NP-MRD: Showing NP-Card for (E)-synoilide B (NP0037098)

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Record Information

Version

2.0

Created at

2021-06-20 20:06:06 UTC

Updated at

2021-06-30 00:09:06 UTC

NP-MRD ID

NP0037098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(E)-synoilide B

Provided By

JEOL Database JEOL Logo

Description

2-(3,5-Dibromo-4-hydroxybenzoyl)-3-(3-bromo-4-hydroxyphenyl)fumaric acid dimethyl ester belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. (E)-synoilide B is found in Synoicum sp. (E)-synoilide B was first documented in 2012 (Won, T. H., et al.). Based on a literature review very few articles have been published on 2-(3,5-Dibromo-4-hydroxybenzoyl)-3-(3-bromo-4-hydroxyphenyl)fumaric acid dimethyl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122063D          

 42 43  0  0  0  0            999 V2000
   -4.0272    1.5603   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    0.9777   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392    1.0466    0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312    1.5945    0.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669    0.4492    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6728    1.2156    1.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3201    0.7030    2.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    2.6413    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1984    3.1172   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908    4.4679   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2895    5.0652   -2.0136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.2293    5.3421    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5100    6.6623    0.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838    4.8569    2.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755    6.0115    3.6522 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075    3.5112    2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854   -0.7975    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803   -1.2311    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -0.5805    0.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2172   -2.4359    1.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841   -2.9186    1.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -1.7156   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4920   -2.0960   -1.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728   -2.9582   -2.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -3.4458   -2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1931   -4.2834   -2.9322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -3.0816   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5282   -3.7411   -0.1490 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1216   -2.2202   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187    1.4193   -2.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0530    2.6338   -1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9125    1.0621   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    2.4480   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5821    7.1126    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186    3.1341    3.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -3.8719    2.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355   -2.2176    2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -3.0898    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580   -1.7201   -2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9463   -3.2484   -3.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9885   -4.5522   -2.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.9490    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
  3  2  1  0  0  0  0
  8 16  1  0  0  0  0
  3  4  2  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 17 22  1  0  0  0  0
 10 11  1  0  0  0  0
 17 18  1  0  0  0  0
 16 14  2  0  0  0  0
 18 19  2  0  0  0  0
 14 15  1  0  0  0  0
 18 20  1  0  0  0  0
  9  8  2  0  0  0  0
 20 21  1  0  0  0  0
  6  7  2  0  0  0  0
 22 29  2  0  0  0  0
 14 12  1  0  0  0  0
 29 27  1  0  0  0  0
  6  5  1  0  0  0  0
 27 25  2  0  0  0  0
 12 10  2  0  0  0  0
 25 24  1  0  0  0  0
  5 17  2  0  0  0  0
 24 23  2  0  0  0  0
 23 22  1  0  0  0  0
 10  9  1  0  0  0  0
 25 26  1  0  0  0  0
  5  3  1  0  0  0  0
 27 28  1  0  0  0  0
  9 33  1  0  0  0  0
 16 35  1  0  0  0  0
 13 34  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 21 36  1  0  0  0  0
 21 37  1  0  0  0  0
 21 38  1  0  0  0  0
 29 42  1  0  0  0  0
 24 40  1  0  0  0  0
 23 39  1  0  0  0  0
 26 41  1  0  0  0  0
M  END

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -4.0272    1.5603   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    0.9777   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392    1.0466    0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312    1.5945    0.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669    0.4492    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6728    1.2156    1.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3201    0.7030    2.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    2.6413    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1984    3.1172   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908    4.4679   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2895    5.0652   -2.0136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.2293    5.3421    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5100    6.6623    0.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838    4.8569    2.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755    6.0115    3.6522 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075    3.5112    2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854   -0.7975    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803   -1.2311    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -0.5805    0.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2172   -2.4359    1.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841   -2.9186    1.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -1.7156   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4920   -2.0960   -1.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728   -2.9582   -2.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -3.4458   -2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1931   -4.2834   -2.9322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -3.0816   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5282   -3.7411   -0.1490 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1216   -2.2202   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187    1.4193   -2.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0530    2.6338   -1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9125    1.0621   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    2.4480   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5821    7.1126    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186    3.1341    3.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -3.8719    2.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355   -2.2176    2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -3.0898    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580   -1.7201   -2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9463   -3.2484   -3.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9885   -4.5522   -2.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.9490    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0
  3  2  1  0
  8 16  1  0
  3  4  2  0
 12 13  1  0
  2  1  1  0
 17 22  1  0
 10 11  1  0
 17 18  1  0
 16 14  2  0
 18 19  2  0
 14 15  1  0
 18 20  1  0
  9  8  2  0
 20 21  1  0
  6  7  2  0
 22 29  2  0
 14 12  1  0
 29 27  1  0
  6  5  1  0
 27 25  2  0
 12 10  2  0
 25 24  1  0
  5 17  2  0
 24 23  2  0
 23 22  1  0
 10  9  1  0
 25 26  1  0
  5  3  1  0
 27 28  1  0
  9 33  1  0
 16 35  1  0
 13 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
 29 42  1  0
 24 40  1  0
 23 39  1  0
 26 41  1  0
M  END


