NP-MRD: Showing NP-Card for 4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole (NP0268266)

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Record Information

Version

2.0

Created at

2022-09-08 13:19:58 UTC

Updated at

2022-09-08 13:19:58 UTC

NP-MRD ID

NP0268266

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole

Description

Beilschmin D belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. 4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole is found in Beilschmiedia tsangii. 4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole was first documented in 2007 (PMID: 17520523). Based on a literature review very few articles have been published on Beilschmin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215192D          

 30 35  0  0  1  0            999 V2000
   -1.9708   -1.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563   -2.1892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563   -3.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419   -3.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419   -4.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726   -4.6642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9263   -4.3286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4783   -4.9417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1458   -4.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595   -3.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7270   -3.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -2.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8870   -1.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806   -3.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669   -4.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8994   -4.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -4.4789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -3.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2343   -3.1514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908   -5.6562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -5.6562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9796   -6.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588   -5.4846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3542   -6.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563   -4.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -4.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -3.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554   -3.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -3.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554   -4.5066    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  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  6  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  1  0  0  0  0
M  END

     RDKit          3D

 52 57  0  0  0  0  0  0  0  0999 V2000
    5.8943    1.9260   -1.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8201    0.6794   -1.3584 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7329    0.0414   -0.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4529    0.5844   -0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3856   -0.1013   -0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0482    0.5160   -0.3331 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0707   -0.4033   -0.6705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -0.3593    0.2408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3653   -0.2591   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132   -1.3440   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5325   -1.2142   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3796   -2.3307   -0.4776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690   -3.5794   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9725    0.0283   -0.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1669    1.1473   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8352    0.9655   -0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9016    2.2415   -1.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2638    1.8671   -1.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2285    0.4541   -1.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6475   -0.9295    1.4759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5587    0.4524    1.4009 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5419    1.1953    2.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    1.0913    1.0049 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5870    2.5698    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -1.3407    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -1.9377    0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8982   -1.2353   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0168   -2.0380   -0.1182 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7148   -3.0789    0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3130   -3.1525    0.7485 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0121    1.8714   -3.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7913    2.4721   -1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0078    2.5882   -1.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390    1.5649   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973    1.3011   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -2.2848    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9789   -3.8410   -0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5392   -3.4427    1.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6249   -4.3704   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2178    1.8636   -0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6915    2.2952   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7446    2.2682   -2.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206    1.5415    3.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0059    2.0687    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519    0.5455    2.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    0.8707    1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5577    3.1299    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0601    3.0037    1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314    2.8552   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7578   -1.8973    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1440   -4.0483    0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0874   -2.8115    1.7890 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 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
  8  9  1  6
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 27  3  1  0
 23  6  1  0
 16  9  1  0
 30 26  1  0
 21  8  1  0
 15 14  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
 25 50  1  0
 29 51  1  0
 29 52  1  0
  6 35  1  6
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  1
 24 47  1  0
 24 48  1  0
 24 49  1  0
 10 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 18 41  1  0
 18 42  1  0
 16 40  1  0
M  END


  Mrv1652309082215192D          

 30 35  0  0  1  0            999 V2000
   -1.9708   -1.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563   -2.1892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563   -3.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419   -3.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419   -4.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726   -4.6642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9263   -4.3286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4783   -4.9417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1458   -4.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595   -3.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7270   -3.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -2.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8870   -1.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806   -3.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669   -4.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8994   -4.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -4.4789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -3.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2343   -3.1514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908   -5.6562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -5.6562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9796   -6.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588   -5.4846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3542   -6.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563   -4.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -4.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -3.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554   -3.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -3.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554   -4.5066    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  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  6  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0268266

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC2=C1OCO2)[C@H]1O[C@]2(O[C@@]2(C)[C@@H]1C)C1=CC(OC)=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O8/c1-11-18(12-5-14(23-3)19-16(6-12)25-9-27-19)29-22(21(11,2)30-22)13-7-15(24-4)20-17(8-13)26-10-28-20/h5-8,11,18H,9-10H2,1-4H3/t11-,18+,21+,22+/m1/s1

> <INCHI_KEY>
CVGWCATWCAZNFN-YMIXRQRSSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.41

> <EXACT_MASS>
414.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.825597598338234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-[(1S,3S,4R,5S)-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2H-1,3-benzodioxole

> <JCHEM_LOGP>
3.6141738256666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8911238107087773

> <JCHEM_POLAR_SURFACE_AREA>
77.14000000000001

> <JCHEM_REFRACTIVITY>
101.909

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-6-[(1S,3S,4R,5S)-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2H-1,3-benzodioxole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.679  -3.316   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.345  -4.086   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.345  -5.626   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.011  -6.396   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.011  -7.936   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.322  -8.706   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.729  -8.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.760  -9.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.005  -8.319   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.844  -6.788   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.090  -5.883   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.929  -4.351   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.522  -3.725   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.497  -6.509   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.658  -8.041   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.412  -8.946   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.165  -8.361   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.935  -7.027   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.904  -5.883   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.530 -10.558   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.990 -10.558   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.829 -12.090   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.483 -10.238   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.661 -11.268   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.345  -8.706   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.679  -7.936   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.679  -6.396   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.143  -5.921   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.049  -7.166   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.143  -8.412   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20   21                                             
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15    9                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    8   21                                                       
CONECT   21   20    8   22   23                                             
CONECT   22   21                                                            
CONECT   23   21    6   24                                                  
CONECT   24   23                                                            
CONECT   25    5   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26    3   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₈

Average Mass

414.4100 Da

Monoisotopic Mass

414.13147 Da

IUPAC Name

4-methoxy-6-[(1S,3S,4R,5S)-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2H-1,3-benzodioxole

Traditional Name

4-methoxy-6-[(1S,3S,4R,5S)-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2H-1,3-benzodioxole

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC2=C1OCO2)[C@H]1O[C@]2(O[C@@]2(C)[C@@H]1C)C1=CC(OC)=C2OCOC2=C1

InChI Identifier

InChI=1S/C22H22O8/c1-11-18(12-5-14(23-3)19-16(6-12)25-9-27-19)29-22(21(11,2)30-22)13-7-15(24-4)20-17(8-13)26-10-28-20/h5-8,11,18H,9-10H2,1-4H3/t11-,18+,21+,22+/m1/s1

InChI Key

CVGWCATWCAZNFN-YMIXRQRSSA-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
Beilschmiedia tsangii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane lignans

Alternative Parents

Substituents

Dibenzylbutane lignan skeleton
Benzodioxole
Anisole
Alkyl aryl ether
Meta-dioxane
Benzenoid
Oxolane
Acetal
Oxacycle
Organoheterocyclic compound
Oxirane
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	3.61	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.91 m³·mol⁻¹	ChemAxon
Polarizability	42.83 Å³	ChemAxon
Number of Rings	6	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

28645302

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71455792

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen JJ, Chou ET, Peng CF, Chen IS, Yang SZ, Huang HY: Novel epoxyfuranoid lignans and antitubercular constituents from the leaves of Beilschmiedia tsangii. Planta Med. 2007 Jun;73(6):567-71. doi: 10.1055/s-2007-967195. Epub 2007 May 22. [PubMed:17520523 ]
LOTUS database [Link]

Showing NP-Card for 4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole (NP0268266)

MOL for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)

3D MOL for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)

3D SDF for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)

3D-SDF for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)

PDB for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)

3D PDB for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)

SMILES for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)

INCHI for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)

Structure for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)

3D Structure for NP0268266 (4-methoxy-6-[(1s,3s,4r,5s)-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-4,5-dimethyl-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-2h-1,3-benzodioxole)