NP-MRD: Showing NP-Card for Bursehernin (NP0138726)

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Record Information

Version

2.0

Created at

2022-06-29 18:33:23 UTC

Updated at

2022-06-29 18:33:23 UTC

NP-MRD ID

NP0138726

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bursehernin

Description

(-)-Bursehernin belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety (-)-bursehernin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Bursehernin is found in Aristolochia tomentosa, Bupleurum salicifolium, Bursera simaruba, Hernandia nymphaeifolia, Hernandia ovigera, Juniperus chinensis, Stellera chamaejasme and Zanthoxylum beecheyanum. It was first documented in 1994 (PMID: 24242108). Based on a literature review a significant number of articles have been published on (-)-bursehernin (PMID: 14987061) (PMID: 19329133) (PMID: 10230514) (PMID: 18680297).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292220332D          

 27 30  0  0  1  0            999 V2000
    8.1758   -0.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5627   -1.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7781   -0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1650   -1.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3803   -1.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2088   -0.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8219    0.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065    0.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4242   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2527    0.7749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5852    1.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922    2.1025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047    1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6252    1.3017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3365   -2.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7234   -2.7079    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -7.2556   -1.1139    0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4662    0.0008    0.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1373   -0.1432    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5739   -1.3977    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -1.6227    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546   -0.5614   -0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0272   -0.7539   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -0.5428    0.4808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3561   -1.4346    1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4931   -1.6061    2.1690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197   -2.0522    1.9726 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190   -1.9642    0.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308   -0.7460    0.1199 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1050    0.4945    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5431    0.4294    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172    0.0212    1.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7729   -0.0516    0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    0.2787   -0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4414    0.6896   -1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0687    0.7624   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2362    0.9536   -2.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5883    1.1093   -2.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6110    0.2994   -0.8995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0313    0.7112   -0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3567    0.9253   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9615    2.1712   -0.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3100    3.3693   -0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4011   -1.7939    0.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2494   -0.8165    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7687   -1.6726    1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1670   -2.2670    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615   -2.6534    0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9173   -1.7911   -1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407   -0.0237   -1.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2872    0.5418    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -2.0645    1.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956   -2.8745    0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605   -0.9758   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5906    1.3263   -0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    0.7569    1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -0.2484    2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4306   -0.3834    1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.0901   -1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7136    2.1887   -1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3065    0.7558   -2.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    1.5475   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8273    3.8301    0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140    3.1756   -1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0234    4.1266   -0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 25  2  0
 25 26  1  0
 26 27  1  0
 25 24  1  0
 24  6  2  0
  6  7  1  0
  7  8  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 20  2  0
 20 19  1  0
 19 18  2  0
 18 23  1  0
 23 22  1  0
 22 21  1  0
 18 17  1  0
 17 16  2  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  9  8  1  0
 16 15  1  0
 21 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 24 46  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  1
 13 38  1  6
 14 39  1  0
 14 40  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 17 42  1  0
 16 41  1  0
 12 36  1  0
 12 37  1  0
  5 32  1  0
  4 31  1  0
M  END


  Mrv1652306292220332D          

 27 30  0  0  1  0            999 V2000
    8.1758   -0.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5627   -1.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7781   -0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1650   -1.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3803   -1.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2088   -0.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8219    0.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065    0.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4242   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2527    0.7749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5852    1.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922    2.1025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047    1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6252    1.3017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3365   -2.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7234   -2.7079    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138726

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C(C[C@@H]2[C@@H](CC3=CC4=C(OCO4)C=C3)COC2=O)C=C1

> <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+/m0/s1

> <INCHI_KEY>
IYBDDRJHJMFFBB-JKSUJKDBSA-N

> <FORMULA>
C21H22O6

> <MOLECULAR_WEIGHT>
370.401

> <EXACT_MASS>
370.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.57105157777349

