Record Information |
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Version | 4.0 |
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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 | 2019-07-23 06:16:03 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. (Wikipedia |
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Structure | |
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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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Disposition | Route of exposure: Biological location: Source: |
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Role | Indirect biological role: Environmental role: Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0zi3-2549000000-930d18ff5e2d26d23e39 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0009000000-358453a180ad1eac44bb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0129000000-cc8a296246aa7e1b7fec | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03dm-0795000000-228bd7c35bed240b45ad | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-01ow-0698000000-a9e4b41be932783b0afd | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-01ow-0698000000-8f6994cc1cf72104baf0 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03dm-0696000000-cbec904cb2f70ad2fab0 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03dl-0693000000-fb2d60cf107761a6c44d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03dl-0693000000-5718e6cf640e3d715757 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03dl-0693000000-0e5df9ae944ec77aec31 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0129000000-36a830cd40ad8fbcdeee | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004s-1359000000-7b6f697fe59d525d48f9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05r0-4931000000-2d664b8d3fd4ebfd86ce | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0009000000-fbc08106b7ba4d66b944 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0019000000-ac9b3c7e9dbdabbc9404 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pbj-0924000000-7060b1a64eec50bf9c96 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0006-3901000000-c340e02baee25cf6196b | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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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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