NP-MRD: Showing NP-Card for marchantin C (NP0039799)

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Record Information

Version

2.0

Created at

2021-06-20 22:07:36 UTC

Updated at

2021-06-30 00:13:20 UTC

NP-MRD ID

NP0039799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

marchantin C

Provided By

JEOL Database JEOL Logo

Description

Marchantin C belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. marchantin C is found in Dumortiera hirsuta, Marchantia chenopoda, Marchantia paleacea, Marchantia polymorpha, Marchantia sp., Monoclea forsteri, Monoclea gottschei, Reboulia hemisphaerica, Schistochila glaucescens and Jungermannia infusca. marchantin C was first documented in 2015 (PMID: 26055979). Based on a literature review a small amount of articles have been published on Marchantin C (PMID: 31103748) (PMID: 28222318) (PMID: 30807033) (PMID: 27318123).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100073D          

 56 60  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212100073D          

 56 60  0  0  0  0            999 V2000
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    4.2619   -0.2353   -1.6580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3346    1.8935   -4.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    2.8089   -5.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7152    1.7222   -3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628   -0.6873   -1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4545   -1.6064   -2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5646   -1.4993    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    2.7534    0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    2.6311   -1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7625    0.0073    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054    1.6817    1.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -0.3491    3.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1688   -0.4610    2.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7624    1.3843    5.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489    3.2535    6.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012    4.3631    5.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131    3.3474    2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3231   -0.1696    3.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486   -1.4050    3.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9590   -1.0757    1.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817    1.7637    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6338    0.3069   -0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6794    1.6623   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105   -1.2367   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -0.3977   -2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 29 30  2  0  0  0  0
  6  5  1  0  0  0  0
 11 12  2  0  0  0  0
  5  4  2  0  0  0  0
 30 25  1  0  0  0  0
  4  3  1  0  0  0  0
 12 13  1  0  0  0  0
  3  2  2  0  0  0  0
  2  7  1  0  0  0  0
 26 27  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
  5 32  1  0  0  0  0
 16 17  1  0  0  0  0
 14  9  1  0  0  0  0
 17 18  2  0  0  0  0
 28 27  2  0  0  0  0
 18 19  1  0  0  0  0
  9 10  2  0  0  0  0
 19 20  2  0  0  0  0
 10 11  1  0  0  0  0
 20 21  1  0  0  0  0
 28 29  1  0  0  0  0
 21 23  2  0  0  0  0
 23 17  1  0  0  0  0
 23 24  1  0  0  0  0
  9  8  1  0  0  0  0
  2  1  1  0  0  0  0
 25 24  1  0  0  0  0
 21 22  1  0  0  0  0
  8  7  1  0  0  0  0
 29 31  1  0  0  0  0
 25 26  2  0  0  0  0
 32 31  1  0  0  0  0
 26 49  1  0  0  0  0
 30 52  1  0  0  0  0
 28 51  1  0  0  0  0
 27 50  1  0  0  0  0
 11 38  1  0  0  0  0
 13 39  1  0  0  0  0
 14 40  1  0  0  0  0
 10 37  1  0  0  0  0
  6 36  1  0  0  0  0
  4 35  1  0  0  0  0
  3 34  1  0  0  0  0
 15 41  1  0  0  0  0
 15 42  1  0  0  0  0
 16 43  1  0  0  0  0
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 18 45  1  0  0  0  0
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 20 47  1  0  0  0  0
  1 33  1  0  0  0  0
 22 48  1  0  0  0  0
 31 53  1  0  0  0  0
 31 54  1  0  0  0  0
 32 55  1  0  0  0  0
 32 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039799

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C([H])=C1OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C(O[H])=C1OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O4/c29-25-16-12-21-8-7-20-3-1-5-24(17-20)32-28-22(4-2-6-26(28)30)13-9-19-10-14-23(15-11-19)31-27(25)18-21/h1-6,10-12,14-18,29-30H,7-9,13H2

> <INCHI_KEY>
BLRFPCOIKKIKNC-UHFFFAOYSA-N

> <FORMULA>
C28H24O4

> <MOLECULAR_WEIGHT>
424.496

> <EXACT_MASS>
424.167459253

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.759510899787564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,15-dioxapentacyclo[22.2.2.1^{3,7}.1^{10,14}.0^{16,21}]triaconta-1(26),3(30),4,6,10(29),11,13,16,18,20,24,27-dodecaene-4,17-diol

