NP-MRD: Showing NP-Card for (-)-cis-Rotenolone (NP0047870)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:19 UTC

Updated at

2022-03-17 20:47:19 UTC

NP-MRD ID

NP0047870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-cis-Rotenolone

Description

(-)-Cis-Rotenolone, also known as 6ab,12ab-rotenolone or rotenolon I, 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 (-)-cis-Rotenolone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (-)-cis-Rotenolone has been detected, but not quantified in, jicama and pulses. (-)-cis-Rotenolone is found in Amorpha fruticosa, Antheroporum pierrei, Apis cerana, Deguelia rufescens, Deguelia spruceana, Derris malaccensis, Derris oblonga, Derris trifoliata, Derris urucu, Erycibe expansa , Lonchocarpus subglaucescens, Lonchocarpus utilis, Millettia ferruginea , Millettia pachycarpa, Neorautanenia amboensis, Neorautanenia mitis , Pachyrrhizus erosus , Piscidia mollois, Sarcolobus globosus, Tephrosia candida, Tephrosia pentaphylla , Tephrosia praecana, Tephrosia purpurea and Tephrosia vogelii. This could make (-)-cis-rotenolone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241220202D          

 31 35  0  0  0  0            999 V2000
   -1.9049   -1.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    0.0697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2370   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804    0.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937    1.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    2.2007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8374    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670    1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    1.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    0.8946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1913    1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    0.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3348   -1.5801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0483   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8957    2.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0707    2.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    3.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049   -2.4051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -2.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370   -1.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764   -0.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    1.7196    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 21  1  0  0  0  0
  1 27  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  4 30  1  6  0  0  0
  5  6  1  0  0  0  0
  5 29  2  0  0  0  0
  6  7  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 25  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 16 31  1  6  0  0  0
M  END


  Mrv0541 02241220202D          

 31 35  0  0  0  0            999 V2000
   -1.9049   -1.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    0.0697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2370   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804    0.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937    1.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    2.2007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8374    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670    1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    0.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    1.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    0.8946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1913    1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    0.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3348   -1.5801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0483   -1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8957    2.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0707    2.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    3.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049   -2.4051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6199   -2.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370   -1.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764   -0.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    1.7196    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 21  1  0  0  0  0
  1 27  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  4 30  1  6  0  0  0
  5  6  1  0  0  0  0
  5 29  2  0  0  0  0
  6  7  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 25  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 16 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0047870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1

> <INCHI_KEY>
JFVKWCYZKMUTLH-AYPBNUJASA-N

> <FORMULA>
C23H22O7

> <MOLECULAR_WEIGHT>
410.4166

> <EXACT_MASS>
410.136553058

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
42.79904288951134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,6R,13R)-13-hydroxy-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

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.728660151333333

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.075276263311958

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2046903864344705

> <JCHEM_POLAR_SURFACE_AREA>
83.45

> <JCHEM_REFRACTIVITY>
106.95830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rotenolone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.556  -2.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.224  -2.180   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.224  -0.640   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.889   0.130   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.442  -0.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.777   0.130   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.112  -0.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.443   0.130   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.443   1.670   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.588   2.702   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.962   4.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.430   3.947   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.112   2.440   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.777   1.670   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.442   2.440   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.889   1.670   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.224   2.440   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.556   1.670   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.556   0.130   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.890  -0.640   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.890  -2.180   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.225  -2.950   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -7.557  -2.180   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.272   5.440   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.732   5.440   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.962   6.775   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.556  -4.490   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.890  -5.259   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.442  -2.180   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.889  -1.410   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0      -0.889   3.210   0.000  0.00  0.00           H+0
CONECT    1    2   21   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   16   30                                             
CONECT    5    4    6   29                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13    9   12   14                                                  
CONECT   14    6   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    4   15   17   31                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19    3   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21    1   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25   11   24   26                                                  
CONECT   26   25                                                            
CONECT   27    1   28                                                       
CONECT   28   27                                                            
CONECT   29    5                                                            
CONECT   30    4                                                            
CONECT   31   16                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
(-)-cis-12a-Hydroxyrotenone	HMDB
1,2,12,12a-Tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-(2R,6ar,12ar)-[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	HMDB
12-Hydroxyrotenone	HMDB
12alpha-Hydroxyrotenone	HMDB
6a-beta,12a-beta-Rotenolone	HMDB
6Ab,12ab-rotenolone	HMDB
Rotenalone	HMDB
Rotenolon I	HMDB
Rotenolone	HMDB
Rotenolone I	HMDB
6 alpha(beta),12 alpha(beta)-Rotenolone	MeSH
Rotenolone, (2R-(2alpha,6aalpha,12aalpha))-isomer	MeSH
Rotenolone, (2R-(2alpha,6abeta,12aalpha))-isomer	MeSH
Rotenolone, (2R-(2alpha,6aalpha,12abeta))-isomer	MeSH

Chemical Formula

C₂₃H₂₂O₇

Average Mass

410.4166 Da

Monoisotopic Mass

410.13655 Da

IUPAC Name

(1R,6R,13R)-13-hydroxy-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

Traditional Name

rotenolone

CAS Registry Number

509-96-6

SMILES

[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C

InChI Identifier

InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1

InChI Key

JFVKWCYZKMUTLH-AYPBNUJASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amorpha fruticosa	Plant	KNApSAcK
Antheroporum pierrei	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Deguelia rufescens	Plant	KNApSAcK
Deguelia spruceana	Plant	KNApSAcK
Derris malaccensis	Plant	KNApSAcK
Derris oblonga	Plant	KNApSAcK
Derris trifoliata	LOTUS Database	35616633
Derris urucu	Plant	KNApSAcK
Erycibe expansa	Plant	KNApSAcK
Lonchocarpus subglaucescens	Plant	KNApSAcK
Lonchocarpus utilis	LOTUS Database	35616633
Millettia ferruginea	Plant	KNApSAcK
Millettia pachycarpa	Plant	KNApSAcK
Neorautanenia amboensis	Plant	KNApSAcK
Neorautanenia mitis	Plant	KNApSAcK
Pachyrhizus erosus	FooDB	KNAPSACK
Pachyrrhizus erosus	Plant	KNApSAcK
Piscidia mollois	Plant	KNApSAcK
Sarcolobus globosus	LOTUS Database	35616633
Tephrosia candida	Plant	KNApSAcK
Tephrosia pentaphylla	Plant	KNApSAcK
Tephrosia praecana	Plant	KNApSAcK
Tephrosia purpurea	Plant	KNApSAcK
Tephrosia vogelii	LOTUS Database	35616633

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
1-benzopyran
Chromane
Benzopyran
Coumaran
Aryl alkyl ketone
Aryl ketone
Anisole
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Ketone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:68051 )
rotenones (C10464 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.4	ALOGPS
logP	2.73	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.08	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.96 m³·mol⁻¹	ChemAxon
Polarizability	42.8 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