NP-MRD: Showing NP-Card for 5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole (NP0309188)

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Record Information

Version

1.0

Created at

2022-09-11 03:36:48 UTC

Updated at

2022-09-11 03:36:48 UTC

NP-MRD ID

NP0309188

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole

Description

Machilin G, also known as lasquim 25, 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. 5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole is found in Machilus thunbergii, Magnolia denudata, Nectandra megapotamica, Piper schmidtii and Piper wightii. It was first documented in 2015 (PMID: 26184150). Based on a literature review a significant number of articles have been published on machilin G (PMID: 31861910) (PMID: 31444858) (PMID: 30354012) (PMID: 27331807).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205362D          

 26 29  0  0  1  0            999 V2000
    9.1393    2.9480    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
    7.8339    2.3668    0.0000 C   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  2  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  1  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
    7.9833    3.7879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8038    3.7016    0.0000 C   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
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  1  0  0  0
  6 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
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -5.8821    0.2284   -2.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5277    0.4856   -1.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538    0.2993   -0.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2352   -0.1480   -1.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9636   -0.3167   -1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7189   -0.0420    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -0.2045    0.7669 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6339    0.3137   -0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657   -0.2520    0.6133 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0100    0.1319   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0371   -0.6932   -0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703   -0.2076   -1.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2523    1.1222   -1.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220    1.9860   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.4777   -0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5633    3.2764   -1.5297 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5503    3.0989   -2.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2082    1.9286   -2.0461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -1.7014    0.5694 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2449   -2.5877    1.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511   -1.6870    0.9669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2416   -1.9550    2.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7614    0.4038    0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0387    0.5874    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0786    1.0376    1.2576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7917    1.3090    2.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4397   -0.7748   -2.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9855    0.1475   -2.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4586    1.0457   -3.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4613   -0.3522   -2.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1838   -0.6623   -1.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3429    0.3523    1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430    0.1064    1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9665   -1.7235   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9820   -0.8737   -1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3192    2.1853   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270    3.9690   -2.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0710    2.9119   -3.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -2.0491   -0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6920   -3.4596    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054   -2.0310    2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754   -3.1083    2.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570   -2.3363    0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1398   -1.3618    2.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162   -1.4959    2.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3967   -3.0254    2.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948    0.6265    1.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7654    1.4417    3.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1310    2.1766    2.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309    0.3993    3.0938 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  6  2  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 24  3  1  0
 21  7  1  0
 15 10  1  0
 14 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
 23 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
  7 32  1  1
  9 33  1  1
 19 39  1  6
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  6
 22 44  1  0
 22 45  1  0
 22 46  1  0
 11 34  1  0
 12 35  1  0
 17 37  1  0
 17 38  1  0
 15 36  1  0
M  END


  Mrv1652309112205362D          

 26 29  0  0  1  0            999 V2000
    9.1393    2.9480    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
    7.8339    2.3668    0.0000 C   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  2  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  1  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
    7.9833    3.7879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8038    3.7016    0.0000 C   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
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  1  0  0  0
  6 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
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309188

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)[C@@H]1O[C@@H]([C@@H](C)[C@H]1C)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O5/c1-12-13(2)21(15-6-8-17-19(10-15)25-11-24-17)26-20(12)14-5-7-16(22-3)18(9-14)23-4/h5-10,12-13,20-21H,11H2,1-4H3/t12-,13+,20-,21+/m1/s1

> <INCHI_KEY>
HSMDOSKNXLVXIP-QVEMZERUSA-N

> <FORMULA>
C21H24O5

> <MOLECULAR_WEIGHT>
356.418

> <EXACT_MASS>
356.162373873

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.63496747395129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2S,3S,4R,5R)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2H-1,3-benzodioxole

> <JCHEM_LOGP>
4.136663865333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9912993313398473

> <JCHEM_POLAR_SURFACE_AREA>
46.150000000000006

> <JCHEM_REFRACTIVITY>
96.75560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2S,3S,4R,5R)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2H-1,3-benzodioxole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      17.060   5.503   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.155   4.257   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.623   4.418   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.718   3.172   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.187   3.333   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.560   4.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.029   4.901   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.998   3.756   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.752   5.914   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.608   6.945   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.259   6.235   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.885   7.641   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.465   5.986   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.997   5.825   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.902   7.071   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.434   6.910   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    9   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    7   22                                                  
CONECT   22   21                                                            
CONECT   23    6   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
5-((2S,3S,4R,5R)-5-(3,4-Dimethoxyphenyl)-3,4-dimethyloxolan-2-yl)-1,3-benzodioxole	MeSH
LASQUIM 25	MeSH

