NP-MRD: Showing NP-Card for dextrobursehernin (NP0030784)

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Record Information

Version

2.0

Created at

2021-06-19 22:03:06 UTC

Updated at

2021-06-29 23:58:58 UTC

NP-MRD ID

NP0030784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dextrobursehernin

Provided By

JEOL Database JEOL Logo

Description

2S,3S-Bursehernin belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. dextrobursehernin is found in Bursera schlechtendalii, Bursera simaruba, Phyllanthus urinaria and Phyllanthus urinaria L. . dextrobursehernin was first documented in 2003 (Chang, C. -C., et al.). Based on a literature review very few articles have been published on 2S,3S-Bursehernin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100033D          

 49 52  0  0  0  0            999 V2000
   -3.3642   -2.9688    1.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566   -1.8080    0.5946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062   -1.6623    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -1.5714   -0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489   -1.4338   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2871   -1.3732    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7853   -1.1895    1.0289 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2151    0.2140    0.5924 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7152    0.2857    0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4070   -0.2866   -0.3098 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2135    1.0763    1.5074 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1618    1.4487    2.3919 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8756    1.3138    1.6016 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5008    2.6438    0.9136 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1564    2.5659    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    2.6035   -1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2118    2.2647    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0177    2.4132    0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5081   -1.4473    2.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8831   -1.5561    2.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5779   -1.5775    3.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255   -0.3204    3.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -3.8015    1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14 15  1  0  0  0  0
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  8 35  1  6  0  0  0
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 12 37  1  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202100033D          

 49 52  0  0  0  0            999 V2000
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 25 26  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  4  5  2  0  0  0  0
 26 27  1  0  0  0  0
 15 16  2  0  0  0  0
  2  1  1  0  0  0  0
  8 13  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  6 24  2  0  0  0  0
 19 20  2  0  0  0  0
 12 11  1  0  0  0  0
 11  9  1  0  0  0  0
  8  9  1  0  0  0  0
 13 12  1  0  0  0  0
 20 15  1  0  0  0  0
  9 10  2  0  0  0  0
  4 31  1  0  0  0  0
 24 46  1  0  0  0  0
  5 32  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
 16 41  1  0  0  0  0
 17 42  1  0  0  0  0
 20 43  1  0  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 27 47  1  0  0  0  0
 27 48  1  0  0  0  0
 27 49  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  8 35  1  6  0  0  0
 13 38  1  1  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030784

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O6/c1-23-17-5-3-14(9-19(17)24-2)8-16-15(11-25-21(16)22)7-13-4-6-18-20(10-13)27-12-26-18/h3-6,9-10,15-16H,7-8,11-12H2,1-2H3/t15-,16+/m1/s1

> <INCHI_KEY>
IYBDDRJHJMFFBB-CVEARBPZSA-N

> <FORMULA>
C21H22O6

> <MOLECULAR_WEIGHT>
370.401

> <EXACT_MASS>
370.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.15934902705878