  Mrv1652306202122063D          

 42 43  0  0  0  0            999 V2000
   -4.0272    1.5603   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    0.9777   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392    1.0466    0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312    1.5945    0.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669    0.4492    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6728    1.2156    1.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3201    0.7030    2.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    2.6413    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1984    3.1172   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908    4.4679   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2895    5.0652   -2.0136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.2293    5.3421    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5100    6.6623    0.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838    4.8569    2.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755    6.0115    3.6522 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075    3.5112    2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854   -0.7975    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803   -1.2311    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -0.5805    0.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2172   -2.4359    1.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841   -2.9186    1.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -1.7156   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4920   -2.0960   -1.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728   -2.9582   -2.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -3.4458   -2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1931   -4.2834   -2.9322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -3.0816   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5282   -3.7411   -0.1490 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1216   -2.2202   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187    1.4193   -2.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0530    2.6338   -1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9125    1.0621   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    2.4480   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5821    7.1126    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186    3.1341    3.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -3.8719    2.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355   -2.2176    2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -3.0898    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580   -1.7201   -2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9463   -3.2484   -3.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9885   -4.5522   -2.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.9490    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
  3  2  1  0  0  0  0
  8 16  1  0  0  0  0
  3  4  2  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 17 22  1  0  0  0  0
 10 11  1  0  0  0  0
 17 18  1  0  0  0  0
 16 14  2  0  0  0  0
 18 19  2  0  0  0  0
 14 15  1  0  0  0  0
 18 20  1  0  0  0  0
  9  8  2  0  0  0  0
 20 21  1  0  0  0  0
  6  7  2  0  0  0  0
 22 29  2  0  0  0  0
 14 12  1  0  0  0  0
 29 27  1  0  0  0  0
  6  5  1  0  0  0  0
 27 25  2  0  0  0  0
 12 10  2  0  0  0  0
 25 24  1  0  0  0  0
  5 17  2  0  0  0  0
 24 23  2  0  0  0  0
 23 22  1  0  0  0  0
 10  9  1  0  0  0  0
 25 26  1  0  0  0  0
  5  3  1  0  0  0  0
 27 28  1  0  0  0  0
  9 33  1  0  0  0  0
 16 35  1  0  0  0  0
 13 34  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 21 36  1  0  0  0  0
 21 37  1  0  0  0  0
 21 38  1  0  0  0  0
 29 42  1  0  0  0  0
 24 40  1  0  0  0  0
 23 39  1  0  0  0  0
 26 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(Br)C([H])=C(C([H])=C1[H])C(\C(=O)OC([H])([H])[H])=C(/C(=O)OC([H])([H])[H])C(=O)C1=C([H])C(Br)=C(O[H])C(Br)=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H13Br3O7/c1-28-18(26)14(8-3-4-13(23)10(20)5-8)15(19(27)29-2)16(24)9-6-11(21)17(25)12(22)7-9/h3-7,23,25H,1-2H3/b15-14+

> <INCHI_KEY>
GMHLSOYTFNFLNQ-CCEZHUSRSA-N

> <FORMULA>
C19H13Br3O7

> <MOLECULAR_WEIGHT>
593.018

> <EXACT_MASS>
589.821142

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
45.444020093611286

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-dimethyl (2E)-2-(3-bromo-4-hydroxyphenyl)-3-[(E)-3,5-dibromo-4-hydroxybenzoyl]but-2-enedioate

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
5.426237612666666

> <ALOGPS_LOGS>
-5.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.010555897790027

