NP-MRD: Showing NP-Card for (16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+ (NP0036355)

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Record Information

Version

2.0

Created at

2021-06-20 19:33:00 UTC

Updated at

2021-06-30 00:07:58 UTC

NP-MRD ID

NP0036355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+

Provided By

JEOL Database JEOL Logo

Description

CHEMBL1923782 belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. (16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+ is found in Machilus yaoshansis. (16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+ was first documented in 2011 (Gan, M., et al.). Based on a literature review very few articles have been published on CHEMBL1923782.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121333D          

100105  0  0  0  0            999 V2000
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   -2.9115   -3.5580    2.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121333D          

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  4  5  2  0  0  0  0
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M  END
> <DATABASE_ID>
NP0036355

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])[C@]3([H])C(=C([H])C([H])([H])[C@@]4([H])[C@]5(C([H])([H])[H])C([H])([H])[C@@]6([H])O[C@@]([H])(C([H])([H])C(=O)[C@@](O[H])(C([H])([H])[H])[C@]6([H])[C@@]5(C([H])([H])[H])C([H])([H])C(=O)[C@@]34C([H])([H])[H])C(O[H])(C([H])([H])[H])C([H])([H])[H])C(C2=O)(C([H])([H])[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C36H52O12/c1-31(2)16-9-10-21-33(5)13-19-28(36(8,45)22(38)12-24(46-19)32(3,4)44)34(33,6)14-23(39)35(21,7)17(16)11-18(29(31)43)47-30-27(42)26(41)25(40)20(15-37)48-30/h9,11,17,19-21,24-28,30,37,40-42,44-45H,10,12-15H2,1-8H3/t17-,19-,20-,21+,24+,25-,26+,27-,28+,30-,33+,34-,35+,36+/m1/s1

> <INCHI_KEY>
IWNXFVRPEIWIJJ-VPLPWDSJSA-N

> <FORMULA>
C36H52O12

> <MOLECULAR_WEIGHT>
676.8

> <EXACT_MASS>
676.345877114

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
71.74132736574913

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R,6S,9R,10R,11R,14R,15R)-9-hydroxy-6-(2-hydroxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-17-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-oxapentacyclo[12.8.0.0^{2,11}.0^{4,10}.0^{15,20}]docosa-16,20-diene-8,13,18-trione

