NP-MRD: Showing NP-Card for (-)-Withanoside VI (NP0073259)

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Record Information

Version

2.0

Created at

2022-04-28 18:32:33 UTC

Updated at

2022-04-28 18:32:33 UTC

NP-MRD ID

NP0073259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Withanoside VI

Description

Withanoside VI belongs to the class of organic compounds known as withanolide glycosides and derivatives. These are withanolides in which at least one hydroxyl group is glycosylated. (-)-Withanoside VI is found in Withania somnifera . (-)-Withanoside VI was first documented in 2005 (PMID: 15956813). Based on a literature review a small amount of articles have been published on Withanoside VI (PMID: 19475989) (PMID: 33647752) (PMID: 25457493) (PMID: 18670181).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220322D          

 55 61  0  0  1  0            999 V2000
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0784   -1.1393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.4594   -2.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2640   -1.3314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9658   -3.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7109   -1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083   -0.2865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9511   -0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4829   -0.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2951   -0.7535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5754    0.0224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3875    0.1676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9193   -0.4631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6390   -1.2390    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8269   -1.3843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1708   -1.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0435    0.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  6  0  0  0
  9 12  1  1  0  0  0
  8 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  1  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  0  0  0  0
 24 28  1  0  0  0  0
 23 29  1  0  0  0  0
 20 30  1  1  0  0  0
 20 31  1  1  0  0  0
 15 32  1  1  0  0  0
  2 33  1  1  0  0  0
 34 33  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 39  1  0  0  0  0
 39 40  1  1  0  0  0
 38 41  1  6  0  0  0
 37 42  1  1  0  0  0
 36 43  1  6  0  0  0
 43 44  1  0  0  0  0
 45 44  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
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 49 50  1  0  0  0  0
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 51 52  1  0  0  0  0
 48 53  1  6  0  0  0
 47 54  1  1  0  0  0
 46 55  1  6  0  0  0
M  END

     RDKit          3D

117123  0  0  0  0  0  0  0  0999 V2000
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 44100  1  0
M  END


  Mrv1652304282220322D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
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  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
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  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
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 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  0  0  0  0
 24 28  1  0  0  0  0
 23 29  1  0  0  0  0
 20 30  1  1  0  0  0
 20 31  1  1  0  0  0
 15 32  1  1  0  0  0
  2 33  1  1  0  0  0
 34 33  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 39  1  0  0  0  0
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 38 41  1  6  0  0  0
 37 42  1  1  0  0  0
 36 43  1  6  0  0  0
 43 44  1  0  0  0  0
 45 44  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 45 50  1  0  0  0  0
 49 51  1  1  0  0  0
 51 52  1  0  0  0  0
 48 53  1  6  0  0  0
 47 54  1  1  0  0  0
 46 55  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0073259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(=O)O[C@H](C1)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C40H62O15/c1-17-12-28(55-35(49)18(17)2)40(5,50)26-9-8-22-21-7-6-19-13-20(14-27(42)39(19,4)23(21)10-11-38(22,26)3)52-37-34(48)32(46)30(44)25(54-37)16-51-36-33(47)31(45)29(43)24(15-41)53-36/h6,20-34,36-37,41-48,50H,7-16H2,1-5H3/t20-,21+,22+,23+,24-,25-,26+,27+,28-,29-,30-,31+,32+,33-,34-,36-,37-,38+,39+,40-/m1/s1

> <INCHI_KEY>
MKCYAASFWFGIJK-BWBMWEGTSA-N

> <FORMULA>
C40H62O15

> <MOLECULAR_WEIGHT>
782.921

> <EXACT_MASS>
782.408871296

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
117

> <JCHEM_AVERAGE_POLARIZABILITY>
83.44535789442148

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(1R)-1-hydroxy-1-[(1S,2R,3S,5R,10S,11S,14S,15S)-3-hydroxy-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethyl]-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
-0.07

