Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:22 UTC |
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Update date | 2019-11-26 03:10:30 UTC |
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Primary ID | FDB014623 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Cucurbitacin E |
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Description | Cucurbitacin e is a member of the class of compounds known as cucurbitacins. Cucurbitacins are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Cucurbitacin e is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitacin e is a bitter tasting compound found in cucumber, muskmelon, and watermelon, which makes cucurbitacin e a potential biomarker for the consumption of these food products. |
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CAS Number | 18444-66-1 |
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Structure | |
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Synonyms | Synonym | Source |
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α-elaterin | biospider | α-elaterine | biospider | a-Elaterin | db_source | Alpha-elaterin | biospider | Alpha-elaterine | biospider | Cucurbitacin E | db_source | Cucurbitacine e | biospider | Cucurbitacine-e | biospider | CUE | biospider | Elaterin, alpha | biospider |
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Predicted Properties | |
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Chemical Formula | C32H44O8 |
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IUPAC name | (3E)-6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate |
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InChI Identifier | InChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+ |
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InChI Key | NDYMQXYDSVBNLL-OUKQBFOZSA-N |
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Isomeric SMILES | CC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(C=C(O)C(=O)C4(C)C)C3(C)C(=O)CC12C |
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Average Molecular Weight | 556.687 |
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Monoisotopic Molecular Weight | 556.303618384 |
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Classification |
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Description | Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Cucurbitacins |
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Direct Parent | Cucurbitacins |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Cucurbitacin skeleton
- 22-oxosteroid
- 21-oxosteroid
- 20-hydroxysteroid
- Steroid ester
- 3-oxo-delta-1-steroid
- 3-oxosteroid
- 2-hydroxysteroid
- 16-hydroxysteroid
- Hydroxysteroid
- Oxosteroid
- 11-oxosteroid
- Delta-1-steroid
- Cyclohexenone
- Acyloin
- Cyclic alcohol
- Alpha-hydroxy ketone
- Tertiary alcohol
- Alpha,beta-unsaturated ketone
- Acryloyl-group
- Enone
- Cyclic ketone
- Secondary alcohol
- Carboxylic acid ester
- Ketone
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Enol
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Alcohol
- Organooxygen compound
- Organic oxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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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 | C 69.04%; H 7.97%; O 22.99% | DFC |
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Melting Point | Mp 234° | 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]20D -64.3 (CHCl3) | DFC |
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Spectroscopic UV Data | 269 () (EtOH) (Berdy) | DFC |
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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 | splash10-052r-0002490000-a5e7e9b592435eef0ac6 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-009j-1304920000-793e79191adae98d3d5c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f7a-3359320000-f318c31d8a8c88c66927 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4j-3900380000-b3d176e28ee25f6c446f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4j-5903010000-cda6c5f37c8ec8d27f4c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9105300000-01af65138619a59e0c02 | 2016-08-03 | 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 | C08797 |
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Pubchem Compound ID | 5353547 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 543904 |
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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 | JPP60-I:JSZ09-S |
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EAFUS ID | Not Available |
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Dr. Duke ID | CUCURBITACIN-E |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003686 |
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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 gibberellin | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | 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 | insectifuge | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | Insectiphile | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | 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).
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