NP-MRD: Showing NP-Card for (+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan (NP0036086)

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Record Information

Version

1.0

Created at

2021-06-20 19:21:13 UTC

Updated at

2021-06-30 00:07:33 UTC

NP-MRD ID

NP0036086

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan

Provided By

JEOL Database JEOL Logo

Description

(+)-(8S,8'R)-9-acetoxy-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)-9-acetoxy-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)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121213D          

 60 61  0  0  0  0            999 V2000
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    0.4531   -0.3159   -2.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0019   -0.8582   -0.2212 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1016   -1.8058    3.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3413   -0.8478    3.9035 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5  4  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121213D          

 60 61  0  0  0  0            999 V2000
   -0.2369    1.0075   -5.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8100   -2.0228   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5090   -2.2043   -2.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -1.4423   -3.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714   -1.6396   -5.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3211    1.4065   -6.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1522    0.4459   -4.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.4131   -2.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492   -1.6630   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    0.0695   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359   -1.8650    1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135    0.1615    2.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3307   -0.7039    3.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7534   -2.9752    3.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3336   -3.1881    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095   -3.9159    3.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4850    0.1709    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3260   -1.2949    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5740   -0.2474    3.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8653    0.3748    2.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    2.2243    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    1.6783    2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053    2.3402   -0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    3.5190   -4.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7741    2.1267   -3.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4058    3.6962   -2.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0657    4.5805   -2.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2049    4.0739    0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    4.1766    1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2955    2.5903    1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960    2.5836    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -2.6439   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -2.9403   -2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4651   -1.0237   -5.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
 21 18  1  0  0  0  0
  3  2  1  0  0  0  0
 23 24  1  0  0  0  0
  2  1  1  0  0  0  0
 29 30  1  0  0  0  0
  5 27  2  0  0  0  0
 18 19  1  0  0  0  0
 18 17  2  0  0  0  0
 19 20  1  0  0  0  0
 23 21  2  0  0  0  0
 24 25  1  0  0  0  0
 17 16  1  0  0  0  0
  5  6  1  0  0  0  0
 15 13  1  0  0  0  0
 13  7  1  0  0  0  0
  7  6  1  0  0  0  0
 16 26  2  0  0  0  0
 13 14  1  0  0  0  0
  3 29  1  0  0  0  0
  7  8  1  0  0  0  0
 15 16  1  0  0  0  0
 26 23  1  0  0  0  0
 29 28  2  0  0  0  0
  9 10  1  0  0  0  0
 28 27  1  0  0  0  0
 10 11  1  0  0  0  0
 21 22  1  0  0  0  0
 10 12  2  0  0  0  0
  8  9  1  0  0  0  0
 26 57  1  0  0  0  0
 17 49  1  0  0  0  0
 22 53  1  0  0  0  0
 20 50  1  0  0  0  0
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 20 52  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
 28 59  1  0  0  0  0
  4 34  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 30 60  1  0  0  0  0
 27 58  1  0  0  0  0
 15 47  1  0  0  0  0
 15 48  1  0  0  0  0
 13 43  1  6  0  0  0
  7 37  1  1  0  0  0
  6 35  1  0  0  0  0
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 14 44  1  0  0  0  0
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 14 46  1  0  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036086

> <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])OC(=O)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/C23H30O7/c1-14(8-17-11-21(28-4)23(26)22(12-17)29-5)18(13-30-15(2)24)9-16-6-7-19(25)20(10-16)27-3/h6-7,10-12,14,18,25-26H,8-9,13H2,1-5H3/t14-,18-/m1/s1

> <INCHI_KEY>
TZDZTWKCXMIGJR-RDTXWAMCSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.52285126685939

