NP-MRD: Showing NP-Card for methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate (NP0226856)

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Record Information

Version

2.0

Created at

2022-09-06 06:01:22 UTC

Updated at

2022-09-06 06:01:22 UTC

NP-MRD ID

NP0226856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate

Description

Methyl (5R)-5-{2-hydroxy-6-methoxy-4-[(E)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate 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. Based on a literature review very few articles have been published on methyl (5R)-5-{2-hydroxy-6-methoxy-4-[(E)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062208012D          

 33 35  0  0  1  0            999 V2000
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  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
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  2  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
   -2.9080    5.9059   -2.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8598    4.4945   -2.6926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9680    3.9399   -1.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081    4.6930   -0.4449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082    2.4575   -1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306    2.1219    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9940    0.6714    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9782   -0.2307    0.0093 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4117   -1.6330    0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133   -2.3364   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -3.6506    0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073   -4.2461    1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5995   -5.4884    1.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632   -6.1687    1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1303   -5.5952    0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7242   -4.3628   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548   -0.1722    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1592   -1.3758   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965   -2.4739   -0.5837 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051   -1.4530   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753   -0.3489    0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -0.5079    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5262    0.4842    0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.3705    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7080    1.5383    0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0936    1.5243    0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7674    0.3401    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0463   -0.7997    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6571   -0.7853    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501    0.8186    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2437    0.8677    0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3042    2.0801    0.6920 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4806    3.1849    1.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5989    6.1478   -3.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8809    6.2547   -3.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1846    6.3933   -1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934    2.0315   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8237    2.0582   -1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5233    2.7654    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1727    2.4300    0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9994    0.2778   -0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2800    0.5958    1.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2088   -0.4292   -1.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8927   -1.9362    1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7734   -1.8969   -0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -3.7473    2.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1429   -5.9259    2.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8726   -7.1414    1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8989   -6.1689   -0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -3.9072   -1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346   -3.3399   -0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397   -2.3855   -0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1655   -1.4617   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961    1.4590    0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2109    2.4895    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6382    2.4438    0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8597    0.3474    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5325   -1.7420   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1203   -1.6935   -0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2109    1.7015    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1559    3.4579    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725    2.9983    1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1321    4.0599    1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 21 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 16 11  1  0
 31 17  1  0
 29 24  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  6
  9 44  1  0
 10 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 19 51  1  0
 20 52  1  0
 22 53  1  0
 23 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 33 61  1  0
 33 62  1  0
 33 63  1  0
M  END


  Mrv1652309062208012D          

 33 35  0  0  1  0            999 V2000
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
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 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
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 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  2  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCC[C@H](\C=C\C1=CC=CC=C1)C1=C(O)C=C(\C=C\C2=CC=CC=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C29H30O4/c1-32-27-21-24(17-16-22-10-5-3-6-11-22)20-26(30)29(27)25(14-9-15-28(31)33-2)19-18-23-12-7-4-8-13-23/h3-8,10-13,16-21,25,30H,9,14-15H2,1-2H3/b17-16+,19-18+/t25-/m1/s1

> <INCHI_KEY>
TVJWBELILIIXPA-NVAYANGASA-N

> <FORMULA>
C29H30O4

> <MOLECULAR_WEIGHT>
442.555

> <EXACT_MASS>
442.214409446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.34268837549594

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (5R,6E)-5-{2-hydroxy-6-methoxy-4-[(E)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate

> <JCHEM_LOGP>
6.999937346666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.65907915543032

> <JCHEM_PKA_STRONGEST_BASIC>
-4.847407530025187

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
134.7988

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5R,6E)-5-{2-hydroxy-6-methoxy-4-[(E)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.669 -16.940   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    8   18   31                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   21   31                                                       
CONECT   31   30   17   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl (5R)-5-{2-hydroxy-6-methoxy-4-[(e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoic acid	Generator

Chemical Formula

C₂₉H₃₀O₄

Average Mass

442.5550 Da

Monoisotopic Mass

442.21441 Da

IUPAC Name

methyl (5R,6E)-5-{2-hydroxy-6-methoxy-4-[(E)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate

Traditional Name

methyl (5R,6E)-5-{2-hydroxy-6-methoxy-4-[(E)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)CCC[C@H](\C=C\C1=CC=CC=C1)C1=C(O)C=C(\C=C\C2=CC=CC=C2)C=C1OC

InChI Identifier

InChI=1S/C29H30O4/c1-32-27-21-24(17-16-22-10-5-3-6-11-22)20-26(30)29(27)25(14-9-15-28(31)33-2)19-18-23-12-7-4-8-13-23/h3-8,10-13,16-21,25,30H,9,14-15H2,1-2H3/b17-16+,19-18+/t25-/m1/s1

InChI Key

TVJWBELILIIXPA-NVAYANGASA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Norlignan skeleton
Linear 1,3-diarylpropanoid
Cinnamylphenol
Stilbene
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Methoxyphenol
Monoterpenoid
Anisole
Methoxybenzene
Phenoxy compound
Styrene
Phenol ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Fatty acid methyl ester
Phenol
Alkyl aryl ether
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Methyl ester
Carboxylic acid ester
Ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	7	ChemAxon
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	134.8 m³·mol⁻¹	ChemAxon
Polarizability	51.34 Å³	ChemAxon
Number of Rings	3	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

163194410

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate (NP0226856)

MOL for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)

3D MOL for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)

3D SDF for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)

3D-SDF for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)

PDB for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)

3D PDB for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)

SMILES for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)

INCHI for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)

Structure for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)

3D Structure for NP0226856 (methyl (5r,6e)-5-{2-hydroxy-6-methoxy-4-[(1e)-2-phenylethenyl]phenyl}-7-phenylhept-6-enoate)