NP-MRD: Showing NP-Card for (+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan (NP0036084)

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Record Information

Version

1.0

Created at

2021-06-20 19:21:08 UTC

Updated at

2021-06-30 00:07:33 UTC

NP-MRD ID

NP0036084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan

Provided By

JEOL Database JEOL Logo

Description

(+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety (+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan 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. (+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan is found in Machilus robusta. It was first documented in 2011 (PMID: 21627109). Based on a literature review very few articles have been published on (+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121213D          

 54 55  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121213D          

 54 55  0  0  0  0            999 V2000
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   -2.4537    4.9175   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    5.0926    1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755    4.5308    0.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2340    2.4056    2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930    3.0470    2.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    1.5000    3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.7552    4.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6607    0.4681    5.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -0.4686    5.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050   -2.8464    3.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691   -1.5012   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545   -1.8504    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3354   -3.1538   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    0.1838    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6676    5.0210   -0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638    4.2493   -0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    0.8627   -0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 19  1  0  0  0  0
 25 24  2  0  0  0  0
 24 23  1  0  0  0  0
 17 18  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
 17 14  1  0  0  0  0
  3  2  1  0  0  0  0
 19 20  1  0  0  0  0
  2  1  1  0  0  0  0
 25 26  1  0  0  0  0
  5 23  2  0  0  0  0
 14 15  1  0  0  0  0
 14 13  2  0  0  0  0
 15 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 21  1  0  0  0  0
 13 12  1  0  0  0  0
  5  6  1  0  0  0  0
 11  9  1  0  0  0  0
  9  7  1  0  0  0  0
  7  6  1  0  0  0  0
 12 22  2  0  0  0  0
  9 10  1  0  0  0  0
  3 25  1  0  0  0  0
  7  8  1  0  0  0  0
 11 12  1  0  0  0  0
 22 51  1  0  0  0  0
 13 43  1  0  0  0  0
 18 47  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 24 53  1  0  0  0  0
  4 30  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 26 54  1  0  0  0  0
 23 52  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
  9 37  1  6  0  0  0
  7 33  1  6  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C1=C([H])C(OC([H])([H])[H])=C(O[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-13(8-15-6-7-17(22)18(10-15)24-3)14(2)9-16-11-19(25-4)21(23)20(12-16)26-5/h6-7,10-14,22-23H,8-9H2,1-5H3/t13-,14+/m0/s1

> <INCHI_KEY>
GFMUBOWRQZASFJ-UONOGXRCSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.45

> <EXACT_MASS>
360.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.52835224565595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2R,3S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2,6-dimethoxyphenol

