NP-MRD: Showing NP-Card for scaphopetalone (NP0030664)

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Record Information

Version

2.0

Created at

2021-06-19 21:57:35 UTC

Updated at

2021-06-29 23:58:47 UTC

NP-MRD ID

NP0030664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

scaphopetalone

Provided By

JEOL Database JEOL Logo

Description

Scaphopetalone belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position. scaphopetalone is found in Scaphopetalum thonneri. scaphopetalone was first documented in 2003 (PMID: 12560041). Based on a literature review very few articles have been published on Scaphopetalone (PMID: 26080555).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123573D          

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M  END

     RDKit          3D

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  Mrv1652306192123573D          

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   -1.0170   -1.9534   -4.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5879    0.7499   -3.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066    0.2307   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7459    1.3306   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304    0.0832   -1.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509    2.0868   -2.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270    0.6153   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    2.3899    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966    3.1888    4.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0  0  0  0
  8  7  2  0  0  0  0
 22 23  1  0  0  0  0
 12  9  2  0  0  0  0
 12 13  1  0  0  0  0
 16 15  2  0  0  0  0
  9 10  1  0  0  0  0
 15 12  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  6 21  1  0  0  0  0
  5 24  1  0  0  0  0
 21 18  1  0  0  0  0
 24 25  2  0  0  0  0
 18 17  1  0  0  0  0
 25 26  1  0  0  0  0
 16  7  1  0  0  0  0
 26  3  2  0  0  0  0
 21 22  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 26 27  1  0  0  0  0
 18 19  1  0  0  0  0
  3  2  1  0  0  0  0
  9  8  1  0  0  0  0
  2  1  1  0  0  0  0
  8 33  1  0  0  0  0
 15 40  1  0  0  0  0
  6 32  1  1  0  0  0
 21 47  1  6  0  0  0
 18 43  1  1  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 20 46  1  0  0  0  0
 23 50  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 24 51  1  0  0  0  0
 25 52  1  0  0  0  0
  4 31  1  0  0  0  0
 27 53  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030664

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])[C@]1([H])C2=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C2C([H])([H])[C@]([H])(C([H])([H])O[H])[C@@]1([H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O6/c1-25-18-7-12(4-5-17(18)24)21-15-9-20(27-3)19(26-2)8-13(15)6-14(10-22)16(21)11-23/h4-5,7-9,14,16,21-24H,6,10-11H2,1-3H3/t14-,16-,21-/m1/s1

> <INCHI_KEY>
PDWZFAROGANMAJ-IUSZMWJPSA-N

> <FORMULA>
C21H26O6

> <MOLECULAR_WEIGHT>
374.433

> <EXACT_MASS>
374.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.76335386502748

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1R,2S,3S)-2,3-bis(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-yl]-2-methoxyphenol