> <ALOGPS_LOGP>
6.39

> <JCHEM_LOGP>
7.466169106666667

> <ALOGPS_LOGS>
-5.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.97620841007556

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.35617342191392

> <JCHEM_PKA_STRONGEST_BASIC>
-3.424911602387287

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
125.1198

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.33e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,15-dioxapentacyclo[22.2.2.1^{3,7}.1^{10,14}.0^{16,21}]triaconta-1(26),3(30),4,6,10(29),11,13,16,18,20,24,27-dodecaene-4,17-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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   -0.0992    1.9997    3.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548    1.6168    1.9085 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6259    0.8915    1.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739   -0.0025    2.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1744   -0.7071    2.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0254   -0.5185    1.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6873    0.3789    0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    1.0720    0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    0.5909   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619   -0.2353   -1.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5628   -0.6873   -1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1688   -0.4610    2.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3012    4.3631    5.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131    3.3474    2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3231   -0.1696    3.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486   -1.4050    3.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9590   -1.0757    1.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817    1.7637    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6338    0.3069   -0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6794    1.6623   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105   -1.2367   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -0.3977   -2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0
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  6  5  1  0
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 12 15  1  0
 13 14  2  0
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  5 32  1  0
 16 17  1  0
 14  9  1  0
 17 18  2  0
 28 27  2  0
 18 19  1  0
  9 10  2  0
 19 20  2  0
 10 11  1  0
 20 21  1  0
 28 29  1  0
 21 23  2  0
 23 17  1  0
 23 24  1  0
  9  8  1  0
  2  1  1  0
 25 24  1  0
 21 22  1  0
  8  7  1  0
 29 31  1  0
 25 26  2  0
 32 31  1  0
 26 49  1  0
 30 52  1  0
 28 51  1  0
 27 50  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 10 37  1  0
  6 36  1  0
  4 35  1  0
  3 34  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
  1 33  1  0
 22 48  1  0
 31 53  1  0
 31 54  1  0
 32 55  1  0
 32 56  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       0.536   2.302  -5.107  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.412   1.684  -4.260  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.749   2.050  -4.316  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.668   1.431  -3.465  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.254   0.437  -2.563  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.899   0.082  -2.514  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.978   0.721  -3.350  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.360   0.390  -3.352  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.989   0.497  -2.133  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.538  -0.656  -1.578  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.167  -0.589  -0.336  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.274   0.635   0.344  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.763   1.795  -0.253  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.119   1.728  -1.489  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.897   0.683   1.719  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.932   0.233   2.827  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.272   1.378   3.564  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.854   1.845   4.757  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.286   2.905   5.468  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.135   3.527   4.992  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.446   3.082   3.811  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.546   3.760   3.366  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.099   2.000   3.107  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.455   1.617   1.909  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.626   0.892   1.938  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.974  -0.003   2.950  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.174  -0.707   2.865  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.025  -0.519   1.774  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.687   0.379   0.752  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.474   1.072   0.839  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.622   0.591  -0.417  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.262  -0.235  -1.658  0.00  0.00           C+0
HETATM   33  H   UNK     0      -0.335   1.894  -4.945  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.077   2.809  -5.020  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.715   1.722  -3.519  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.563  -0.687  -1.823  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.454  -1.606  -2.097  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.565  -1.499   0.107  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.837   2.753   0.257  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.713   2.631  -1.935  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.763   0.007   1.709  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.305   1.682   1.918  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.505  -0.349   3.561  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.169  -0.461   2.454  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.762   1.384   5.142  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.749   3.253   6.388  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.301   4.363   5.531  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.813   3.347   2.525  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.323  -0.170   3.802  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.449  -1.405   3.652  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.959  -1.076   1.732  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.182   1.764   0.051  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.634   0.307  -0.097  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.679   1.662  -0.648  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.910  -1.237  -1.378  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.174  -0.398  -2.248  0.00  0.00           H+0
CONECT    1    2   33                                                       
CONECT    2    3    7    1                                                  
CONECT    3    4    2   34                                                  
CONECT    4    5    3   35                                                  
CONECT    5    6    4   32                                                  
CONECT    6    7    5   36                                                  
CONECT    7    6    2    8                                                  
CONECT    8    9    7                                                       
CONECT    9   14   10    8                                                  
CONECT   10    9   11   37                                                  
CONECT   11   12   10   38                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14   39                                                  
CONECT   14   13    9   40                                                  
CONECT   15   12   16   41   42                                             
CONECT   16   15   17   43   44                                             
CONECT   17   16   18   23                                                  
CONECT   18   17   19   45                                                  
CONECT   19   18   20   46                                                  
CONECT   20   19   21   47                                                  
CONECT   21   20   23   22                                                  
CONECT   22   21   48                                                       
CONECT   23   21   17   24                                                  
CONECT   24   23   25                                                       
CONECT   25   30   24   26                                                  
CONECT   26   27   25   49                                                  
CONECT   27   26   28   50                                                  
CONECT   28   27   29   51                                                  
CONECT   29   30   28   31                                                  
CONECT   30   29   25   52                                                  
CONECT   31   29   32   53   54                                             
CONECT   32    5   31   55   56                                             
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    6                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   22                                                            
CONECT   49   26                                                            
CONECT   50   27                                                            
CONECT   51   28                                                            
CONECT   52   30                                                            
CONECT   53   31                                                            
CONECT   54   31                                                            
CONECT   55   32                                                            
CONECT   56   32                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  120    0
END

