Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:10:45 UTC |
---|
Update date | 2019-11-26 03:08:32 UTC |
---|
Primary ID | FDB013518 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Uvaol |
---|
Description | Constituent of olive oil and Osmanthus fragrans (sweet osmanthus)
Uvaol is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Uvaol exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619) |
---|
CAS Number | 545-46-0 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
(3.beta.)-urs-12-ene-3,28-diol | HMDB | (3beta)-Urs-12-ene-3,28-diol | biospider | Urs-12-ene-3,28-diol | biospider | Urs-12-ene-3beta,28-diol | biospider | Uvaol | db_source |
|
---|
Predicted Properties | |
---|
Chemical Formula | C30H50O2 |
---|
IUPAC name | 8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol |
---|
InChI Identifier | InChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3 |
---|
InChI Key | XUARCIYIVXVTAE-UHFFFAOYSA-N |
---|
Isomeric SMILES | CC1CCC2(CO)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C |
---|
Average Molecular Weight | 442.7168 |
---|
Monoisotopic Molecular Weight | 442.381080844 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Prenol lipids |
---|
Sub Class | Triterpenoids |
---|
Direct Parent | Triterpenoids |
---|
Alternative Parents | |
---|
Substituents | - Triterpenoid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
|
---|
Molecular Framework | Aliphatic homopolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Ontology | No ontology term |
---|
Physico-Chemical Properties |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 81.39%; H 11.38%; O 7.23% | DFC |
---|
Melting Point | Mp 232-233° | DFC |
---|
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]D +70 (c, 0.93 in CHCl3) | DFC |
---|
Spectroscopic UV Data | [neutral] lmax 205 () (MeOH) (Berdy) | DFC |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Not Available |
---|
MS/MS | Type | Description | Splash Key | View |
---|
Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004l-0000900000-1b790f5e9eb5bf2bf90e | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-056r-1231900000-29ce819c5908fe6bde31 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pvj-7694100000-2b9064a475a1e08a9d51 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0000900000-7faf32cca5b2bea1eab2 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-006x-0001900000-ae3e9b87b7df659c3633 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0005-1009600000-56d6425409f73e689b7c | 2016-08-03 | View Spectrum |
|
---|
NMR | Not Available |
---|
External Links |
---|
ChemSpider ID | 83774 |
---|
ChEMBL ID | CHEMBL399873 |
---|
KEGG Compound ID | Not Available |
---|
Pubchem Compound ID | 92802 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB02391 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | JFD07-X:JDW15-B |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | UVAOL |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00032467 |
---|
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 |
---|
Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti-proliferative | | An agent that inhibits cell growth and division, particularly in cancer cells, preventing tumor expansion. It plays a biological role in regulating cell cycles and has therapeutic applications in cancer treatment, such as chemotherapy and targeted therapy, with key medical uses in managing various types of cancer and other proliferative diseases. | DUKE | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | Cytotoxic | 52209 | An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells. | DUKE | Lipoxygenase inhibitor | 35856 | An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases. | DUKE |
|
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | show |
---|
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).
|
---|