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
1.9263323916666666

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.135428604769775

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.055839579616189

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6036864610462302

> <JCHEM_POLAR_SURFACE_AREA>
88.38000000000001

> <JCHEM_REFRACTIVITY>
102.35490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1R,2S,3S)-2,3-bis(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-yl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
   -2.2916    1.1642    4.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1048    1.8901    4.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3967    1.4853    2.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    0.4902    2.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495    0.1694    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769   -0.9286   -0.0030 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5563   -2.1397    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9413   -2.6804    1.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7993   -3.7804    1.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1112   -4.2486    2.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182   -3.8131    2.9833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -4.4110    0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0666   -5.5025    0.3689 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4799   -6.2023   -0.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590   -3.8945   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985   -2.7797   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917   -2.2851   -2.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352   -1.5079   -2.4561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1124   -1.1013   -3.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2756   -0.0617   -4.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5841   -0.3417   -1.4377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7809    0.6268   -1.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572    1.4080   -2.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2634    0.8584    0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6415    1.8566    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8108    2.1604    2.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2059    3.1444    3.6394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124    1.5770    5.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744    0.1057    4.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378    1.2888    3.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -0.0551    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3546   -1.3175    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5888   -2.2432    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765   -4.0961    4.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5120   -2.7233    2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925   -4.3012    2.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1082   -5.5709   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0847   -7.0563   -0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199   -6.5933   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1948   -4.3481   -1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -3.1446   -3.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4007   -1.6578   -2.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248   -2.1852   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1555   -0.7718   -3.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170   -1.9534   -4.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5879    0.7499   -3.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066    0.2307   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7459    1.3306   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304    0.0832   -1.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509    2.0868   -2.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270    0.6153   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    2.3899    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966    3.1888    4.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
  8  7  2  0
 22 23  1  0
 12  9  2  0
 12 13  1  0
 16 15  2  0
  9 10  1  0
 15 12  1  0
 13 14  1  0
 16 17  1  0
 10 11  1  0
  7  6  1  0
  6  5  1  0
  6 21  1  0
  5 24  1  0
 21 18  1  0
 24 25  2  0
 18 17  1  0
 25 26  1  0
 16  7  1  0
 26  3  2  0
 21 22  1  0
  3  4  1  0
  4  5  2  0
 26 27  1  0
 18 19  1  0
  3  2  1  0
  9  8  1  0
  2  1  1  0
  8 33  1  0
 15 40  1  0
  6 32  1  1
 21 47  1  6
 18 43  1  1
 17 41  1  0
 17 42  1  0
 22 48  1  0
 22 49  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 23 50  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 24 51  1  0
 25 52  1  0
  4 31  1  0
 27 53  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.292   1.164   4.381  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.105   1.890   4.082  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.397   1.485   2.980  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.774   0.490   2.077  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.050   0.169   0.978  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.377  -0.929  -0.003  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.556  -2.140   0.047  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.941  -2.680   1.286  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.799  -3.780   1.356  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.111  -4.249   2.609  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.418  -3.813   2.983  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.258  -4.411   0.195  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.067  -5.503   0.369  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.480  -6.202  -0.796  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.859  -3.894  -1.039  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.999  -2.780  -1.123  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.592  -2.285  -2.488  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.735  -1.508  -2.456  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.112  -1.101  -3.887  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.276  -0.062  -4.369  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.584  -0.342  -1.438  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.781   0.627  -1.458  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.757   1.408  -2.652  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.263   0.858   0.809  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.642   1.857   1.704  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.811   2.160   2.774  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.206   3.144   3.639  0.00  0.00           O+0
HETATM   28  H   UNK     0      -2.712   1.577   5.303  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.074   0.106   4.559  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.038   1.289   3.589  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.704  -0.055   2.206  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.355  -1.317   0.320  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.589  -2.243   2.217  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.576  -4.096   4.028  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.512  -2.723   2.912  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.192  -4.301   2.383  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.108  -5.571  -1.433  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.085  -7.056  -0.476  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.620  -6.593  -1.350  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.195  -4.348  -1.967  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.482  -3.145  -3.162  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.401  -1.658  -2.883  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.525  -2.185  -2.099  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.155  -0.772  -3.945  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.017  -1.953  -4.569  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.588   0.750  -3.912  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.307   0.231  -1.734  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.746   1.331  -0.622  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.730   0.083  -1.414  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.451   2.087  -2.556  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.927   0.615  -0.019  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.578   2.390   1.573  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.497   3.189   4.309  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3   26    4    2                                                  
CONECT    4    3    5   31                                                  
CONECT    5    6   24    4                                                  
CONECT    6    7    5   21   32                                             
CONECT    7    8    6   16                                                  
CONECT    8    7    9   33                                                  
CONECT    9   12   10    8                                                  
CONECT   10    9   11                                                       
CONECT   11   10   34   35   36                                             
CONECT   12    9   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13   37   38   39                                             
CONECT   15   16   12   40                                                  
CONECT   16   15   17    7                                                  
CONECT   17   16   18   41   42                                             
CONECT   18   21   17   19   43                                             
CONECT   19   20   18   44   45                                             
CONECT   20   19   46                                                       
CONECT   21    6   18   22   47                                             
CONECT   22   23   21   48   49                                             
CONECT   23   22   50                                                       
CONECT   24    5   25   51                                                  
CONECT   25   24   26   52                                                  
CONECT   26   25    3   27                                                  
CONECT   27   26   53                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    6                                                            
CONECT   33    8                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   27                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