RDKit          3D

56 60  0  0  0  0  0  0  0  0999 V2000
    0.5361    2.3022   -5.1072 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119    1.6844   -4.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7495    2.0497   -4.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6682    1.4307   -3.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    0.4366   -2.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986    0.0824   -2.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9779    0.7206   -3.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3604    0.3897   -3.3520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893    0.4965   -2.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5384   -0.6562   -1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672   -0.5888   -0.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738    0.6351    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7627    1.7952   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192    1.7277   -1.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8967    0.6830    1.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317    0.2331    2.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723    1.3778    3.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8544    1.8449    4.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2863    2.9053    5.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1350    3.5270    4.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    3.0822    3.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5463    3.7601    3.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0992    1.9997    3.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548    1.6168    1.9085 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6259    0.8915    1.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739   -0.0025    2.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1744   -0.7071    2.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0254   -0.5185    1.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6873    0.3789    0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    1.0720    0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    0.5909   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619   -0.2353   -1.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    1.8935   -4.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    2.8089   -5.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7152    1.7222   -3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628   -0.6873   -1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4545   -1.6064   -2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5646   -1.4993    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    2.7534    0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    2.6311   -1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7625    0.0073    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054    1.6817    1.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -0.3491    3.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1688   -0.4610    2.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7624    1.3843    5.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489    3.2535    6.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012    4.3631    5.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8131    3.3474    2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3231   -0.1696    3.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486   -1.4050    3.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9590   -1.0757    1.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817    1.7637    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6338    0.3069   -0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6794    1.6623   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105   -1.2367   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -0.3977   -2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0
 29 30  2  0
  6  5  1  0
 11 12  2  0
  5  4  2  0
 30 25  1  0
  4  3  1  0
 12 13  1  0
  3  2  2  0
  2  7  1  0
 26 27  1  0
 12 15  1  0
 13 14  2  0
 15 16  1  0
  5 32  1  0
 16 17  1  0
 14  9  1  0
 17 18  2  0
 28 27  2  0
 18 19  1  0
  9 10  2  0
 19 20  2  0
 10 11  1  0
 20 21  1  0
 28 29  1  0
 21 23  2  0
 23 17  1  0
 23 24  1  0
  9  8  1  0
  2  1  1  0
 25 24  1  0
 21 22  1  0
  8  7  1  0
 29 31  1  0
 25 26  2  0
 32 31  1  0
 26 49  1  0
 30 52  1  0
 28 51  1  0
 27 50  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 10 37  1  0
  6 36  1  0
  4 35  1  0
  3 34  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
  1 33  1  0
 22 48  1  0
 31 53  1  0
 31 54  1  0
 32 55  1  0
 32 56  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₈H₂₄O₄

Average Mass

424.4960 Da

Monoisotopic Mass

424.16746 Da

IUPAC Name

2,15-dioxapentacyclo[22.2.2.1^{3,7}.1^{10,14}.0^{16,21}]triaconta-1(26),3(30),4,6,10(29),11,13,16,18,20,24,27-dodecaene-4,17-diol

