NP-MRD: Showing NP-Card for endiandrin A (NP0033075)

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Record Information

Version

2.0

Created at

2021-06-19 23:43:24 UTC

Updated at

2021-06-30 00:02:39 UTC

NP-MRD ID

NP0033075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

endiandrin A

Provided By

JEOL Database JEOL Logo

Description

ENDIANDRIN A belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms. endiandrin A is found in Endiandra anthropophagorum and Eudiandra anthropophagorum. endiandrin A was first documented in 2007 (PMID: 17583952). Based on a literature review a small amount of articles have been published on ENDIANDRIN A (PMID: 23152905) (PMID: 19138858).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101433D          

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     RDKit          3D

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  Mrv1652306202101433D          

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 15 16  1  0  0  0  0
 21 22  2  0  0  0  0
  3  2  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
 22 23  1  0  0  0  0
 17 18  1  0  0  0  0
  7  6  1  0  0  0  0
 18 19  1  0  0  0  0
  7 30  1  1  0  0  0
  6 29  1  6  0  0  0
 11 38  1  1  0  0  0
  9 34  1  6  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
 21 46  1  0  0  0  0
 22 47  1  0  0  0  0
  4 28  1  0  0  0  0
 20 45  1  0  0  0  0
 14 40  1  0  0  0  0
 13 39  1  0  0  0  0
 24 48  1  0  0  0  0
 16 41  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])[C@@]1([H])[C@]([H])(C2=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C2[H])[C@@]([H])(C([H])([H])[H])[C@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-11-12(2)20(14-6-8-16(22)18(10-14)24-4)19(11)13-5-7-15(21)17(9-13)23-3/h5-12,19-22H,1-4H3/t11-,12-,19-,20-/m0/s1

> <INCHI_KEY>
QDBUCXMBHJMGCN-HIGYNYDNSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.408

> <EXACT_MASS>
328.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.11056178761513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1R,2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dimethylcyclobutyl]-2-methoxyphenol