RDKit          3D

53 55  0  0  0  0  0  0  0  0999 V2000
   -2.2916    1.1642    4.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1048    1.8901    4.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3967    1.4853    2.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    0.4902    2.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495    0.1694    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769   -0.9286   -0.0030 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5563   -2.1397    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9413   -2.6804    1.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7993   -3.7804    1.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1112   -4.2486    2.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182   -3.8131    2.9833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -4.4110    0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0666   -5.5025    0.3689 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4799   -6.2023   -0.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590   -3.8945   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985   -2.7797   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917   -2.2851   -2.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352   -1.5079   -2.4561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1124   -1.1013   -3.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2756   -0.0617   -4.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5841   -0.3417   -1.4377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7809    0.6268   -1.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572    1.4080   -2.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2634    0.8584    0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6415    1.8566    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8108    2.1604    2.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2059    3.1444    3.6394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124    1.5770    5.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744    0.1057    4.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378    1.2888    3.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -0.0551    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3546   -1.3175    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5888   -2.2432    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765   -4.0961    4.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5120   -2.7233    2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925   -4.3012    2.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1082   -5.5709   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0847   -7.0563   -0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199   -6.5933   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1948   -4.3481   -1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -3.1446   -3.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4007   -1.6578   -2.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248   -2.1852   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1555   -0.7718   -3.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170   -1.9534   -4.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5879    0.7499   -3.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066    0.2307   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7459    1.3306   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304    0.0832   -1.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509    2.0868   -2.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270    0.6153   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    2.3899    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966    3.1888    4.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8  7  2  0
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  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
9,4'.9'-Trihydroxy-4,5,3'-trimethoxyaryltetralinlignan	MeSH

Chemical Formula

C₂₁H₂₆O₆

Average Mass

374.4330 Da

Monoisotopic Mass

374.17294 Da

IUPAC Name

4-[(1R,2S,3S)-2,3-bis(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-yl]-2-methoxyphenol

Traditional Name

4-[(1R,2S,3S)-2,3-bis(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-yl]-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])C2=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C2C([H])([H])[C@]([H])(C([H])([H])O[H])[C@@]1([H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C21H26O6/c1-25-18-7-12(4-5-17(18)24)21-15-9-20(27-3)19(26-2)8-13(15)6-14(10-22)16(21)11-23/h4-5,7-9,14,16,21-24H,6,10-11H2,1-3H3/t14-,16-,21-/m1/s1

InChI Key

PDWZFAROGANMAJ-IUSZMWJPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Scaphopetalum thonneri	JEOL database	Vardamides, J. C., et al., Phytochemistry 62, 647 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

9,9p-dihydroxyaryltetralin lignans

Direct Parent

9,9p-dihydroxyaryltetralin lignans

Alternative Parents

Substituents

9,9p-dihydroxyaryltetralin lignan
Methoxyphenol
Tetralin
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.58	ALOGPS
logP	1.93	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	102.35 m³·mol⁻¹	ChemAxon
Polarizability	40.76 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	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

552876

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

637239

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chai YQ, Zhao GH, Wang RJ, Cao MG, Wu HB, Tang SA, Duan HQ: [Anti-tumor metastatic constituents from Rhodiola wallichiana]. Zhongguo Zhong Yao Za Zhi. 2015 Jan;40(2):258-63. [PubMed:26080555 ]
Vardamides JC, Azebaze AG, Nkengfack AE, Van Heerden FR, Fomum ZT, Ngando TM, Conrad J, Vogler B, Kraus W: Scaphopetalone and scaphopetalumate, a lignan and a triterpene ester from Scaphopetalum thonneri. Phytochemistry. 2003 Feb;62(4):647-50. doi: 10.1016/s0031-9422(02)00616-7. [PubMed:12560041 ]
Vardamides, J. C., et al. (2003). Vardamides, J. C., et al., Phytochemistry 62, 647 (2003). Phytochem..

Showing NP-Card for scaphopetalone (NP0030664)

MOL for NP0030664 (scaphopetalone)

3D MOL for NP0030664 (scaphopetalone)

3D SDF for NP0030664 (scaphopetalone)

3D-SDF for NP0030664 (scaphopetalone)

PDB for NP0030664 (scaphopetalone)

3D PDB for NP0030664 (scaphopetalone)

SMILES for NP0030664 (scaphopetalone)

INCHI for NP0030664 (scaphopetalone)

Structure for NP0030664 (scaphopetalone)

3D Structure for NP0030664 (scaphopetalone)