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      15.261  -0.933   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.117  -1.963   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.652  -1.488   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.508  -2.518   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.043  -2.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.723  -0.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.868   0.495   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.332   0.019   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.259  -0.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.938   1.446   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.692   3.604   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.199   3.925   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.969   2.591   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.500   2.430   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      11.828  -4.024   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.684  -5.055   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19                                                       
CONECT   26    4   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
(-)-5'-Desmethoxy-yatein	ChEBI
(3R-trans)-4-(1,3-Benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]dihydro-2(3H)-furanone	ChEBI
(R,R)-4-(1,3-Benzodioxol-5-ylmethyl)-3-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one	ChEBI
Bursehernin	ChEBI
(3R-trans)-4-(1,3-Benzodioxol-5-ylmethyl)-3-((3,4-dimethoxyphenyl)methyl)dihydro-2(3H)-furanone	MeSH

Chemical Formula

C₂₁H₂₂O₆

Average Mass

370.4010 Da

Monoisotopic Mass

370.14164 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

40456-51-7

SMILES

COC1=C(OC)C=C(C[C@@H]2[C@@H](CC3=CC4=C(OCO4)C=C3)COC2=O)C=C1

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+/m0/s1

InChI Key

IYBDDRJHJMFFBB-JKSUJKDBSA-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
Aristolochia tomentosa	LOTUS Database	35616633
Bupleurum salicifolium	LOTUS Database	35616633
Bursera simaruba	LOTUS Database	35616633
Hernandia nymphaeifolia	LOTUS Database	35616633
Hernandia ovigera	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Stellera chamaejasme	LOTUS Database	35616633
Zanthoxylum beecheyanum	LOTUS Database	35616633

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
Tetrahydrofuran
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00036847

Chemspider ID

85282

KEGG Compound ID

Not Available

BioCyc ID

CPD-17599

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94504

PDB ID

Not Available

ChEBI ID

90893

Good Scents ID

Not Available

References

General References

Pettit GR, Meng Y, Gearing RP, Herald DL, Pettit RK, Doubek DL, Chapuis JC, Tackett LP: Antineoplastic agents. 522. Hernandia peltata (Malaysia) and Hernandia nymphaeifolia (Republic of Maldives). J Nat Prod. 2004 Feb;67(2):214-20. doi: 10.1021/np030125s. [PubMed:14987061 ]
Maldini M, Montoro P, Piacente S, Pizza C: Phenolic compounds from Bursera simaruba Sarg. bark: phytochemical investigation and quantitative analysis by tandem mass spectrometry. Phytochemistry. 2009 Mar;70(5):641-9. doi: 10.1016/j.phytochem.2009.02.009. Epub 2009 Mar 28. [PubMed:19329133 ]
Lim YH, Leem MJ, Shin DH, Chang HB, Hong SW, Moon EY, Lee DK, Yoon SJ, Woo WS: Cytotoxic constituents from the roots of Anthriscus sylvestris. Arch Pharm Res. 1999 Apr;22(2):208-12. doi: 10.1007/BF02976548. [PubMed:10230514 ]
DeMartino MP, Chen K, Baran PS: Intermolecular enolate heterocoupling: scope, mechanism, and application. J Am Chem Soc. 2008 Aug 27;130(34):11546-60. doi: 10.1021/ja804159y. Epub 2008 Aug 5. [PubMed:18680297 ]
Gonzalez JA, Estevez-Braun A, Estevez-Reyes R, Ravelo AG: Inhibition of potato cyst nematode hatch by lignans fromBupleurum salicifolium (Unbelliferae). J Chem Ecol. 1994 Mar;20(3):517-24. doi: 10.1007/BF02059594. [PubMed:24242108 ]

Showing NP-Card for Bursehernin (NP0138726)

MOL for NP0138726 (Bursehernin)

3D MOL for NP0138726 (Bursehernin)

3D SDF for NP0138726 (Bursehernin)

3D-SDF for NP0138726 (Bursehernin)

PDB for NP0138726 (Bursehernin)

3D PDB for NP0138726 (Bursehernin)

SMILES for NP0138726 (Bursehernin)

INCHI for NP0138726 (Bursehernin)

Structure for NP0138726 (Bursehernin)

3D Structure for NP0138726 (Bursehernin)