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
0.8300330336666656

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.764321786066592

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.109591737554977

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923571073396

> <JCHEM_POLAR_SURFACE_AREA>
200.28

> <JCHEM_REFRACTIVITY>
172.63170000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,6S,9R,10R,11R,14R,15R)-9-hydroxy-6-(2-hydroxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-17-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-oxapentacyclo[12.8.0.0^{2,11}.0^{4,10}.0^{15,20}]docosa-16,20-diene-8,13,18-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 34 85  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      -1.652  -5.370   1.332  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.510  -3.981   1.993  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.912  -3.558   2.473  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.579  -4.131   3.212  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.221  -5.214   3.682  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.110  -2.881   3.878  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.299  -2.965   5.190  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.715  -2.791   5.399  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.142  -1.467   5.061  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.514  -1.211   5.401  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.837   0.245   5.029  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.709   0.476   3.627  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.460  -2.201   4.704  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.804  -2.030   5.168  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.030  -3.639   5.002  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.849  -4.544   4.242  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.557  -3.859   4.667  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.209  -5.197   5.055  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.179  -1.727   3.204  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.565  -1.557   1.749  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.896  -2.897   1.083  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.642  -3.093  -0.226  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.034  -2.102  -1.167  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.209  -0.687  -0.603  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.839   0.380  -1.053  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.286  -0.040  -0.642  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.901   0.633  -2.575  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.455   2.076  -2.714  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.752   1.976  -3.296  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.620   3.127  -3.238  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.721   2.887  -4.314  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.888   3.867  -4.188  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.164   2.898  -5.740  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.264   1.572  -4.086  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.876   4.449  -3.398  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.461   4.923  -2.024  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.117   5.803  -1.461  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.220   4.265  -1.365  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.005   4.905   0.013  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.093   4.589  -2.180  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.426   2.722  -1.287  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.393   1.806  -0.543  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.062   2.206  -0.953  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.444   1.786   0.988  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.504   0.726   1.542  0.00  0.00           C+0
HETATM   46  O   UNK     0       1.210   1.008   2.517  0.00  0.00           O+0
HETATM   47  C   UNK     0       0.491  -0.708   0.946  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.920  -1.302   1.132  0.00  0.00           C+0
HETATM   49  H   UNK     0      -0.684  -5.753   0.987  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.051  -6.107   2.040  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.339  -5.344   0.478  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.334  -4.307   3.154  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.906  -2.609   3.020  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.600  -3.446   1.627  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.842  -2.920   6.481  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.623  -1.297   6.490  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.860   0.503   5.319  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.154   0.932   5.540  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.750   0.582   3.438  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.463  -2.043   3.618  0.00  0.00           H+0
HETATM   61  H   UNK     0       6.307  -2.763   4.758  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.226  -3.882   6.054  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.425  -5.420   4.354  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.428  -3.799   3.580  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.292  -5.354   4.729  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.078  -0.821   3.751  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.502  -0.996   1.800  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.869  -4.047  -0.698  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.640  -2.060  -2.079  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.932  -2.520  -1.481  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.143  -0.382  -1.094  0.00  0.00           H+0
HETATM   72  H   UNK     0      -3.060   0.559  -1.131  0.00  0.00           H+0
HETATM   73  H   UNK     0      -2.481   0.052   0.424  0.00  0.00           H+0
HETATM   74  H   UNK     0      -2.503  -1.071  -0.936  0.00  0.00           H+0
HETATM   75  H   UNK     0      -1.520  -0.103  -3.101  0.00  0.00           H+0
HETATM   76  H   UNK     0       0.101   0.577  -3.017  0.00  0.00           H+0
HETATM   77  H   UNK     0      -0.811   2.600  -3.427  0.00  0.00           H+0
HETATM   78  H   UNK     0      -4.112   3.076  -2.257  0.00  0.00           H+0
HETATM   79  H   UNK     0      -5.603   4.893  -4.438  0.00  0.00           H+0
HETATM   80  H   UNK     0      -6.713   3.575  -4.849  0.00  0.00           H+0
HETATM   81  H   UNK     0      -6.294   3.858  -3.170  0.00  0.00           H+0
HETATM   82  H   UNK     0      -4.945   2.630  -6.462  0.00  0.00           H+0
HETATM   83  H   UNK     0      -3.766   3.879  -6.016  0.00  0.00           H+0
HETATM   84  H   UNK     0      -3.369   2.154  -5.862  0.00  0.00           H+0
HETATM   85  H   UNK     0      -4.486   0.997  -3.937  0.00  0.00           H+0
HETATM   86  H   UNK     0      -2.001   4.384  -4.051  0.00  0.00           H+0
HETATM   87  H   UNK     0      -3.518   5.234  -3.810  0.00  0.00           H+0
HETATM   88  H   UNK     0      -1.029   6.000  -0.053  0.00  0.00           H+0
HETATM   89  H   UNK     0      -1.779   4.600   0.725  0.00  0.00           H+0
HETATM   90  H   UNK     0      -0.020   4.671   0.423  0.00  0.00           H+0
HETATM   91  H   UNK     0       0.092   5.541  -2.073  0.00  0.00           H+0
HETATM   92  H   UNK     0      -2.400   2.582  -0.801  0.00  0.00           H+0
HETATM   93  H   UNK     0       1.326   3.190  -0.554  0.00  0.00           H+0
HETATM   94  H   UNK     0       1.822   1.525  -0.561  0.00  0.00           H+0
