NP-MRD: Showing NP-Card for Rotenonone (NP0051487)

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Record Information

Version

2.0

Created at

2022-04-27 22:50:02 UTC

Updated at

2022-04-27 22:50:03 UTC

NP-MRD ID

NP0051487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rotenonone

Description

Rotenonone belongs to the class of organic compounds known as rotenoids. These are phenolic compounds containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many rotenoids contain an additional ring, e.G. Rotenone. They are isoflavonoids characterized by the presence of an extra carbon atom in an additional heterocyclic ring. Thus, rotenonone is considered to be a flavonoid. Rotenonone is found in Amorpha canescens, Neorautanenia amboensis and Tephrosia villosa. Rotenonone was first documented in 1984 (PMID: 6511834). Based on a literature review very few articles have been published on rotenonone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200502D          

 30 34  0  0  1  0            999 V2000
    5.2623    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607    1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0358    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141    0.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816   -0.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403    0.0524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0666    0.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8484   -0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691    0.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8359   -1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908   -0.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659   -0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876    1.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860    1.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176   -1.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425   -1.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441   -1.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887    1.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    2.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9353    0.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587   -0.2705    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  8 10  1  1  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 18 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
    7.1803    0.3951   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3462   -0.4864   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7873   -1.2995    0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077   -0.6571   -0.8862 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9594   -0.3530    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8044    0.0474   -0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2898    0.4510   -1.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4294    0.8797   -2.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822    0.8835   -2.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839    0.4826   -1.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596    0.4889   -1.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171    0.8728   -1.9886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1653    0.0744    0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2360   -0.3409    1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -0.3285    0.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493    0.0585   -0.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813   -0.7472    2.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556   -1.1205    3.1995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9501   -0.7488    2.6395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8865   -0.3753    1.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2229   -0.3958    2.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1812    0.0030    1.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5502   -0.0098    1.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9677   -0.4365    2.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7953    0.4166    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7511    0.8180   -0.8728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3507    1.2448   -2.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4465    0.4490   -0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985    0.0505    0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6730    0.3209   -1.8531 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8872    1.0041   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1818    0.5518   -0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9571   -1.8780    1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5468   -2.0216    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1897   -0.6493    1.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385   -1.6565   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878   -1.2856    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3538    0.4717    0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369    1.1879   -3.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060    1.2158   -3.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4703   -0.7326    3.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0677   -0.6873    2.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4093   -1.3279    3.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8720    0.3482    3.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7501    2.1811   -2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2719    1.3886   -2.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7514    0.4755   -2.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104    0.7767   -1.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 22  1  0
 22 25  2  0
 25 26  1  0
 26 27  1  0
 25 28  1  0
 28 29  2  0
 29 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  2  0
 17 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7 30  1  0
 30  4  1  0
  4  5  1  0
  5  6  1  0
  6 16  2  0
 16 15  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 20 21  2  0
 21 22  1  0
 13 29  1  0
 16 10  1  0
 15 14  1  0
  6  7  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
 28 48  1  0
  9 40  1  0
  8 39  1  0
  4 36  1  6
  5 37  1  0
  5 38  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  1 31  1  0
  1 32  1  0
 21 41  1  0
M  END


  Mrv1652304282200502D          

 30 34  0  0  1  0            999 V2000
    5.2623    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607    1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0358    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141    0.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816   -0.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403    0.0524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0666    0.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8484   -0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691    0.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8359   -1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908   -0.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659   -0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876    1.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860    1.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176   -1.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425   -1.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441   -1.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887    1.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    2.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9353    0.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587   -0.2705    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  8 10  1  1  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 18 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(OC(=O)C3=C2C(=O)C2=CC=C4O[C@H](CC4=C2O3)C(C)=C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H18O7/c1-10(2)15-8-13-14(28-15)6-5-11-20(24)19-12-7-17(26-3)18(27-4)9-16(12)29-23(25)22(19)30-21(11)13/h5-7,9,15H,1,8H2,2-4H3/t15-/m1/s1

