NP-MRD: Showing NP-Card for 2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin (NP0029773)

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Record Information

Version

2.0

Created at

2021-06-19 21:18:31 UTC

Updated at

2021-06-29 23:57:21 UTC

NP-MRD ID

NP0029773

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin

Provided By

JEOL Database JEOL Logo

Description

2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin is found in Hyaloseris salicifolia. 2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin was first documented in 2000 (De Riscala, E.C., et al.). Based on a literature review very few articles have been published on (3aR,4aalpha,9aalpha)-3a,4,4a,5,6,7,8,8a,9,9a-Decahydro-7alpha-(6-O-acetyl-beta-D-glucopyranosyloxy)-8beta-hydroxy-8abeta-methyl-3,5-bis(methylene)naphtho[2,3-b]furan-2(3H)-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123183D          

 65 68  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192123183D          

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   -3.8419   -3.7599   -0.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0295   -3.9694    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701   -5.9935   -0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786   -7.3140   -0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -7.9317   -2.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -5.6612    0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0868   -4.1732   -0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2401   -3.8232   -1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -3.0463    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
 22 24  1  0  0  0  0
 33 32  1  0  0  0  0
 32 31  1  0  0  0  0
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 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
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  4  3  1  0  0  0  0
 31 29  1  0  0  0  0
 29 27  1  0  0  0  0
 27 26  1  0  0  0  0
 25 26  1  0  0  0  0
 29 30  2  3  0  0  0
  6 18  1  0  0  0  0
  2  1  2  3  0  0  0
  4  5  1  0  0  0  0
 18 16  1  0  0  0  0
 20 21  1  0  0  0  0
 16 14  1  0  0  0  0
 22 23  1  6  0  0  0
  4 20  1  0  0  0  0
 27 28  2  0  0  0  0
  3  2  1  0  0  0  0
 33 65  1  1  0  0  0
  2 33  1  0  0  0  0
  9 10  1  0  0  0  0
 22 20  1  0  0  0  0
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 11 12  1  0  0  0  0
 14  8  1  0  0  0  0
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  8  9  1  0  0  0  0
  6  5  1  0  0  0  0
  6 39  1  6  0  0  0
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 12 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029773

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@]([H])(O[C@@]2([H])C([H])([H])C(=C([H])[H])[C@]3([H])C([H])([H])[C@]4([H])C(=C([H])[H])C(=O)O[C@]4([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]2([H])O[H])O[C@]([H])(C([H])([H])OC(=O)C([H])([H])[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O10/c1-9-5-14(32-22-19(27)18(26)17(25)16(33-22)8-30-11(3)24)20(28)23(4)7-15-12(6-13(9)23)10(2)21(29)31-15/h12-20,22,25-28H,1-2,5-8H2,3-4H3/t12-,13+,14+,15-,16-,17-,18+,19-,20-,22-,23-/m1/s1

> <INCHI_KEY>
CMLLFFQDBYXUFG-PHRLGUNSSA-N

> <FORMULA>
C23H32O10

> <MOLECULAR_WEIGHT>
468.499

> <EXACT_MASS>
468.19954723

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.43920622684281

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3aR,4aS,7S,8S,8aR,9aR)-8-hydroxy-8a-methyl-3,5-dimethylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
-0.43

