NP-MRD: Showing NP-Card for (+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan (NP0036081)

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Record Information

Version

1.0

Created at

2021-06-20 19:21:00 UTC

Updated at

2021-06-30 00:07:33 UTC

NP-MRD ID

NP0036081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan

Provided By

JEOL Database JEOL Logo

Description

(+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5-methoxy-2,7'-cyclolignan belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton (+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5-methoxy-2,7'-cyclolignan is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan is found in Machilus robusta. It was first documented in 2011 (PMID: 21627109). Based on a literature review a small amount of articles have been published on (+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5-methoxy-2,7'-cyclolignan (PMID: 24010288) (PMID: 29281889).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121213D          

 45 47  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121213D          

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 22 41  1  0  0  0  0
 22 42  1  0  0  0  0
 22 43  1  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
 18 35  1  0  0  0  0
 15 33  1  0  0  0  0
 17 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1O[H])[C@@]1([H])C2=C([H])C(O[H])=C(OC([H])([H])[H])C([H])=C2C([H])([H])[C@]([H])(C([H])([H])[H])[C@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O4/c1-10-6-13-8-18(23-3)17(22)9-14(13)19(11(10)2)12-4-5-15(20)16(21)7-12/h4-5,7-11,19-22H,6H2,1-3H3/t10-,11-,19-/m0/s1

> <INCHI_KEY>
GSOJAKKBDGPDIS-ADWYPQAOSA-N

> <FORMULA>
C19H22O4

> <MOLECULAR_WEIGHT>
314.381

> <EXACT_MASS>
314.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.704201771854855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S,2S,3S)-7-hydroxy-6-methoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]benzene-1,2-diol

