NP-MRD: Showing NP-Card for Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid (NP0056430)

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Record Information

Version

1.0

Created at

2022-04-28 02:12:59 UTC

Updated at

2022-04-28 02:12:59 UTC

NP-MRD ID

NP0056430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid

Description

2-[(2R,3R,4S)-8-[(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]Henicosa-2(11),3(8),9,15,17,19-hexaen-7-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]acetic acid belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid is found in Arachniodes carvifolia, Arachniodes exilis, Arachniodes sporadosora, Loxogramme saziran, Polystichum polyblepharum and Polystichum tsus-simense. Based on a literature review very few articles have been published on 2-[(2R,3R,4S)-8-[(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]Henicosa-2(11),3(8),9,15,17,19-hexaen-7-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204122D          

 67 76  0  0  1  0            999 V2000
   -1.6425   10.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0591   11.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622   11.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487   10.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321    9.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   10.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    9.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569    8.7962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3234    9.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2196    9.0776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4331    8.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475    7.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444    8.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475    7.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331    6.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    7.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    7.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    8.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103    7.8682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7103    7.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9959    6.6307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9959    5.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    5.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    4.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    4.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103    4.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103    5.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    5.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393    5.3932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1393    4.5682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4248    4.1557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4248    3.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393    2.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537    3.3307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393    2.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537    4.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537    5.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537    6.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5682    7.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2827    6.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2827    5.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5682    5.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9972    7.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5682    7.8682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    3.3307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331    5.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    6.6307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    8.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    9.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393    9.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537    9.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537    8.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393    7.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5682    9.5182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393   10.3432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180    5.9633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9298    9.9291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749    8.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4906    7.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3085    7.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8108    8.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4951    9.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6771    9.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9973    9.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6287    8.3655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482   10.1619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   12.1827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 30 36  1  6  0  0  0
 29 37  1  6  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 42  1  0  0  0  0
 40 43  1  0  0  0  0
 39 44  1  0  0  0  0
 25 45  1  0  0  0  0
 23 46  1  0  0  0  0
 20 47  1  6  0  0  0
 19 48  1  6  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 48 53  1  0  0  0  0
 51 54  1  0  0  0  0
 50 55  1  0  0  0  0
 15 56  1  0  0  0  0
  9 57  1  6  0  0  0
  8 58  1  1  0  0  0
 58 59  2  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 58 63  1  0  0  0  0
 62 64  1  0  0  0  0
 61 65  1  0  0  0  0
  4 66  1  0  0  0  0
  2 67  1  0  0  0  0
M  END

     RDKit          3D

105114  0  0  0  0  0  0  0  0999 V2000
   -8.1051   -2.6063   -1.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6925   -1.9430   -0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6469   -1.1784   -0.2461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2883   -2.0177   -0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9734   -0.8454    0.5045 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5930   -0.9321    0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2325   -1.3708    2.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119   -1.6913    3.1176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846   -1.4724    2.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818   -1.1458    1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -1.2651    1.9522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2282   -0.7119    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -0.5090   -0.7423 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0157    0.1313   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    1.4901   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9550    2.2978   -0.7619 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    2.1257   -0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230    1.3855    0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3831   -0.0148    0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1777   -0.6095   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -1.9907   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318   -2.6881   -0.7041 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5417   -3.6403   -1.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275   -4.9763   -1.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816   -5.8522   -2.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -5.3085   -3.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -6.1435   -4.7203 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897   -3.9440   -3.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982   -3.4360   -4.7510 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -3.0955   -2.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.8731   -1.4304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6527   -1.6051   -2.7318 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5926   -0.7178    0.6488 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7846   -0.8010   -0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885   -1.8143   -1.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1228   -2.8636   -1.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1222   -1.8648   -1.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0913   -0.9022   -1.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2383   -0.9138   -2.6498 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9227    0.1017   -0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8039    0.1453   -0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7559    1.2104    0.7371 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5406    1.4235    1.4482 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6882    2.4321    2.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6109    3.0843    3.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135    4.0366    4.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0681    4.3928    4.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2803    5.3722    5.4696 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1538    3.7536    3.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4114    4.1365    4.3375 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414    2.8007    2.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6147    1.9936    0.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215    0.0892    1.9118 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0480   -0.5895    2.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6011   -0.6045    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0011   -0.1350   -1.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0909    0.8163   -1.2036 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6575    2.1632   -0.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0541    2.4049    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6611    3.6887    0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8843    4.7590    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4909    6.0381    0.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4860    4.5634   -1.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7170    5.6526   -2.0560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8640    3.2890   -1.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2042    0.4125   -0.2820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4156    1.4418    0.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4332   -0.7583   -0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0656   -3.0001    0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6326   -1.8366   -1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7376   -0.8453    1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1884   -1.6720    3.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554   -1.8020    3.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2912   -1.5812    2.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8305    0.0396   -1.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8381    1.9441   -1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066    3.2096   -0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -3.3168    0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4115   -6.9109   -2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282204122D          

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M  END
> <DATABASE_ID>
NP0056430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](CC(O)=O)C2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C([C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC1=C3[C@@H]3[C@@H](O)[C@@](OC4=C3C(O)=CC(O)=C4)(O1)C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C47H38O20/c48-18-10-26(55)34-30(11-18)66-47(17-3-6-22(51)25(54)9-17)46(63)39(34)37-31(67-47)14-29(58)36-38(41(62)43(65-45(36)37)16-2-5-21(50)24(53)8-16)35-28(57)13-27(56)33-19(12-32(59)60)40(61)42(64-44(33)35)15-1-4-20(49)23(52)7-15/h1-11,13-14,19,38-43,46,48-58,61-63H,12H2,(H,59,60)/t19-,38-,39+,40+,41+,42+,43+,46+,47-/m0/s1