> <JCHEM_LOGP>
-0.2774495873333318

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.110922391932963

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.198891091862286

> <JCHEM_PKA_STRONGEST_BASIC>
-3.356726889953669

> <JCHEM_POLAR_SURFACE_AREA>
151.98000000000002

> <JCHEM_REFRACTIVITY>
110.63919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3aR,4aS,7S,8S,8aR,9aR)-8-hydroxy-8a-methyl-3,5-dimethylidene-2-oxo-octahydronaphtho[2,3-b]furan-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
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 22 20  1  0
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 14  8  1  0
 11 13  2  0
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 12 45  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.373  -1.321  -0.793  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.221  -1.498  -0.124  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.403  -0.354   0.650  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.858  -0.095   0.224  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.558   0.819   1.097  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.000   2.140   1.129  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.921   2.181   2.056  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.319   3.484   2.160  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.890   3.385   3.102  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.452   3.055   4.431  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.465   2.852   5.316  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.907   2.522   6.666  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.659   2.925   5.059  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.344   4.520   2.643  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.778   5.833   2.638  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.566   4.506   1.723  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.567   5.386   2.258  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.123   3.093   1.580  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.202   3.125   0.632  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.662  -1.417   0.254  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001  -1.161  -0.187  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.025  -2.571  -0.580  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.061  -2.212  -2.087  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.855  -3.864  -0.347  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.209  -5.164  -0.823  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.328  -5.337  -2.240  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.343  -6.184  -2.660  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.263  -6.705  -3.755  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.377  -6.320  -1.540  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.595  -7.238  -1.512  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.728  -5.299  -0.515  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.085  -4.015  -0.728  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.573  -2.797  -0.057  0.00  0.00           C+0
HETATM   34  H   UNK     0       1.850  -2.111  -1.363  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.888  -0.363  -0.794  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.365  -0.581   1.723  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.187   0.560   0.516  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.898   0.332  -0.785  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.657   2.413   0.122  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.065   3.767   1.171  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.432   4.337   3.127  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.557   2.591   2.744  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.730   2.366   7.370  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.319   1.602   6.609  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.293   3.350   7.026  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.667   4.305   3.669  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.530   6.436   2.814  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.307   4.920   0.740  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.371   5.212   1.727  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.554   2.760   2.532  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.461   2.195   0.491  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.754  -1.737   1.302  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.328  -0.444   0.387  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.091  -2.083  -2.438  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.526  -1.283  -2.305  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.607  -2.983  -2.713  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.842  -3.760  -0.816  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.030  -3.969   0.733  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.770  -5.994  -0.368  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.279  -7.314  -0.673  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.732  -7.932  -2.338  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.588  -5.661   0.509  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.087  -4.173  -0.306  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.240  -3.823  -1.797  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.638  -3.046   1.014  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2    1    3   33                                                  
CONECT    3    4    2   36   37                                             
CONECT    4    3    5   20   38                                             
CONECT    5    4    6                                                       
CONECT    6    7   18    5   39                                             
CONECT    7    8    6                                                       
CONECT    8    7   14    9   40                                             
CONECT    9   10    8   41   42                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   43   44   45                                             
CONECT   13   11                                                            
CONECT   14   15   16    8   46                                             
CONECT   15   14   47                                                       
CONECT   16   17   18   14   48                                             
CONECT   17   16   49                                                       
CONECT   18   19    6   16   50                                             
CONECT   19   18   51                                                       
CONECT   20   21    4   22   52                                             
CONECT   21   20   53                                                       
CONECT   22   24   23   20   33                                             
CONECT   23   22   54   55   56                                             
CONECT   24   22   25   57   58                                             
CONECT   25   24   31   26   59                                             
CONECT   26   27   25                                                       
CONECT   27   29   26   28                                                  
CONECT   28   27                                                            
CONECT   29   31   27   30                                                  
CONECT   30   29   60   61                                                  
CONECT   31   32   25   29   62                                             
CONECT   32   33   31   63   64                                             
CONECT   33   32   65    2   22                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    6                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   30                                                            
CONECT   61   30                                                            
CONECT   62   31                                                            
CONECT   63   32                                                            
CONECT   64   32                                                            
CONECT   65   33                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

