NP-MRD: Showing NP-Card for 11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside (NP0033762)

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Record Information

Version

2.0

Created at

2021-06-20 17:41:21 UTC

Updated at

2021-06-30 00:03:44 UTC

NP-MRD ID

NP0033762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside

Provided By

JEOL Database JEOL Logo

Description

11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside is found in Staehelina fruticosa. 11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside was first documented in 2008 (Kotsos, M. P., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119413D          

 62 65  0  0  0  0            999 V2000
    2.2480   -1.7158    1.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0536   -0.9167    0.4270 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8810    0.1584    1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    0.0552    2.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898    1.2760    0.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469    1.0320   -0.9038 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1889   -0.0964   -0.5293 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6311   -0.9421   -1.6838 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8682   -0.2200   -2.8085 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3076    0.6532   -2.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3626    0.0002   -1.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0436    0.2630   -0.1939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7983   -0.5569    0.7011 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.0170   -2.7635    1.5549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5083   -4.1995    1.3688 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.4235    2.2811   -1.2876 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.3569    0.3218    0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4601   -1.4876   -2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766   -1.7162   -1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5968    0.3400   -3.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870   -0.9900   -3.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4701   -4.2953    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
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 27 30  1  0  0  0  0
 10 24  2  0  0  0  0
 18 15  1  0  0  0  0
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 10  9  1  0  0  0  0
 30  6  1  0  0  0  0
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 22 23  1  0  0  0  0
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  6  5  1  0  0  0  0
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M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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    3.0536   -0.9167    0.4270 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.4831    0.0552    2.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898    1.2760    0.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469    1.0320   -0.9038 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1889   -0.0964   -0.5293 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6311   -0.9421   -1.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682   -0.2200   -2.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3076    0.6532   -2.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7983   -0.5569    0.7011 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202119413D          

 62 65  0  0  0  0            999 V2000
    2.2480   -1.7158    1.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0536   -0.9167    0.4270 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8810    0.1584    1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1889   -0.0964   -0.5293 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6311   -0.9421   -1.6838 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8682   -0.2200   -2.8085 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.3626    0.0002   -1.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0436    0.2630   -0.1939 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1980    3.4681   -1.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8570   -0.5186    0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4701   -4.2953    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204   -4.4696    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3756    2.4566   -2.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8326    2.0423   -4.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6839    4.3925   -3.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714    4.2196   -2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7960    3.2977   -4.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5245    2.1810   -3.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2095    1.6316   -4.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205    2.4344   -0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 30  1  0  0  0  0
 10 24  2  0  0  0  0
 18 15  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
 10  9  1  0  0  0  0
 30  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  6  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 25 26  1  0  0  0  0
  6  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  7  2  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 22  1  0  0  0  0
  2  1  1  0  0  0  0
 22 20  1  0  0  0  0
 30 29  1  0  0  0  0
 29 27  1  0  0  0  0
 20 18  1  0  0  0  0
  3  4  2  0  0  0  0
 25 24  1  0  0  0  0
 16 17  1  0  0  0  0
 27 28  1  6  0  0  0
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 13 12  1  0  0  0  0
 15 16  1  0  0  0  0
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 17 47  1  0  0  0  0
 28 59  1  0  0  0  0
 28 60  1  0  0  0  0
 28 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1([H])O[C@]([H])(OC([H])([H])C2=C([H])/C([H])([H])C([H])([H])[C@]3(O[C@]3([H])[C@@]3([H])OC(=O)[C@@]([H])(C([H])([H])[H])[C@]3([H])C([H])([H])C\2([H])[H])C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O9/c1-10-12-6-5-11(4-3-7-21(2)18(30-21)17(12)29-19(10)26)9-27-20-16(25)15(24)14(23)13(8-22)28-20/h4,10,12-18,20,22-25H,3,5-9H2,1-2H3/b11-4+/t10-,12-,13-,14-,15+,16-,17-,18+,20-,21+/m0/s1

> <INCHI_KEY>
PPEZJRDHOXFQGZ-ZIRAYCBSSA-N

> <FORMULA>
C21H32O9

> <MOLECULAR_WEIGHT>
428.478

> <EXACT_MASS>
428.20463261

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.45610585425593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,7E,11S,12S)-4,12-dimethyl-8-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
-0.12196890833333357