> <ALOGPS_LOGP>
4.20

> <JCHEM_LOGP>
4.271485815999999

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.494939831840531

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.892690099941849

> <JCHEM_PKA_STRONGEST_BASIC>
-4.590468995405362

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
93.67660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1R,2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dimethylcyclobutyl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
   -4.0164    2.1027    0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763    2.2641    1.7502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171    1.4264    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    0.4549    0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941   -0.3600    0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5308   -1.4357   -0.8339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0225   -2.8801   -0.5297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0866   -3.9119   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -2.8956   -1.9833 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8430   -3.6491   -2.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6467   -1.3368   -1.8758 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4048   -0.4162   -3.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005   -0.9114   -4.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805   -0.0797   -5.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355    1.2735   -5.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2508    2.0690   -6.4594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0323    1.8222   -4.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565    3.1737   -4.0274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    3.7638   -2.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917    0.9757   -2.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -0.1462    1.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126    0.8186    2.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283    1.5933    2.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7656    2.5358    3.3597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720    2.3207   -0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4465    1.1015    1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7717    2.8257    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5657    0.3014   -0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5022   -1.4712   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7711   -2.9082    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -3.7108    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892   -3.9118   -0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -4.9161   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -3.2257   -2.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839   -4.7263   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2423   -3.4708   -3.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6035   -3.3426   -1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5935   -1.0397   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5733   -1.9699   -4.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1795   -0.4858   -6.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    2.9678   -6.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267    3.6516   -2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506    3.3522   -2.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4412    4.8345   -2.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2109    1.3702   -1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800   -0.7423    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2491    0.9638    2.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483    2.9472    3.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  3  2  0
  9 10  1  0
  3  4  1  0
  4  5  2  0
  6 11  1  0
 12 20  2  0
  7  8  1  0
 20 17  1  0
 11  9  1  0
 17 15  2  0
 11 12  1  0
 15 14  1  0
  9  7  1  0
 14 13  2  0
 13 12  1  0
  5 21  1  0
 23 24  1  0
 15 16  1  0
 21 22  2  0
  3  2  1  0
  6  5  1  0
  2  1  1  0
 22 23  1  0
 17 18  1  0
  7  6  1  0
 18 19  1  0
  7 30  1  1
  6 29  1  6
 11 38  1  1
  9 34  1  6
 10 35  1  0
 10 36  1  0
 10 37  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
 21 46  1  0
 22 47  1  0
  4 28  1  0
 20 45  1  0
 14 40  1  0
 13 39  1  0
 24 48  1  0
 16 41  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 19 42  1  0
 19 43  1  0
 19 44  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      -4.016   2.103   0.914  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.876   2.264   1.750  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.817   1.426   1.513  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.739   0.455   0.512  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.594  -0.360   0.339  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.531  -1.436  -0.834  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.023  -2.880  -0.530  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.087  -3.912  -0.208  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.542  -2.896  -1.983  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.843  -3.649  -2.183  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.647  -1.337  -1.876  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.405  -0.416  -3.152  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.401  -0.911  -4.471  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.181  -0.080  -5.572  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.036   1.274  -5.368  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.251   2.069  -6.459  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.032   1.822  -4.085  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.257   3.174  -4.027  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.251   3.764  -2.732  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.192   0.976  -2.997  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.474  -0.146   1.235  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.413   0.819   2.242  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.728   1.593   2.369  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.766   2.536   3.360  0.00  0.00           O+0
HETATM   25  H   UNK     0      -3.772   2.321  -0.131  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.447   1.101   1.021  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.772   2.826   1.236  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.566   0.301  -0.177  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.502  -1.471  -1.357  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.771  -2.908   0.230  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.533  -3.711   0.771  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.889  -3.912  -0.953  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.652  -4.916  -0.180  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.208  -3.226  -2.717  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.684  -4.726  -2.071  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.242  -3.471  -3.186  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.603  -3.343  -1.457  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.593  -1.040  -1.396  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.573  -1.970  -4.653  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.180  -0.486  -6.579  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.366   2.968  -6.094  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.727   3.652  -2.251  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.051   3.352  -2.107  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.441   4.835  -2.852  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.211   1.370  -1.985  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.380  -0.742   1.145  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.249   0.964   2.919  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.648   2.947   3.282  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3   23    4    2                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4   21    6                                                  
CONECT    6   11    5    7   29                                             
CONECT    7    8    9    6   30                                             
CONECT    8    7   31   32   33                                             
CONECT    9   10   11    7   34                                             
CONECT   10    9   35   36   37                                             
CONECT   11    6    9   12   38                                             
CONECT   12   20   11   13                                                  
CONECT   13   14   12   39                                                  
CONECT   14   15   13   40                                                  
CONECT   15   17   14   16                                                  
CONECT   16   15   41                                                       
CONECT   17   20   15   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   42   43   44                                             
CONECT   20   12   17   45                                                  
CONECT   21    5   22   46                                                  
CONECT   22   21   23   47                                                  
CONECT   23    3   24   22                                                  
CONECT   24   23   48                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   16                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   24                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  100    0
END

RDKit          3D

48 50  0  0  0  0  0  0  0  0999 V2000
   -4.0164    2.1027    0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763    2.2641    1.7502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171    1.4264    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    0.4549    0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941   -0.3600    0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5308   -1.4357   -0.8339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0225   -2.8801   -0.5297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0866   -3.9119   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -2.8956   -1.9833 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8430   -3.6491   -2.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6467   -1.3368   -1.8758 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4048   -0.4162   -3.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005   -0.9114   -4.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805   -0.0797   -5.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355    1.2735   -5.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2508    2.0690   -6.4594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0323    1.8222   -4.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565    3.1737   -4.0274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    3.7638   -2.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917    0.9757   -2.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -0.1462    1.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126    0.8186    2.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283    1.5933    2.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7656    2.5358    3.3597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720    2.3207   -0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4465    1.1015    1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7717    2.8257    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5657    0.3014   -0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5022   -1.4712   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7711   -2.9082    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -3.7108    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892   -3.9118   -0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -4.9161   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -3.2257   -2.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839   -4.7263   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2423   -3.4708   -3.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6035   -3.3426   -1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5935   -1.0397   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5733   -1.9699   -4.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1795   -0.4858   -6.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    2.9678   -6.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267    3.6516   -2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506    3.3522   -2.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4412    4.8345   -2.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2109    1.3702   -1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800   -0.7423    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2491    0.9638    2.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483    2.9472    3.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  3  2  0
  9 10  1  0
  3  4  1  0
  4  5  2  0
  6 11  1  0
 12 20  2  0
  7  8  1  0
 20 17  1  0
 11  9  1  0
 17 15  2  0
 11 12  1  0
 15 14  1  0
  9  7  1  0
 14 13  2  0
 13 12  1  0
  5 21  1  0
 23 24  1  0
 15 16  1  0
 21 22  2  0
  3  2  1  0
  6  5  1  0
  2  1  1  0
 22 23  1  0
 17 18  1  0
  7  6  1  0
 18 19  1  0
  7 30  1  1
  6 29  1  6
 11 38  1  1
  9 34  1  6
 10 35  1  0
 10 36  1  0
 10 37  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
 21 46  1  0
 22 47  1  0
  4 28  1  0
 20 45  1  0
 14 40  1  0
 13 39  1  0
 24 48  1  0
 16 41  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4080 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

