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Showing NP-Card for Rotenone (NP0000579)

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Record Information
Version1.0
Created at2012-09-11 19:16:54 UTC
Updated at2024-05-05 00:32:50 UTC
NP-MRD IDNP0000579
Secondary Accession NumbersNone
Natural Product Identification
Common NameRotenone
DescriptionRotenone 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.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0000579 (Rotenone)

Not Available

3D MOL for NP0000579 (Rotenone)

Not Available

3D SDF for NP0000579 (Rotenone)

Not Available

3D-SDF for NP0000579 (Rotenone)

Not Available

PDB for NP0000579 (Rotenone)

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3D PDB for NP0000579 (Rotenone)

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SMILES for NP0000579 (Rotenone)

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INCHI for NP0000579 (Rotenone)

Not Available
View in JSmol
Synonyms
ValueSource
(-)-cis-RotenoneChEBI
(-)-RotenoneChEBI
5'beta-RotenoneChEBI
[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)-oneChEBI
BarbascoChEBI
CanexChEBI
DactinolChEBI
DerrisChEBI
NoxfireChEBI
ParaderilChEBI
TubatoxinChEBI
5'b-RotenoneGenerator
5'Β-rotenoneGenerator
[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)-oneGenerator
[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)-oneGenerator
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, 9ciHMDB
DerrinHMDB
Derris, jmafHMDB
Dri-kilHMDB
NicoulineHMDB
NoxfishHMDB
TubotoxinHMDB
Chemical FormulaC23H22O6
Average Mass394.4172 Da
Monoisotopic Mass394.14164 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number83-79-4
SMILESNot Available
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
InChI KeyJUVIOZPCNVVQFO-HBGVWJBISA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Amorpha fruticosa
Antheroporum pierrei
Derris brevipes
Derris ecliptaPlant
Derris ellipticaPlant
Derris malaccensisPlant
Derris trifoliataPlant
Erycibe expansaPlant
Leguminosae-
Lonchocarpus spp.Plant
Lonchocarpus utilis
Milletia pachycarpa-
Millettia pachycarpaPlant
Millettia pachyloba
Millettia pervilleanaPlant
Millettia reticulataPlant
Millettia spp.Plant
Neorautanenia mitis
Pachyrhizus erosusFooDB
Pachyrhizus tuberosusPlant
Pachyrrhizus erosusPlant
Papilionoideae-
Piscidia erythrinaPlant
Piscidia piscipula
Spatholobus parviflorus
Taxus chinensisPlant
Taxus fuanaPlant
Taxus wallichiana var. yunnanensisPlant
Tephrosia interrupta Engl.Plant
Tephrosia leiocarpa
Tephrosia linearis
Tephrosia linearis (Willd.) Pers.Plant
Tephrosia pentaphylla
Tephrosia purpureaPlant
Tephrosia spp.Plant
Tephrosia strigosa
Tephrosia villosa
Tephrosia vogelii
Verbascum thapsusPlant
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassRotenoids
Direct ParentRotenones
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point163 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0002 mg/mL at 20 °CNot Available
LogP4.10Not Available
Predicted PropertiesNot Available
HMDB IDHMDB0034436
DrugBank IDDB11457
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012837
KNApSAcK IDC00002568
Chemspider ID6500
KEGG Compound IDC07593
BioCyc IDCPD-5741
BiGG IDNot Available
Wikipedia LinkRotenone
METLIN IDNot Available
PubChem Compound6758
PDB IDNot Available
ChEBI ID28201
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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. doi: 10.1093/toxsci/kfh089. Epub 2004 Feb 19. [PubMed:14976342 ]
  4. 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. doi: 10.1021/np0303815. [PubMed:15043430 ]
  5. 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. doi: 10.1016/j.molbrainres.2004.11.007. Epub 2005 Jan 6. [PubMed:15790535 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .