NP-MRD: Showing NP-Card for Rotenone (NP0000579)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2012-09-11 19:16:54 UTC

Updated at

2024-09-03 04:18:16 UTC

NP-MRD ID

NP0000579

Natural Product DOI

https://doi.org/10.57994/1339

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rotenone

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.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305271900282D          

 31 35  0  0  1  0            999 V2000
    3.9940    1.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    1.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361    1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7005    2.5161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8800    2.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130    3.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9380    3.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7005    3.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9940    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651    0.3854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5651    1.2104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2795    1.6229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361    1.2104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361   -1.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -1.2646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -2.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361   -2.0896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -2.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -0.4396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651    2.0354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 30  1  6  0  0  0
 16 31  1  6  0  0  0
M  END


  Mrv1652305271900282D          

 31 35  0  0  1  0            999 V2000
    3.9940    1.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    1.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361    1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7005    2.5161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8800    2.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130    3.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9380    3.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7005    3.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9940    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2795   -0.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651    0.3854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5651    1.2104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2795    1.6229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361    1.2104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361   -1.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -1.2646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -2.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1361   -2.0896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -2.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -0.4396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651    2.0354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 30  1  6  0  0  0
 16 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000579

> <DATABASE_NAME>
NP-MRD

> <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

> <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_KEY>
JUVIOZPCNVVQFO-HBGVWJBISA-N

> <FORMULA>
C23H22O6

> <MOLECULAR_WEIGHT>
394.4172

> <EXACT_MASS>
394.141638436

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
42.07171729217053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(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

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
3.320177814333334

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.803545634313098

> <JCHEM_PKA_STRONGEST_BASIC>
-4.19837863212729

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
105.7123

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       7.455   2.259   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.789   3.029   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.123   2.259   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.267   3.290   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.641   4.697   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.109   4.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.411   6.030   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.951   6.030   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.641   7.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.123   0.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.789  -0.051   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.455   0.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.122  -0.051   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.122  -1.591   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.788   0.719   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.788   2.259   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.122   3.029   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.454   3.029   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.121   2.259   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.121   0.719   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.454  -0.051   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.454  -1.591   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.121  -2.361   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.787  -1.591   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.787  -0.051   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.547  -2.361   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.547  -3.901   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.121  -3.901   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.787  -4.671   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       4.788  -0.821   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.788   3.799   0.000  0.00  0.00           H+0
CONECT    1    2   12   17                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    1   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21   30                                             
CONECT   16   15   17   18   31                                             
CONECT   17   16    1                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23   29                                                       
CONECT   29   28                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
(-)-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

Chemical Formula

C₂₃H₂₂O₆

Average Mass

394.4172 Da

Monoisotopic Mass

394.14164 Da

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

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

CAS Registry Number

83-79-4

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

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 Key

JUVIOZPCNVVQFO-HBGVWJBISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Amorpha fruticosa		LOTUS database
Antheroporum pierrei		LOTUS database
Derris brevipes		LOTUS database
Derris eclipta	Plant	KNApSAcK
Derris elliptica	Plant	KNApSAcK
Derris malaccensis	Plant	KNApSAcK
Derris trifoliata	Plant	KNApSAcK
Erycibe expansa	Plant	KNApSAcK
Leguminosae	-	KNApSAcK
Lonchocarpus spp.	Plant	KNApSAcK
Lonchocarpus utilis		LOTUS database
Milletia pachycarpa	-	KNApSAcK
Millettia pachycarpa	Plant	KNApSAcK
Millettia pachyloba		LOTUS database
Millettia pervilleana	Plant	KNApSAcK
Millettia reticulata	Plant	KNApSAcK
Millettia spp.	Plant	KNApSAcK
Neorautanenia mitis		LOTUS database
Pachyrhizus erosus	FooDB	KNAPSACK
Pachyrhizus tuberosus	Plant	KNApSAcK
Pachyrrhizus erosus	Plant	KNApSAcK
Papilionoideae	-	KNApSAcK
Piscidia erythrina	Plant	KNApSAcK
Piscidia piscipula		LOTUS database
Spatholobus parviflorus		LOTUS database
Taxus chinensis	Plant	KNApSAcK
Taxus fuana	Plant	KNApSAcK
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK
Tephrosia interrupta Engl.	Plant	KNApSAcK
Tephrosia leiocarpa		LOTUS database
Tephrosia linearis		LOTUS database
Tephrosia linearis (Willd.) Pers.	Plant	KNApSAcK
Tephrosia pentaphylla		LOTUS database
Tephrosia purpurea	Plant	KNApSAcK
Tephrosia spp.	Plant	KNApSAcK
Tephrosia strigosa		LOTUS database
Tephrosia villosa		LOTUS database
Tephrosia vogelii		LOTUS database
Verbascum thapsus	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenones

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:28201 )
rotenones (CHEBI:28201 )
rotenones (C07593 )
Rotenoid flavonoids (C07593 )
Pesticides (C07593 )
Rotenoid flavonoids (LMPK12060007 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
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

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.3	ALOGPS
logP	3.32	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	11.8	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.71 m³·mol⁻¹	ChemAxon
Polarizability	42.07 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034436

DrugBank ID

DB11457

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Rotenone

METLIN ID

Not Available

PubChem Compound

6758

PDB ID

Not Available

ChEBI ID

28201

Good Scents ID

Not Available

References

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 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Rotenone (NP0000579)

MOL for NP0000579 (Rotenone)

3D MOL for NP0000579 (Rotenone)

3D SDF for NP0000579 (Rotenone)

3D-SDF for NP0000579 (Rotenone)

PDB for NP0000579 (Rotenone)

3D PDB for NP0000579 (Rotenone)

SMILES for NP0000579 (Rotenone)

INCHI for NP0000579 (Rotenone)

Structure for NP0000579 (Rotenone)

3D Structure for NP0000579 (Rotenone)