Chemical Formula

C₂₁H₂₄O₅

Average Mass

356.4180 Da

Monoisotopic Mass

356.16237 Da

IUPAC Name

5-[(2S,3S,4R,5R)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2H-1,3-benzodioxole

Traditional Name

5-[(2S,3S,4R,5R)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2H-1,3-benzodioxole

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)[C@@H]1O[C@@H]([C@@H](C)[C@H]1C)C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C21H24O5/c1-12-13(2)21(15-6-8-17-19(10-15)25-11-24-17)26-20(12)14-5-7-16(22-3)18(9-14)23-4/h5-10,12-13,20-21H,11H2,1-4H3/t12-,13+,20-,21+/m1/s1

InChI Key

HSMDOSKNXLVXIP-QVEMZERUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Machilus thunbergii	LOTUS Database	35616633
Magnolia denudata	LOTUS Database	35616633
Nectandra megapotamica	LOTUS Database	35616633
Piper schmidtii	LOTUS Database	35616633
Piper wightii	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
Dimethoxybenzene
O-dimethoxybenzene
Benzodioxole
Methoxybenzene
Anisole
Phenol ether
Phenoxy compound
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxolane
Oxacycle
Organoheterocyclic compound
Acetal
Dialkyl ether
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	4.14	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.76 m³·mol⁻¹	ChemAxon
Polarizability	38.63 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

C00043690

Chemspider ID

8626338

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10450921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cardozo Pinto de Arruda C, de Jesus Hardoim D, Silva Rizk Y, da Silva Freitas de Souza C, Zaverucha do Valle T, Bento Carvalho D, Nosomi Taniwaki N, de Morais Baroni AC, da Silva Calabrese K: A Triazole Hybrid of Neolignans as a Potential Antileishmanial Agent by Triggering Mitochondrial Dysfunction. Molecules. 2019 Dec 20;25(1). pii: molecules25010037. doi: 10.3390/molecules25010037. [PubMed:31861910 ]
das Neves AR, Trefzger OS, Barbosa NV, Honorato AM, Carvalho DB, Moslaves IS, Kadri MCT, Yoshida NC, Kato MJ, Arruda CCP, Baroni ACM: Effect of isoxazole derivatives of tetrahydrofuran neolignans on intracellular amastigotes of Leishmania (Leishmania) amazonensis: A structure-activity relationship comparative study with triazole-neolignan-based compounds. Chem Biol Drug Des. 2019 Dec;94(6):2004-2012. doi: 10.1111/cbdd.13609. Epub 2019 Sep 12. [PubMed:31444858 ]
Trefzger OS, das Neves AR, Barbosa NV, Carvalho DB, Pereira IC, Perdomo RT, Matos MFC, Yoshida NC, Kato MJ, de Albuquerque S, Arruda CCP, Baroni ACM: Design, synthesis and antitrypanosomatid activities of 3,5-diaryl-isoxazole analogues based on neolignans veraguensin, grandisin and machilin G. Chem Biol Drug Des. 2019 Mar;93(3):313-324. doi: 10.1111/cbdd.13417. Epub 2018 Nov 25. [PubMed:30354012 ]
Ponci V, Figueiredo CR, Massaoka MH, de Farias CF, Matsuo AL, Sartorelli P, Lago JH: Neolignans from Nectandra megapotamica (Lauraceae) Display in vitro Cytotoxic Activity and Induce Apoptosis in Leukemia Cells. Molecules. 2015 Jul 15;20(7):12757-68. doi: 10.3390/molecules200712757. [PubMed:26184150 ]
Costa EC, Cassamale TB, Carvalho DB, Bosquiroli LS, Ojeda M, Ximenes TV, Matos MF, Kadri MC, Baroni AC, Arruda CC: Antileishmanial Activity and Structure-Activity Relationship of Triazolic Compounds Derived from the Neolignans Grandisin, Veraguensin, and Machilin G. Molecules. 2016 Jun 20;21(6):802. doi: 10.3390/molecules21060802. [PubMed:27331807 ]
LOTUS database [Link]

Showing NP-Card for 5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole (NP0309188)

MOL for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)

3D MOL for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)

3D SDF for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)

3D-SDF for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)

PDB for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)

3D PDB for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)

SMILES for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)

INCHI for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)

Structure for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)

3D Structure for NP0309188 (5-[(2s,3s,4r,5r)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2h-1,3-benzodioxole)