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
4.351994053

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.309227725831688

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.314674710527578

> <JCHEM_PKA_STRONGEST_BASIC>
-4.887199278703527

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
89.6869

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2S,3S)-7-hydroxy-6-methoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -3.3569   -1.1056   -4.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4440   -0.2663   -3.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374   -0.5889   -2.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7277   -1.6439   -2.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486   -1.8664   -1.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1003   -1.0255   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    0.0349   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681    0.2406   -1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6503    1.2868   -1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823   -1.2155    0.8750 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7587   -0.1160    1.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0847    0.2311    2.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411    1.2114    2.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6758    1.8491    1.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6102    2.8087    1.9309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695    1.5224    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289    2.1956   -0.6435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    0.5428    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -2.6247    0.9744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6496   -3.6558    1.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227   -3.0126   -0.3744 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7902   -4.3348   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123   -3.0513   -1.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545   -1.0702   -5.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609   -0.7253   -5.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6490   -2.1332   -4.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -2.3187   -3.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    0.7068    0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686    1.2464   -2.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -1.1318    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921   -0.2663    3.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2864    1.4739    3.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048    3.1086    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6543    1.9103   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    0.2898   -0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1677   -2.5958    1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506   -3.3483    2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4959   -3.7733    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1880   -4.6372    1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7632   -2.2405   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -4.5004   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128   -4.3241    0.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230   -5.1909   -0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210   -3.9616   -1.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213   -3.0974   -2.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 23  1  0
  6 10  1  0
 10 19  1  0
 19 21  1  0
 21 23  1  0
  2  1  1  0
 19 20  1  0
  7  6  2  0
 21 22  1  0
  8  9  1  0
 10 11  1  0
  5  6  1  0
 11 12  2  0
  3  8  2  0
 12 13  1  0
  5  4  2  0
 13 14  2  0
  4  3  1  0
 14 16  1  0
 16 18  2  0
 18 11  1  0
  3  2  1  0
 14 15  1  0
  8  7  1  0
 16 17  1  0
  7 28  1  0
  4 27  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  9 29  1  0
 10 30  1  1
 19 36  1  1
 21 40  1  6
 23 44  1  0
 23 45  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 12 31  1  0
 13 32  1  0
 18 35  1  0
 15 33  1  0
 17 34  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      -3.357  -1.106  -4.935  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.444  -0.266  -3.789  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.637  -0.589  -2.729  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.728  -1.644  -2.674  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.949  -1.866  -1.519  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.100  -1.026  -0.398  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.020   0.035  -0.462  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.768   0.241  -1.614  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.650   1.287  -1.633  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.282  -1.216   0.875  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.759  -0.116   1.116  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.085   0.231   2.444  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.041   1.211   2.718  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.676   1.849   1.666  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.610   2.809   1.931  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.369   1.522   0.349  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.029   2.196  -0.644  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.423   0.543   0.065  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.374  -2.625   0.974  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.650  -3.656   1.480  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.023  -3.013  -0.374  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.790  -4.335  -0.307  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.012  -3.051  -1.506  0.00  0.00           C+0
HETATM   24  H   UNK     0      -2.354  -1.070  -5.375  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.061  -0.725  -5.682  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.649  -2.133  -4.695  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.602  -2.319  -3.515  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.151   0.707   0.383  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.069   1.246  -2.514  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.006  -1.132   1.701  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.592  -0.266   3.277  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.286   1.474   3.743  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.905   3.109   1.048  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.654   1.910  -1.495  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.196   0.290  -0.966  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.168  -2.596   1.734  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.051  -3.348   2.453  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.496  -3.773   0.797  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.188  -4.637   1.624  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.763  -2.240  -0.622  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.346  -4.500  -1.237  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.513  -4.324   0.515  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.123  -5.191  -0.168  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.621  -3.962  -1.433  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.521  -3.097  -2.464  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3                                                       
CONECT    3    8    4    2                                                  
CONECT    4    5    3   27                                                  
CONECT    5   23    6    4                                                  
CONECT    6   10    7    5                                                  
CONECT    7    6    8   28                                                  
CONECT    8    9    3    7                                                  
CONECT    9    8   29                                                       
CONECT   10    6   19   11   30                                             
CONECT   11   10   12   18                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   32                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   33                                                       
CONECT   16   14   18   17                                                  
CONECT   17   16   34                                                       
CONECT   18   16   11   35                                                  
CONECT   19   10   21   20   36                                             
CONECT   20   19   37   38   39                                             
CONECT   21   19   23   22   40                                             
CONECT   22   21   41   42   43                                             
CONECT   23    5   21   44   45                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    4                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   15                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   20                                                            
CONECT   38   20                                                            
CONECT   39   20                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
CONECT   42   22                                                            
CONECT   43   22                                                            
CONECT   44   23                                                            
CONECT   45   23                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

RDKit          3D

45 47  0  0  0  0  0  0  0  0999 V2000
   -3.3569   -1.1056   -4.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4440   -0.2663   -3.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374   -0.5889   -2.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7277   -1.6439   -2.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486   -1.8664   -1.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1003   -1.0255   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    0.0349   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681    0.2406   -1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6503    1.2868   -1.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823   -1.2155    0.8750 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7587   -0.1160    1.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0847    0.2311    2.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411    1.2114    2.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6758    1.8491    1.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6102    2.8087    1.9309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695    1.5224    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289    2.1956   -0.6435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    0.5428    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -2.6247    0.9744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6496   -3.6558    1.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227   -3.0126   -0.3744 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7902   -4.3348   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123   -3.0513   -1.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545   -1.0702   -5.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609   -0.7253   -5.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6490   -2.1332   -4.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -2.3187   -3.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    0.7068    0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686    1.2464   -2.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -1.1318    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921   -0.2663    3.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2864    1.4739    3.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048    3.1086    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6543    1.9103   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    0.2898   -0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1677   -2.5958    1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506   -3.3483    2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4959   -3.7733    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1880   -4.6372    1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7632   -2.2405   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -4.5004   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128   -4.3241    0.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230   -5.1909   -0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210   -3.9616   -1.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213   -3.0974   -2.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 23  1  0
  6 10  1  0
 10 19  1  0
 19 21  1  0
 21 23  1  0
  2  1  1  0
 19 20  1  0
  7  6  2  0
 21 22  1  0
  8  9  1  0
 10 11  1  0
  5  6  1  0
 11 12  2  0
  3  8  2  0
 12 13  1  0
  5  4  2  0
 13 14  2  0
  4  3  1  0
 14 16  1  0
 16 18  2  0
 18 11  1  0
  3  2  1  0
 14 15  1  0
  8  7  1  0
 16 17  1  0
  7 28  1  0
  4 27  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  9 29  1  0
 10 30  1  1
 19 36  1  1
 21 40  1  6
 23 44  1  0
 23 45  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 12 31  1  0
 13 32  1  0
 18 35  1  0
 15 33  1  0
 17 34  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₄