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.892639590333333

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.375723502039504

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.589738617081315

> <JCHEM_PKA_STRONGEST_BASIC>
-4.421807515794356

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
102.04679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2R,3S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2,6-dimethoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
    3.1456   -0.9876    0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0970    0.0026    0.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263    1.2843    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3348    1.7204    0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693    3.0669    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637    3.5317    0.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    2.8615   -0.1427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4392    3.3681   -1.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679    3.0164    0.4287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4493    4.4737    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1637    2.4006    1.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    0.9807    2.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6846    0.6910    2.9662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957   -0.6061    3.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7783   -1.0096    3.9861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3879    0.0056    4.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108   -1.6197    2.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149   -2.8948    2.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7035   -1.3638    1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1263   -2.4352    0.5953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1236   -2.2013   -0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819   -0.0571    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253    3.9756   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2213    3.5491   -0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569    2.2147   -0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8347    1.8211   -0.4600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3195   -1.0431    0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7811   -0.8064    1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6541   -1.9564    0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883    1.0297    0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4015    3.3247    1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5007    4.6223    0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3211    1.7849   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947    4.4599   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510    2.9522   -2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034    3.0624   -2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6385    2.4789   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4537    4.9175   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    5.0926    1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755    4.5308    0.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2340    2.4056    2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930    3.0470    2.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    1.5000    3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.7552    4.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6607    0.4681    5.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -0.4686    5.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050   -2.8464    3.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691   -1.5012   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545   -1.8504    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3354   -3.1538   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    0.1838    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6676    5.0210   -0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638    4.2493   -0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    0.8627   -0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 19  1  0
 25 24  2  0
 24 23  1  0
 17 18  1  0
  5  4  1  0
  4  3  2  0
 17 14  1  0
  3  2  1  0
 19 20  1  0
  2  1  1  0
 25 26  1  0
  5 23  2  0
 14 15  1  0
 14 13  2  0
 15 16  1  0
 19 17  2  0
 20 21  1  0
 13 12  1  0
  5  6  1  0
 11  9  1  0
  9  7  1  0
  7  6  1  0
 12 22  2  0
  9 10  1  0
  3 25  1  0
  7  8  1  0
 11 12  1  0
 22 51  1  0
 13 43  1  0
 18 47  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 24 53  1  0
  4 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 26 54  1  0
 23 52  1  0
 11 41  1  0
 11 42  1  0
  9 37  1  6
  7 33  1  6
  6 31  1  0
  6 32  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
  8 34  1  0
  8 35  1  0
  8 36  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       3.146  -0.988   0.816  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.097   0.003   0.436  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.626   1.284   0.306  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.335   1.720   0.602  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.969   3.067   0.410  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564   3.532   0.729  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.523   2.861  -0.143  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.439   3.368  -1.592  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.968   3.016   0.429  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.449   4.474   0.460  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.164   2.401   1.839  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.668   0.981   2.005  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.685   0.691   2.966  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.196  -0.606   3.107  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.778  -1.010   3.986  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.388   0.006   4.776  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.711  -1.620   2.288  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.215  -2.895   2.430  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.704  -1.364   1.335  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.126  -2.435   0.595  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.124  -2.201  -0.388  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.182  -0.057   1.207  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.925   3.976  -0.067  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.221   3.549  -0.354  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.557   2.215  -0.166  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.835   1.821  -0.460  0.00  0.00           O+0
HETATM   27  H   UNK     0       2.320  -1.043   0.099  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.781  -0.806   1.832  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.654  -1.956   0.814  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.588   1.030   0.980  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.402   3.325   1.792  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.501   4.622   0.627  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.321   1.785  -0.199  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.495   4.460  -1.646  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.251   2.952  -2.198  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.503   3.062  -2.058  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.639   2.479  -0.257  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.454   4.918  -0.540  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.821   5.093   1.108  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.475   4.531   0.840  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.234   2.406   2.087  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.693   3.047   2.591  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.308   1.500   3.584  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.879   0.755   4.146  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.661   0.468   5.452  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.159  -0.469   5.391  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.405  -2.846   3.181  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.769  -1.501  -1.152  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.054  -1.850   0.069  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.335  -3.154  -0.883  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.954   0.184   0.483  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.668   5.021  -0.220  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.964   4.249  -0.724  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.848   0.863  -0.270  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   25                                                  
CONECT    4    5    3   30                                                  
CONECT    5    4   23    6                                                  
CONECT    6    5    7   31   32                                             
CONECT    7    9    6    8   33                                             
CONECT    8    7   34   35   36                                             
CONECT    9   11    7   10   37                                             
CONECT   10    9   38   39   40                                             
CONECT   11    9   12   41   42                                             
CONECT   12   13   22   11                                                  
CONECT   13   14   12   43                                                  
CONECT   14   17   15   13                                                  
CONECT   15   14   16                                                       
CONECT   16   15   44   45   46                                             
CONECT   17   18   14   19                                                  
CONECT   18   17   47                                                       
CONECT   19   22   20   17                                                  
CONECT   20   19   21                                                       
CONECT   21   20   48   49   50                                             
CONECT   22   19   12   51                                                  
CONECT   23   24    5   52                                                  
CONECT   24   25   23   53                                                  
CONECT   25   24   26    3                                                  
CONECT   26   25   54                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   18                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   26                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  110    0
END

