NP-MRD: Showing NP-Card for 4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol (NP0199646)

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Record Information

Version

2.0

Created at

2022-09-04 18:19:50 UTC

Updated at

2022-09-04 18:19:50 UTC

NP-MRD ID

NP0199646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol

Description

Machilin D 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. 4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol is found in Machilus thunbergii and Saururus chinensis. 4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol was first documented in 2009 (PMID: 19898804). Based on a literature review a small amount of articles have been published on Machilin D (PMID: 34596250) (PMID: 32033472) (PMID: 30272133) (PMID: 25466017).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042220192D          

 25 26  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  1  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
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 13 21  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
  4 25  1  0  0  0  0
M  END

     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
    7.0814   -1.5416    1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6376   -1.3490    1.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3360   -0.9314    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9644   -0.7315    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -0.9608    0.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -0.7426    0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3398   -0.3034   -0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951   -0.0798   -1.3535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422   -0.2384   -0.6990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9396   -1.2335   -1.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7991    1.1209   -0.6794 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9775    1.5608   -2.0090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417    1.1714    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160    2.3203   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0076    2.4781    0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4600    1.4731    1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6691    1.5964    2.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7250    0.3300    1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1913   -0.6645    2.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4247   -1.8676    2.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5207    0.1966    0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4272   -0.0790   -1.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2005    0.3665   -2.9924 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2214    0.6257   -3.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226   -0.2837   -1.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6486   -1.8269    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4270   -0.5772    2.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1831   -2.3387    2.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357   -1.5729    2.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1713   -0.7414   -0.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0580   -1.3081    1.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -0.9277    1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517   -0.5880    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9915   -0.9128   -1.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108   -1.3646   -2.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731   -2.2319   -1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0728    1.8269   -0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4425    0.8862   -2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956    3.1378   -0.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6238    3.3646    0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2327    2.4392    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5004   -1.6453    3.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1705   -2.2481    1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0156   -2.6447    3.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575   -0.6929    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776   -0.2472   -4.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974    1.5216   -3.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361    0.8912   -4.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5589   -0.0972   -1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 21  2  0
 21 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 13 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  4 25  1  0
 25 22  2  0
 22 23  1  0
 23 24  1  0
 16 18  1  0
 22  7  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 11 37  1  1
 12 38  1  0
  9 33  1  1
 10 34  1  0
 10 35  1  0
 10 36  1  0
  6 32  1  0
  5 31  1  0
  3 30  1  0
  2 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 25 49  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
M  END


  Mrv1652309042220192D          

 25 26  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  1  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
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 13 21  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
  4 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@H](O)C(C)OC1=CC=C(\C=C\C)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O5/c1-5-6-14-7-10-17(19(11-14)24-4)25-13(2)20(22)15-8-9-16(21)18(12-15)23-3/h5-13,20-22H,1-4H3/b6-5+/t13?,20-/m1/s1

> <INCHI_KEY>
WCFYXOLUODJLKB-PFAYCKMXSA-N

> <FORMULA>
C20H24O5

> <MOLECULAR_WEIGHT>
344.407

> <EXACT_MASS>
344.162373873

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.4120602159436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S)-1-hydroxy-2-{2-methoxy-4-[(1E)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol

> <JCHEM_LOGP>
3.83071696

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.559406249881832

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908823992051904

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4843091925129297

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
97.7822

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S)-1-hydroxy-2-{2-methoxy-4-[(1E)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   13                                                       
CONECT   22    7   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22    4                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₅

Average Mass

344.4070 Da

Monoisotopic Mass

344.16237 Da

IUPAC Name

4-[(1S)-1-hydroxy-2-{2-methoxy-4-[(1E)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol

Traditional Name

4-[(1S)-1-hydroxy-2-{2-methoxy-4-[(1E)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@H](O)C(C)OC1=CC=C(\C=C\C)C=C1OC

InChI Identifier

InChI=1S/C20H24O5/c1-5-6-14-7-10-17(19(11-14)24-4)25-13(2)20(22)15-8-9-16(21)18(12-15)23-3/h5-13,20-22H,1-4H3/b6-5+/t13?,20-/m1/s1

InChI Key

WCFYXOLUODJLKB-PFAYCKMXSA-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

Species Name	Source	Reference
Machilus thunbergii	LOTUS Database	35616633
Saururus chinensis	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

Neolignan skeleton
Methoxyphenol
Phenylpropane
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Ether
Aromatic alcohol
Organic oxygen compound
Alcohol
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	3.83	ChemAxon
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.78 m³·mol⁻¹	ChemAxon
Polarizability	37.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00032491

Chemspider ID

17462663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16397289

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee YK, Seo CS, Lee CS, Lee KS, Kang SJ, Jahng Y, Chang HW, Son JK: Inhibition of DNA topoisomerases I and II and cytotoxicity by lignans from Saururus chinensis. Arch Pharm Res. 2009 Oct;32(10):1409-15. doi: 10.1007/s12272-009-2010-7. Epub 2009 Nov 8. [PubMed:19898804 ]
Chen H, Luo Y, Liu J, Chen J, Chen Y, Li X: Comparative pharmacokinetic study of six lignans in normal and diabetic rats after oral administration of Saururus chinensis extract by LC-MS/MS. Biomed Chromatogr. 2022 Feb;36(2):e5253. doi: 10.1002/bmc.5253. Epub 2021 Oct 28. [PubMed:34596250 ]
Zhen X, Choi HS, Kim JH, Kim SL, Liu R, Yun BS, Lee DS: Machilin D, a Lignin Derived from Saururus chinensis, Suppresses Breast Cancer Stem Cells and Inhibits NF-kappaB Signaling. Biomolecules. 2020 Feb 5;10(2). pii: biom10020245. doi: 10.3390/biom10020245. [PubMed:32033472 ]
Chen H, Ji T, Chen J, Li X: Matrix Solid-Phase Dispersion Combined with HPLC-DAD for Simultaneous Determination of Nine Lignans in Saururus chinensis. J Chromatogr Sci. 2019 Feb 1;57(2):186-193. doi: 10.1093/chromsci/bmy090. [PubMed:30272133 ]
Cao GY, Xu W, Yang XW, Gonzalez FJ, Li F: New neolignans from the seeds of Myristica fragrans that inhibit nitric oxide production. Food Chem. 2015 Apr 15;173:231-7. doi: 10.1016/j.foodchem.2014.09.170. Epub 2014 Oct 13. [PubMed:25466017 ]
LOTUS database [Link]

Showing NP-Card for 4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol (NP0199646)

MOL for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)

3D MOL for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)

3D SDF for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)

3D-SDF for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)

PDB for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)

3D PDB for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)

SMILES for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)

INCHI for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)

Structure for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)

3D Structure for NP0199646 (4-[(1s)-1-hydroxy-2-{2-methoxy-4-[(1e)-prop-1-en-1-yl]phenoxy}propyl]-2-methoxyphenol)