> <JCHEM_LOGP>
-0.19521931833333345

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.419403355956561

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.904694859271254

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9932169824289083

> <JCHEM_POLAR_SURFACE_AREA>
245.28999999999996

> <JCHEM_REFRACTIVITY>
193.31560000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-[(1R)-1-hydroxy-1-[(1S,2R,3S,5R,10S,11S,14S,15S)-3-hydroxy-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethyl]-3,4-dimethyl-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.480  -2.127   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.033  -2.696   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.613  -4.122   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.668  -5.338   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.858  -5.127   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.438  -3.701   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.963  -3.490   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.493  -2.485   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.803  -6.343   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.248  -6.765   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.194  -2.425   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.762  -0.535   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.067   0.406   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.512  -1.585   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      14.497  -3.939   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      18.575  -0.500   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      19.568  -1.678   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      21.084  -1.407   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      21.607   0.042   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      23.123   0.313   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      24.116  -0.864   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      23.593  -2.313   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      22.077  -2.584   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      24.586  -3.490   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      26.101  -3.219   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      25.632  -0.593   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      23.647   1.761   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      20.615   1.219   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8    4   10   12                                             
CONECT   10    9    1   11                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19   32                                             
CONECT   16   15    7   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   30   31                                             
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21                                                       
CONECT   28   24                                                            
CONECT   29   23                                                            
CONECT   30   20                                                            
CONECT   31   20                                                            
CONECT   32   15                                                            
CONECT   33    2   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   43                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37   39   41                                                  
CONECT   39   38   34   40                                                  
CONECT   40   39                                                            
CONECT   41   38                                                            
CONECT   42   37                                                            
CONECT   43   36   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   50                                                  
CONECT   46   45   47   55                                                  
CONECT   47   46   48   54                                                  
CONECT   48   47   49   53                                                  
CONECT   49   48   50   51                                                  
CONECT   50   49   45                                                       
CONECT   51   49   52                                                       
CONECT   52   51                                                            
CONECT   53   48                                                            
CONECT   54   47                                                            
CONECT   55   46                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  122    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₆₂O₁₅

Average Mass

782.9210 Da

Monoisotopic Mass

782.40887 Da

IUPAC Name

(6R)-6-[(1R)-1-hydroxy-1-[(1S,2R,3S,5R,10S,11S,14S,15S)-3-hydroxy-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethyl]-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)O[C@H](C1)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C40H62O15/c1-17-12-28(55-35(49)18(17)2)40(5,50)26-9-8-22-21-7-6-19-13-20(14-27(42)39(19,4)23(21)10-11-38(22,26)3)52-37-34(48)32(46)30(44)25(54-37)16-51-36-33(47)31(45)29(43)24(15-41)53-36/h6,20-34,36-37,41-48,50H,7-16H2,1-5H3/t20-,21+,22+,23+,24-,25-,26+,27+,28-,29-,30-,31+,32+,33-,34-,36-,37-,38+,39+,40-/m1/s1

InChI Key

MKCYAASFWFGIJK-BWBMWEGTSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Withania somnifera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolide glycosides and derivatives. These are withanolides in which at least one hydroxyl group is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolide glycosides and derivatives

Alternative Parents

Substituents

Withanolide-glycoside
Diterpene glycoside
Steroidal glycoside
20-hydroxysteroid
Diterpene lactone
Diterpenoid
1-hydroxysteroid
Hydroxysteroid
Delta-5-steroid
Terpene glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Dihydropyranone
Pyran
Oxane
Tertiary alcohol
Enoate ester
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Acetal
Oxacycle
Organic oxygen compound
Organooxygen compound
Carbonyl group
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.07	ALOGPS
logP	-0.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	245.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	193.32 m³·mol⁻¹	ChemAxon
Polarizability	83.45 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00033495

Chemspider ID

52083084

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91827019

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tohda C, Kuboyama T, Komatsu K: Search for natural products related to regeneration of the neuronal network. Neurosignals. 2005;14(1-2):34-45. [PubMed:15956813 ]
Ahuja A, Kaur D, Sharada M, Kumar A, Suri KA, Dutt P: Glycowithanolides accumulation in in vitro shoot cultures of Indian ginseng (Withania somnifera Dunal). Nat Prod Commun. 2009 Apr;4(4):479-82. [PubMed:19475989 ]
Patel CN, Goswami D, Jaiswal DG, Parmar RM, Solanki HA, Pandya HA: Pinpointing the potential hits for hindering interaction of SARS-CoV-2 S-protein with ACE2 from the pool of antiviral phytochemicals utilizing molecular docking and molecular dynamics (MD) simulations. J Mol Graph Model. 2021 Jun;105:107874. doi: 10.1016/j.jmgm.2021.107874. Epub 2021 Feb 22. [PubMed:33647752 ]
Zhang H, Cao CM, Gallagher RJ, Day VW, Kindscher K, Timmermann BN: Withanolides from Physalis coztomatl. Phytochemistry. 2015 Jan;109:147-53. doi: 10.1016/j.phytochem.2014.10.012. Epub 2014 Nov 8. [PubMed:25457493 ]
Tohda C: [Overcoming several neurodegenerative diseases by traditional medicines: the development of therapeutic medicines and unraveling pathophysiological mechanisms]. Yakugaku Zasshi. 2008 Aug;128(8):1159-67. doi: 10.1248/yakushi.128.1159. [PubMed:18670181 ]

Showing NP-Card for (-)-Withanoside VI (NP0073259)

MOL for NP0073259 ((-)-Withanoside VI)

3D MOL for NP0073259 ((-)-Withanoside VI)

3D SDF for NP0073259 ((-)-Withanoside VI)

3D-SDF for NP0073259 ((-)-Withanoside VI)

PDB for NP0073259 ((-)-Withanoside VI)

3D PDB for NP0073259 ((-)-Withanoside VI)

SMILES for NP0073259 ((-)-Withanoside VI)

INCHI for NP0073259 ((-)-Withanoside VI)

Structure for NP0073259 ((-)-Withanoside VI)

3D Structure for NP0073259 ((-)-Withanoside VI)