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200070387218357

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210510846183771

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083552309145

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
102.9375

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,7E,11S,12S)-4,12-dimethyl-8-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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    0.3410    2.7063   -3.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5598    2.9076   -2.6689 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5752    2.4754   -3.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1980    3.4681   -1.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4235    2.2811   -1.2876 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.3569    0.3218    0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4601   -1.4876   -2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8714    4.2196   -2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7960    3.2977   -4.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5245    2.1810   -3.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2095    1.6316   -4.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205    2.4344   -0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 30  1  0
 10 24  2  0
 18 15  1  0
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 10  9  1  0
 30  6  1  0
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 22 23  1  0
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  2  1  1  0
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 29 27  1  0
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 25 24  1  0
 16 17  1  0
 27 28  1  6
 27 26  1  0
 13 12  1  0
 15 16  1  0
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 18 48  1  1
 19 49  1  0
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 21 51  1  0
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 15 44  1  6
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 17 47  1  0
 28 59  1  0
 28 60  1  0
 28 61  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       2.248  -1.716   1.438  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.054  -0.917   0.427  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.881   0.158   1.080  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.483   0.055   2.136  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.890   1.276   0.300  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.147   1.032  -0.904  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.189  -0.096  -0.529  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.631  -0.942  -1.684  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.868  -0.220  -2.809  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.308   0.653  -2.420  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.363   0.000  -1.554  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.044   0.263  -0.194  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.798  -0.557   0.701  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.314  -1.898   0.653  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.017  -2.764   1.555  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.508  -4.199   1.369  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.309  -5.143   2.072  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.823  -2.293   3.006  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.544  -3.126   3.922  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.302  -0.847   3.141  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.020  -0.387   4.471  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.610   0.039   2.109  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.156   1.364   2.195  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.494   1.918  -2.860  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.341   2.706  -3.840  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.355   3.653  -3.182  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.560   2.908  -2.669  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.575   2.475  -3.688  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.198   3.468  -1.512  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.424   2.281  -1.288  0.00  0.00           C+0
HETATM   31  H   UNK     0       1.615  -1.066   2.051  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.914  -2.256   2.120  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.608  -2.452   0.943  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.739  -1.575  -0.121  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.860   0.709  -1.670  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.357   0.322   0.048  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.460  -1.488  -2.155  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.977  -1.716  -1.264  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.597   0.340  -3.396  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.487  -0.990  -3.493  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.403  -1.076  -1.760  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.356   0.412  -1.770  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.857  -0.519   0.410  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.087  -2.756   1.307  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.470  -4.295   1.706  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.520  -4.470   0.308  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.473  -4.770   2.965  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.764  -2.351   3.286  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.523  -2.640   4.774  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.392  -0.792   3.033  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.172   0.580   4.448  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.544   0.129   2.351  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.721   1.871   1.480  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.376   2.457  -2.509  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.833   2.042  -4.559  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.356   3.311  -4.435  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.684   4.393  -3.922  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.871   4.220  -2.376  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.796   3.298  -4.377  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.524   2.181  -3.229  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.209   1.632  -4.279  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.521   2.434  -0.709  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    7    1   34                                             
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6   30    7    5   35                                             
CONECT    7    8    6    2   36                                             
CONECT    8    7    9   37   38                                             
CONECT    9   10    8   39   40                                             
CONECT   10   24    9   11                                                  
CONECT   11   10   12   41   42                                             
CONECT   12   11   13                                                       
CONECT   13   14   22   12   43                                             
CONECT   14   15   13                                                       
CONECT   15   18   14   16   44                                             
CONECT   16   17   15   45   46                                             
CONECT   17   16   47                                                       
CONECT   18   15   19   20   48                                             
CONECT   19   18   49                                                       
CONECT   20   21   22   18   50                                             
CONECT   21   20   51                                                       
CONECT   22   23   13   20   52                                             
CONECT   23   22   53                                                       
CONECT   24   10   25   54                                                  
CONECT   25   26   24   55   56                                             
CONECT   26   25   27   57   58                                             
CONECT   27   30   29   28   26                                             
CONECT   28   27   59   60   61                                             
CONECT   29   30   27                                                       
CONECT   30   27    6   29   62                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   30                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
    2.2480   -1.7158    1.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0536   -0.9167    0.4270 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8810    0.1584    1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    0.0552    2.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898    1.2760    0.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469    1.0320   -0.9038 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1889   -0.0964   -0.5293 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6311   -0.9421   -1.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682   -0.2200   -2.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3076    0.6532   -2.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3626    0.0002   -1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0436    0.2630   -0.1939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7983   -0.5569    0.7011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3144   -1.8981    0.6530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0170   -2.7635    1.5549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5083   -4.1995    1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -5.1428    2.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8233   -2.2934    3.0064 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5438   -3.1257    3.9217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3018   -0.8473    3.1413 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0200   -0.3872    4.4711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104    0.0389    2.1090 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1564    1.3640    2.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936    1.9182   -2.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3410    2.7063   -3.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547    3.6527   -3.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598    2.9076   -2.6689 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5752    2.4754   -3.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1980    3.4681   -1.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4235    2.2811   -1.2876 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6153   -1.0658    2.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9135   -2.2555    2.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6080   -2.4518    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7393   -1.5745   -0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    0.7091   -1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3569    0.3218    0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4601   -1.4876   -2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766   -1.7162   -1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5968    0.3400   -3.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870   -0.9900   -3.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026   -1.0761   -1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3562    0.4118   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -0.5186    0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873   -2.7562    1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4701   -4.2953    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204   -4.4696    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -4.7696    2.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7636   -2.3507    3.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5225   -2.6396    4.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922   -0.7919    3.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1717    0.5799    4.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443    0.1285    2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213    1.8710    1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756    2.4566   -2.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8326    2.0423   -4.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3556    3.3109   -4.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839    4.3925   -3.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714    4.2196   -2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7960    3.2977   -4.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5245    2.1810   -3.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2095    1.6316   -4.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205    2.4344   -0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 30  1  0
 10 24  2  0
 18 15  1  0
 15 14  1  0
 14 13  1  0
 10  9  1  0
 30  6  1  0
  7  8  1  0
  8  9  1  0
  7  6  1  0
 18 19  1  0
 20 21  1  0
 22 23  1  0
 25 26  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
  7  2  1  0
 10 11  1  0
 11 12  1  0
 13 22  1  0
  2  1  1  0
 22 20  1  0
 30 29  1  0
 29 27  1  0
 20 18  1  0
  3  4  2  0
 25 24  1  0
 16 17  1  0
 27 28  1  6
 27 26  1  0
 13 12  1  0
 15 16  1  0
 13 43  1  6
 18 48  1  1
 19 49  1  0
 20 50  1  6
 21 51  1  0
 22 52  1  1
 23 53  1  0
 16 45  1  0
 16 46  1  0
 15 44  1  6
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 24 54  1  0
 30 62  1  1
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
  7 36  1  1
  6 35  1  6
  2 34  1  6
 11 41  1  0
 11 42  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 17 47  1  0
 28 59  1  0
 28 60  1  0
 28 61  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₉

