NP-MRD: Showing NP-Card for 22-dehydro-20-deoxy-ajugasterone C (NP0039376)

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Record Information

Version

2.0

Created at

2021-06-20 21:49:34 UTC

Updated at

2021-06-30 00:12:40 UTC

NP-MRD ID

NP0039376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-dehydro-20-deoxy-ajugasterone C

Provided By

JEOL Database JEOL Logo

Description

22-dehydro-20-deoxy-ajugasterone C is found in Serratula wolffii. 22-dehydro-20-deoxy-ajugasterone C was first documented in 2010 (Takacs, M., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123493D          

 75 78  0  0  0  0            999 V2000
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   -0.1077   -1.0142   -4.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
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 26 27  1  6
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 23 21  1  0
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 33 75  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
 14 54  1  0
 24 62  1  0
 30 70  1  0
M  END


  Mrv1652306202123493D          

 75 78  0  0  0  0            999 V2000
   -0.8551   -4.9600   -7.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1148   -4.3595   -6.2444 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4591   -5.4051   -5.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4663   -2.3360   -4.7077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1077   -1.0142   -4.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7921   -0.1836   -3.2987 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1707    1.0824   -4.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726    0.0807   -1.9565 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.0459    2.6188    1.4891 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.7982    2.4516   -1.1021 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8033    0.9193   -0.8584 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2769    0.4348   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
 20 21  1  0  0  0  0
 13 14  1  6  0  0  0
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  6  7  2  0  0  0  0
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 24 62  1  0  0  0  0
 30 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039376

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@@]2([H])C(=O)C([H])=C3[C@@]([H])([C@]([H])(O[H])C([H])([H])[C@]4(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@@]34O[H])[C@@]([H])(C(=O)C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@@]2(C([H])([H])[H])C([H])([H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O6/c1-14(2)6-7-19(28)15(3)16-8-9-27(33)18-11-20(29)17-10-21(30)22(31)12-25(17,4)24(18)23(32)13-26(16,27)5/h11,14-17,21-24,30-33H,6-10,12-13H2,1-5H3/t15-,16+,17-,21+,22-,23+,24-,25-,26+,27+/m0/s1

> <INCHI_KEY>
NPBZEMOJGSURAF-YLMCTCPGSA-N

> <FORMULA>
C27H42O6

> <MOLECULAR_WEIGHT>
462.627

> <EXACT_MASS>
462.298139072

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.65508459170949

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,5R,7R,11S,14R,15R,17R)-4,5,11,17-tetrahydroxy-2,15-dimethyl-14-[(2S)-6-methyl-3-oxoheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
2.239072381333333

