NP-MRD: Showing NP-Card for (2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+ (NP0031840)

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Record Information

Version

2.0

Created at

2021-06-19 22:48:24 UTC

Updated at

2021-06-30 00:00:40 UTC

NP-MRD ID

NP0031840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+

Provided By

JEOL Database JEOL Logo

Description

CHEMBL492169 belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. (2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+ is found in Peperomia duclouxii and Peperomia heyneana. (2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+ was first documented in 2006 (Li, N., et al.). Based on a literature review very few articles have been published on CHEMBL492169.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100483D          

 52 55  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202100483D          

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   -3.7752   -0.6944   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6197    3.4981    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    5.5907    1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6376    4.8749    3.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8539   -1.8569   -1.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101   -1.7997   -5.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -2.5416   -4.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8595   -0.8687   -3.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2438   -3.1520   -2.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 24 19  1  0  0  0  0
  6  5  1  0  0  0  0
 14 15  2  0  0  0  0
  5  4  1  0  0  0  0
 19 20  1  0  0  0  0
  4  3  2  0  0  0  0
  3 29  1  0  0  0  0
 19 16  2  0  0  0  0
 26 25  1  0  0  0  0
 25  5  2  0  0  0  0
 26 29  2  0  0  0  0
 16 15  1  0  0  0  0
 14 13  1  0  0  0  0
  8  9  2  0  0  0  0
  6  7  2  0  0  0  0
 12 38  1  1  0  0  0
 12 13  1  0  0  0  0
  3  2  1  0  0  0  0
 12  7  1  0  0  0  0
  2  1  1  0  0  0  0
 14 21  1  0  0  0  0
 16 17  1  0  0  0  0
 21 20  2  0  0  0  0
 17 18  1  0  0  0  0
 20 22  1  0  0  0  0
 26 27  1  0  0  0  0
 22 23  1  0  0  0  0
 29 30  1  0  0  0  0
 23 24  1  0  0  0  0
 27 28  1  0  0  0  0
 21 45  1  0  0  0  0
 23 46  1  0  0  0  0
 23 47  1  0  0  0  0
 15 41  1  0  0  0  0
  6 35  1  0  0  0  0
 13 39  1  0  0  0  0
 13 40  1  0  0  0  0
 11 36  1  0  0  0  0
 11 37  1  0  0  0  0
  4 34  1  0  0  0  0
 25 48  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 18 42  1  0  0  0  0
 18 43  1  0  0  0  0
 18 44  1  0  0  0  0
 30 52  1  0  0  0  0
 28 49  1  0  0  0  0
 28 50  1  0  0  0  0
 28 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C(\C([H])=C2\C(=O)OC([H])([H])[C@@]2([H])C([H])([H])C2=C([H])C(OC([H])([H])[H])=C3OC([H])([H])OC3=C2[H])C([H])=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O8/c1-25-16-6-13(7-17(26-2)20(16)23)5-15-14(10-28-22(15)24)4-12-8-18(27-3)21-19(9-12)29-11-30-21/h5-9,14,23H,4,10-11H2,1-3H3/b15-5+/t14-/m1/s1

> <INCHI_KEY>
OOJSDEWTOLBIRE-YWKRCKIVSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.41

> <EXACT_MASS>
414.131467668

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.82630958063658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,4S)-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.2273310686666665

