAS Number | 439-89-4 |
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Structure | |
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Synonyms | Synonym | Source |
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4-(2-Hydroxyethyl)-5-vinylnicotinic acid gamma-lactone | ChEBI | 4-(2-Hydroxyethyl)-5-vinylnicotinate g-lactone | Generator | 4-(2-Hydroxyethyl)-5-vinylnicotinate gamma-lactone | Generator | 4-(2-Hydroxyethyl)-5-vinylnicotinate γ-lactone | Generator | 4-(2-Hydroxyethyl)-5-vinylnicotinic acid g-lactone | Generator | 4-(2-Hydroxyethyl)-5-vinylnicotinic acid γ-lactone | Generator | 5-Ethenyl-3,4-dihydro-1H-pyrano(3,4-c)pyridin-1-one | MeSH | 4-(2-hydroxyethyl)-5-vinylnicotinic acid gamma-lactone | biospider | 5-ethenyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-one | biospider | From schultesia guianensis malme (mata-zombando) | biospider | Gencianina | biospider | Gentianine | biospider |
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Predicted Properties | |
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Chemical Formula | C10H9NO2 |
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IUPAC name | 5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one |
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InChI Identifier | InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2 |
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InChI Key | DFNZYFAJQPLJFI-UHFFFAOYSA-N |
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Isomeric SMILES | C=CC1=C2CCOC(=O)C2=CN=C1 |
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Average Molecular Weight | 175.184 |
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Monoisotopic Molecular Weight | 175.063328537 |
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Classification |
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Description | Belongs to the class of organic compounds known as pyranopyridines. These are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyranopyridines |
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Sub Class | Not Available |
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Direct Parent | Pyranopyridines |
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Alternative Parents | |
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Substituents | - Pyranopyridine
- Pyridine carboxylic acid
- Pyridine
- Heteroaromatic compound
- Carboxylic acid ester
- Lactone
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Azacycle
- Oxacycle
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic nitrogen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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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 | Not Available | |
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Melting Point | Not Available | |
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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 | Not Available | |
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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 | Gentianine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fsj-0900000000-82c909a9b8a7607cde1c | 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 | splash10-004i-0900000000-6952936c6079ddf5ab09 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0900000000-d238492324797d68c5ad | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fc0-6900000000-d741083b91716f4a2491 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-c019889916cceb899160 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-7551bf35931ac9e53b04 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ufu-2900000000-909507d1ec10bd79325e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-dd76f78fc523efac1e38 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0900000000-ab54bf6cf5b9da2d0589 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-2900000000-eba85c05b3d25808d631 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-e1e7a7636061f9624da0 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-6c25d3fbd9a60487381a | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0v4j-9600000000-e569d0287224ee966744 | 2021-10-21 | 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 | C06525 |
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Pubchem Compound ID | 354616 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28981 |
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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 | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | GENTIANINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001977 |
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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 | Descriptor | ID | Definition | Reference |
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analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | anti anaphylactic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti arthritic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti edemic | | | DUKE | anti histaminic | 37956 | Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti meningitic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti psychotic | 35476 | Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. | DUKE | anti rheumatic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti shigellic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti staphylococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti streptococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | ataractic | | | DUKE | central nervous system paralytic | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | central nervous system stimulant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | corticosterogenic | | | DUKE | emetic | | | DUKE | hypoglycemic | 35526 | A drug which lowers the blood glucose level. | DUKE | hypotensive | | | DUKE | myorelaxant | | | DUKE | neurotoxic | 50910 | A poison that interferes with the functions of the nervous system. | 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 | sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | 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 | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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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 | — 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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