Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:10:41 UTC |
---|
Update date | 2019-11-26 03:08:23 UTC |
---|
Primary ID | FDB013409 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Acteoside |
---|
Description | Acteoside, also known as kusaginin or verbascoside, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Acteoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Acteoside is found, on average, in the highest concentration within a few different foods, such as common verbena, lemon verbena, and olives. Acteoside has also been detected, but not quantified in, a few different foods, such as bitter gourds, fruits, and sesames. This could make acteoside a potential biomarker for the consumption of these foods. |
---|
CAS Number | 61276-17-3 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
Kusaginin | HMDB | Verbascoside | HMDB | 6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid | Generator | Acteoside | MeSH |
|
---|
Predicted Properties | |
---|
Chemical Formula | C29H36O15 |
---|
IUPAC name | 6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
---|
InChI Identifier | InChI=1S/C29H36O15/c1-13-22(36)23(37)24(38)29(41-13)44-27-25(39)28(40-9-8-15-3-6-17(32)19(34)11-15)42-20(12-30)26(27)43-21(35)7-4-14-2-5-16(31)18(33)10-14/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/b7-4+ |
---|
InChI Key | FBSKJMQYURKNSU-QPJJXVBHSA-N |
---|
Isomeric SMILES | CC1OC(OC2C(O)C(OCCC3=CC(O)=C(O)C=C3)OC(CO)C2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C(O)C(O)C1O |
---|
Average Molecular Weight | 624.5871 |
---|
Monoisotopic Molecular Weight | 624.205420482 |
---|
Classification |
---|
Description | belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. |
---|
Kingdom | Organic compounds |
---|
Super Class | Phenylpropanoids and polyketides |
---|
Class | Cinnamic acids and derivatives |
---|
Sub Class | Hydroxycinnamic acids and derivatives |
---|
Direct Parent | Coumaric acids and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Coumaric acid or derivatives
- Cinnamic acid ester
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Tyrosol derivative
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Fatty acid ester
- Phenol
- Monocyclic benzene moiety
- Fatty acyl
- Oxane
- Benzenoid
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Carboxylic acid ester
- Polyol
- Acetal
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Oxacycle
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Primary alcohol
- Alcohol
- Aromatic heteromonocyclic compound
|
---|
Molecular Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Industrial application: Biological role: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Not Available | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 55.77%; H 5.81%; O 38.42% | DFC |
---|
Melting Point | Not Available | |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | [a]20D -84.9 (c, 1.15 in MeOH) | 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 | splash10-0c01-8920533000-c097428fe1e65a0969d1 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00gv-9700035000-c5b8ef4573cf92ca120f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-06vi-0610905000-d3e010321fe0d919d876 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-08g0-0902400000-dd983ed069c1287efa62 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-07vs-0936300000-3704d6fa7e12bff5166c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-024i-1711907000-8d66cf1f56e75f6558ad | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ta-1931400000-86ecba3eeab93093ef6c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01t9-2912000000-635e9beb27d765412134 | JSpectraViewer |
|
---|
External Links |
---|
ChemSpider ID | 4572852 |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | C10501 |
---|
Pubchem Compound ID | 5459010 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | 468 |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB34843 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | DVR38-T:HWS46-Y |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | VERBASCOSIDE |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00002783 |
---|
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 | Not Available |
---|
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 |
---|
aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | 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 bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti feedant | | | DUKE | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | anti hypertensive | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti staph | | | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | hypertensive | | | DUKE | immunosuppressant | 35705 | An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. | DUKE | lipoxygenase inhibitor | 35856 | A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. | 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 | phytoalexin | 26115 | A toxin made by a plant that acts against an organism attacking it. | DUKE | protein kinase C inhibitor | 37700 | An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13). | 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 | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
|
---|