NP-MRD: Showing NP-Card for deguelin (NP0031058)

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Record Information

Version

2.0

Created at

2021-06-19 22:14:54 UTC

Updated at

2024-09-03 04:22:36 UTC

NP-MRD ID

NP0031058

Natural Product DOI

https://doi.org/10.57994/2914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

deguelin

Provided By

JEOL Database JEOL Logo

Description

Legumelin 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, legumelin is considered to be a flavonoid. deguelin is found in Amorpha fruticosa, Chadsia grevei, Derris trifoliata, Lonchocarpus utilis, Millettia dura, Millettia pachycarpa, Tephrosia candida and Tephrosia linearis. deguelin was first documented in 2024 (PMID: 38579352). Based on a literature review very few articles have been published on Legumelin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100143D          

 51 55  0  0  0  0            999 V2000
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   -0.9253    3.2924    4.9580 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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  Mrv1652306202100143D          

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   -1.4913    1.1003   -7.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387   -0.3803   -6.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0088    0.3427   -6.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    2.6053   -5.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    3.3042   -6.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5563    3.3569   -4.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0  0  0  0
  8  3  2  0  0  0  0
 12 13  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 17 18  2  0  0  0  0
 11  6  1  0  0  0  0
 14 19  2  0  0  0  0
 19 18  1  0  0  0  0
 11 21  1  0  0  0  0
  5 23  1  0  0  0  0
 17 29  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 29  1  0  0  0  0
 23 22  1  0  0  0  0
 26 27  1  6  0  0  0
 22 21  1  0  0  0  0
 26 28  1  0  0  0  0
 16 15  2  0  0  0  0
 19 20  1  0  0  0  0
 14 12  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  0  0  0  0
  9 10  1  0  0  0  0
 17 16  1  0  0  0  0
  3  2  1  0  0  0  0
  6  7  2  0  0  0  0
  2  1  1  0  0  0  0
 20 21  1  0  0  0  0
 12 11  1  0  0  0  0
 21 41  1  6  0  0  0
  7  8  1  0  0  0  0
 11 38  1  1  0  0  0
 16 40  1  0  0  0  0
 15 39  1  0  0  0  0
 22 42  1  0  0  0  0
 22 43  1  0  0  0  0
  7 34  1  0  0  0  0
  4 33  1  0  0  0  0
 24 44  1  0  0  0  0
 25 45  1  0  0  0  0
 27 46  1  0  0  0  0
 27 47  1  0  0  0  0
 27 48  1  0  0  0  0
 28 49  1  0  0  0  0
 28 50  1  0  0  0  0
 28 51  1  0  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031058

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C2=C(O[C@]3([H])C([H])([H])OC4=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C4[C@]3([H])C2=O)C2=C1OC(C([H])=C2[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1

> <INCHI_KEY>
ORDAZKGHSNRHTD-UXHICEINSA-N

> <FORMULA>
C23H22O6

> <MOLECULAR_WEIGHT>
394.423

> <EXACT_MASS>
394.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
41.87083001132794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
3.3042058106666667