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.066210889167806

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.501918476591076

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8691454103495655

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
126.25590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,5R,7R,11S,14R,15R,17R)-4,5,11,17-tetrahydroxy-2,15-dimethyl-14-[(2S)-6-methyl-3-oxoheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
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    0.4214   -2.0531   -1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785   -1.5775   -1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -1.3462    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -1.4634    0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4323    2.0034    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0314   -0.4085    2.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941    2.5339    3.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967    4.2516    5.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7110    2.6999    6.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    2.6874    5.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0615    3.7583    7.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678    4.5647    4.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2589    6.0094    5.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2095    3.0000    3.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045    4.6193    2.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    5.4475    1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683    4.5150    2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118    5.3257    3.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1265    2.4731    1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674    4.2646    0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495    4.2222   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0353    2.7079   -1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7600    2.7549   -1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714    0.7226   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3556   -0.6532   -0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818    0.8580    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 29 31  1  0
 21 22  1  0
 31 32  1  0
 15 13  1  0
 32 13  1  0
 26 25  1  0
 10  8  1  0
 29 28  1  0
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  8  6  1  0
 28 26  1  0
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  5  4  1  0
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  4  2  1  0
 17 16  1  0
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 13 12  1  0
 32 33  1  1
 19 20  1  0
  2  3  1  0
 20 21  1  0
 13 14  1  6
 12 11  1  0
  6  7  2  0
 25 23  1  0
 23 24  1  0
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  8 45  1  1
 26 27  1  6
 19 56  1  6
 15 28  1  0
 17 18  2  0
 23 21  1  0
 29 30  1  0
  8  9  1  0
 22 60  1  0
 25 63  1  0
 25 64  1  0
 29 69  1  6
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 28 68  1  6
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 27 66  1  0
 27 67  1  0
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 31 71  1  0
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  9 46  1  0
  9 47  1  0
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  5 43  1  0
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  2 37  1  6
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  3 38  1  0
  3 39  1  0
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 14 54  1  0
 24 62  1  0
 30 70  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      -0.855  -4.960  -7.265  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.115  -4.359  -6.244  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.459  -5.405  -5.183  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.492  -3.082  -5.636  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.466  -2.336  -4.708  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.108  -1.014  -4.220  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.224  -0.617  -4.553  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.792  -0.184  -3.299  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.171   1.082  -4.064  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.073   0.081  -1.956  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.271  -1.243  -1.215  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.182  -0.957   0.296  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.065   0.569   0.390  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.414   1.034   0.232  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.468   1.209   1.650  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.444   0.585   2.837  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.963   1.225   4.061  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.965   0.567   5.101  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.513   2.651   3.993  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.312   3.327   5.361  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.162   3.619   5.639  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.267   4.348   6.869  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.791   4.466   4.527  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.264   5.795   4.588  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.560   3.878   3.132  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.914   3.479   2.810  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.767   4.762   2.615  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.046   2.619   1.489  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.562   3.303   0.171  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.840   3.577   0.246  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.798   2.452  -1.102  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.803   0.919  -0.858  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.277   0.435  -0.720  0.00  0.00           C+0
HETATM   34  H   UNK     0      -1.081  -4.239  -8.058  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.799  -5.252  -6.792  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.423  -5.849  -7.737  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.038  -4.092  -6.775  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.825  -6.326  -5.649  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.417  -5.659  -4.576  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.247  -5.048  -4.513  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.412  -3.329  -5.089  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.792  -2.410  -6.451  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.402  -2.119  -5.235  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.690  -2.942  -3.825  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.705  -0.764  -3.120  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.310   1.750  -4.183  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.969   1.634  -3.562  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.532   0.836  -5.069  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.883   0.576  -2.187  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.421  -2.053  -1.471  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.278  -1.577  -1.487  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.071  -1.346   0.806  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.693  -1.463   0.718  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.432   2.003   0.371  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.031  -0.409   2.972  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.594   2.534   3.832  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.897   4.252   5.426  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.711   2.700   6.169  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.727   2.687   5.752  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.062   3.758   7.572  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.868   4.565   4.710  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.259   6.009   5.545  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.210   3.000   3.030  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.905   4.619   2.403  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.304   5.447   1.897  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.768   4.515   2.243  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.912   5.326   3.539  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.127   2.473   1.347  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.067   4.265   0.036  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.050   4.222  -0.457  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.035   2.708  -1.847  0.00  0.00           H+0
HETATM   72  H   UNK     0       1.760   2.755  -1.533  0.00  0.00           H+0
HETATM   73  H   UNK     0       2.871   0.723  -1.593  0.00  0.00           H+0
HETATM   74  H   UNK     0       2.356  -0.653  -0.632  0.00  0.00           H+0
HETATM   75  H   UNK     0       2.782   0.858   0.151  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    4    1    3   37                                             
CONECT    3    2   38   39   40                                             
CONECT    4    5    2   41   42                                             
CONECT    5    6    4   43   44                                             
CONECT    6    8    5    7                                                  
CONECT    7    6                                                            
CONECT    8   10    6   45    9                                             
CONECT    9    8   46   47   48                                             
CONECT   10   11    8   32   49                                             
CONECT   11   10   12   50   51                                             
CONECT   12   13   11   52   53                                             
CONECT   13   15   32   12   14                                             
CONECT   14   13   54                                                       
CONECT   15   13   16   28                                                  
CONECT   16   15   17   55                                                  
CONECT   17   19   16   18                                                  
CONECT   18   17                                                            
CONECT   19   26   17   20   56                                             
CONECT   20   19   21   57   58                                             
CONECT   21   22   20   23   59                                             
CONECT   22   21   60                                                       
CONECT   23   25   24   21   61                                             
CONECT   24   23   62                                                       
CONECT   25   26   23   63   64                                             
CONECT   26   25   28   19   27                                             
CONECT   27   26   65   66   67                                             
CONECT   28   29   26   15   68                                             
CONECT   29   31   28   30   69                                             
CONECT   30   29   70                                                       
CONECT   31   29   32   71   72                                             
CONECT   32   31   13   33   10                                             
CONECT   33   32   73   74   75                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    2                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    4                                                            
CONECT   43    5                                                            
CONECT   44    5                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   11                                                            
CONECT   51   11                                                            
CONECT   52   12                                                            
CONECT   53   12                                                            
CONECT   54   14                                                            
CONECT   55   16                                                            
CONECT   56   19                                                            
CONECT   57   20                                                            
CONECT   58   20                                                            
CONECT   59   21                                                            
CONECT   60   22                                                            
CONECT   61   23                                                            
CONECT   62   24                                                            
CONECT   63   25                                                            
CONECT   64   25                                                            
CONECT   65   27                                                            
CONECT   66   27                                                            
CONECT   67   27                                                            
CONECT   68   28                                                            
CONECT   69   29                                                            
CONECT   70   30                                                            
CONECT   71   31                                                            
CONECT   72   31                                                            
CONECT   73   33                                                            
CONECT   74   33                                                            
CONECT   75   33                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  156    0
END

