Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 19:16:54 UTC |
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Update Date | 2022-03-07 02:54:06 UTC |
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HMDB ID | HMDB0034436 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Rotenone |
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Description | Rotenone is found in jicama. Rotenone is widely distributed in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean).Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinson's disease. |
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Structure | [H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1 |
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Synonyms | Value | Source |
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(-)-cis-Rotenone | ChEBI | (-)-Rotenone | ChEBI | 5'beta-Rotenone | ChEBI | [2R-(2alpha,6Aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one | ChEBI | Barbasco | ChEBI | Canex | ChEBI | Dactinol | ChEBI | Derris | ChEBI | Noxfire | ChEBI | Paraderil | ChEBI | Tubatoxin | ChEBI | 5'b-Rotenone | Generator | 5'Β-rotenone | Generator | [2R-(2a,6Aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one | Generator | [2R-(2Α,6aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one | Generator | 1,2,12,12a-tetrahydro-8,9-Dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one, 9ci | HMDB | Derrin | HMDB | Derris, jmaf | HMDB | Dri-kil | HMDB | Nicouline | HMDB | Noxfish | HMDB | Tubotoxin | HMDB |
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Chemical Formula | C23H22O6 |
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Average Molecular Weight | 394.4172 |
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Monoisotopic Molecular Weight | 394.141638436 |
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IUPAC Name | (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one |
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Traditional Name | (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one |
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CAS Registry Number | 83-79-4 |
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SMILES | [H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C |
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InChI Identifier | InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1 |
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InChI Key | JUVIOZPCNVVQFO-HBGVWJBISA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Isoflavonoids |
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Sub Class | Rotenoids |
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Direct Parent | Rotenones |
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Alternative Parents | |
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Substituents | - Rotenone or derivatives
- 8-prenylated isoflavanone
- Isoflavanone
- Isoflavan
- Chromone
- Chromane
- 1-benzopyran
- Benzopyran
- Coumaran
- Anisole
- Aryl alkyl ketone
- Aryl ketone
- Alkyl aryl ether
- Benzenoid
- Ketone
- Ether
- Oxacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 163 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0002 mg/mL at 20 °C | Not Available | LogP | 4.10 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Rotenone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0zi3-2549000000-930d18ff5e2d26d23e39 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Rotenone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Rotenone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0006-3901000000-c340e02baee25cf6196b | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone LC-ESI-QTOF , positive-QTOF | splash10-0002-0009000000-358453a180ad1eac44bb | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone LC-ESI-QTOF , positive-QTOF | splash10-0002-0129000000-cc8a296246aa7e1b7fec | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone LC-ESI-QTOF , positive-QTOF | splash10-03dm-0795000000-228bd7c35bed240b45ad | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF | splash10-01ow-0698000000-a9e4b41be932783b0afd | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF | splash10-01ow-0698000000-8f6994cc1cf72104baf0 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF | splash10-03dm-0696000000-cbec904cb2f70ad2fab0 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF | splash10-03dl-0693000000-fb2d60cf107761a6c44d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF | splash10-03dl-0693000000-5718e6cf640e3d715757 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOF | splash10-03dl-0693000000-0e5df9ae944ec77aec31 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 20V, Negative-QTOF | splash10-03dl-4669000000-0fb03940864d95c2078a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 55V, Positive-QTOF | splash10-03dl-0693000000-33cf33e1c5d6e621df3a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 45V, Positive-QTOF | splash10-03dl-0693000000-209ca7e024f911e3b7d9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 10V, Negative-QTOF | splash10-0006-1449000000-3bc2601b53c203b7fa83 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 20V, Positive-QTOF | splash10-01oy-0964000000-acfb0099b12ab168b4a8 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 40V, Positive-QTOF | splash10-0007-0910000000-7b2d8dce16788bdf7747 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 15V, Positive-QTOF | splash10-0002-0129000000-64fb6c845a91bd3fb4b7 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 10V, Positive-QTOF | splash10-0002-0009000000-9e8d4cec92e24203cdbd | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 20V, Positive-QTOF | splash10-03dm-0695000000-e9e1241f5910716f0c92 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rotenone 20V, Positive-QTOF | splash10-03dm-0695000000-4af2f040a67e164c6325 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rotenone 10V, Positive-QTOF | splash10-0002-0129000000-36a830cd40ad8fbcdeee | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rotenone 20V, Positive-QTOF | splash10-004s-1359000000-7b6f697fe59d525d48f9 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rotenone 40V, Positive-QTOF | splash10-05r0-4931000000-2d664b8d3fd4ebfd86ce | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rotenone 10V, Negative-QTOF | splash10-0006-0009000000-fbc08106b7ba4d66b944 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rotenone 20V, Negative-QTOF | splash10-0006-0019000000-ac9b3c7e9dbdabbc9404 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rotenone 40V, Negative-QTOF | splash10-0pbj-0924000000-7060b1a64eec50bf9c96 | 2017-07-26 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB11457 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB012837 |
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KNApSAcK ID | C00002568 |
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Chemspider ID | 6500 |
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KEGG Compound ID | C07593 |
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BioCyc ID | CPD-5741 |
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BiGG ID | Not Available |
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Wikipedia Link | Rotenone |
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METLIN ID | Not Available |
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PubChem Compound | 6758 |
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PDB ID | Not Available |
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ChEBI ID | 28201 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1280741 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Khar A, Ali AM, Begum Z, Pardhasaradhi BV, Varalakshmi C: Induction of apoptosis in AK-5 cells by rotenone involves participation of caspases. Indian J Biochem Biophys. 1999 Apr;36(2):77-81. [PubMed:10549166 ]
- Tapias V, Cannon JR, Greenamyre JT: Melatonin treatment potentiates neurodegeneration in a rat rotenone Parkinson's disease model. J Neurosci Res. 2010 Feb 1;88(2):420-7. doi: 10.1002/jnr.22201. [PubMed:19681169 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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