> <INCHI_KEY>
PCFVIHJYMQZKLI-YHWZNFJUSA-N

> <FORMULA>
C47H38O20

> <MOLECULAR_WEIGHT>
922.801

> <EXACT_MASS>
922.195643624

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
87.62624316891939

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2R,3R,4S)-8-[(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaen-7-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]acetic acid

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
4.400469821333333

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.626132112641951

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2548048592504455

> <JCHEM_PKA_STRONGEST_BASIC>
-5.216365311029041

> <JCHEM_POLAR_SURFACE_AREA>
357.44000000000005

> <JCHEM_REFRACTIVITY>
227.44260000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S)-8-[(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaen-7-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -3.066  20.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.977  21.254   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.489  20.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.091  19.367   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.180  18.279   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  18.677   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001  17.907   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.400  16.420   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.470  17.181   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.410  16.945   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.808  15.457   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.142  14.687   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.630  15.086   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.142  13.147   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.808  12.377   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.525  13.147   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.525  14.687   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.859  15.457   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.193  14.687   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.193  13.147   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.859  12.377   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.859  10.837   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.525  10.067   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.525   8.527   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.859   7.757   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.193   8.527   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.193  10.067   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.526  10.837   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.860  10.067   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.860   8.527   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.526   7.757   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.526   6.217   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.860   5.447   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.194   6.217   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.860   3.907   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.194   7.757   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.194  10.837   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.194  12.377   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.527  13.147   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.861  12.377   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.861  10.837   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.527  10.067   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      11.195  13.147   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       8.527  14.687   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       1.859   6.217   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -0.808  10.837   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       4.526  12.377   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.526  15.457   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.526  16.997   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.860  17.767   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.194  16.997   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       7.194  15.457   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.860  14.687   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       8.527  17.767   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       5.860  19.307   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -1.714  11.131   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -1.736  18.534   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      -5.926  16.219   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -6.516  14.796   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -8.043  14.595   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -8.980  15.817   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -8.391  17.239   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -6.864  17.440   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      -9.328  18.461   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0     -10.507  15.616   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       1.397  18.969   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      -2.376  22.741   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   67                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   66                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13   58                                             
CONECT    9    8   10   57                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   56                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   11   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   48                                                  
CONECT   20   19   21   47                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   46                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   45                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   22   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31   36                                                  
CONECT   31   30   26   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   30                                                            
CONECT   37   29   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41   37                                                       
CONECT   43   40                                                            
CONECT   44   39                                                            
CONECT   45   25                                                            
CONECT   46   23                                                            
CONECT   47   20                                                            
CONECT   48   19   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   55                                                  
CONECT   51   50   52   54                                                  
CONECT   52   51   53                                                       
CONECT   53   52   48                                                       
CONECT   54   51                                                            
CONECT   55   50                                                            
CONECT   56   15                                                            
CONECT   57    9                                                            
CONECT   58    8   59   63                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   65                                                  
CONECT   62   61   63   64                                                  
CONECT   63   62   58                                                       
CONECT   64   62                                                            
CONECT   65   61                                                            
CONECT   66    4                                                            
CONECT   67    2                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  152    0
END

View in JSmol

Synonyms

Value	Source
2-[(2R,3R,4S)-8-[(1R,5R,6R,7S,13S,21R)-5,13-Bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.0,.0,.0,]henicosa-2(11),3(8),9,15,17,19-hexaen-7-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]acetate	Generator

Chemical Formula

C₄₇H₃₈O₂₀

Average Mass

922.8010 Da

Monoisotopic Mass

922.19564 Da

IUPAC Name

2-[(2R,3R,4S)-8-[(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaen-7-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]acetic acid

Traditional Name

[(2R,3R,4S)-8-[(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaen-7-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]acetic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](CC(O)=O)C2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C([C@@H]1[C@@H](O)[C@H](OC3=C1C(O)=CC1=C3[C@@H]3[C@@H](O)[C@@](OC4=C3C(O)=CC(O)=C4)(O1)C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)=C(O)C=C2O

InChI Identifier

InChI=1S/C47H38O20/c48-18-10-26(55)34-30(11-18)66-47(17-3-6-22(51)25(54)9-17)46(63)39(34)37-31(67-47)14-29(58)36-38(41(62)43(65-45(36)37)16-2-5-21(50)24(53)8-16)35-28(57)13-27(56)33-19(12-32(59)60)40(61)42(64-44(33)35)15-1-4-20(49)23(52)7-15/h1-11,13-14,19,38-43,46,48-58,61-63H,12H2,(H,59,60)/t19-,38-,39+,40+,41+,42+,43+,46+,47-/m0/s1

InChI Key

PCFVIHJYMQZKLI-YHWZNFJUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Arachniodes carvifolia	LOTUS Database	35616633
Arachniodes exilis	Plant	KNApSAcK
Arachniodes sporadosora	Plant	KNApSAcK
Loxogramme saziran	Plant	KNApSAcK
Polystichum polyblepharum	Plant	KNApSAcK
Polystichum tsus-simense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

B-type proanthocyanidin
A-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Pyranoflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Pyranochromene
Chromane
Benzopyran
1-benzopyran
Catechol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Ether
Organoheterocyclic compound
Polyol
Acetal
Monocarboxylic acid or derivatives
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen 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	3.37	ALOGPS
logP	4.4	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.25	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	357.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	227.44 m³·mol⁻¹	ChemAxon
Polarizability	87.63 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163087453

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid (NP0056430)

MOL for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)

3D MOL for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)

3D SDF for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)

3D-SDF for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)

PDB for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)

3D PDB for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)

SMILES for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)

INCHI for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)

Structure for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)

3D Structure for NP0056430 (Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-dryopteric acid)