NP-MRD: Showing NP-Card for eupalinilide G (NP0027469)

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Record Information

Version

2.0

Created at

2021-06-19 19:37:07 UTC

Updated at

2021-06-29 23:53:36 UTC

NP-MRD ID

NP0027469

Secondary Accession Numbers

None

Natural Product Identification

Common Name

eupalinilide G

Provided By

JEOL Database JEOL Logo

Description

eupalinilide G is found in Eupatorium lindleyanum. eupalinilide G was first documented in 2016 (PMID: 30204384). Based on a literature review very few articles have been published on Eupalinilide G.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121373D          

 52 56  0  0  0  0            999 V2000
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   -2.7763   -0.7899    0.1981 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


  Mrv1652306192121373D          

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    2.3609    2.2318    3.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7915    1.9993    4.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798    2.8186    0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    5.0811    1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483    4.9940    2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590    6.0411    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5010   -1.9736   -0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 33  1  6  0  0  0
 18 19  1  0  0  0  0
  7 32  1  6  0  0  0
 28 19  1  0  0  0  0
  3  4  2  0  0  0  0
  8  9  1  0  0  0  0
  2  1  2  3  0  0  0
 13 14  1  6  0  0  0
 20 21  1  0  0  0  0
 28  6  1  0  0  0  0
 21 23  1  0  0  0  0
  7  8  1  0  0  0  0
 21 22  2  0  0  0  0
  9 11  1  0  0  0  0
 15 16  1  0  0  0  0
  8 15  1  0  0  0  0
 23 24  1  0  0  0  0
  7  6  1  0  0  0  0
 23 25  2  0  0  0  0
 13  7  1  0  0  0  0
 25 26  1  0  0  0  0
  6  5  1  0  0  0  0
 26 27  1  0  0  0  0
  5  3  1  0  0  0  0
  9 10  1  0  0  0  0
  3  2  1  0  0  0  0
 15 17  1  1  0  0  0
 11 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
 28  2  1  0  0  0  0
 15 18  1  0  0  0  0
 19 20  1  0  0  0  0
 16 17  1  0  0  0  0
  9 34  1  6  0  0  0
 18 42  1  0  0  0  0
 18 43  1  0  0  0  0
 19 44  1  1  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 28 52  1  6  0  0  0
  6 31  1  1  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 24 45  1  0  0  0  0
 24 46  1  0  0  0  0
 24 47  1  0  0  0  0
 25 48  1  0  0  0  0
 26 49  1  0  0  0  0
 26 50  1  0  0  0  0
 27 51  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0027469

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(\[H])=C(\C(=O)O[C@]1([H])C([H])([H])[C@@]2(OC2([H])[H])[C@]2([H])[C@]([H])(O[H])[C@@]3([H])O[C@@]3(C([H])([H])[H])[C@]2([H])[C@@]2([H])OC(=O)C(=C([H])[H])[C@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O8/c1-8(4-5-21)17(23)26-10-6-20(7-25-20)12-13(19(3)16(28-19)14(12)22)15-11(10)9(2)18(24)27-15/h4,10-16,21-22H,2,5-7H2,1,3H3/b8-4+/t10-,11-,12+,13+,14+,15+,16-,19+,20+/m1/s1

> <INCHI_KEY>
FGUYAMCTGOJAHQ-GQEGKNDZSA-N

> <FORMULA>
C20H24O8

> <MOLECULAR_WEIGHT>
392.404

> <EXACT_MASS>
392.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.77499722129485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,2'S,6'R,7'R,10'S,11'S,12'R,14'S)-11'-hydroxy-14'-methyl-5'-methylidene-4'-oxo-3',13'-dioxaspiro[oxirane-2,9'-tetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecane]-7'-yl (2E)-4-hydroxy-2-methylbut-2-enoate

