NP-MRD: Showing NP-Card for 4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol (NP0322366)

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Record Information

Version

2.0

Created at

2022-09-12 01:05:57 UTC

Updated at

2022-09-12 01:05:57 UTC

NP-MRD ID

NP0322366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

Description

Talaumidin belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton. 4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol is found in Aristolochia arcuata, Magnolia liliifera, Myristica fragrans and Virola surinamensis. 4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol was first documented in 2005 (PMID: 15684486). Based on a literature review a significant number of articles have been published on Talaumidin (PMID: 17764190) (PMID: 20332453) (PMID: 32391327) (PMID: 32009033) (PMID: 29721999) (PMID: 29454919).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203052D          

 25 28  0  0  1  0            999 V2000
    8.5050    0.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6845    0.9457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3490    1.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5285    1.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1929    2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    2.6255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8204    2.0124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530    3.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5399    3.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    3.3400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2955    4.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6779    3.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4983    3.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8339    2.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6544    2.2805    0.0000 O   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
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  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
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  6  0  0  0
  5 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
   -3.8758    3.5245    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6640    2.3678    0.5900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1318    1.1042    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150    0.9410    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225   -0.3309   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -0.5445   -0.5241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0310    0.2067    0.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335   -0.5603    0.5998 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3228    0.1192    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2049   -0.0121    1.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4383    0.6454    1.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984    1.4359    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9145    1.5716   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6857    0.9064   -0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5367    2.4042   -1.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078    2.9695   -0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    2.1822    0.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0234   -1.8252   -0.2561 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6432   -2.9916    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980   -1.9874   -0.4119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8332   -2.8057   -1.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1470   -1.4267   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4953   -1.2859    0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9575    0.0117    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2977    0.1356    0.8625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6015    3.7591   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265    3.3641    1.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4564    4.3593    0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1545    1.8022   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7643   -0.2628   -1.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234   -0.9186    1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973   -0.6178    2.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1141    0.5226    2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0173    1.0366   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5913    2.8651   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5889    4.0431   -0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120   -1.6416   -1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5439   -2.8965    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923   -3.0812    0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933   -3.9078    0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901   -2.4693    0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -3.8194   -1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195   -2.3258   -2.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0900   -3.0089   -2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8038   -2.4546   -0.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1418   -2.1446    0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7030    1.0413    1.0186 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
  4  5  1  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 17  1  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  2  0
 24  3  1  0
 20  6  1  0
 14  9  1  0
 13 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
  6 30  1  6
  8 31  1  1
 18 37  1  6
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  1
 21 42  1  0
 21 43  1  0
 21 44  1  0
 10 32  1  0
 11 33  1  0
 16 35  1  0
 16 36  1  0
 14 34  1  0
M  END


  Mrv1652309122203052D          

 25 28  0  0  1  0            999 V2000
    8.5050    0.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6845    0.9457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3490    1.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5285    1.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1929    2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    2.6255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8204    2.0124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530    3.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5399    3.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    3.3400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2955    4.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6779    3.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4983    3.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8339    2.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6544    2.2805    0.0000 O   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
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  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
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  6  0  0  0
  5 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@H]1O[C@@H]([C@@H](C)[C@@H]1C)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O5/c1-11-12(2)20(14-5-7-16-18(9-14)24-10-23-16)25-19(11)13-4-6-15(21)17(8-13)22-3/h4-9,11-12,19-21H,10H2,1-3H3/t11-,12-,19-,20-/m0/s1

> <INCHI_KEY>
JPDORDSJPIKURD-HIGYNYDNSA-N

> <FORMULA>
C20H22O5

> <MOLECULAR_WEIGHT>
342.391

> <EXACT_MASS>
342.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.08097879200726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S,3S,4S,5S)-5-(2H-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

> <JCHEM_LOGP>
3.990769809333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.910800516313147

> <JCHEM_PKA_STRONGEST_BASIC>
-4.049220177016412

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
92.27330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S,3S,4S,5S)-5-(2H-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      15.876   1.604   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.344   1.765   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.718   3.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.187   3.333   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.560   4.740   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.029   4.901   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.998   3.756   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.752   5.914   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.608   6.945   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.259   6.235   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.885   7.641   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.465   5.986   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.997   5.825   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.623   4.418   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.155   4.257   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    8   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    6   21                                                  
CONECT   21   20                                                            
CONECT   22    5   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₅

Average Mass

342.3910 Da

Monoisotopic Mass

342.14672 Da

IUPAC Name

4-[(2S,3S,4S,5S)-5-(2H-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

Traditional Name

4-[(2S,3S,4S,5S)-5-(2H-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@H]1O[C@@H]([C@@H](C)[C@@H]1C)C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C20H22O5/c1-11-12(2)20(14-5-7-16-18(9-14)24-10-23-16)25-19(11)13-4-6-15(21)17(8-13)22-3/h4-9,11-12,19-21H,10H2,1-3H3/t11-,12-,19-,20-/m0/s1

