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 |
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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 | An agent that induces abortion, disrupting pregnancy by blocking progesterone or causing uterine contractions. Therapeutically, it's used to terminate early pregnancies, manage ectopic pregnancies, or treat miscarriages. Key medical uses include medical abortion, pregnancy termination, and menstrual regulation. | DUKE | Cathartic | 75325 | An agent that induces bowel movements, relieving constipation by stimulating intestinal motility. Its biological role is to increase water and electrolyte secretion in the gut. Therapeutically, cathartics are used to treat constipation, prepare the bowel for surgery or exams, and manage opioid-induced constipation. Key medical uses include laxative therapy and colonoscopy preparation. | DUKE | Central nervous system stimulant | 35470 | An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood. | DUKE | Coagulant | | An agent that causes blood or another liquid to coagulate, playing a crucial biological role in wound healing and hemostasis. Therapeutically, coagulants are used to treat bleeding disorders, such as hemophilia, and to prevent excessive bleeding during surgery, with key medical uses including trauma treatment and transfusion medicine. | DUKE | Parasympathicomimetic | | An agent that mimics the parasympathetic nervous system, promoting relaxation and reducing stress. It has therapeutic applications in managing glaucoma, asthma, and gastrointestinal disorders, and is used to treat conditions such as bradycardia, bowel obstruction, and salivation disorders. | DUKE | Purgative | 50503 | An agent that stimulates bowel movements, promoting the elimination of waste and toxins from the digestive system. It plays a biological role in maintaining gut health and is therapeutically used to treat constipation, prepare the bowel for surgical procedures, and manage certain medical conditions, such as fecal impaction. | DUKE | Utero tonic | 52217 | An agent that stimulates and strengthens the uterine muscles, aiding in childbirth and reducing postpartum bleeding. Therapeutically, it is used to induce labor, manage uterine atony, and treat menstrual disorders, promoting overall reproductive health. | 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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