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
-0.2138076506666658

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.57036931419459

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.740951600864143

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5521985984284923

> <JCHEM_POLAR_SURFACE_AREA>
118.12000000000002

> <JCHEM_REFRACTIVITY>
94.0381

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'S,6'R,7'R,10'S,11'S,12'R,14'S)-11'-hydroxy-14'-methyl-5'-methylidene-4'-oxo-3',13'-dioxaspiro[oxirane-2,9'-tetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecane]-7'-yl (2E)-4-hydroxy-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -3.1403   -1.0519    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7763   -0.7899    0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -0.1997   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9261   -0.0690   -0.6283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0104    0.1517   -1.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5941    0.1060   -1.5752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8506   -0.1559   -2.8965 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6647   -0.4819   -2.7724 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3717    0.8979   -2.7541 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3246    1.4889   -1.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246    1.7282   -3.6791 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0907    1.0790   -4.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8318    1.1066   -3.7712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0573    1.9038   -4.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0848   -1.5062   -1.7530 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0084   -2.6204   -2.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054   -2.8306   -2.0482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1159   -1.1976   -0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2199   -0.8276    0.3851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1589    0.5390    0.8578 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5623    0.7720    1.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -0.0905    2.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    2.2374    2.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3098    2.5390    3.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2661    3.1535    1.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3694    4.6372    1.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    5.0704    0.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627   -0.9734   -0.5041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1522   -0.8461    1.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4564   -1.4815    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349    1.1021   -1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3591   -0.9580   -3.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295   -0.9169   -3.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    0.8248   -3.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546    2.3624   -1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6661    2.7956   -3.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636    1.2573   -4.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8774    2.6660   -4.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981    2.4230   -3.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6823   -3.0914   -1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859   -2.6084   -3.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8865   -0.4433   -0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4816   -2.0918    0.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443   -1.4835    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724    3.5983    3.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609    2.2318    3.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7915    1.9993    4.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798    2.8186    0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    5.0811    1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483    4.9940    2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590    6.0411    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5010   -1.9736   -0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 33  1  6
 18 19  1  0
  7 32  1  6
 28 19  1  0
  3  4  2  0
  8  9  1  0
  2  1  2  3
 13 14  1  6
 20 21  1  0
 28  6  1  0
 21 23  1  0
  7  8  1  0
 21 22  2  0
  9 11  1  0
 15 16  1  0
  8 15  1  0
 23 24  1  0
  7  6  1  0
 23 25  2  0
 13  7  1  0
 25 26  1  0
  6  5  1  0
 26 27  1  0
  5  3  1  0
  9 10  1  0
  3  2  1  0
 15 17  1  1
 11 13  1  0
 11 12  1  0
 13 12  1  0
 28  2  1  0
 15 18  1  0
 19 20  1  0
 16 17  1  0
  9 34  1  6
 18 42  1  0
 18 43  1  0
 19 44  1  1
 14 37  1  0
 14 38  1  0
 14 39  1  0
 28 52  1  6
  6 31  1  1
  1 29  1  0
  1 30  1  0
 16 40  1  0
 16 41  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 10 35  1  0
 11 36  1  6
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      -3.140  -1.052   1.460  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.776  -0.790   0.198  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.725  -0.200  -0.770  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.926  -0.069  -0.628  0.00  0.00           O+0
HETATM    5  O   UNK     0      -3.010   0.152  -1.869  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.594   0.106  -1.575  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.851  -0.156  -2.897  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.665  -0.482  -2.772  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.372   0.898  -2.754  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.325   1.489  -1.467  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.525   1.728  -3.679  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.091   1.079  -4.880  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.832   1.107  -3.771  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.057   1.904  -4.047  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.085  -1.506  -1.753  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.008  -2.620  -2.230  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.605  -2.831  -2.048  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.116  -1.198  -0.281  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.220  -0.828   0.385  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.159   0.539   0.858  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.562   0.772   1.981  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.073  -0.091   2.681  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.678   2.237   2.269  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.310   2.539   3.597  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.266   3.154   1.368  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.369   4.637   1.449  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.019   5.070   0.261  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.463  -0.973  -0.504  0.00  0.00           C+0
HETATM   29  H   UNK     0      -4.152  -0.846   1.803  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.456  -1.482   2.183  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.335   1.102  -1.195  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.359  -0.958  -3.447  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.930  -0.917  -3.751  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.413   0.825  -3.083  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.755   2.362  -1.518  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.666   2.796  -3.666  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.864   1.257  -4.407  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.877   2.666  -4.813  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.398   2.423  -3.146  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.682  -3.091  -1.523  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.386  -2.608  -3.245  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.887  -0.443  -0.089  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.482  -2.092   0.245  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.344  -1.484   1.257  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.272   3.598   3.861  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.361   2.232   3.596  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.792   1.999   4.397  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.180   2.819   0.433  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.630   5.081   1.482  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.948   4.994   2.302  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.059   6.041   0.308  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.501  -1.974  -0.953  0.00  0.00           H+0
CONECT    1    2   29   30                                                  
CONECT    2    1    3   28                                                  
CONECT    3    4    5    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6   28    7    5   31                                             
CONECT    7   32    8    6   13                                             
CONECT    8   33    9    7   15                                             
CONECT    9    8   11   10   34                                             
CONECT   10    9   35                                                       
CONECT   11    9   13   12   36                                             
CONECT   12   11   13                                                       
CONECT   13   14    7   11   12                                             
CONECT   14   13   37   38   39                                             
CONECT   15   16    8   17   18                                             
CONECT   16   15   17   40   41                                             
CONECT   17   15   16                                                       
CONECT   18   19   15   42   43                                             
CONECT   19   18   28   20   44                                             
CONECT   20   21   19                                                       
CONECT   21   20   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23   45   46   47                                             
CONECT   25   23   26   48                                                  
CONECT   26   25   27   49   50                                             
CONECT   27   26   51                                                       
CONECT   28   19    6    2   52                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   24                                                            
CONECT   46   24                                                            
CONECT   47   24                                                            
CONECT   48   25                                                            
CONECT   49   26                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   28                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