InChI Key

JPDORDSJPIKURD-HIGYNYDNSA-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
Aristolochia arcuata	LOTUS Database	35616633
Magnolia liliifera	LOTUS Database	35616633
Myristica fragrans	LOTUS Database	35616633
Virola surinamensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,7'-epoxylignans

Alternative Parents

Substituents

7,7p-epoxylignan
Dibenzylbutane lignan skeleton
Methoxyphenol
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxolane
Ether
Acetal
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
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	3.99	ChemAxon
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.27 m³·mol⁻¹	ChemAxon
Polarizability	37.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9748471

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11573701

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim H, Wooten CM, Park Y, Hong J: Stereoselective synthesis of tetrahydrofuran lignans via BF(3) x OEt(2)-promoted reductive deoxygenation/epimerization of cyclic hemiketal: synthesis of (-)-odoratisol C, (-)-futokadsurin A, (-)-veraguensin, (+)-fragransin A(2), (+)-galbelgin, and (+)-talaumidin. Org Lett. 2007 Sep 27;9(20):3965-8. doi: 10.1021/ol7016388. Epub 2007 Sep 1. [PubMed:17764190 ]
Pusztai R, Abrantes M, Serly J, Duarte N, Molnar J, Ferreira MJ: Antitumor-promoting activity of lignans: inhibition of human cytomegalovirus IE gene expression. Anticancer Res. 2010 Feb;30(2):451-4. [PubMed:20332453 ]
Zhai H, Inoue T, Moriyama M, Esumi T, Mitsumoto Y, Fukuyama Y: Neuroprotective effects of 2,5-diaryl-3,4-dimethyltetrahydrofuran neolignans. Biol Pharm Bull. 2005 Feb;28(2):289-93. doi: 10.1248/bpb.28.289. [PubMed:15684486 ]
Harada K, Kubo M, Fukuyama Y: Chemistry and Neurotrophic Activities of (-)-Talaumidin and Its Derivatives. Front Chem. 2020 Apr 23;8:301. doi: 10.3389/fchem.2020.00301. eCollection 2020. [PubMed:32391327 ]
Harada K: [Development of New Neurotrophic Compounds Based on Talaumidin]. Yakugaku Zasshi. 2020;140(2):129-137. doi: 10.1248/yakushi.19-00167. [PubMed:32009033 ]
Koriyama Y, Furukawa A, Sugitani K, Kubo M, Harada K, Fukuyama Y: Talaumidin Promotes Neurite Outgrowth of Staurosporine-Differentiated RGC-5 Cells Through PI3K/Akt-Dependent Pathways. Adv Exp Med Biol. 2018;1074:649-653. doi: 10.1007/978-3-319-75402-4_79. [PubMed:29721999 ]
Harada K, Zaha K, Bando R, Irimaziri R, Kubo M, Koriyama Y, Fukuyama Y: Structure-activity relationships of talaumidin derivatives: Their neurite-outgrowth promotion in vitro and optic nerve regeneration in vivo. Eur J Med Chem. 2018 Mar 25;148:86-94. doi: 10.1016/j.ejmech.2018.02.014. Epub 2018 Feb 9. [PubMed:29454919 ]
Harada K, Kubo M, Horiuchi H, Ishii A, Esumi T, Hioki H, Fukuyama Y: Systematic Asymmetric Synthesis of All Diastereomers of (-)-Talaumidin and Their Neurotrophic Activity. J Org Chem. 2015 Jul 17;80(14):7076-88. doi: 10.1021/acs.joc.5b00945. Epub 2015 Jul 6. [PubMed:26108800 ]
Xue P, Wang LP, Jiao XZ, Jiang YJ, Xiao Q, Luo ZG, Xie P, Liang XT: Total synthesis of (-)-talaumidin and (-)-galbelgin. J Asian Nat Prod Res. 2009;11(3):281-7. doi: 10.1080/10286020802675191. [PubMed:19408154 ]
Abrantes M, Mil-Homens T, Duarte N, Lopes D, Cravo P, Madureira Md, Ferreira MJ: Antiplasmodial activity of lignans and extracts from Pycnanthus angolensis. Planta Med. 2008 Sep;74(11):1408-12. doi: 10.1055/s-2008-1081317. Epub 2008 Jul 31. [PubMed:18671202 ]
LOTUS database [Link]

Showing NP-Card for 4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol (NP0322366)

MOL for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D MOL for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D SDF for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D-SDF for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

PDB for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D PDB for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

SMILES for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

INCHI for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

Structure for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D Structure for NP0322366 (4-[(2s,3s,4s,5s)-5-(2h-1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)