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-methylbutyl acetate

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.975040113999999

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.137442810267105

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.498102599306632

> <JCHEM_PKA_STRONGEST_BASIC>
-4.420992175732088

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
113.05000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-methylbutyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
   -0.2369    1.0075   -5.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1016   -1.8058    3.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236   -3.0567    3.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9834   -0.2750    2.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5464    1.6388    1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8166    2.3711    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3703    3.6570   -3.0375 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1908    4.3728   -2.6309 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8100   -2.0228   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5090   -2.2043   -2.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -1.4423   -3.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714   -1.6396   -5.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3095   -3.9159    3.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4850    0.1709    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3260   -1.2949    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5740   -0.2474    3.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8653    0.3748    2.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    2.2243    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    1.6783    2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053    2.3402   -0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    3.5190   -4.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7741    2.1267   -3.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4058    3.6962   -2.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0657    4.5805   -2.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2049    4.0739    0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    4.1766    1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9960    2.5836    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -2.6439   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -2.9403   -2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4651   -1.0237   -5.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  2  0
 21 18  1  0
  3  2  1  0
 23 24  1  0
  2  1  1  0
 29 30  1  0
  5 27  2  0
 18 19  1  0
 18 17  2  0
 19 20  1  0
 23 21  2  0
 24 25  1  0
 17 16  1  0
  5  6  1  0
 15 13  1  0
 13  7  1  0
  7  6  1  0
 16 26  2  0
 13 14  1  0
  3 29  1  0
  7  8  1  0
 15 16  1  0
 26 23  1  0
 29 28  2  0
  9 10  1  0
 28 27  1  0
 10 11  1  0
 21 22  1  0
 10 12  2  0
  8  9  1  0
 26 57  1  0
 17 49  1  0
 22 53  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 28 59  1  0
  4 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 60  1  0
 27 58  1  0
 15 47  1  0
 15 48  1  0
 13 43  1  6
  7 37  1  1
  6 35  1  0
  6 36  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  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      -0.237   1.008  -5.061  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.907   0.160  -5.022  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.138  -0.502  -3.844  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.453  -0.316  -2.642  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.792  -1.061  -1.495  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.002  -0.858  -0.221  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.788  -0.865   1.116  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.203  -0.742   2.291  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.060  -1.895   2.311  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.102  -1.806   3.182  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.924  -3.057   3.129  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.341  -0.848   3.904  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.950   0.179   1.189  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.983  -0.275   2.238  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.546   1.639   1.513  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.817   2.371   0.413  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.474   2.660  -0.797  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.818   3.337  -1.826  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.370   3.657  -3.038  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.698   3.217  -3.288  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.512   3.725  -1.625  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.191   4.373  -2.631  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.183   3.465  -0.422  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.481   3.909  -0.375  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.198   3.664   0.831  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.510   2.794   0.598  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.810  -2.023  -1.587  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.509  -2.204  -2.780  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.172  -1.442  -3.889  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.871  -1.640  -5.049  0.00  0.00           O+0
HETATM   31  H   UNK     0      -0.321   1.407  -6.076  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.126   1.855  -4.380  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.152   0.446  -4.846  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.349   0.413  -2.569  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.749  -1.663  -0.202  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.578   0.070  -0.294  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.236  -1.865   1.196  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.814   0.162   2.182  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.331  -0.704   3.246  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.753  -2.975   3.837  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.334  -3.188   2.125  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.309  -3.916   3.410  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.485   0.171   0.232  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.326  -1.295   2.033  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.574  -0.247   3.252  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.865   0.375   2.216  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.453   2.224   1.724  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.970   1.678   2.445  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.505   2.340  -0.911  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.963   3.519  -4.306  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.774   2.127  -3.235  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.406   3.696  -2.604  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.066   4.580  -2.253  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.205   4.074   0.709  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.730   4.177   1.678  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.296   2.590   1.020  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.996   2.584   1.545  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.072  -2.644  -0.735  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.304  -2.940  -2.848  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.465  -1.024  -5.690  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   29                                                  
CONECT    4    5    3   34                                                  
CONECT    5    4   27    6                                                  
CONECT    6    5    7   35   36                                             
CONECT    7   13    6    8   37                                             
CONECT    8    7    9   38   39                                             
CONECT    9   10    8                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   40   41   42                                             
CONECT   12   10                                                            
CONECT   13   15    7   14   43                                             
CONECT   14   13   44   45   46                                             
CONECT   15   13   16   47   48                                             
CONECT   16   17   26   15                                                  
CONECT   17   18   16   49                                                  
CONECT   18   21   19   17                                                  
CONECT   19   18   20                                                       
CONECT   20   19   50   51   52                                             
CONECT   21   18   23   22                                                  
CONECT   22   21   53                                                       
CONECT   23   24   21   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   54   55   56                                             
CONECT   26   16   23   57                                                  
CONECT   27    5   28   58                                                  
CONECT   28   29   27   59                                                  
CONECT   29   30    3   28                                                  
CONECT   30   29   60                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   17                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   20                                                            
CONECT   53   22                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   30                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  122    0
END