RDKit          3D

52 56  0  0  0  0  0  0  0  0999 V2000
   -3.1403   -1.0519    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7763   -0.7899    0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -0.1997   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9261   -0.0690   -0.6283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0104    0.1517   -1.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5941    0.1060   -1.5752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8506   -0.1559   -2.8965 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6647   -0.4819   -2.7724 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3717    0.8979   -2.7541 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3246    1.4889   -1.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246    1.7282   -3.6791 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0907    1.0790   -4.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8318    1.1066   -3.7712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0573    1.9038   -4.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0848   -1.5062   -1.7530 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0084   -2.6204   -2.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054   -2.8306   -2.0482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1159   -1.1976   -0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2199   -0.8276    0.3851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1589    0.5390    0.8578 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5623    0.7720    1.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -0.0905    2.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    2.2374    2.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3098    2.5390    3.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2661    3.1535    1.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3694    4.6372    1.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    5.0704    0.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627   -0.9734   -0.5041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1522   -0.8461    1.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4564   -1.4815    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349    1.1021   -1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3591   -0.9580   -3.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295   -0.9169   -3.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    0.8248   -3.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546    2.3624   -1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6661    2.7956   -3.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636    1.2573   -4.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8774    2.6660   -4.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981    2.4230   -3.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6823   -3.0914   -1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859   -2.6084   -3.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8865   -0.4433   -0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4816   -2.0918    0.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443   -1.4835    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724    3.5983    3.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609    2.2318    3.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7915    1.9993    4.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798    2.8186    0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    5.0811    1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483    4.9940    2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590    6.0411    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5010   -1.9736   -0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 33  1  6
 18 19  1  0
  7 32  1  6
 28 19  1  0
  3  4  2  0
  8  9  1  0
  2  1  2  3
 13 14  1  6
 20 21  1  0
 28  6  1  0
 21 23  1  0
  7  8  1  0
 21 22  2  0
  9 11  1  0
 15 16  1  0
  8 15  1  0
 23 24  1  0
  7  6  1  0
 23 25  2  0
 13  7  1  0
 25 26  1  0
  6  5  1  0
 26 27  1  0
  5  3  1  0
  9 10  1  0
  3  2  1  0
 15 17  1  1
 11 13  1  0
 11 12  1  0
 13 12  1  0
 28  2  1  0
 15 18  1  0
 19 20  1  0
 16 17  1  0
  9 34  1  6
 18 42  1  0
 18 43  1  0
 19 44  1  1
 14 37  1  0
 14 38  1  0
 14 39  1  0
 28 52  1  6
  6 31  1  1
  1 29  1  0
  1 30  1  0
 16 40  1  0
 16 41  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 10 35  1  0
 11 36  1  6
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₈

Average Mass

392.4040 Da

Monoisotopic Mass

392.14712 Da

IUPAC Name

(1'S,2R,2'S,6'R,7'R,10'S,11'S,12'R,14'S)-11'-hydroxy-14'-methyl-5'-methylidene-4'-oxo-3',13'-dioxaspiro[oxirane-2,9'-tetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecane]-7'-yl (2E)-4-hydroxy-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C(\[H])=C(\C(=O)O[C@]1([H])C([H])([H])[C@@]2(OC2([H])[H])[C@]2([H])[C@]([H])(O[H])[C@@]3([H])O[C@@]3(C([H])([H])[H])[C@]2([H])[C@@]2([H])OC(=O)C(=C([H])[H])[C@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H24O8/c1-8(4-5-21)17(23)26-10-6-20(7-25-20)12-13(19(3)16(28-19)14(12)22)15-11(10)9(2)18(24)27-15/h4,10-16,21-22H,2,5-7H2,1,3H3/b8-4+/t10-,11-,12+,13+,14+,15+,16-,19+,20+/m1/s1

InChI Key

FGUYAMCTGOJAHQ-GQEGKNDZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Eupatorium lindleyanum	JEOL database	Huo, L., et al, J. Nat. Prod. 67, 1470 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ambrosanolides and secoambrosanolides

Alternative Parents

Substituents

Secoambrosanolide
Guaianolide-skeleton
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Gamma butyrolactone
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary 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	0.59	ALOGPS
logP	-0.21	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.74	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.04 m³·mol⁻¹	ChemAxon
Polarizability	38.77 Å³	ChemAxon
Number of Rings	5	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

9649655

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11474825

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yu XQ, Liu CX, Zou K, He HB, Wang JZ, Wu YH, Xu YC: [Research on Chemical Constituents and Anti-tumor Activity of Eupatorium chinense]. Zhong Yao Cai. 2016 Aug;39(8):1782-5. [PubMed:30204384 ]
Huo, L., et al. (2004). Huo, L., et al, J. Nat. Prod. 67, 1470 (2004). J. Nat. Prod..

Showing NP-Card for eupalinilide G (NP0027469)

MOL for NP0027469 (eupalinilide G)

3D MOL for NP0027469 (eupalinilide G)

3D SDF for NP0027469 (eupalinilide G)

3D-SDF for NP0027469 (eupalinilide G)

PDB for NP0027469 (eupalinilide G)

3D PDB for NP0027469 (eupalinilide G)

SMILES for NP0027469 (eupalinilide G)

INCHI for NP0027469 (eupalinilide G)

Structure for NP0027469 (eupalinilide G)

3D Structure for NP0027469 (eupalinilide G)