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.018882794869648

> <JCHEM_PKA_STRONGEST_BASIC>
-6.758904466446984

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
115.3189

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-dimethyl (2E)-2-(3-bromo-4-hydroxyphenyl)-3-[(E)-3,5-dibromo-4-hydroxybenzoyl]but-2-enedioate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -4.0272    1.5603   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    0.9777   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392    1.0466    0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312    1.5945    0.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669    0.4492    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6728    1.2156    1.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3201    0.7030    2.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    2.6413    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1984    3.1172   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908    4.4679   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2895    5.0652   -2.0136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.2293    5.3421    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5100    6.6623    0.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838    4.8569    2.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755    6.0115    3.6522 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075    3.5112    2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854   -0.7975    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803   -1.2311    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -0.5805    0.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2172   -2.4359    1.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841   -2.9186    1.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -1.7156   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4920   -2.0960   -1.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728   -2.9582   -2.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -3.4458   -2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1931   -4.2834   -2.9322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -3.0816   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5282   -3.7411   -0.1490 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1216   -2.2202   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187    1.4193   -2.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0530    2.6338   -1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9125    1.0621   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    2.4480   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5821    7.1126    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186    3.1341    3.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -3.8719    2.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355   -2.2176    2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -3.0898    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580   -1.7201   -2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9463   -3.2484   -3.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9885   -4.5522   -2.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.9490    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0
  3  2  1  0
  8 16  1  0
  3  4  2  0
 12 13  1  0
  2  1  1  0
 17 22  1  0
 10 11  1  0
 17 18  1  0
 16 14  2  0
 18 19  2  0
 14 15  1  0
 18 20  1  0
  9  8  2  0
 20 21  1  0
  6  7  2  0
 22 29  2  0
 14 12  1  0
 29 27  1  0
  6  5  1  0
 27 25  2  0
 12 10  2  0
 25 24  1  0
  5 17  2  0
 24 23  2  0
 23 22  1  0
 10  9  1  0
 25 26  1  0
  5  3  1  0
 27 28  1  0
  9 33  1  0
 16 35  1  0
 13 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
 29 42  1  0
 24 40  1  0
 23 39  1  0
 26 41  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      -4.027   1.560  -1.755  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.836   0.978  -1.224  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.739   1.047   0.127  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.531   1.595   0.877  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.467   0.449   0.582  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.673   1.216   1.582  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.320   0.703   2.640  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.364   2.641   1.298  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.198   3.117  -0.008  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.091   4.468  -0.224  0.00  0.00           C+0
HETATM   11 Br   UNK     0       0.290   5.065  -2.014  0.00  0.00          Br+0
HETATM   12  C   UNK     0       0.229   5.342   0.858  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.510   6.662   0.626  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.084   4.857   2.161  0.00  0.00           C+0
HETATM   15 Br   UNK     0       0.276   6.011   3.652  0.00  0.00          Br+0
HETATM   16  C   UNK     0      -0.208   3.511   2.385  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.085  -0.798   0.227  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.280  -1.231   0.620  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.285  -0.581   0.372  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.217  -2.436   1.235  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.484  -2.919   1.681  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.914  -1.716  -0.581  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.492  -2.096  -1.864  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.273  -2.958  -2.637  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.472  -3.446  -2.129  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.193  -4.283  -2.932  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.898  -3.082  -0.852  0.00  0.00           C+0
HETATM   28 Br   UNK     0      -5.528  -3.741  -0.149  0.00  0.00          Br+0
HETATM   29  C   UNK     0      -3.122  -2.220  -0.075  0.00  0.00           C+0
HETATM   30  H   UNK     0      -4.019   1.419  -2.839  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.053   2.634  -1.544  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.912   1.062  -1.348  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.269   2.448  -0.862  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.582   7.113   1.487  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.319   3.134   3.400  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.323  -3.872   2.192  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.936  -2.218   2.390  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.149  -3.090   0.828  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.558  -1.720  -2.278  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.946  -3.248  -3.632  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.989  -4.552  -2.437  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.453  -1.949   0.926  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    6   17    3                                                  
CONECT    6    8    7    5                                                  
CONECT    7    6                                                            
CONECT    8    6   16    9                                                  
CONECT    9    8   10   33                                                  
CONECT   10   11   12    9                                                  
CONECT   11   10                                                            
CONECT   12   13   14   10                                                  
CONECT   13   12   34                                                       
CONECT   14   16   15   12                                                  
CONECT   15   14                                                            
CONECT   16    8   14   35                                                  
CONECT   17   22   18    5                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   36   37   38                                             
CONECT   22   17   29   23                                                  
CONECT   23   24   22   39                                                  
CONECT   24   25   23   40                                                  
CONECT   25   27   24   26                                                  
CONECT   26   25   41                                                       
CONECT   27   29   25   28                                                  
CONECT   28   27                                                            
CONECT   29   22   27   42                                                  
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    9                                                            
CONECT   34   13                                                            
CONECT   35   16                                                            
CONECT   36   21                                                            
CONECT   37   21                                                            
CONECT   38   21                                                            
CONECT   39   23                                                            
CONECT   40   24                                                            
CONECT   41   26                                                            
CONECT   42   29                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