RDKit          3D

60 61  0  0  0  0  0  0  0  0999 V2000
   -0.2369    1.0075   -5.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9073    0.1603   -5.0222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1384   -0.5023   -3.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531   -0.3159   -2.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922   -1.0612   -1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0019   -0.8582   -0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -0.8650    1.1162 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2034   -0.7416    2.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597   -1.8950    2.3105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016   -1.8058    3.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236   -3.0567    3.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413   -0.8478    3.9035 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501    0.1792    1.1893 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9834   -0.2750    2.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5464    1.6388    1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8166    2.3711    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    2.6601   -0.7968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175    3.3375   -1.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703    3.6570   -3.0375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6980    3.2173   -3.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5116    3.7248   -1.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908    4.3728   -2.6309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1829    3.4645   -0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4809    3.9089   -0.3745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1976    3.6643    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096    2.7944    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8100   -2.0228   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5090   -2.2043   -2.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -1.4423   -3.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714   -1.6396   -5.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3211    1.4065   -6.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1260    1.8546   -4.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522    0.4459   -4.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.4131   -2.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492   -1.6630   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    0.0695   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359   -1.8650    1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135    0.1615    2.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3307   -0.7039    3.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7534   -2.9752    3.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3336   -3.1881    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095   -3.9159    3.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4850    0.1709    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3260   -1.2949    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5740   -0.2474    3.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8653    0.3748    2.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    2.2243    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    1.6783    2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053    2.3402   -0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    3.5190   -4.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7741    2.1267   -3.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4058    3.6962   -2.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0657    4.5805   -2.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2049    4.0739    0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    4.1766    1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2955    2.5903    1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960    2.5836    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -2.6439   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -2.9403   -2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4651   -1.0237   -5.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  2  0
 21 18  1  0
  3  2  1  0
 23 24  1  0
  2  1  1  0
 29 30  1  0
  5 27  2  0
 18 19  1  0
 18 17  2  0
 19 20  1  0
 23 21  2  0
 24 25  1  0
 17 16  1  0
  5  6  1  0
 15 13  1  0
 13  7  1  0
  7  6  1  0
 16 26  2  0
 13 14  1  0
  3 29  1  0
  7  8  1  0
 15 16  1  0
 26 23  1  0
 29 28  2  0
  9 10  1  0
 28 27  1  0
 10 11  1  0
 21 22  1  0
 10 12  2  0
  8  9  1  0
 26 57  1  0
 17 49  1  0
 22 53  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 28 59  1  0
  4 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 60  1  0
 27 58  1  0
 15 47  1  0
 15 48  1  0
 13 43  1  6
  7 37  1  1
  6 35  1  0
  6 36  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₇

Average Mass

418.4860 Da

Monoisotopic Mass

418.19915 Da

IUPAC Name

(2S,3R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-methylbutyl acetate

Traditional Name

(2S,3R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-methylbutyl acetate

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])OC(=O)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/C23H30O7/c1-14(8-17-11-21(28-4)23(26)22(12-17)29-5)18(13-30-15(2)24)9-16-6-7-19(25)20(10-16)27-3/h6-7,10-12,14,18,25-26H,8-9,13H2,1-5H3/t14-,18-/m1/s1

InChI Key

TZDZTWKCXMIGJR-RDTXWAMCSA-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

Not Available

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

Classification

Not classified

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	3.75	ALOGPS
logP	3.98	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	113.05 m³·mol⁻¹	ChemAxon
Polarizability	44.52 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

26629056

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

68163

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)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan (NP0036086)

MOL for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D MOL for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D SDF for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D-SDF for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

PDB for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D PDB for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

SMILES for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

INCHI for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

Structure for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)

3D Structure for NP0036086 ((+)-(8S,8'R)-9-acetoxy-4,4'-dihydroxy-3,3',5'-trimethoxylignan)