Average Mass

428.4780 Da

Monoisotopic Mass

428.20463 Da

IUPAC Name

(1S,2R,4R,7E,11S,12S)-4,12-dimethyl-8-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

Traditional Name

(1S,2R,4R,7E,11S,12S)-4,12-dimethyl-8-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@]1([H])O[C@]([H])(OC([H])([H])C2=C([H])/C([H])([H])C([H])([H])[C@]3(O[C@]3([H])[C@@]3([H])OC(=O)[C@@]([H])(C([H])([H])[H])[C@]3([H])C([H])([H])C\2([H])[H])C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C21H32O9/c1-10-12-6-5-11(4-3-7-21(2)18(30-21)17(12)29-19(10)26)9-27-20-16(25)15(24)14(23)13(8-22)28-20/h4,10,12-18,20,22-25H,3,5-9H2,1-2H3/b11-4+/t10-,12-,13-,14-,15+,16-,17-,18+,20-,21+/m0/s1

InChI Key

PPEZJRDHOXFQGZ-ZIRAYCBSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Staehelina fruticosa	JEOL database	Kotsos, M. P., et al, J. Nat. Prod. 71, 847 (2008)

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	0.04	ALOGPS
logP	-0.12	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.94 m³·mol⁻¹	ChemAxon
Polarizability	43.46 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

Not Available

References

General References

Kotsos, M. P., et al. (2008). Kotsos, M. P., et al, J. Nat. Prod. 71, 847 (2008) . J. Nat. Prod..

Showing NP-Card for 11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside (NP0033762)

MOL for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)

3D MOL for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)

3D SDF for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)

3D-SDF for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)

PDB for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)

3D PDB for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)

SMILES for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)

INCHI for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)

Structure for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)

3D Structure for NP0033762 (11beta, 13-dihydroparthenolide-14-O-beta-D-glucopyranoside)