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.261087979938798

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2684269841713744

> <JCHEM_POLAR_SURFACE_AREA>
92.68000000000002

> <JCHEM_REFRACTIVITY>
106.75950000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,4S)-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -2.1827   -4.5294    0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -3.9094    1.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031   -3.3985    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095   -3.0720    0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1658   -2.5105    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091   -2.1144    0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -1.0590    1.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638   -0.6565    2.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8690   -1.0844    1.9577 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845    0.3101    3.1465 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0679    0.4054    3.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4277   -0.1125    2.0540 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1900    1.0002    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426    1.6615    1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334    0.9746    0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009    1.5445    0.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7904    0.9697    0.6288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7462   -0.3700    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529    2.8099    1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5145    3.4822    1.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7441    2.9389    1.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    4.7069    2.4432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2204    4.7359    2.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7797    3.5391    1.7737 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0223   -2.2901   -1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191   -2.6024   -1.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -2.4108   -3.2260 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849   -1.8759   -4.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2413   -3.1468   -1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4183   -3.3907   -1.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -3.7824    0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186   -5.2916   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051   -5.0379    1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2199   -3.2577    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2930   -2.7023    0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7980   -0.2075    4.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036    1.4431    3.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4939   -0.6274    2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2182    0.5993   -0.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9878    1.7537    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261   -0.0123    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135   -1.0415    0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2051   -0.4311   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -0.6944   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6197    3.4981    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    5.5907    1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6376    4.8749    3.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8539   -1.8569   -1.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101   -1.7997   -5.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -2.5416   -4.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8595   -0.8687   -3.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2438   -3.1520   -2.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 24 19  1  0
  6  5  1  0
 14 15  2  0
  5  4  1  0
 19 20  1  0
  4  3  2  0
  3 29  1  0
 19 16  2  0
 26 25  1  0
 25  5  2  0
 26 29  2  0
 16 15  1  0
 14 13  1  0
  8  9  2  0
  6  7  2  0
 12 38  1  1
 12 13  1  0
  3  2  1  0
 12  7  1  0
  2  1  1  0
 14 21  1  0
 16 17  1  0
 21 20  2  0
 17 18  1  0
 20 22  1  0
 26 27  1  0
 22 23  1  0
 29 30  1  0
 23 24  1  0
 27 28  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
 15 41  1  0
  6 35  1  0
 13 39  1  0
 13 40  1  0
 11 36  1  0
 11 37  1  0
  4 34  1  0
 25 48  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 30 52  1  0
 28 49  1  0
 28 50  1  0
 28 51  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      -2.183  -4.529   0.537  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.029  -3.909   1.089  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.103  -3.398   0.222  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.109  -3.072   0.839  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.166  -2.510   0.112  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.409  -2.114   0.777  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.487  -1.059   1.602  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.764  -0.657   2.230  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.869  -1.084   1.958  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.484   0.310   3.147  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.068   0.405   3.329  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.428  -0.113   2.054  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.190   1.000   1.017  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.843   1.662   1.201  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.333   0.975   0.804  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.601   1.545   0.971  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.790   0.970   0.629  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.746  -0.370   0.152  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.653   2.810   1.530  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.515   3.482   1.914  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.744   2.939   1.766  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.782   4.707   2.443  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.220   4.736   2.344  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.780   3.539   1.774  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.022  -2.290  -1.262  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.819  -2.602  -1.894  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.539  -2.411  -3.226  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.585  -1.876  -4.031  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.241  -3.147  -1.145  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.418  -3.391  -1.808  0.00  0.00           O+0
HETATM   31  H   UNK     0      -2.871  -3.782   0.129  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.919  -5.292  -0.204  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.705  -5.038   1.353  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.220  -3.258   1.906  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.293  -2.702   0.536  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.798  -0.208   4.198  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.804   1.443   3.554  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.494  -0.627   2.303  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.218   0.599  -0.005  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.988   1.754   1.057  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.226  -0.012   0.362  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.313  -1.042   0.900  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.205  -0.431  -0.798  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.775  -0.694  -0.031  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.620   3.498   2.079  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.511   5.591   1.722  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.638   4.875   3.348  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.854  -1.857  -1.809  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.210  -1.800  -5.056  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.454  -2.542  -4.043  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.859  -0.869  -3.701  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.244  -3.152  -2.740  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1                                                       
CONECT    3    4   29    2                                                  
CONECT    4    5    3   34                                                  
CONECT    5    6    4   25                                                  
CONECT    6    5    7   35                                                  
CONECT    7    8    6   12                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   36   37                                             
CONECT   12   11   38   13    7                                             
CONECT   13   14   12   39   40                                             
CONECT   14   15   13   21                                                  
CONECT   15   14   16   41                                                  
CONECT   16   19   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   42   43   44                                             
CONECT   19   24   20   16                                                  
CONECT   20   19   21   22                                                  
CONECT   21   14   20   45                                                  
CONECT   22   20   23                                                       
CONECT   23   22   24   46   47                                             
CONECT   24   19   23                                                       
CONECT   25   26    5   48                                                  
CONECT   26   25   29   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   49   50   51                                             
CONECT   29    3   26   30                                                  
CONECT   30   29   52                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36   11                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   15                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
CONECT   44   18                                                            
CONECT   45   21                                                            
CONECT   46   23                                                            
CONECT   47   23                                                            
CONECT   48   25                                                            
CONECT   49   28                                                            
CONECT   50   28                                                            
CONECT   51   28                                                            
CONECT   52   30                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  110    0
END