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.5221466220000006

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.358653592560326

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
97.43950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S)-4-(2H-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -3.3642   -2.9688    1.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566   -1.8080    0.5946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062   -1.6623    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -1.5714   -0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489   -1.4338   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2871   -1.3732    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7853   -1.1895    1.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.2140    0.5924 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7152    0.2857    0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4070   -0.2866   -0.3098 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2135    1.0763    1.5074 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1618    1.4487    2.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8756    1.3138    1.6016 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5008    2.6438    0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1564    2.5659    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    2.6035   -1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1537    2.4595   -1.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2771    2.2810   -1.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    2.2647    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0177    2.4132    0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288    2.0771    0.8850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2562    1.9092   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5430    2.0996   -1.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5081   -1.4473    2.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8831   -1.5561    2.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5779   -1.5775    3.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255   -0.3204    3.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -3.8015    1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678   -2.7280    2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2581   -3.2922    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205   -1.6164   -1.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273   -1.3706   -1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387   -1.4036    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2587   -1.9483    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269    0.4451   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365    2.4640    2.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1822    0.7656    3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0642    1.0339    2.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497    3.4489    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788    2.9412    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753    2.7272   -1.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2204    2.4744   -2.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    2.3857    2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6826    0.8994   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0752    2.6359   -0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721   -1.3964    3.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6656   -0.3374    4.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089    0.5076    3.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0355   -0.1605    2.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 19 18  1  0
  6  7  1  0
 14 13  1  0
  8  7  1  0
  3 25  2  0
 24 25  1  0
 18 23  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
  6  5  1  0
 25 26  1  0
  3  4  1  0
  3  2  1  0
  4  5  2  0
 26 27  1  0
 15 16  2  0
  2  1  1  0
  8 13  1  0
 16 17  1  0
 17 18  2  0
  6 24  2  0
 19 20  2  0
 12 11  1  0
 11  9  1  0
  8  9  1  0
 13 12  1  0
 20 15  1  0
  9 10  2  0
  4 31  1  0
 24 46  1  0
  5 32  1  0
 14 39  1  0
 14 40  1  0
  7 33  1  0
  7 34  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  8 35  1  6
 13 38  1  1
 12 36  1  0
 12 37  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      -3.364  -2.969   1.253  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.857  -1.808   0.595  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.506  -1.662   0.774  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.739  -1.571  -0.386  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.649  -1.434  -0.302  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.287  -1.373   0.945  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.785  -1.190   1.029  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.215   0.214   0.592  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.715   0.286   0.517  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.407  -0.287  -0.310  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.213   1.076   1.507  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.162   1.449   2.392  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.876   1.314   1.602  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.501   2.644   0.914  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.156   2.566   0.224  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.075   2.603  -1.187  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.154   2.459  -1.841  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.277   2.281  -1.064  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.212   2.265   0.308  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.018   2.413   0.980  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.429   2.077   0.885  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.256   1.909  -0.286  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.543   2.100  -1.526  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.508  -1.447   2.108  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.883  -1.556   2.022  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.578  -1.577   3.203  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.225  -0.320   3.413  0.00  0.00           C+0
HETATM   28  H   UNK     0      -2.651  -3.801   1.248  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.668  -2.728   2.276  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.258  -3.292   0.711  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.220  -1.616  -1.359  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.227  -1.371  -1.222  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.139  -1.404   2.046  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.259  -1.948   0.392  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.827   0.445  -0.405  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.337   2.464   2.761  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.182   0.766   3.248  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.064   1.034   2.282  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.450   3.449   1.658  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.279   2.941   0.199  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.975   2.727  -1.786  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.220   2.474  -2.923  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.001   2.386   2.064  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.683   0.899  -0.275  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.075   2.636  -0.240  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.972  -1.396   3.089  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.666  -0.337   4.415  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.509   0.508   3.375  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.035  -0.161   2.695  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3   25    4    2                                                  
CONECT    4    3    5   31                                                  
CONECT    5    6    4   32                                                  
CONECT    6    7    5   24                                                  
CONECT    7    6    8   33   34                                             
CONECT    8    7   13    9   35                                             
CONECT    9   11    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12    9                                                       
CONECT   12   11   13   36   37                                             
CONECT   13   14    8   12   38                                             
CONECT   14   15   13   39   40                                             
CONECT   15   14   16   20                                                  
CONECT   16   15   17   41                                                  
CONECT   17   16   18   42                                                  
CONECT   18   19   23   17                                                  
CONECT   19   18   21   20                                                  
CONECT   20   19   15   43                                                  
CONECT   21   22   19                                                       
CONECT   22   23   21   44   45                                             
CONECT   23   18   22                                                       
CONECT   24   25    6   46                                                  
CONECT   25    3   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   47   48   49                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   20                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   24                                                            
CONECT   47   27                                                            
CONECT   48   27                                                            
CONECT   49   27                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  104    0
END