HETATM   95  H   UNK     0       1.204   2.248  -2.036  0.00  0.00           H+0
HETATM   96  H   UNK     0      -0.122   2.745   1.402  0.00  0.00           H+0
HETATM   97  H   UNK     0      -1.446   1.604   1.384  0.00  0.00           H+0
HETATM   98  H   UNK     0       2.224  -1.339   2.182  0.00  0.00           H+0
HETATM   99  H   UNK     0       2.667  -0.685   0.618  0.00  0.00           H+0
HETATM  100  H   UNK     0       2.001  -2.320   0.740  0.00  0.00           H+0
CONECT    1    2   49   50   51                                             
CONECT    2    1    4   21    3                                             
CONECT    3    2   52   53   54                                             
CONECT    4    6    2    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8   17    9    7   55                                             
CONECT    9   10    8                                                       
CONECT   10   13    9   11   56                                             
CONECT   11   12   10   57   58                                             
CONECT   12   11   59                                                       
CONECT   13   15   10   14   60                                             
CONECT   14   13   61                                                       
CONECT   15   17   13   16   62                                             
CONECT   16   15   63                                                       
CONECT   17    8   15   18   64                                             
CONECT   18   17   65                                                       
CONECT   19    6   20   66                                                  
CONECT   20   19   21   47   67                                             
CONECT   21    2   20   22                                                  
CONECT   22   21   23   68                                                  
CONECT   23   22   24   69   70                                             
CONECT   24   25   47   23   71                                             
CONECT   25   24   42   27   26                                             
CONECT   26   25   72   73   74                                             
CONECT   27   25   28   75   76                                             
CONECT   28   27   41   29   77                                             
CONECT   29   28   30                                                       
CONECT   30   29   35   31   78                                             
CONECT   31   30   32   33   34                                             
CONECT   32   31   79   80   81                                             
CONECT   33   31   82   83   84                                             
CONECT   34   31   85                                                       
CONECT   35   36   30   86   87                                             
CONECT   36   38   35   37                                                  
CONECT   37   36                                                            
CONECT   38   41   39   40   36                                             
CONECT   39   38   88   89   90                                             
CONECT   40   38   91                                                       
CONECT   41   42   38   28   92                                             
CONECT   42   44   25   41   43                                             
CONECT   43   42   93   94   95                                             
CONECT   44   42   45   96   97                                             
CONECT   45   47   44   46                                                  
CONECT   46   45                                                            
CONECT   47   45   48   20   24                                             
CONECT   48   47   98   99  100                                             
CONECT   49    1                                                            
CONECT   50    1                                                            
CONECT   51    1                                                            
CONECT   52    3                                                            
CONECT   53    3                                                            
CONECT   54    3                                                            
CONECT   55    8                                                            
CONECT   56   10                                                            
CONECT   57   11                                                            
CONECT   58   11                                                            
CONECT   59   12                                                            
CONECT   60   13                                                            
CONECT   61   14                                                            
CONECT   62   15                                                            
CONECT   63   16                                                            
CONECT   64   17                                                            
CONECT   65   18                                                            
CONECT   66   19                                                            
CONECT   67   20                                                            
CONECT   68   22                                                            
CONECT   69   23                                                            
CONECT   70   23                                                            
CONECT   71   24                                                            
CONECT   72   26                                                            
CONECT   73   26                                                            
CONECT   74   26                                                            
CONECT   75   27                                                            
CONECT   76   27                                                            
CONECT   77   28                                                            
CONECT   78   30                                                            
CONECT   79   32                                                            
CONECT   80   32                                                            
CONECT   81   32                                                            
CONECT   82   33                                                            
CONECT   83   33                                                            
CONECT   84   33                                                            
CONECT   85   34                                                            
CONECT   86   35                                                            
CONECT   87   35                                                            
CONECT   88   39                                                            
CONECT   89   39                                                            
CONECT   90   39                                                            
CONECT   91   40                                                            
CONECT   92   41                                                            
CONECT   93   43                                                            
CONECT   94   43                                                            
CONECT   95   43                                                            
CONECT   96   44                                                            
CONECT   97   44                                                            
CONECT   98   48                                                            
CONECT   99   48                                                            
CONECT  100   48                                                            
MASTER        0    0    0    0    0    0    0    0  100    0  210    0
END