RDKit          3D

42 43  0  0  0  0  0  0  0  0999 V2000
   -4.0272    1.5603   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    0.9777   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392    1.0466    0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312    1.5945    0.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669    0.4492    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6728    1.2156    1.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3201    0.7030    2.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    2.6413    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1984    3.1172   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908    4.4679   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2895    5.0652   -2.0136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.2293    5.3421    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5100    6.6623    0.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838    4.8569    2.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755    6.0115    3.6522 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075    3.5112    2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854   -0.7975    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803   -1.2311    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -0.5805    0.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2172   -2.4359    1.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841   -2.9186    1.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -1.7156   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4920   -2.0960   -1.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728   -2.9582   -2.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -3.4458   -2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1931   -4.2834   -2.9322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -3.0816   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5282   -3.7411   -0.1490 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1216   -2.2202   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187    1.4193   -2.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0530    2.6338   -1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9125    1.0621   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    2.4480   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5821    7.1126    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186    3.1341    3.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -3.8719    2.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355   -2.2176    2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -3.0898    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580   -1.7201   -2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9463   -3.2484   -3.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9885   -4.5522   -2.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.9490    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0
  3  2  1  0
  8 16  1  0
  3  4  2  0
 12 13  1  0
  2  1  1  0
 17 22  1  0
 10 11  1  0
 17 18  1  0
 16 14  2  0
 18 19  2  0
 14 15  1  0
 18 20  1  0
  9  8  2  0
 20 21  1  0
  6  7  2  0
 22 29  2  0
 14 12  1  0
 29 27  1  0
  6  5  1  0
 27 25  2  0
 12 10  2  0
 25 24  1  0
  5 17  2  0
 24 23  2  0
 23 22  1  0
 10  9  1  0
 25 26  1  0
  5  3  1  0
 27 28  1  0
  9 33  1  0
 16 35  1  0
 13 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
 29 42  1  0
 24 40  1  0
 23 39  1  0
 26 41  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-(3,5-Dibromo-4-hydroxybenzoyl)-3-(3-bromo-4-hydroxyphenyl)fumarate dimethyl ester	Generator

Chemical Formula

C₁₉H₁₃Br₃O₇

Average Mass

593.0180 Da

Monoisotopic Mass

589.82114 Da

IUPAC Name

1,4-dimethyl (2E)-2-(3-bromo-4-hydroxyphenyl)-3-[(E)-3,5-dibromo-4-hydroxybenzoyl]but-2-enedioate

Traditional Name

1,4-dimethyl (2E)-2-(3-bromo-4-hydroxyphenyl)-3-[(E)-3,5-dibromo-4-hydroxybenzoyl]but-2-enedioate

CAS Registry Number

Not Available

SMILES

[H]OC1=C(Br)C([H])=C(C([H])=C1[H])C(\C(=O)OC([H])([H])[H])=C(/C(=O)OC([H])([H])[H])C(=O)C1=C([H])C(Br)=C(O[H])C(Br)=C1[H]

InChI Identifier

InChI=1S/C19H13Br3O7/c1-28-18(26)14(8-3-4-13(23)10(20)5-8)15(19(27)29-2)16(24)9-6-11(21)17(25)12(22)7-9/h3-7,23,25H,1-2H3/b15-14+

InChI Key

GMHLSOYTFNFLNQ-CCEZHUSRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Synoicum sp.	JEOL database	Won, T. H., et al, J. Nat. Prod. 75, 2055 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retrochalcones

Alternative Parents

Substituents

Retrochalcone
Cinnamylphenol
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
2-halophenol
2-bromophenol
Benzoyl
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Halobenzene
Bromobenzene
Beta-keto acid
Phenol
Alpha-branched alpha,beta-unsaturated-ketone
Dicarboxylic acid or derivatives
Keto acid
Fatty acyl
Aryl halide
Aryl bromide
Monocyclic benzene moiety
Benzenoid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Carbonyl group
Organic oxygen compound
Organohalogen compound
Organobromide
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.54	ALOGPS
logP	5.43	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	5.02	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	115.32 m³·mol⁻¹	ChemAxon
Polarizability	45.44 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

29215369

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102313460

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Won, T. H., et al. (2012). Won, T. H., et al, J. Nat. Prod. 75, 2055 (2012). J. Nat. Prod..

Showing NP-Card for (E)-synoilide B (NP0037098)

MOL for NP0037098 ((E)-synoilide B)

3D MOL for NP0037098 ((E)-synoilide B)

3D SDF for NP0037098 ((E)-synoilide B)

3D-SDF for NP0037098 ((E)-synoilide B)

PDB for NP0037098 ((E)-synoilide B)

3D PDB for NP0037098 ((E)-synoilide B)

SMILES for NP0037098 ((E)-synoilide B)

INCHI for NP0037098 ((E)-synoilide B)

Structure for NP0037098 ((E)-synoilide B)

3D Structure for NP0037098 ((E)-synoilide B)