Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:00 UTC |
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Update date | 2019-11-26 02:56:33 UTC |
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Primary ID | FDB001521 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Verbenalin |
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Description | Verbenalin, also known as cornin (glycoside) or cornin iridoid, is a member of the class of compounds known as iridoid o-glycosides. Iridoid o-glycosides are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Thus, verbenalin is considered to be an isoprenoid lipid molecule. Verbenalin is soluble (in water) and a very weakly acidic compound (based on its pKa). Verbenalin is a bitter tasting compound found in common verbena, which makes verbenalin a potential biomarker for the consumption of this food product. Verbenalin is a chemical compound, classified as an iridoid glucoside, that is found in Verbena officinalis. It is one of the sleep-promoting (soporific) components in Verbena officinalis . |
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CAS Number | 548-37-8 |
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Structure | |
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Synonyms | Synonym | Source |
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Cornin (glycoside) | Kegg | Methyl (1S,4as,7S,7ar)-7-methyl-5-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylic acid | Generator | Cornin iridoid | MeSH |
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Predicted Properties | |
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Chemical Formula | C17H24O10 |
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IUPAC name | methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate |
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InChI Identifier | InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1 |
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InChI Key | HLXRWTJXGMHOFN-XJSNKYLASA-N |
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Isomeric SMILES | COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@@H](C)CC(=O)[C@H]12 |
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Average Molecular Weight | 388.3665 |
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Monoisotopic Molecular Weight | 388.136946988 |
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Classification |
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Description | Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene glycosides |
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Direct Parent | Iridoid O-glycosides |
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Alternative Parents | |
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Substituents | - Iridoid o-glycoside
- Hexose monosaccharide
- Glycosyl compound
- Iridoid-skeleton
- O-glycosyl compound
- Bicyclic monoterpenoid
- Monoterpenoid
- Monosaccharide
- Oxane
- Vinylogous ester
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Methyl ester
- Secondary alcohol
- Ketone
- Carboxylic acid ester
- Polyol
- Carboxylic acid derivative
- Acetal
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Oxacycle
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- Organooxygen compound
- Primary alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | - terpene glycoside (CHEBI:9954 )
- Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (C09802 )
- Iridoids (C09802 )
- Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (LMPR0102070016 )
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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 | 211 mg/mL at 18 oC | BEILSTEIN |
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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 | Not Available |
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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 | splash10-01t9-0896000000-437cd88fa73a5c4d7b90 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06vj-0951000000-1242e64dbb52b6178f09 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kb-3920000000-da78294fdb00d24514e0 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004r-1589000000-d3de7f2ed7d905736e35 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-2963000000-a5eb145f50523b35dd20 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0036-8920000000-cae9774ae18e15ccbe46 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004r-0197000000-08dc874beea6d15b7630 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4l-0982000000-cccb82751b52776fa64a | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05r0-7792000000-390fc7ee43f9dc8ee78d | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0379000000-9c71e3d58bd848370ba7 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05ot-2944000000-ed555a3f148b5df753ed | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4m-9631000000-3f8cf1006bc884d2333e | 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 | Not Available |
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Pubchem Compound ID | Not Available |
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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 | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | VERBENALIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003102 |
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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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abortifacient | 50691 | A chemical substance that interrupts pregnancy after implantation. | DUKE | cathartic | 75325 | Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic. | 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 | coagulant | | | DUKE | parasympathicomimetic | | | DUKE | purgative | 50503 | An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic. | DUKE | utero tonic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | 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). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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