NP-MRD: Showing NP-Card for 4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol (NP0256310)

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Record Information

Version

1.0

Created at

2022-09-07 21:05:20 UTC

Updated at

2022-09-07 21:05:21 UTC

NP-MRD ID

NP0256310

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

Description

Verrucosin 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,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol is found in Bicuiba oleifera and Myristica fragrans. It was first documented in 2016 (PMID: 27419473). Based on a literature review a significant number of articles have been published on Verrucosin (PMID: 29336005) (PMID: 28914420) (PMID: 26805808) (PMID: 26786026).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072223052D          

 25 27  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4257   -5.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052   -5.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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  1  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
  9 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

 49 51  0  0  0  0  0  0  0  0999 V2000
    4.0704    2.9718   -1.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8998    1.9847   -1.0761 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3548    0.9742   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9755    0.8772   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -0.1272    0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0011   -0.1836    0.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2737    0.0155   -0.3152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0253   -0.2266    0.1931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0849   -0.0588   -0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9516   -0.5378   -2.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9936   -0.3659   -2.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1647    0.2888   -2.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2035    0.4582   -3.5245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2969    0.7697   -1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4803    1.4151   -0.9872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7387    1.9508    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2495    0.5845   -0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8461   -1.6233    0.7419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5820   -2.6344   -0.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -1.4262    1.5109 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0733   -1.1787    2.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -1.0336    1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6876   -0.9464    1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956    0.0608    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5628    0.1610    0.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7236    3.8271   -2.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342    3.3895   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230    2.5904   -2.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    1.6391   -0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6772    0.6817    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0952    0.4747    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -1.0536   -2.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813   -0.7457   -3.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1109    0.1109   -4.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8571    1.1005    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6219    2.5924    0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8461    2.5411    0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    0.9898    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6435   -1.9222    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2726   -2.3646   -0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024   -2.8544   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059   -3.6270    0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664   -2.3241    1.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557   -0.2150    3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4777   -1.9578    3.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0174   -1.0190    3.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839   -1.8530    1.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3812   -1.6572    1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1954   -0.5132    0.4750 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 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 24  3  1  0
 20  6  1  0
 17  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
  6 30  1  1
  8 31  1  1
 18 39  1  1
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  1
 21 44  1  0
 21 45  1  0
 21 46  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END


  Mrv1652309072223052D          

 25 27  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4257   -5.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052   -5.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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  1  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
  9 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>
NP0256310

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O5/c1-11-12(2)20(14-6-8-16(22)18(10-14)24-4)25-19(11)13-5-7-15(21)17(9-13)23-3/h5-12,19-22H,1-4H3/t11-,12-,19-,20+/m0/s1

> <INCHI_KEY>
GMXMKSFJQLFOSO-HKKFXGGESA-N

> <FORMULA>
C20H24O5

> <MOLECULAR_WEIGHT>
344.407

> <EXACT_MASS>
344.162373873

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.89802091472485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S,3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

> <JCHEM_LOGP>
3.906299754333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.211830511977292

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.609770520649167

> <JCHEM_PKA_STRONGEST_BASIC>
-4.075937576695324

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
94.95050000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S,3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.580  -3.215   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.009  -5.926   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.819  -8.417   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.724  -9.663   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.288  -8.578   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.661  -9.985   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.130 -10.146   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.382  -7.333   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334   3.850   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   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14    9                                                       
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   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₅

Average Mass

344.4070 Da

Monoisotopic Mass

344.16237 Da

IUPAC Name

4-[(2S,3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol

Traditional Name

4-[(2S,3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-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=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C20H24O5/c1-11-12(2)20(14-6-8-16(22)18(10-14)24-4)25-19(11)13-5-7-15(21)17(9-13)23-3/h5-12,19-22H,1-4H3/t11-,12-,19-,20+/m0/s1

InChI Key

GMXMKSFJQLFOSO-HKKFXGGESA-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
Bicuiba oleifera	LOTUS Database	35616633
Myristica fragrans	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
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxolane
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.91	ChemAxon
pKa (Strongest Acidic)	9.61	ChemAxon
pKa (Strongest Basic)	-4.1	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	4	ChemAxon
Refractivity	94.95 m³·mol⁻¹	ChemAxon
Polarizability	36.9 Å³	ChemAxon
Number of Rings	3	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

C00037984

Chemspider ID

8911559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10736226

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Morikawa T, Hachiman I, Ninomiya K, Hata H, Sugawara K, Muraoka O, Matsuda H: Degranulation inhibitors from the arils of Myristica fragrans in antigen-stimulated rat basophilic leukemia cells. J Nat Med. 2018 Mar;72(2):464-473. doi: 10.1007/s11418-017-1170-x. Epub 2018 Jan 15. [PubMed:29336005 ]
Ban NK, Thoa NTK, Linh TM, Trang DT, Van Kiem P, Nhiem NX, Tai BH, Van Minh C, Song JH, Ko HJ, Kim SH: Labdane-type diterpenoids from Vitex limonifolia and their antivirus activities. J Nat Med. 2018 Jan;72(1):290-297. doi: 10.1007/s11418-017-1125-2. Epub 2017 Sep 15. [PubMed:28914420 ]
Morikawa T, Hachiman I, Matsuo K, Nishida E, Ninomiya K, Hayakawa T, Yoshie O, Muraoka O, Nakayama T: Neolignans from the Arils of Myristica fragrans as Potent Antagonists of CC Chemokine Receptor 3. J Nat Prod. 2016 Aug 26;79(8):2005-13. doi: 10.1021/acs.jnatprod.6b00262. Epub 2016 Jul 15. [PubMed:27419473 ]
Wu N, Xu W, Cao GY, Yang YF, Yang XB, Yang XW: The Blood-Brain Barrier Permeability of Lignans and Malabaricones from the Seeds of Myristica fragrans in the MDCK-pHaMDR Cell Monolayer Model. Molecules. 2016 Jan 22;21(2):134. doi: 10.3390/molecules21020134. [PubMed:26805808 ]
Wukirsari T, Nishiwaki H, Nishi K, Sugahara T, Akiyama K, Kishida T, Yamauchi S: Effect of the structure of dietary epoxylignan on its cytotoxic activity: relationship between the structure and the activity of 7,7'-epoxylignan and the introduction of apoptosis by caspase 3/7. Biosci Biotechnol Biochem. 2016;80(4):669-75. doi: 10.1080/09168451.2015.1123603. Epub 2016 Jan 20. [PubMed:26786026 ]
LOTUS database [Link]

Showing NP-Card for 4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol (NP0256310)

MOL for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D MOL for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D SDF for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D-SDF for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

PDB for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D PDB for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

SMILES for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

INCHI for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

Structure for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)

3D Structure for NP0256310 (4-[(2s,3s,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol)