Rotenone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Rotenone
Accession Number
DB11457
Type
Small Molecule
Groups
Vet approved
Description

Rotenone is an isoflavone compound that naturally occurs in the jicama vine plant as well as many Fabaceae plants. It has broad spectrum insecticide and pesticide activity and is also toxic to fish.

Structure
Thumb
Synonyms
  • (−)-cis-rotenone
  • (−)-rotenone
  • (12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-one
  • [2R-(2α,6aα,12aα)]-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
  • 5'β-rotenone
  • Dactinol
  • Tubatoxin
External IDs
NSC-26258
Categories
UNII
03L9OT429T
CAS number
83-79-4
Weight
Average: 394.4172
Monoisotopic: 394.141638436
Chemical Formula
C23H22O6
InChI Key
JUVIOZPCNVVQFO-HBGVWJBISA-N
InChI
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
IUPAC Name
(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-12-one
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Yang SP, Yu XB, Huang JG, Xu HH: Rotenone alpha-oxime. Acta Crystallogr C. 2003 Jul;59(Pt 7):o392-3. Epub 2003 Jun 20. [PubMed:12855867]
  2. OLIVER WT, ROE CK: Rotenone poisoning of swine. J Am Vet Med Assoc. 1957 May 1;130(9):410-1. [PubMed:13428625]
  3. SANTI R, TOTH CE: TOXICOLOGY OF ROTENONE. Farmaco Sci. 1965 Apr;20:270-9. [PubMed:14333191]
  4. Santi R, Ferrari M, Toth E: Pharmacological properties of rotenone. Farmaco Sci. 1966 Oct;21(10):689-703. [PubMed:6008413]
  5. BRYAN JT, LINCOLN WR: Determination of rotenone in pharmaceuticals. J Am Pharm Assoc Am Pharm Assoc. 1959 Jun;48(6):330-2. [PubMed:13654088]
  6. DANZEL L: [Derris and other rotenone plants]. Prod Pharm. 1951 Oct;6(10):487-9. [PubMed:14892110]
  7. Gosalvez M: Carcinogenesis with the insecticide rotenone. Life Sci. 1983 Feb 21;32(8):809-16. [PubMed:6338335]
  8. Gosalvez M, Diaz-Gil JJ: Rotenone: a possible environmental carcinogen? Eur J Cancer. 1978 Dec;14(12):1403-4. [PubMed:738345]
  9. Acree F Jr, Jacobson M, Haller HL: AMORPHA FRUTICOSA CONTAINS NO ROTENONE. Science. 1944 Feb 4;99(2562):99-100. [PubMed:17753901]
  10. Tanner CM, Kamel F, Ross GW, Hoppin JA, Goldman SM, Korell M, Marras C, Bhudhikanok GS, Kasten M, Chade AR, Comyns K, Richards MB, Meng C, Priestley B, Fernandez HH, Cambi F, Umbach DM, Blair A, Sandler DP, Langston JW: Rotenone, paraquat, and Parkinson's disease. Environ Health Perspect. 2011 Jun;119(6):866-72. doi: 10.1289/ehp.1002839. Epub 2011 Jan 26. [PubMed:21269927]
  11. 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]
  12. 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]
  13. Newhouse K, Hsuan SL, Chang SH, Cai B, Wang Y, Xia Z: Rotenone-induced apoptosis is mediated by p38 and JNK MAP kinases in human dopaminergic SH-SY5Y cells. Toxicol Sci. 2004 May;79(1):137-46. Epub 2004 Feb 19. [PubMed:14976342]
  14. Cao S, Schilling JK, Miller JS, Andriantsiferana R, Rasamison VE, Kingston DG: Cytotoxic compounds from Mundulea chapelieri from the Madagascar Rainforest. J Nat Prod. 2004 Mar;67(3):454-6. [PubMed:15043430]
  15. Testa CM, Sherer TB, Greenamyre JT: Rotenone induces oxidative stress and dopaminergic neuron damage in organotypic substantia nigra cultures. Brain Res Mol Brain Res. 2005 Mar 24;134(1):109-18. Epub 2005 Jan 6. [PubMed:15790535]
  16. Morikawa T, Xu F, Matsuda H, Yoshikawa M: Structures of new flavonoids, erycibenins D, E, and F, and NO production inhibitors from Erycibe expansa originating in Thailand. Chem Pharm Bull (Tokyo). 2006 Nov;54(11):1530-4. [PubMed:17077549]
  17. Meurers BH, Zhu C, Fernagut PO, Richter F, Hsia YC, Fleming SM, Oh M, Elashoff D, Dicarlo CD, Seaman RL, Chesselet MF: Low dose rotenone treatment causes selective transcriptional activation of cell death related pathways in dopaminergic neurons in vivo. Neurobiol Dis. 2009 Feb;33(2):182-92. doi: 10.1016/j.nbd.2008.10.001. Epub 2008 Oct 26. [PubMed:19013527]
  18. Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
External Links
Human Metabolome Database
HMDB0034436
KEGG Compound
C07593
PubChem Compound
6758
PubChem Substance
347827979
ChemSpider
6500
BindingDB
50135527
ChEBI
28201
ChEMBL
CHEMBL429023
Wikipedia
Rotenone

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0129 mg/mLALOGPS
logP2.3ALOGPS
logP3.32ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)11.8ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.22 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.71 m3·mol-1ChemAxon
Polarizability42.06 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0006-3901000000-c340e02baee25cf6196b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0009000000-358453a180ad1eac44bb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0129000000-cc8a296246aa7e1b7fec
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03dm-0795000000-228bd7c35bed240b45ad
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01ow-0698000000-a9e4b41be932783b0afd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01ow-0698000000-8f6994cc1cf72104baf0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03dm-0696000000-cbec904cb2f70ad2fab0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03dl-0693000000-fb2d60cf107761a6c44d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03dl-0693000000-5718e6cf640e3d715757
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03dl-0693000000-0e5df9ae944ec77aec31
1H NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Isoflavonoids
Sub Class
Rotenoids
Direct Parent
Rotenones
Alternative Parents
8-prenylated isoflavanones / Chromones / Coumarans / Aryl alkyl ketones / Anisoles / Alkyl aryl ethers / Oxacyclic compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Rotenone or derivatives / 8-prenylated isoflavanone / Isoflavanone / Isoflavan / Chromone / Chromane / 1-benzopyran / Benzopyran / Coumaran / Anisole
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound, rotenones (CHEBI:28201) / rotenones, Rotenoid flavonoids, Pesticides (C07593) / Rotenoid flavonoids (LMPK12060007)

Drug created on February 25, 2016 11:54 / Updated on June 04, 2019 07:21