Traditional Name

2,15-dioxapentacyclo[22.2.2.1^{3,7}.1^{10,14}.0^{16,21}]triaconta-1(26),3(30),4,6,10(29),11,13,16,18,20,24,27-dodecaene-4,17-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C2C([H])=C1OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C(O[H])=C1OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])C2([H])[H]

InChI Identifier

InChI=1S/C28H24O4/c29-25-16-12-21-8-7-20-3-1-5-24(17-20)32-28-22(4-2-6-26(28)30)13-9-19-10-14-23(15-11-19)31-27(25)18-21/h1-6,10-12,14-18,29-30H,7-9,13H2

InChI Key

BLRFPCOIKKIKNC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Dumortiera hirsuta	LOTUS Database	35616633
Marchantia chenopoda	LOTUS Database	35616633
Marchantia paleacea	LOTUS Database	35616633
Marchantia polymorpha	Plant	KNApSAcK
Marchantia sp.	JEOL database	Tori, M., et al, Tetrahedron Lett. 39, 4735 (1985)
Monoclea forsteri	Plant	KNApSAcK
Monoclea gottschei	Plant	KNApSAcK
Reboulia hemisphaerica	LOTUS Database	35616633
Schistochila glaucescens	Plant	KNApSAcK
Solenostoma infuscum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Oxyneolignan skeleton
Diaryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.39	ALOGPS
logP	7.47	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	8.36	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	125.12 m³·mol⁻¹	ChemAxon
Polarizability	45.76 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

4477608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319272

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang XL, Ji XT, Sun B, Qian LL, Hu XL, Lou HX, Yuan HQ: Anti-cancer effect of marchantin C via inducing lung cancer cellular senescence associated with less secretory phenotype. Biochim Biophys Acta Gen Subj. 2019 Oct;1863(10):1443-1457. doi: 10.1016/j.bbagen.2019.05.006. Epub 2019 May 16. [PubMed:31103748 ]
Sun B, Li L, Hu QW, Zheng HB, Tang H, Niu HM, Yuan HQ, Lou HX: Design, synthesis, biological evaluation and molecular modeling study of novel macrocyclic bisbibenzyl analogues as antitubulin agents. Eur J Med Chem. 2017 Mar 31;129:186-208. doi: 10.1016/j.ejmech.2017.02.021. Epub 2017 Feb 10. [PubMed:28222318 ]
Anchang KY, Novakovic M, Bukvicki D, Asakawa Y: Bis-bibenzyls from the Cameroon Liverwort Marchantia debilis. Nat Prod Commun. 2016 Sep;11(9):1317-1318. [PubMed:30807033 ]
Sun B, Li L, Hu QW, Xie F, Zheng HB, Niu HM, Yuan HQ, Lou HX: Design, synthesis and biological evaluation of novel macrocyclic bisbibenzyl analogues as tubulin polymerization inhibitors. Eur J Med Chem. 2016 Oct 4;121:484-499. doi: 10.1016/j.ejmech.2016.06.007. Epub 2016 Jun 8. [PubMed:27318123 ]
Kageyama A, Ishizaki K, Kohchi T, Matsuura H, Takahashi K: Abscisic acid induces biosynthesis of bisbibenzyls and tolerance to UV-C in the liverwort Marchantia polymorpha. Phytochemistry. 2015 Sep;117:547-553. doi: 10.1016/j.phytochem.2015.05.009. Epub 2015 Jun 5. [PubMed:26055979 ]
Tori, M., et al. (1985). Tori, M., et al, Tetrahedron Lett. 39, 4735 (1985). Tetrahedron Lett.

Showing NP-Card for marchantin C (NP0039799)

MOL for NP0039799 (marchantin C)

3D MOL for NP0039799 (marchantin C)

3D SDF for NP0039799 (marchantin C)

3D-SDF for NP0039799 (marchantin C)

PDB for NP0039799 (marchantin C)

3D PDB for NP0039799 (marchantin C)

SMILES for NP0039799 (marchantin C)

INCHI for NP0039799 (marchantin C)

Structure for NP0039799 (marchantin C)

3D Structure for NP0039799 (marchantin C)