RDKit          3D

54 55  0  0  0  0  0  0  0  0999 V2000
    3.1456   -0.9876    0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0970    0.0026    0.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263    1.2843    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3348    1.7204    0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693    3.0669    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637    3.5317    0.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    2.8615   -0.1427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4392    3.3681   -1.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679    3.0164    0.4287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4493    4.4737    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1637    2.4006    1.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    0.9807    2.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6846    0.6910    2.9662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957   -0.6061    3.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7783   -1.0096    3.9861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3879    0.0056    4.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108   -1.6197    2.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149   -2.8948    2.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7035   -1.3638    1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1263   -2.4352    0.5953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1236   -2.2013   -0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819   -0.0571    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253    3.9756   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2213    3.5491   -0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569    2.2147   -0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8347    1.8211   -0.4600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3195   -1.0431    0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7811   -0.8064    1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6541   -1.9564    0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883    1.0297    0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4015    3.3247    1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5007    4.6223    0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3211    1.7849   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947    4.4599   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510    2.9522   -2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034    3.0624   -2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6385    2.4789   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4537    4.9175   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    5.0926    1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755    4.5308    0.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2340    2.4056    2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930    3.0470    2.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    1.5000    3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.7552    4.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6607    0.4681    5.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -0.4686    5.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050   -2.8464    3.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691   -1.5012   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545   -1.8504    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3354   -3.1538   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    0.1838    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6676    5.0210   -0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638    4.2493   -0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    0.8627   -0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 19  1  0
 25 24  2  0
 24 23  1  0
 17 18  1  0
  5  4  1  0
  4  3  2  0
 17 14  1  0
  3  2  1  0
 19 20  1  0
  2  1  1  0
 25 26  1  0
  5 23  2  0
 14 15  1  0
 14 13  2  0
 15 16  1  0
 19 17  2  0
 20 21  1  0
 13 12  1  0
  5  6  1  0
 11  9  1  0
  9  7  1  0
  7  6  1  0
 12 22  2  0
  9 10  1  0
  3 25  1  0
  7  8  1  0
 11 12  1  0
 22 51  1  0
 13 43  1  0
 18 47  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 24 53  1  0
  4 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 26 54  1  0
 23 52  1  0
 11 41  1  0
 11 42  1  0
  9 37  1  6
  7 33  1  6
  6 31  1  0
  6 32  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₅

Average Mass

360.4500 Da

Monoisotopic Mass

360.19367 Da

IUPAC Name

4-[(2R,3S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2,6-dimethoxyphenol

Traditional Name

4-[(2R,3S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2,6-dimethoxyphenol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C1=C([H])C(OC([H])([H])[H])=C(O[H])C(OC([H])([H])[H])=C1[H]

InChI Identifier

InChI=1S/C21H28O5/c1-13(8-15-6-7-17(22)18(10-15)24-3)14(2)9-16-11-19(25-4)21(23)20(12-16)26-5/h6-7,10-14,22-23H,8-9H2,1-5H3/t13-,14+/m0/s1

InChI Key

GFMUBOWRQZASFJ-UONOGXRCSA-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 dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane lignans

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:68161 )
dimethoxybenzene (CHEBI:68161 )
lignan (CHEBI:68161 )

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	4.5	ALOGPS
logP	4.89	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	102.05 m³·mol⁻¹	ChemAxon
Polarizability	39.53 Å³	ChemAxon
Number of Rings	2	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

26629054

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

68161

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 ]
Li, Y., et al. (2011). Li, Y., et al, J. Nat. Prod. 74, 1444 (2011). J. Nat. Prod..

Showing NP-Card for (+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan (NP0036084)

MOL for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D MOL for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D SDF for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D-SDF for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

PDB for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D PDB for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

SMILES for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

INCHI for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

Structure for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D Structure for NP0036084 ((+)-(8S,8'R)-4,4'-dihydroxy-3,3',5'-trimethoxylignan)