NP-MRD: Showing NP-Card for (1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+ (NP0032863)

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Record Information

Version

2.0

Created at

2021-06-19 23:33:54 UTC

Updated at

2021-06-30 00:02:18 UTC

NP-MRD ID

NP0032863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+

Provided By

JEOL Database JEOL Logo

Description

CHEMBL376820 belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. (1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+ is found in Peperomia duclouxii and Peperomia heyneana. (1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+ was first documented in 2007 (Li, N., et al.). Based on a literature review very few articles have been published on CHEMBL376820.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101333D          

 51 55  0  0  0  0            999 V2000
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     RDKit          3D

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  Mrv1652306202101333D          

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    1.4877   -4.7850   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -5.7990    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.2997   -3.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7357   -5.6483   -3.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7837   -4.9346   -2.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4152    3.1776   -1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    6.2842   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1018    7.9840   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 13 14  1  0  0  0  0
  6  7  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 19  2  0  0  0  0
  5 25  2  0  0  0  0
 20 21  2  0  0  0  0
 21 14  1  0  0  0  0
 20 19  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 25 26  1  0  0  0  0
 19 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 20  1  0  0  0  0
  3  4  2  0  0  0  0
 10 38  1  1  0  0  0
  6  5  1  0  0  0  0
  9 37  1  1  0  0  0
 28 26  2  0  0  0  0
 16 17  1  0  0  0  0
 28  3  1  0  0  0  0
 17 18  1  0  0  0  0
  9 13  1  0  0  0  0
  3  2  1  0  0  0  0
 13 12  1  0  0  0  0
  2  1  1  0  0  0  0
 12 11  1  0  0  0  0
 26 27  1  0  0  0  0
 11 10  1  0  0  0  0
 28 29  1  0  0  0  0
  4 33  1  0  0  0  0
 25 49  1  0  0  0  0
  6 34  1  6  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
 13 41  1  6  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 15 42  1  0  0  0  0
 21 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 18 43  1  0  0  0  0
 18 44  1  0  0  0  0
 18 45  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 27 50  1  0  0  0  0
 29 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032863

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])C(OC([H])([H])[H])=C([H])C(=C1[H])[C@]1([H])OC([H])([H])[C@@]2([H])[C@@]([H])(OC([H])([H])[C@@]12[H])C1=C([H])C(OC([H])([H])[H])=C2OC([H])([H])OC2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O8/c1-24-15-4-10(3-14(22)18(15)23)19-12-7-27-20(13(12)8-26-19)11-5-16(25-2)21-17(6-11)28-9-29-21/h3-6,12-13,19-20,22-23H,7-9H2,1-2H3/t12-,13-,19+,20+/m1/s1

> <INCHI_KEY>
VVGTYCADBJEFMD-VLSDQLEDSA-N

> <FORMULA>
C21H22O8

> <MOLECULAR_WEIGHT>
402.399

> <EXACT_MASS>
402.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
41.57677877985782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1R,3aS,4R,6aS)-4-(7-methoxy-2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-3-methoxybenzene-1,2-diol