4-[(1R,2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dimethylcyclobutyl]-2-methoxyphenol

Traditional Name

4-[(1R,2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dimethylcyclobutyl]-2-methoxyphenol

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])[C@@]1([H])[C@]([H])(C2=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C2[H])[C@@]([H])(C([H])([H])[H])[C@]1([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H24O4/c1-11-12(2)20(14-6-8-16(22)18(10-14)24-4)19(11)13-5-7-15(21)17(9-13)23-3/h5-12,19-22H,1-4H3/t11-,12-,19-,20-/m0/s1

InChI Key

QDBUCXMBHJMGCN-HIGYNYDNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Endiandra anthropophagorum	JEOL database	Davis, R. A., et al, J. Nat. Prod. 70, 1118 (2007)
Eudiandra anthropophagorum	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Cyclobutane lignans

Sub Class

Not Available

Direct Parent

Cyclobutane lignans

Alternative Parents

Substituents

Cyclobutane lignan skeleton
Dibenzylbutane lignan skeleton
Stilbene
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.2	ALOGPS
logP	4.27	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.89	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.68 m³·mol⁻¹	ChemAxon
Polarizability	37.11 Å³	ChemAxon
Number of Rings	3	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

23286937

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16756780

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kuntzsch D, Bergann T, Dames P, Fromm A, Fromm M, Davis RA, Melzig MF, Schulzke JD: The plant-derived glucocorticoid receptor agonist Endiandrin A acts as co-stimulator of colonic epithelial sodium channels (ENaC) via SGK-1 and MAPKs. PLoS One. 2012;7(11):e49426. doi: 10.1371/journal.pone.0049426. Epub 2012 Nov 13. [PubMed:23152905 ]
Davis RA, Barnes EC, Longden J, Avery VM, Healy PC: Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum. Bioorg Med Chem. 2009 Feb 1;17(3):1387-92. doi: 10.1016/j.bmc.2008.12.030. Epub 2008 Dec 24. [PubMed:19138858 ]
Davis RA, Carroll AR, Duffy S, Avery VM, Guymer GP, Forster PI, Quinn RJ: Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum. J Nat Prod. 2007 Jul;70(7):1118-21. doi: 10.1021/np070073x. Epub 2007 Jun 21. [PubMed:17583952 ]
Davis, R. A., et al. (2007). Davis, R. A., et al, J. Nat. Prod. 70, 1118 (2007). J. Nat. Prod..

Showing NP-Card for endiandrin A (NP0033075)

MOL for NP0033075 (endiandrin A)

3D MOL for NP0033075 (endiandrin A)

3D SDF for NP0033075 (endiandrin A)

3D-SDF for NP0033075 (endiandrin A)

PDB for NP0033075 (endiandrin A)

3D PDB for NP0033075 (endiandrin A)

SMILES for NP0033075 (endiandrin A)

INCHI for NP0033075 (endiandrin A)

Structure for NP0033075 (endiandrin A)

3D Structure for NP0033075 (endiandrin A)