RDKit          3D

49 52  0  0  0  0  0  0  0  0999 V2000
   -3.3642   -2.9688    1.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566   -1.8080    0.5946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062   -1.6623    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -1.5714   -0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489   -1.4338   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2871   -1.3732    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7853   -1.1895    1.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.2140    0.5924 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7152    0.2857    0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4070   -0.2866   -0.3098 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2135    1.0763    1.5074 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1618    1.4487    2.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8756    1.3138    1.6016 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5008    2.6438    0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1564    2.5659    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    2.6035   -1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1537    2.4595   -1.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2771    2.2810   -1.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    2.2647    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0177    2.4132    0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288    2.0771    0.8850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2562    1.9092   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5430    2.0996   -1.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5081   -1.4473    2.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8831   -1.5561    2.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5779   -1.5775    3.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255   -0.3204    3.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -3.8015    1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678   -2.7280    2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2581   -3.2922    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205   -1.6164   -1.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273   -1.3706   -1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387   -1.4036    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2587   -1.9483    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269    0.4451   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365    2.4640    2.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1822    0.7656    3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0642    1.0339    2.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497    3.4489    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788    2.9412    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753    2.7272   -1.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2204    2.4744   -2.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    2.3857    2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6826    0.8994   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0752    2.6359   -0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721   -1.3964    3.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6656   -0.3374    4.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089    0.5076    3.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0355   -0.1605    2.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 19 18  1  0
  6  7  1  0
 14 13  1  0
  8  7  1  0
  3 25  2  0
 24 25  1  0
 18 23  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
  6  5  1  0
 25 26  1  0
  3  4  1  0
  3  2  1  0
  4  5  2  0
 26 27  1  0
 15 16  2  0
  2  1  1  0
  8 13  1  0
 16 17  1  0
 17 18  2  0
  6 24  2  0
 19 20  2  0
 12 11  1  0
 11  9  1  0
  8  9  1  0
 13 12  1  0
 20 15  1  0
  9 10  2  0
  4 31  1  0
 24 46  1  0
  5 32  1  0
 14 39  1  0
 14 40  1  0
  7 33  1  0
  7 34  1  0
 16 41  1  0
 17 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  8 35  1  6
 13 38  1  1
 12 36  1  0
 12 37  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₆

Average Mass

370.4010 Da

Monoisotopic Mass

370.14164 Da

IUPAC Name

(3S,4S)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

Traditional Name

(3S,4S)-4-(2H-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H22O6/c1-23-17-5-3-14(9-19(17)24-2)8-16-15(11-25-21(16)22)7-13-4-6-18-20(10-13)27-12-26-18/h3-6,9-10,15-16H,7-8,11-12H2,1-2H3/t15-,16+/m1/s1

InChI Key

IYBDDRJHJMFFBB-CVEARBPZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bursera schlechtendalii	LOTUS Database	35616633
Bursera simaruba	LOTUS Database	35616633
Phyllanthus urinaria	JEOL database	Chang, C. -C., et al., Phytochemistry 63, 825 (2003)
Phyllanthus urinaria L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
O-dimethoxybenzene
Dimethoxybenzene
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	3.58	ALOGPS
logP	3.52	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	97.44 m³·mol⁻¹	ChemAxon
Polarizability	37.16 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	Yes	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

13084307

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15941633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chang, C. -C., et al. (2003). Chang, C. -C., et al., Phytochemistry 63, 825 (2003). Phytochem..

Showing NP-Card for dextrobursehernin (NP0030784)

MOL for NP0030784 (dextrobursehernin)

3D MOL for NP0030784 (dextrobursehernin)

3D SDF for NP0030784 (dextrobursehernin)

3D-SDF for NP0030784 (dextrobursehernin)

PDB for NP0030784 (dextrobursehernin)

3D PDB for NP0030784 (dextrobursehernin)

SMILES for NP0030784 (dextrobursehernin)

INCHI for NP0030784 (dextrobursehernin)

Structure for NP0030784 (dextrobursehernin)

3D Structure for NP0030784 (dextrobursehernin)