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.724479793029548

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204904948066979

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
107.21800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -0.8096    4.7006    4.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9253    3.2924    4.9580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796    2.5337    4.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024    1.4153    3.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709    0.5400    2.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.7809    2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5348    1.8777    2.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0171    2.7577    3.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124    3.8179    4.0431 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493    4.0177    3.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517   -0.1715    1.0603 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1309    0.4870   -0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087    0.8165    0.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211    0.7577   -1.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732    1.4422   -2.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865    1.7326   -3.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0509    1.3514   -3.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6076    0.6642   -2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0943    0.3505   -1.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784   -0.3246   -0.4804 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611   -1.0372    0.4407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6289   -1.5630    1.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2681   -0.5183    2.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0032    0.2849   -2.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6063    0.6291   -3.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179    1.3904   -5.0813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9783    0.5676   -6.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    2.7338   -5.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253    1.6917   -4.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7115    5.1617    5.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489    4.9883    3.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437    5.0875    5.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912    1.2285    4.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    2.0256    2.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    4.8883    4.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814    3.1594    3.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825    4.2387    2.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -0.8404    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1082    1.7585   -2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8874    2.2661   -4.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010   -1.8882   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -2.1757    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633   -2.1938    2.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5273   -0.2539   -2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6492    0.3600   -4.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4913    1.1003   -7.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387   -0.3803   -6.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0088    0.3427   -6.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    2.6053   -5.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    3.3042   -6.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5563    3.3569   -4.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
  8  3  2  0
 12 13  2  0
  3  4  1  0
  4  5  2  0
 17 18  2  0
 11  6  1  0
 14 19  2  0
 19 18  1  0
 11 21  1  0
  5 23  1  0
 17 29  1  0
 18 24  1  0
 24 25  2  0
 25 26  1  0
 26 29  1  0
 23 22  1  0
 26 27  1  6
 22 21  1  0
 26 28  1  0
 16 15  2  0
 19 20  1  0
 14 12  1  0
  8  9  1  0
  5  6  1  0
  9 10  1  0
 17 16  1  0
  3  2  1  0
  6  7  2  0
  2  1  1  0
 20 21  1  0
 12 11  1  0
 21 41  1  6
  7  8  1  0
 11 38  1  1
 16 40  1  0
 15 39  1  0
 22 42  1  0
 22 43  1  0
  7 34  1  0
  4 33  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.810   4.701   4.777  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.925   3.292   4.958  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.280   2.534   4.014  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.002   1.415   3.589  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.471   0.540   2.645  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.788   0.781   2.091  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.535   1.878   2.563  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.017   2.758   3.525  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.712   3.818   4.043  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.049   4.018   3.603  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.352  -0.172   1.060  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.131   0.487  -0.052  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.309   0.817   0.076  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.421   0.758  -1.317  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.073   1.442  -2.347  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.387   1.733  -3.524  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.051   1.351  -3.669  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.608   0.664  -2.643  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.094   0.351  -1.464  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.578  -0.325  -0.480  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.261  -1.037   0.441  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.629  -1.563   1.564  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.268  -0.518   2.306  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.003   0.285  -2.833  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.606   0.629  -3.974  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.918   1.390  -5.081  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.978   0.568  -6.374  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.627   2.734  -5.291  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.525   1.692  -4.860  0.00  0.00           O+0
HETATM   30  H   UNK     0      -1.712   5.162   5.192  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.749   4.988   3.721  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.044   5.088   5.342  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.991   1.228   4.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.537   2.026   2.170  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.448   4.888   4.133  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.681   3.159   3.853  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.083   4.239   2.531  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.048  -0.840   1.587  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.108   1.759  -2.235  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.887   2.266  -4.328  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.701  -1.888  -0.097  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.433  -2.176   1.141  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.063  -2.194   2.261  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.527  -0.254  -2.052  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.649   0.360  -4.122  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.491   1.100  -7.199  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.439  -0.380  -6.258  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.009   0.343  -6.670  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.686   2.605  -5.538  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.151   3.304  -6.098  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.556   3.357  -4.391  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1                                                       
CONECT    3    8    4    2                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4   23    6                                                  
CONECT    6   11    5    7                                                  
CONECT    7    6    8   34                                                  
CONECT    8    3    9    7                                                  
CONECT    9    8   10                                                       
CONECT   10    9   35   36   37                                             
CONECT   11    6   21   12   38                                             
CONECT   12   13   14   11                                                  
CONECT   13   12                                                            
CONECT   14   15   19   12                                                  
CONECT   15   14   16   39                                                  
CONECT   16   15   17   40                                                  
CONECT   17   18   29   16                                                  
CONECT   18   17   19   24                                                  
CONECT   19   14   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   11   22   20   41                                             
CONECT   22   23   21   42   43                                             
CONECT   23    5   22                                                       
CONECT   24   18   25   44                                                  
CONECT   25   24   26   45                                                  
CONECT   26   25   29   27   28                                             
CONECT   27   26   46   47   48                                             
CONECT   28   26   49   50   51                                             
CONECT   29   17   26                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    7                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
CONECT   43   22                                                            
CONECT   44   24                                                            
CONECT   45   25                                                            
CONECT   46   27                                                            
CONECT   47   27                                                            
CONECT   48   27                                                            
CONECT   49   28                                                            
CONECT   50   28                                                            
CONECT   51   28                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

RDKit          3D

51 55  0  0  0  0  0  0  0  0999 V2000
   -0.8096    4.7006    4.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9253    3.2924    4.9580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796    2.5337    4.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024    1.4153    3.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709    0.5400    2.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.7809    2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5348    1.8777    2.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0171    2.7577    3.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124    3.8179    4.0431 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493    4.0177    3.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517   -0.1715    1.0603 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1309    0.4870   -0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3087    0.8165    0.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211    0.7577   -1.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732    1.4422   -2.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865    1.7326   -3.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0509    1.3514   -3.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6076    0.6642   -2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0943    0.3505   -1.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784   -0.3246   -0.4804 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611   -1.0372    0.4407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6289   -1.5630    1.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2681   -0.5183    2.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0032    0.2849   -2.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6063    0.6291   -3.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179    1.3904   -5.0813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9783    0.5676   -6.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    2.7338   -5.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253    1.6917   -4.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7115    5.1617    5.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489    4.9883    3.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437    5.0875    5.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912    1.2285    4.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    2.0256    2.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    4.8883    4.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814    3.1594    3.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825    4.2387    2.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -0.8404    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1082    1.7585   -2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8874    2.2661   -4.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010   -1.8882   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -2.1757    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633   -2.1938    2.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5273   -0.2539   -2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6492    0.3600   -4.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4913    1.1003   -7.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387   -0.3803   -6.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0088    0.3427   -6.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    2.6053   -5.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    3.3042   -6.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5563    3.3569   -4.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
  8  3  2  0
 12 13  2  0
  3  4  1  0
  4  5  2  0
 17 18  2  0
 11  6  1  0
 14 19  2  0
 19 18  1  0
 11 21  1  0
  5 23  1  0
 17 29  1  0
 18 24  1  0
 24 25  2  0
 25 26  1  0
 26 29  1  0
 23 22  1  0
 26 27  1  6
 22 21  1  0
 26 28  1  0
 16 15  2  0
 19 20  1  0
 14 12  1  0
  8  9  1  0
  5  6  1  0
  9 10  1  0
 17 16  1  0
  3  2  1  0
  6  7  2  0
  2  1  1  0
 20 21  1  0
 12 11  1  0
 21 41  1  6
  7  8  1  0
 11 38  1  1
 16 40  1  0
 15 39  1  0
 22 42  1  0
 22 43  1  0
  7 34  1  0
  4 33  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