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.9009930149999998

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.024129843872615

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.405211860802808

> <JCHEM_PKA_STRONGEST_BASIC>
-3.762112117667194

> <JCHEM_POLAR_SURFACE_AREA>
95.84000000000002

> <JCHEM_REFRACTIVITY>
100.86710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1R,3aS,4R,6aS)-4-(7-methoxy-2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-3-methoxybenzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -1.1916    7.0672   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2162    7.1647   -0.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9559    6.0640   -0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4560    4.8343   -1.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269    3.7743   -1.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8040    2.4260   -2.2092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5299    2.5399   -2.7530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3846    1.5962   -2.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852    0.5969   -1.4131 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7242    1.4175   -1.0581 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8351    0.3962   -1.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848   -0.6107   -2.0076 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -0.4693   -2.3497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6371   -1.7926   -2.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2163   -2.7848   -1.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -3.9979   -1.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5842   -5.0138   -0.3191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280   -4.8841    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190   -4.1834   -1.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4361   -3.2271   -2.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7725   -2.0288   -3.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5486   -3.6014   -3.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7796   -4.9126   -3.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8260   -5.2831   -1.9899 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136    3.9677   -1.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2048    5.1865   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5533    5.3611   -1.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377    6.2222   -0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769    7.4079   -0.4413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4393    6.8802   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324    8.0289   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    6.3011   -0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131    4.6712   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334    2.0651   -3.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9787    2.1511   -1.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0679    1.1507   -2.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9606    0.1493   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.9190   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9031   -0.0953   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175    0.8084   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0704   -0.1507   -3.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632   -2.5795   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756   -4.0459    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -4.7850   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -5.7990    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.2997   -3.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7357   -5.6483   -3.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7837   -4.9346   -2.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4152    3.1776   -1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    6.2842   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1018    7.9840   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
  5 25  2  0
 20 21  2  0
 21 14  1  0
 20 19  1  0
  7  8  1  0
  8  9  1  0
 10  6  1  0
 10  9  1  0
 25 26  1  0
 19 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
  3  4  2  0
 10 38  1  1
  6  5  1  0
  9 37  1  1
 28 26  2  0
 16 17  1  0
 28  3  1  0
 17 18  1  0
  9 13  1  0
  3  2  1  0
 13 12  1  0
  2  1  1  0
 12 11  1  0
 26 27  1  0
 11 10  1  0
 28 29  1  0
  4 33  1  0
 25 49  1  0
  6 34  1  6
  8 35  1  0
  8 36  1  0
 13 41  1  6
 11 39  1  0
 11 40  1  0
 15 42  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 50  1  0
 29 51  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.192   7.067  -0.826  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.216   7.165  -0.638  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.956   6.064  -0.986  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.456   4.834  -1.423  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.327   3.774  -1.757  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.804   2.426  -2.209  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.530   2.540  -2.753  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.385   1.596  -2.095  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.485   0.597  -1.413  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.724   1.418  -1.058  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.835   0.396  -1.049  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.485  -0.611  -2.008  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.090  -0.469  -2.350  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.637  -1.793  -2.229  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.216  -2.785  -1.307  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.904  -3.998  -1.172  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.584  -5.014  -0.319  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.628  -4.884   0.411  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.019  -4.183  -1.971  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.436  -3.227  -2.868  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.773  -2.029  -3.021  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.549  -3.601  -3.556  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.780  -4.913  -3.002  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.826  -5.283  -1.990  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.714   3.968  -1.638  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.205   5.186  -1.196  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.553   5.361  -1.079  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.338   6.222  -0.873  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.877   7.408  -0.441  0.00  0.00           O+0
HETATM   30  H   UNK     0      -1.439   6.880  -1.876  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.632   8.029  -0.546  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.623   6.301  -0.173  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.613   4.671  -1.520  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.433   2.065  -3.033  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.979   2.151  -1.361  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.068   1.151  -2.824  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.961   0.149  -0.533  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.620   1.919  -0.089  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.903  -0.095  -0.073  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.817   0.808  -1.294  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.070  -0.151  -3.400  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.663  -2.579  -0.703  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.576  -4.046   1.114  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.488  -4.785  -0.260  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.766  -5.799   0.996  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.129  -1.300  -3.741  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.736  -5.648  -3.813  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.784  -4.935  -2.563  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.415   3.178  -1.892  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.653   6.284  -0.768  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.102   7.984  -0.284  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1                                                       
CONECT    3    4   28    2                                                  
CONECT    4    5    3   33                                                  
CONECT    5    4   25    6                                                  
CONECT    6    7   10    5   34                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   35   36                                             
CONECT    9    8   10   37   13                                             
CONECT   10    6    9   38   11                                             
CONECT   11   12   10   39   40                                             
CONECT   12   13   11                                                       
CONECT   13   14    9   12   41                                             
CONECT   14   13   15   21                                                  
CONECT   15   14   16   42                                                  
CONECT   16   15   19   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   43   44   45                                             
CONECT   19   16   20   24                                                  
CONECT   20   21   19   22                                                  
CONECT   21   20   14   46                                                  
CONECT   22   23   20                                                       
CONECT   23   24   22   47   48                                             
CONECT   24   19   23                                                       
CONECT   25    5   26   49                                                  
CONECT   26   25   28   27                                                  
CONECT   27   26   50                                                       
CONECT   28   26    3   29                                                  
CONECT   29   28   51                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    6                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   13                                                            
CONECT   42   15                                                            
CONECT   43   18                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   21                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   25                                                            
CONECT   50   27                                                            
CONECT   51   29                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