RDKit          3D

52 55  0  0  0  0  0  0  0  0999 V2000
   -2.1827   -4.5294    0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -3.9094    1.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031   -3.3985    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095   -3.0720    0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1658   -2.5105    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091   -2.1144    0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -1.0590    1.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638   -0.6565    2.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8690   -1.0844    1.9577 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845    0.3101    3.1465 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0679    0.4054    3.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4277   -0.1125    2.0540 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1900    1.0002    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426    1.6615    1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334    0.9746    0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009    1.5445    0.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7904    0.9697    0.6288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7462   -0.3700    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529    2.8099    1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5145    3.4822    1.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7441    2.9389    1.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    4.7069    2.4432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2204    4.7359    2.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7797    3.5391    1.7737 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0223   -2.2901   -1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191   -2.6024   -1.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -2.4108   -3.2260 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849   -1.8759   -4.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2413   -3.1468   -1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4183   -3.3907   -1.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -3.7824    0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186   -5.2916   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051   -5.0379    1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2199   -3.2577    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2930   -2.7023    0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7980   -0.2075    4.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036    1.4431    3.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4939   -0.6274    2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2182    0.5993   -0.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9878    1.7537    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261   -0.0123    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135   -1.0415    0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2051   -0.4311   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -0.6944   -0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6197    3.4981    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    5.5907    1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6376    4.8749    3.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8539   -1.8569   -1.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101   -1.7997   -5.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -2.5416   -4.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8595   -0.8687   -3.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2438   -3.1520   -2.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 24 19  1  0
  6  5  1  0
 14 15  2  0
  5  4  1  0
 19 20  1  0
  4  3  2  0
  3 29  1  0
 19 16  2  0
 26 25  1  0
 25  5  2  0
 26 29  2  0
 16 15  1  0
 14 13  1  0
  8  9  2  0
  6  7  2  0
 12 38  1  1
 12 13  1  0
  3  2  1  0
 12  7  1  0
  2  1  1  0
 14 21  1  0
 16 17  1  0
 21 20  2  0
 17 18  1  0
 20 22  1  0
 26 27  1  0
 22 23  1  0
 29 30  1  0
 23 24  1  0
 27 28  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
 15 41  1  0
  6 35  1  0
 13 39  1  0
 13 40  1  0
 11 36  1  0
 11 37  1  0
  4 34  1  0
 25 48  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 30 52  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₈

Average Mass

414.4100 Da

Monoisotopic Mass

414.13147 Da

IUPAC Name

(3E,4S)-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one

Traditional Name

(3E,4S)-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C(\C([H])=C2\C(=O)OC([H])([H])[C@@]2([H])C([H])([H])C2=C([H])C(OC([H])([H])[H])=C3OC([H])([H])OC3=C2[H])C([H])=C1OC([H])([H])[H]

InChI Identifier

InChI=1S/C22H22O8/c1-25-16-6-13(7-17(26-2)20(16)23)5-15-14(10-28-22(15)24)4-12-8-18(27-3)21-19(9-12)29-11-30-21/h5-9,14,23H,4,10-11H2,1-3H3/b15-5+/t14-/m1/s1

InChI Key

OOJSDEWTOLBIRE-YWKRCKIVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

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
Peperomia duclouxii	JEOL database	Li, N., et al, J. Nat. Prod. 69, 234 (2006)
Peperomia heyneana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Benzodioxole
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Ether
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.69	ALOGPS
logP	3.23	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.26	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.76 m³·mol⁻¹	ChemAxon
Polarizability	41.83 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	Yes	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

9829283

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11654545

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li, N., et al. (2006). Li, N., et al, J. Nat. Prod. 69, 234 (2006). J. Nat. Prod..

Showing NP-Card for (2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+ (NP0031840)

MOL for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)

3D MOL for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)

3D SDF for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)

3D-SDF for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)

PDB for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)

3D PDB for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)

SMILES for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)

INCHI for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)

Structure for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)

3D Structure for NP0031840 ((2E,3S)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(5-methoxy-3,4-methylene+)