NP-MRD: Showing NP-Card for Sumatrol (NP0051490)

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Record Information

Version

2.0

Created at

2022-04-27 22:50:12 UTC

Updated at

2022-04-27 22:50:12 UTC

NP-MRD ID

NP0051490

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sumatrol

Description

Sumatrol 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. Thus, sumatrol is considered to be a flavonoid. Sumatrol is found in Crotalaria burha, Crotalaria burhia , Dahlstedtia pinnata, Derris elliptica, Derris malaccensis, Derris oblonga, Macaranga indica, Millettia auriculata , Millettia extensa, Piscidia erythrina, Tephrosia pentaphylla, Tephrosia toxicaria and Tephrosia villosa. Sumatrol was first documented in 2002 (PMID: 12112286). Based on a literature review a small amount of articles have been published on Sumatrol (PMID: 14510590) (PMID: 30152494) (PMID: 29259888) (PMID: 20803155).

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  1  0  0  0  0  0  0  0  0  0
    2.3643    0.3874    0.0000 C   0  0  1  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
    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
    3.6342    2.5118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  8 10  1  1  0  0  0
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  5 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
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 18 19  2  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
 19 22  1  0  0  0  0
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 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
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 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
  3 30  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -7.1289    0.3128    1.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9740    0.4598    1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6480   -0.4111   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0252    1.4909    1.4790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6951    0.9124    1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8560    1.0865    0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263    1.9356   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036    2.2403   -1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3866    0.3651    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1260   -0.5915   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5116   -0.5414   -0.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1615    0.5230    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -1.6353   -0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425   -2.6089   -1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6032   -3.6794   -2.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165   -1.6838   -0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3884   -0.7191   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9046   -0.7562   -0.1731 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2900    0.2782   -1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657    0.6855   -2.1154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7422    2.3461    0.3938 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2474    1.4745    2.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2509    0.4679    0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7104    1.4682   -0.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705   -4.1143   -1.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967   -4.5108   -2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2156   -3.2528   -3.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697   -2.4974   -1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370   -1.7612   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
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 19 18  2  0
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 28 29  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 22 19  1  0
 28 27  1  0
 16 17  1  0
 11 12  1  0
  7  6  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
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 27 52  1  6
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  5 37  1  0
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 10 40  1  0
  3 33  1  0
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  3 35  1  0
  1 31  1  0
  1 32  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  1  0  0  0  0  0  0  0  0  0
    2.3643    0.3874    0.0000 C   0  0  1  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
    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
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  1  2  2  0  0  0  0
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  3  4  2  0  0  0  0
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  1  6  1  0  0  0  0
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  7  8  1  0  0  0  0
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  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
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
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 22 23  2  0  0  0  0
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 24 25  2  0  0  0  0
 18 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
  3 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051490

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@H]1[C@@H](CO2)OC2=C3C[C@@H](OC3=CC(O)=C2C1=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O7/c1-10(2)14-6-12-16(29-14)7-13(24)21-22(25)20-11-5-17(26-3)18(27-4)8-15(11)28-9-19(20)30-23(12)21/h5,7-8,14,19-20,24H,1,6,9H2,2-4H3/t14-,19-,20+/m1/s1

> <INCHI_KEY>
ZPEHYKMRUBEPSQ-XMCHAPAWSA-N

> <FORMULA>
C23H22O7

> <MOLECULAR_WEIGHT>
410.422

> <EXACT_MASS>
410.136553048

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.794052139413374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6R,13S)-10-hydroxy-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>
3.24

> <JCHEM_LOGP>
3.6666124926666677

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.225609766137502

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.95894882310975

> <JCHEM_PKA_STRONGEST_BASIC>
-4.202420153458372

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
107.69319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R,13S)-10-hydroxy-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                                 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  C   UNK     0       0.543  -0.552   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.166   3.460   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.625   4.782   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.746   0.817   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.536  -0.505   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.784   4.689   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
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   25                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   14                                                       
CONECT   22   19   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   18                                                       
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23   29                                                       
CONECT   29   28                                                            
CONECT   30    3                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₇