RDKit          3D

51 55  0  0  0  0  0  0  0  0999 V2000
   -1.1916    7.0672   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2162    7.1647   -0.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9559    6.0640   -0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4560    4.8343   -1.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269    3.7743   -1.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8040    2.4260   -2.2092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5299    2.5399   -2.7530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3846    1.5962   -2.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852    0.5969   -1.4131 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7242    1.4175   -1.0581 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8351    0.3962   -1.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848   -0.6107   -2.0076 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -0.4693   -2.3497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6371   -1.7926   -2.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2163   -2.7848   -1.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -3.9979   -1.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5842   -5.0138   -0.3191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280   -4.8841    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190   -4.1834   -1.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4361   -3.2271   -2.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7725   -2.0288   -3.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5486   -3.6014   -3.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7796   -4.9126   -3.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8260   -5.2831   -1.9899 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136    3.9677   -1.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2048    5.1865   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5533    5.3611   -1.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377    6.2222   -0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769    7.4079   -0.4413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4393    6.8802   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324    8.0289   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    6.3011   -0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131    4.6712   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334    2.0651   -3.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9787    2.1511   -1.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0679    1.1507   -2.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9606    0.1493   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.9190   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9031   -0.0953   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175    0.8084   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0704   -0.1507   -3.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632   -2.5795   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756   -4.0459    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -4.7850   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -5.7990    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.2997   -3.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7357   -5.6483   -3.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7837   -4.9346   -2.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4152    3.1776   -1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    6.2842   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1018    7.9840   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
  5 25  2  0
 20 21  2  0
 21 14  1  0
 20 19  1  0
  7  8  1  0
  8  9  1  0
 10  6  1  0
 10  9  1  0
 25 26  1  0
 19 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
  3  4  2  0
 10 38  1  1
  6  5  1  0
  9 37  1  1
 28 26  2  0
 16 17  1  0
 28  3  1  0
 17 18  1  0
  9 13  1  0
  3  2  1  0
 13 12  1  0
  2  1  1  0
 12 11  1  0
 26 27  1  0
 11 10  1  0
 28 29  1  0
  4 33  1  0
 25 49  1  0
  6 34  1  6
  8 35  1  0
  8 36  1  0
 13 41  1  6
 11 39  1  0
 11 40  1  0
 15 42  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 50  1  0
 29 51  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₈

Average Mass

402.3990 Da

Monoisotopic Mass

402.13147 Da

IUPAC Name

5-[(1R,3aS,4R,6aS)-4-(7-methoxy-2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-3-methoxybenzene-1,2-diol

Traditional Name

5-[(1R,3aS,4R,6aS)-4-(7-methoxy-2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-3-methoxybenzene-1,2-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C(O[H])C(OC([H])([H])[H])=C([H])C(=C1[H])[C@]1([H])OC([H])([H])[C@@]2([H])[C@@]([H])(OC([H])([H])[C@@]12[H])C1=C([H])C(OC([H])([H])[H])=C2OC([H])([H])OC2=C1[H]

InChI Identifier

InChI=1S/C21H22O8/c1-24-15-4-10(3-14(22)18(15)23)19-12-7-27-20(13(12)8-26-19)11-5-16(25-2)21-17(6-11)28-9-29-21/h3-6,12-13,19-20,22-23H,7-9H2,1-2H3/t12-,13-,19+,20+/m1/s1

InChI Key

VVGTYCADBJEFMD-VLSDQLEDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Peperomia duclouxii	JEOL database	Li, N., et al, J. Nat. Prod. 70, 544 (2007)
Peperomia heyneana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Not Available

Direct Parent

Furanoid lignans

Alternative Parents

Substituents

Furanoid lignan
Furofuran lignan skeleton
Methoxyphenol
Benzodioxole
Anisole
Phenoxy compound
Catechol
Furofuran
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Oxolane
Ether
Dialkyl ether
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	2.01	ALOGPS
logP	1.9	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.87 m³·mol⁻¹	ChemAxon
Polarizability	41.58 Å³	ChemAxon
Number of Rings	5	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

17342815

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16215160

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li, N., et al. (2007). Li, N., et al, J. Nat. Prod. 70, 544 (2007) . J. Nat. Prod..

Showing NP-Card for (1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+ (NP0032863)

MOL for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)

3D MOL for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)

3D SDF for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)

3D-SDF for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)

PDB for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)

3D PDB for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)

SMILES for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)

INCHI for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)

Structure for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)

3D Structure for NP0032863 ((1S,2R,5S,6R)-2-(5-methoxy-3,4-methylenedioxyphenyl)-6-(3,4-dihydroxy-5-m+)