RDKit          3D

75 78  0  0  0  0  0  0  0  0999 V2000
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    0.1148   -4.3595   -6.2444 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4591   -5.4051   -5.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922   -3.0824   -5.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663   -2.3360   -4.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1077   -1.0142   -4.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2240   -0.6167   -4.5528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7921   -0.1836   -3.2987 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1707    1.0824   -4.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726    0.0807   -1.9565 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2708   -1.2434   -1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822   -0.9566    0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0653    0.5687    0.3896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4139    1.0338    0.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    1.2094    1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441    0.5853    2.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9634    1.2250    4.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9646    0.5669    5.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5128    2.6512    3.9928 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3117    3.3267    5.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2670    4.3477    6.8685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913    4.4661    4.5273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2643    5.7950    4.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603    3.8775    3.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9139    3.4794    2.8101 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7671    4.7623    2.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0459    2.6188    1.4891 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5624    3.3027    0.1708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8398    3.5773    0.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7982    2.4516   -1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8033    0.9193   -0.8584 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2769    0.4348   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810   -4.2395   -8.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7993   -5.2518   -6.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -5.8489   -7.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -4.0923   -6.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8246   -6.3264   -5.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169   -5.6585   -4.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2471   -5.0484   -4.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4115   -3.3294   -5.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7918   -2.4101   -6.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4018   -2.1195   -5.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6903   -2.9419   -3.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7054   -0.7636   -3.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101    1.7497   -4.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9686    1.6341   -3.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5319    0.8361   -5.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8826    0.5759   -2.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214   -2.0531   -1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785   -1.5775   -1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -1.3462    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -1.4634    0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4323    2.0034    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0314   -0.4085    2.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941    2.5339    3.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967    4.2516    5.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7110    2.6999    6.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    2.6874    5.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0615    3.7583    7.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678    4.5647    4.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2589    6.0094    5.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2095    3.0000    3.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045    4.6193    2.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    5.4475    1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683    4.5150    2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118    5.3257    3.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1265    2.4731    1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674    4.2646    0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495    4.2222   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0353    2.7079   -1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7600    2.7549   -1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714    0.7226   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3556   -0.6532   -0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818    0.8580    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
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 15 13  1  0
 32 13  1  0
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 29 28  1  0
 15 16  2  0
  8  6  1  0
 28 26  1  0
  6  5  1  0
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  2  3  1  0
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  6  7  2  0
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  8 45  1  1
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  1 36  1  0
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  3 38  1  0
  3 39  1  0
  3 40  1  0
 14 54  1  0
 24 62  1  0
 30 70  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₆

Average Mass

462.6270 Da

Monoisotopic Mass

462.29814 Da

IUPAC Name

(1S,2R,4S,5R,7R,11S,14R,15R,17R)-4,5,11,17-tetrahydroxy-2,15-dimethyl-14-[(2S)-6-methyl-3-oxoheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1S,2R,4S,5R,7R,11S,14R,15R,17R)-4,5,11,17-tetrahydroxy-2,15-dimethyl-14-[(2S)-6-methyl-3-oxoheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@@]2([H])C(=O)C([H])=C3[C@@]([H])([C@]([H])(O[H])C([H])([H])[C@]4(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@@]34O[H])[C@@]([H])(C(=O)C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@@]2(C([H])([H])[H])C([H])([H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C27H42O6/c1-14(2)6-7-19(28)15(3)16-8-9-27(33)18-11-20(29)17-10-21(30)22(31)12-25(17,4)24(18)23(32)13-26(16,27)5/h11,14-17,21-24,30-33H,6-10,12-13H2,1-5H3/t15-,16+,17-,21+,22-,23+,24-,25-,26+,27+/m0/s1

InChI Key

NPBZEMOJGSURAF-YLMCTCPGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Serratula wolffii	JEOL database	Takacs, M., et al, Mag. Reson. Chem. 48, 386 (2010)

Chemical Taxonomy

Classification

Not classified

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	2.11	ALOGPS
logP	2.24	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.5	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.26 m³·mol⁻¹	ChemAxon
Polarizability	52.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Takacs, M., et al. (2010). Takacs, M., et al, Mag. Reson. Chem. 48, 386 (2010). Mag. Reson. Chem..

Showing NP-Card for 22-dehydro-20-deoxy-ajugasterone C (NP0039376)

MOL for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)

3D MOL for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)

3D SDF for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)

3D-SDF for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)

PDB for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)

3D PDB for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)

SMILES for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)

INCHI for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)

Structure for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)

3D Structure for NP0039376 (22-dehydro-20-deoxy-ajugasterone C)