View in JSmol

Synonyms

Value	Source
(-)-cis-Deguelin	MetaCyc
13,13a-dihydro-9,10-Dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7ah)-one	MeSH

Chemical Formula

C₂₃H₂₂O₆

Average Mass

394.4230 Da

Monoisotopic Mass

394.14164 Da

IUPAC Name

(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one

Traditional Name

(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C2=C(O[C@]3([H])C([H])([H])OC4=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C4[C@]3([H])C2=O)C2=C1OC(C([H])=C2[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1

InChI Key

ORDAZKGHSNRHTD-UXHICEINSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amorpha fruticosa	LOTUS Database	35616633
Amorpha fruticosa L.	KNApSAcK Database	22123792
Chadsia grevei	LOTUS Database	35616633
Deguelia spruceana	KNApSAcK Database	22123792
Derris elliptica	KNApSAcK Database	22123792
Derris malaccensis	KNApSAcK Database	22123792
Derris trifoliata	JEOL database	Yenesew, A., et al, Phytochemistry 66, 653 (2005)
Erycibe expansa	KNApSAcK Database	22123792
Lonchocarpus salvadorensis	KNApSAcK Database	22123792
Lonchocarpus unifoliolatus	KNApSAcK Database	22123792
Lonchocarpus utilis	LOTUS Database	35616633
Millettia dura	LOTUS Database	35616633
Millettia oblata ssp. teitensis		Not Available
Millettia pachycarpa	LOTUS Database	35616633
Millettia taiwaniana	KNApSAcK Database	22123792
Mundulea sericea	KNApSAcK Database	22123792
Piscidia mollis	KNApSAcK Database	22123792
Piscidia piscipula	KNApSAcK Database	22123792
Tephrosia abbottiae	KNApSAcK Database	22123792
Tephrosia candida	LOTUS Database	35616633
Tephrosia falciformis	KNApSAcK Database	22123792
Tephrosia fulvinervis	KNApSAcK Database	22123792
Tephrosia interrupta Engl.	KNApSAcK Database	22123792
Tephrosia linearis	LOTUS Database	35616633
Tephrosia linearis (Willd.) Pers.	KNApSAcK Database	22123792
Tephrosia nitens	KNApSAcK Database	22123792
Tephrosia purpurea	KNApSAcK Database	22123792
Tephrosia strigosa	KNApSAcK Database	22123792
Tephrosia vogelii	KNApSAcK Database	22123792

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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.97 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.93	ALOGPS
logP	3.3	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	11.72	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	2	ChemAxon
Refractivity	107.22 m³·mol⁻¹	ChemAxon
Polarizability	41.87 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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1588271

References

General References

Kiganda I, Bogaerts J, Wieske LHE, Deyou T, Atilaw Y, Uwamariya C, Miah M, Said J, Ndakala A, Akala HM, Herrebout W, Trybala E, Bergstrom T, Yenesew A, Erdelyi M: Antiviral Rotenoids and Isoflavones Isolated from Millettia oblata ssp. teitensis. J Nat Prod. 2024 Apr 26;87(4):1003-1012. doi: 10.1021/acs.jnatprod.3c01288. Epub 2024 Apr 5. [PubMed:38579352 ]
Yenesew, A., et al. (2005). Yenesew, A., et al, Phytochemistry 66, 653 (2005) . Phytochem..
DOI: 10.1021/acs.jnatprod.3c01288
PMID: 38579352

Showing NP-Card for deguelin (NP0031058)

MOL for NP0031058 (deguelin)

3D MOL for NP0031058 (deguelin)

3D SDF for NP0031058 (deguelin)

3D-SDF for NP0031058 (deguelin)

PDB for NP0031058 (deguelin)

3D PDB for NP0031058 (deguelin)

SMILES for NP0031058 (deguelin)

INCHI for NP0031058 (deguelin)

Structure for NP0031058 (deguelin)

3D Structure for NP0031058 (deguelin)