Average Mass

410.4220 Da

Monoisotopic Mass

410.13655 Da

IUPAC Name

(1S,6R,13S)-10-hydroxy-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)-10-hydroxy-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

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@H]1[C@@H](CO2)OC2=C3C[C@@H](OC3=CC(O)=C2C1=O)C(C)=C

InChI Identifier

InChI=1S/C23H22O7/c1-10(2)14-6-12-16(29-14)7-13(24)21-22(25)20-11-5-17(26-3)18(27-4)8-15(11)28-9-19(20)30-23(12)21/h5,7-8,14,19-20,24H,1,6,9H2,2-4H3/t14-,19-,20+/m1/s1

InChI Key

ZPEHYKMRUBEPSQ-XMCHAPAWSA-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
Crotalaria burha	Plant	KNApSAcK
Crotalaria burhia	Plant	KNApSAcK
Dahlstedtia pinnata	LOTUS Database	35616633
Derris elliptica	LOTUS Database	35616633
Derris malaccensis	Plant	KNApSAcK
Derris oblonga	Plant	KNApSAcK
Macaranga indica	LOTUS Database	35616633
Millettia auriculata	Plant	KNApSAcK
Millettia extensa	LOTUS Database	35616633
Piscidia erythrina	Plant	KNApSAcK
Tephrosia pentaphylla	LOTUS Database	35616633
Tephrosia toxicaria	Plant	KNApSAcK
Tephrosia villosa	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
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoflavanones (CHEBI:9358 )
rotenones (C10532 )
Rotenoid flavonoids (C10532 )
Rotenoid flavonoids (LMPK12060024 )

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	3.24	ALOGPS
logP	3.67	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.96	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	107.69 m³·mol⁻¹	ChemAxon
Polarizability	42.79 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

C00002575

Chemspider ID

391143

KEGG Compound ID

C10532

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442824

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jang DS, Park EJ, Kang YH, Hawthorne ME, Vigo JS, Graham JG, Cabieses F, Fong HH, Mehta RG, Pezzuto JM, Kinghorn AD: Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria. J Nat Prod. 2003 Sep;66(9):1166-70. doi: 10.1021/np0302100. [PubMed:14510590 ]
Russell DA, Freudenreich JJ, Stewart HL, Bond AD, Sore HF, Spring DR: Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol. Org Biomol Chem. 2018 Sep 11;16(35):6395-6398. doi: 10.1039/c8ob01919c. [PubMed:30152494 ]
Vats S: Larvicidal activity and in vitro regulation of rotenoids from Cassia tora L. 3 Biotech. 2018 Jan;8(1):13. doi: 10.1007/s13205-017-1038-5. Epub 2017 Dec 11. [PubMed:29259888 ]
Kamal R, Mathur N: Rotenoids from Lablab purpureus L. and their bioefficacy against human disease vectors. Parasitol Res. 2010 Nov;107(6):1481-8. doi: 10.1007/s00436-010-2023-7. Epub 2010 Aug 28. [PubMed:20803155 ]
Blatt CT, Chavez D, Chai H, Graham JG, Cabieses F, Farnsworth NR, Cordell GA, Pezzuto JM, Kinghorn AD: Cytotoxic flavonoids from the stem bark of Lonchocarpus aff. fluvialis. Phytother Res. 2002 Jun;16(4):320-5. doi: 10.1002/ptr.889. [PubMed:12112286 ]

Showing NP-Card for Sumatrol (NP0051490)

MOL for NP0051490 (Sumatrol)

3D MOL for NP0051490 (Sumatrol)

3D SDF for NP0051490 (Sumatrol)

3D-SDF for NP0051490 (Sumatrol)

PDB for NP0051490 (Sumatrol)

3D PDB for NP0051490 (Sumatrol)

SMILES for NP0051490 (Sumatrol)

INCHI for NP0051490 (Sumatrol)

Structure for NP0051490 (Sumatrol)

3D Structure for NP0051490 (Sumatrol)