> <INCHI_KEY>
CWZIPBGXMLRVIC-OAHLLOKOSA-N

> <FORMULA>
C23H18O7

> <MOLECULAR_WEIGHT>
406.39

> <EXACT_MASS>
406.10525292

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
42.24514067247324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R)-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-1(13),3,8,10,14,16,18-heptaene-12,21-dione

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.2137210833333327

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.394602348266238

> <JCHEM_POLAR_SURFACE_AREA>
80.29

> <JCHEM_REFRACTIVITY>
107.3483

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-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-1(13),3,8,10,14,16,18-heptaene-12,21-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.823   1.975   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.073   3.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.534   3.343   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.743   2.022   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.493   0.676   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.033   0.653   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.046  -0.507   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.462   0.098   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.324   1.632   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.784  -0.692   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.129   0.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.760  -2.232   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.703  -0.645   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.163  -0.622   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.413   0.723   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.204   2.045   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.454   3.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.874   0.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.083  -0.575   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.833  -1.920   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.373  -1.944   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.122  -3.289   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.543  -0.552   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.166   3.460   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.625   4.782   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.746   0.817   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.536  -0.505   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    1                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15    4   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19   26                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21                                                            
CONECT   23   19   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   18                                                       
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₁₈O₇

Average Mass

406.3900 Da

Monoisotopic Mass

406.10525 Da

IUPAC Name

(6R)-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-1(13),3,8,10,14,16,18-heptaene-12,21-dione

Traditional Name

(6R)-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-1(13),3,8,10,14,16,18-heptaene-12,21-dione

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(OC(=O)C3=C2C(=O)C2=CC=C4O[C@H](CC4=C2O3)C(C)=C)=C1

InChI Identifier

InChI=1S/C23H18O7/c1-10(2)15-8-13-14(28-15)6-5-11-20(24)19-12-7-17(26-3)18(27-4)9-16(12)29-23(25)22(19)30-21(11)13/h5-7,9,15H,1,8H2,2-4H3/t15-/m1/s1

InChI Key

CWZIPBGXMLRVIC-OAHLLOKOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amorpha canescens	Plant	KNApSAcK
Neorautanenia amboensis	Plant	KNApSAcK
Tephrosia villosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rotenoids. These are phenolic compounds containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many rotenoids contain an additional ring, e.G. Rotenone. They are isoflavonoids characterized by the presence of an extra carbon atom in an additional heterocyclic ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenoids

Alternative Parents

Substituents

Chromeno-3,4b-chromene
Isoflavone
Chromone
Coumarin
Benzopyran
1-benzopyran
Coumaran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:8898 )
oxacycle (CHEBI:8898 )
rotenones (C10525 )
Rotenoid flavonoids (C10525 )
Rotenoid flavonoids (LMPK12060070 )

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	3.16	ALOGPS
logP	3.21	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	80.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.35 m³·mol⁻¹	ChemAxon
Polarizability	42.25 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002569

Chemspider ID

391138

KEGG Compound ID

C10525

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442819

PDB ID

Not Available

ChEBI ID

8898

Good Scents ID

Not Available

References

General References

Bushway RJ: High-performance liquid chromatographic analysis of rotenone and rotenonone in water by direct injection. J Chromatogr. 1984 Oct 26;303(1):263-6. doi: 10.1016/s0021-9673(01)96074-1. [PubMed:6511834 ]

Showing NP-Card for Rotenonone (NP0051487)

MOL for NP0051487 (Rotenonone)

3D MOL for NP0051487 (Rotenonone)

3D SDF for NP0051487 (Rotenonone)

3D-SDF for NP0051487 (Rotenonone)

PDB for NP0051487 (Rotenonone)

3D PDB for NP0051487 (Rotenonone)

SMILES for NP0051487 (Rotenonone)

INCHI for NP0051487 (Rotenonone)

Structure for NP0051487 (Rotenonone)

3D Structure for NP0051487 (Rotenonone)