RDKit          3D

100105  0  0  0  0  0  0  0  0999 V2000
   -1.6522   -5.3700    1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097   -3.9812    1.9932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9115   -3.5580    2.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5790   -4.1311    3.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -5.2140    3.6816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099   -2.8806    3.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2988   -2.9651    5.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7148   -2.7907    5.3991 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1415   -1.4666    5.0609 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5141   -1.2107    5.4012 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8369    0.2449    5.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7090    0.4756    3.6268 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4600   -2.2008    4.7035 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8043   -2.0301    5.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0303   -3.6390    5.0022 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8495   -4.5443    4.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571   -3.8593    4.6672 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2090   -5.1972    5.0547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1785   -1.7266    3.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645   -1.5572    1.7485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8957   -2.8966    1.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6421   -3.0934   -0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339   -2.1015   -1.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2091   -0.6870   -0.6034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8392    0.3795   -1.0533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2863   -0.0398   -0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9005    0.6327   -2.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4552    2.0760   -2.7142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7522    1.9765   -3.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199    3.1271   -3.2378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7215    2.8866   -4.3135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8882    3.8674   -4.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642    2.8978   -5.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2640    1.5724   -4.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761    4.4488   -3.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4605    4.9234   -2.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1170    5.8032   -1.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2203    4.2651   -1.3645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0054    4.9050    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0933    4.5889   -2.1797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4256    2.7216   -1.2871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3930    1.8063   -0.5428 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0618    2.2061   -0.9528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443    1.7855    0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5039    0.7258    1.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102    1.0084    2.5170 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910   -0.7081    0.9461 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9199   -1.3018    1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6843   -5.7534    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0509   -6.1071    2.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3391   -5.3442    0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3340   -4.3067    3.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9063   -2.6094    3.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5997   -3.4460    1.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8423   -2.9202    6.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231   -1.2974    6.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8598    0.5030    5.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539    0.9321    5.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7503    0.5821    3.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4630   -2.0427    3.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3073   -2.7629    4.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2256   -3.8825    6.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249   -5.4198    4.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282   -3.7991    3.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -5.3537    4.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0775   -0.8208    3.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5204   -0.1028   -3.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8105    2.6004   -3.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1125    3.0758   -2.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6032    4.8928   -4.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7126    3.5747   -4.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2942    3.8584   -3.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3693    2.1536   -5.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    0.9974   -3.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    4.3836   -4.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0920    5.5412   -2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4001    2.5817   -0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264    3.1902   -0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.5252   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043    2.2475   -2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1221    2.7450    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2240   -1.3390    2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -0.6853    0.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0011   -2.3202    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₅₂O₁₂

Average Mass

676.8000 Da

Monoisotopic Mass

676.34588 Da

IUPAC Name

(1S,2S,4R,6S,9R,10R,11R,14R,15R)-9-hydroxy-6-(2-hydroxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-17-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-oxapentacyclo[12.8.0.0^{2,11}.0^{4,10}.0^{15,20}]docosa-16,20-diene-8,13,18-trione

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])[C@]3([H])C(=C([H])C([H])([H])[C@@]4([H])[C@]5(C([H])([H])[H])C([H])([H])[C@@]6([H])O[C@@]([H])(C([H])([H])C(=O)[C@@](O[H])(C([H])([H])[H])[C@]6([H])[C@@]5(C([H])([H])[H])C([H])([H])C(=O)[C@@]34C([H])([H])[H])C(O[H])(C([H])([H])[H])C([H])([H])[H])C(C2=O)(C([H])([H])[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C36H52O12/c1-31(2)16-9-10-21-33(5)13-19-28(36(8,45)22(38)12-24(46-19)32(3,4)44)34(33,6)14-23(39)35(21,7)17(16)11-18(29(31)43)47-30-27(42)26(41)25(40)20(15-37)48-30/h9,11,17,19-21,24-28,30,37,40-42,44-45H,10,12-15H2,1-8H3/t17-,19-,20-,21+,24+,25-,26+,27-,28+,30-,33+,34-,35+,36+/m1/s1

InChI Key

IWNXFVRPEIWIJJ-VPLPWDSJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Machilus yaoshansis	JEOL database	Gan, M., et al, J. Nat. Prod. 74, 2431 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Diterpene glycoside
20-hydroxysteroid
Diterpenoid
3-oxo-delta-1-steroid
3-oxosteroid
14-alpha-methylsteroid
Hydroxysteroid
11-oxosteroid
Oxosteroid
Delta-1-steroid
Terpene glycoside
Glycosyl compound
O-glycosyl compound
Oxepane
Cyclohexenone
Oxane
Acyloin
Monosaccharide
Tertiary alcohol
Secondary alcohol
Ketone
Cyclic ketone
Polyol
Acetal
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

glycoside (CHEBI:68909 )
cucurbitacin (CHEBI:68909 )

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	2.07	ALOGPS
logP	0.83	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	172.63 m³·mol⁻¹	ChemAxon
Polarizability	71.74 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

28482756

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56655721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gan, M., et al. (2011). Gan, M., et al, J. Nat. Prod. 74, 2431 (2011). J. Nat. Prod..

Showing NP-Card for (16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+ (NP0036355)

MOL for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)

3D MOL for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)

3D SDF for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)

3D-SDF for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)

PDB for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)

3D PDB for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)

SMILES for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)

INCHI for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)

Structure for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)

3D Structure for NP0036355 ((16alpha,20R,24S)-16,24-epoxy-2,20,25-trihydroxycucurbita-1,5-diene-3,11,+)