RDKit          3D

65 68  0  0  0  0  0  0  0  0999 V2000
    1.3728   -1.3207   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -1.4975   -0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032   -0.3542    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576   -0.0951    0.2244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5580    0.8191    1.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    2.1397    1.1291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9207    2.1814    2.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3190    3.4837    2.1598 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8896    3.3851    3.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524    3.0546    4.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4654    2.8522    5.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9073    2.5215    6.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586    2.9250    5.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3442    4.5200    2.6430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7784    5.8332    2.6384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5661    4.5060    1.7229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5675    5.3861    2.2582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1230    3.0926    1.5797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2025    3.1252    0.6322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -1.4170    0.2544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0011   -1.1611   -0.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0246   -2.5711   -0.5797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0610   -2.2117   -2.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551   -3.8639   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090   -5.1640   -0.8231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3276   -5.3370   -2.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433   -6.1845   -2.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2629   -6.7047   -3.7553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768   -6.3201   -1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5954   -7.2376   -1.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7284   -5.2989   -0.5154 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0845   -4.0149   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733   -2.7967   -0.0573 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8497   -2.1113   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -0.3633   -0.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652   -0.5814    1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    0.5597    0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    0.3318   -0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6567    2.4128    0.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651    3.7674    1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    4.3370    3.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567    2.5911    2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7298    2.3661    7.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    1.6023    6.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2928    3.3504    7.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6673    4.3054    3.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5300    6.4360    2.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3073    4.9195    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712    5.2118    1.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538    2.7603    2.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4613    2.1946    0.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7538   -1.7372    1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -0.4441    0.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0912   -2.0831   -2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5262   -1.2826   -2.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6074   -2.9835   -2.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8419   -3.7599   -0.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0295   -3.9694    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701   -5.9935   -0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786   -7.3140   -0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -7.9317   -2.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -5.6612    0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0868   -4.1732   -0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2401   -3.8232   -1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -3.0463    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
 22 24  1  0
 33 32  1  0
 32 31  1  0
 25 24  1  0
 25 31  1  0
 14 15  1  0
 16 17  1  0
 18 19  1  0
  4  3  1  0
 31 29  1  0
 29 27  1  0
 27 26  1  0
 25 26  1  0
 29 30  2  3
  6 18  1  0
  2  1  2  3
  4  5  1  0
 18 16  1  0
 20 21  1  0
 16 14  1  0
 22 23  1  6
  4 20  1  0
 27 28  2  0
  3  2  1  0
 33 65  1  1
  2 33  1  0
  9 10  1  0
 22 20  1  0
 10 11  1  0
 22 33  1  0
 11 12  1  0
 14  8  1  0
 11 13  2  0
  8  9  1  0
  6  5  1  0
  6 39  1  6
 14 46  1  1
 15 47  1  0
 16 48  1  6
 17 49  1  0
 18 50  1  1
 19 51  1  0
  9 41  1  0
  9 42  1  0
  8 40  1  6
  4 38  1  6
  3 36  1  0
  3 37  1  0
 20 52  1  1
 32 63  1  0
 32 64  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  1
 31 62  1  1
 30 60  1  0
 30 61  1  0
  1 34  1  0
  1 35  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
 12 43  1  0
 12 44  1  0
 12 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3AR,4aalpha,9aalpha)-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-7a-(6-O-acetyl-b-D-glucopyranosyloxy)-8b-hydroxy-8abeta-methyl-3,5-bis(methylene)naphtho[2,3-b]furan-2(3H)-one	Generator
(3AR,4aalpha,9aalpha)-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-7α-(6-O-acetyl-β-D-glucopyranosyloxy)-8β-hydroxy-8abeta-methyl-3,5-bis(methylene)naphtho[2,3-b]furan-2(3H)-one	Generator

Chemical Formula

C₂₃H₃₂O₁₀

Average Mass

468.4990 Da

Monoisotopic Mass

468.19955 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-{[(3aR,4aS,7S,8S,8aR,9aR)-8-hydroxy-8a-methyl-3,5-dimethylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6R)-6-{[(3aR,4aS,7S,8S,8aR,9aR)-8-hydroxy-8a-methyl-3,5-dimethylidene-2-oxo-octahydronaphtho[2,3-b]furan-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])[C@]([H])(O[C@@]2([H])C([H])([H])C(=C([H])[H])[C@]3([H])C([H])([H])[C@]4([H])C(=C([H])[H])C(=O)O[C@]4([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]2([H])O[H])O[C@]([H])(C([H])([H])OC(=O)C([H])([H])[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C23H32O10/c1-9-5-14(32-22-19(27)18(26)17(25)16(33-22)8-30-11(3)24)20(28)23(4)7-15-12(6-13(9)23)10(2)21(29)31-15/h12-20,22,25-28H,1-2,5-8H2,3-4H3/t12-,13+,14+,15-,16-,17-,18+,19-,20-,22-,23-/m1/s1

InChI Key

CMLLFFQDBYXUFG-PHRLGUNSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Dinoseris salicifolia	JEOL database	De Riscala, E.C., et al, Phytochemistry 53, 873 (2000)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Terpene glycoside
Sesquiterpenoid
Naphthofuran
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Enoate ester
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Carbonyl group
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	-0.43	ALOGPS
logP	-0.28	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.64 m³·mol⁻¹	ChemAxon
Polarizability	48.44 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102237450

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

De Riscala, E.C., et al. (2000). De Riscala, E.C., et al, Phytochemistry 53, 873 (2000). Phytochem..

Showing NP-Card for 2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin (NP0029773)

MOL for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)

3D MOL for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)

3D SDF for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)

3D-SDF for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)

PDB for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)

3D PDB for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)

SMILES for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)

INCHI for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)

Structure for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)

3D Structure for NP0029773 (2-O-(6'-O-acetyl-beta-D-glucopyranosyl)-ivasperin)