Average Mass

314.3810 Da

Monoisotopic Mass

314.15181 Da

IUPAC Name

4-[(1S,2S,3S)-7-hydroxy-6-methoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]benzene-1,2-diol

Traditional Name

4-[(1S,2S,3S)-7-hydroxy-6-methoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1O[H])[C@@]1([H])C2=C([H])C(O[H])=C(OC([H])([H])[H])C([H])=C2C([H])([H])[C@]([H])(C([H])([H])[H])[C@]1([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C19H22O4/c1-10-6-13-8-18(23-3)17(22)9-14(13)19(11(10)2)12-4-5-15(20)16(21)7-12/h4-5,7-11,19-22H,6H2,1-3H3/t10-,11-,19-/m0/s1

InChI Key

GSOJAKKBDGPDIS-ADWYPQAOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Machilus robusta	JEOL database	Li, Y., et al, J. Nat. Prod. 74, 1444 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
Tetralin
Catechol
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

catechols (CHEBI:68158 )
monomethoxybenzene (CHEBI:68158 )
lignan (CHEBI:68158 )

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	3.52	ALOGPS
logP	4.35	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.69 m³·mol⁻¹	ChemAxon
Polarizability	34.7 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

26646737

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

68158

Good Scents ID

Not Available

References

General References

Li Y, Cheng W, Zhu C, Yao C, Xiong L, Tian Y, Wang S, Lin S, Hu J, Yang Y, Guo Y, Yang Y, Li Y, Yuan Y, Chen N, Shi J: Bioactive neolignans and lignans from the bark of Machilus robusta. J Nat Prod. 2011 Jun 24;74(6):1444-52. doi: 10.1021/np2001896. Epub 2011 May 31. [PubMed:21627109 ]
Bu PB, Li YR, Jiang M, Wang XL, Wang F, Lin S, Zhu CG, Shi JG: [Lignans from Machilus robusta]. Zhongguo Zhong Yao Za Zhi. 2013 Jun;38(11):1740-6. [PubMed:24010288 ]
Guo JM, Ba MY, Yang Y, Yao CS, Yu M, Shi JG, Guo Y: Discovery of a semi-synthesized cyclolignan as a potent HIV-1 non-nucleoside reverse transcriptase inhibitor. J Asian Nat Prod Res. 2019 Jan;21(1):76-85. doi: 10.1080/10286020.2017.1417266. Epub 2017 Dec 27. [PubMed:29281889 ]
Li, Y., et al. (2011). Li, Y., et al, J. Nat. Prod. 74, 1444 (2011). J. Nat. Prod..

Showing NP-Card for (+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan (NP0036081)

MOL for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)

3D MOL for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)

3D SDF for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)

3D-SDF for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)

PDB for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)

3D PDB for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)

SMILES for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)

INCHI for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)

Structure for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)

3D Structure for NP0036081 ((+)-(7'S,8S,8'S)-3',4,4'-trihydroxy-5,-methoxy-2,7'-cyclolignan)