| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:49 UTC |
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| Update date | 2019-11-26 03:08:46 UTC |
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| Primary ID | FDB013641 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Lupeol |
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| Description | Lupeol is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Lupeol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Lupeol can be found in a number of food items such as canola, wild carrot, annual wild rice, and european plum, which makes lupeol a potential biomarker for the consumption of these food products. Lupeol is a pharmacologically active triterpenoid. It has several potential medicinal properties . |
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| CAS Number | 545-47-1 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C30H50O |
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| IUPAC name | 1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol |
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| InChI Identifier | InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3 |
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| InChI Key | MQYXUWHLBZFQQO-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(=C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12 |
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| Average Molecular Weight | 426.7174 |
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| Monoisotopic Molecular Weight | 426.386166222 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
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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 | Triterpenoids |
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| Direct Parent | Triterpenoids |
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| Alternative Parents | |
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| Substituents | - Triterpenoid
- Steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic 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 |
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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 | C 84.44%; H 11.81%; O 3.75% | DFC |
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| Melting Point | Mp 215-216° | DFC |
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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 | [a]D +26.4 (CHCl3) | DFC |
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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 | Lupeol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03dj-0119400000-544f7e1713d3a6d84864 | Spectrum | | Predicted GC-MS | Lupeol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Lupeol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Lupeol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | 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 | splash10-0a6r-0011900000-5050c1fe6f79cc640e40 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6r-0579800000-bb52e352c147b0af98ca | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gbj-2597100000-25942c8a036898062a7a | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000900000-d739c6a879f3b6b778eb | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0000900000-a2c05f9b1d8dd849100d | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-1009500000-dc899db3dbe40f34e43e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0004900000-ae22da79c014597e8506 | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-055r-2790300000-09360cec56fad60faf46 | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-053i-4942000000-207dff202d58aa074685 | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000900000-590c9e4adfdd12b64d93 | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0000900000-590c9e4adfdd12b64d93 | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-0000900000-390655f1ec092e7b7517 | 2021-10-12 | 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 | C08628 |
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| Pubchem Compound ID | 259846 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 606123 |
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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 | JFT17-C:JFT13-Y |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | LUPEOL |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00003749 |
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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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| anti angiogenic | 48422 | An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. | DUKE | | anti Epstein-Barr virus | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti edemic | | | DUKE | | anti flu | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti hyperglycemic | | | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti lithic | | | DUKE | | anti malarial | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti oxalate | | | 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 peroxidant | | | DUKE | | anti prostaglandin | 49020 | A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. | DUKE | | anti rheumatic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti urethrotic | | | DUKE | | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | | FPTase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | hypotensive | | | 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 | | topoisomerase-II inhibitor | 50750 | A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. | 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 | Not Available |
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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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