NP-MRD: Showing NP-Card for 2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal (NP0170997)

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Record Information

Version

2.0

Created at

2022-09-03 07:19:57 UTC

Updated at

2022-09-03 07:19:57 UTC

NP-MRD ID

NP0170997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal

Description

Brevetoxin 2 belongs to the class of organic compounds known as brevetoxins and derivatives. These are a group of cyclic polyether compounds produced naturally by a species of dinoflagellate known as Karenia brevis. They contain a Pentaoxapentacycloheptacos- 23-en-7-one derivative (type a brevetoxin) or a pentaoxapentacyclotetracosa- 8,23-dien-7-one derivative (type b brevetoxin). 2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal is found in Karenia brevis. 2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal was first documented in 2021 (PMID: 34681447). Based on a literature review very few articles have been published on Brevetoxin 2 (PMID: 33868255).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032209192D          

 64 74  0  0  0  0            999 V2000
   -0.6305   -5.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0546   -4.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8795   -4.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2803   -5.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539   -4.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1710   -4.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5717   -3.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966   -3.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7973   -2.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8208   -4.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2215   -3.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456   -4.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0698   -4.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8947   -4.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3188   -5.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1121   -5.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8333   -5.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4070   -5.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2073   -5.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9807   -4.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7810   -4.7193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5813   -4.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.0642   -3.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8645   -3.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9436   -5.7338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1434   -5.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6644   -6.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8406   -6.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5231   -7.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2923   -5.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1447   -7.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6691   -5.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5951   -4.8769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
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 22 23  1  0  0  0  0
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 13 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 10 63  1  0  0  0  0
 63 64  1  0  0  0  0
  6 64  1  0  0  0  0
M  END

     RDKit          3D

134144  0  0  0  0  0  0  0  0999 V2000
   13.7326    0.5312   -2.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4284    0.0311   -0.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3169    0.6551   -0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1985   -0.3318    0.1968 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5913   -0.8801   -1.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3922   -0.1395   -1.5421 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032209192D          

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M  END
> <DATABASE_ID>
NP0170997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2OC3CC4OC(=O)C=C(C)C4OC3(C)CC2OC2CCC3(C)OC4(C)CC5OC6CC7OC8(C)C(O)CC(CC(=C)C=O)OC8CC7OC6\C=C/CC5(C)OC4CC3OC12

> <INCHI_IDENTIFIER>
InChI=1S/C50H70O14/c1-25(24-51)14-28-17-37(52)50(8)41(54-28)19-33-34(61-50)18-32-29(55-33)10-9-12-46(4)42(58-32)23-49(7)40(62-46)21-39-47(5,64-49)13-11-30-44(60-39)26(2)15-31-36(56-30)22-48(6)38(57-31)20-35-45(63-48)27(3)16-43(53)59-35/h9-10,16,24,26,28-42,44-45,52H,1,11-15,17-23H2,2-8H3/b10-9-

> <INCHI_KEY>
LYTCVQQGCSNFJU-KTKRTIGZSA-N

> <FORMULA>
C50H70O14

> <MOLECULAR_WEIGHT>
895.096

> <EXACT_MASS>
894.476556934

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
134

> <JCHEM_AVERAGE_POLARIZABILITY>
98.58001199148346

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(21Z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0^{3,26}.0^{5,24}.0^{7,20}.0^{9,18}.0^{11,16}.0^{30,48}.0^{33,46}.0^{35,44}.0^{37,42}]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.674190557666666

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.896403465084923

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.836735719274277

> <JCHEM_PKA_STRONGEST_BASIC>
-3.307595236702076

> <JCHEM_POLAR_SURFACE_AREA>
155.89999999999998

> <JCHEM_REFRACTIVITY>
230.11659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(21Z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0^{3,26}.0^{5,24}.0^{7,20}.0^{9,18}.0^{11,16}.0^{30,48}.0^{33,46}.0^{35,44}.0^{37,42}]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.177 -10.475   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.969  -9.154   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.508  -9.179   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.257 -10.525   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.221  -7.808   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.319  -7.783   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.067  -6.436   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.607  -6.411   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.355  -5.065   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.399  -7.732   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.147  -6.386   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.939  -7.707   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.730  -9.028   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.270  -9.002   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.062 -10.323   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.543  -9.900   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.889 -10.648   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.960  -9.542   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.454  -9.916   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.031  -8.435   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.525  -8.809   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.018  -9.183   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.486  -7.738   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.912  -7.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.450  -7.847   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.474  -8.997   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      20.823  -8.256   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      22.245  -8.848   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      23.316  -7.742   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      24.809  -8.116   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.387  -6.635   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      25.880  -7.009   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      27.374  -7.383   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      28.445  -6.277   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      28.022  -4.796   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      29.939  -6.651   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      30.362  -8.131   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      31.856  -8.506   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      29.291  -9.238   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      27.797  -8.864   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      26.726  -9.971   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      25.232  -9.596   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      24.161 -10.703   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      22.668 -10.329   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      21.774 -11.583   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      20.236 -11.666   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      19.643 -13.087   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      19.212 -10.515   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      17.863 -11.257   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      16.441 -10.664   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      15.370 -11.771   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      13.876 -11.397   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      12.806 -12.503   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      11.312 -12.129   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      11.924 -13.542   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      10.564 -13.475   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       9.083 -13.898   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       7.737 -13.150   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       7.314 -11.669   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       5.774 -11.695   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0       4.982 -10.374   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       3.442 -10.399   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       2.651  -9.078   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       1.111  -9.103   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   64                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   63                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   61                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   59                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   54                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   52                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24   50                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   48                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   44                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32   42                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   40                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   33   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   30   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   28   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   26   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   22   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   19   53                                                  
CONECT   53   52   54                                                       
CONECT   54   53   17   55   56                                             
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   15   60                                                  
CONECT   60   59   61                                                       
CONECT   61   60   13   62                                                  
CONECT   62   61   63                                                       
CONECT   63   62   10   64                                                  
CONECT   64   63    6                                                       
MASTER        0    0    0    0    0    0    0    0   64    0  148    0
END

View in JSmol

Synonyms

Value	Source
Brevetoxin b	MeSH

Chemical Formula

C₅₀H₇₀O₁₄

Average Mass

895.0960 Da

Monoisotopic Mass

894.47656 Da

IUPAC Name

2-{[(21Z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0^{3,26}.0^{5,24}.0^{7,20}.0^{9,18}.0^{11,16}.0^{30,48}.0^{33,46}.0^{35,44}.0^{37,42}]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1CC2OC3CC4OC(=O)C=C(C)C4OC3(C)CC2OC2CCC3(C)OC4(C)CC5OC6CC7OC8(C)C(O)CC(CC(=C)C=O)OC8CC7OC6\C=C/CC5(C)OC4CC3OC12

InChI Identifier

InChI=1S/C50H70O14/c1-25(24-51)14-28-17-37(52)50(8)41(54-28)19-33-34(61-50)18-32-29(55-33)10-9-12-46(4)42(58-32)23-49(7)40(62-46)21-39-47(5,64-49)13-11-30-44(60-39)26(2)15-31-36(56-30)22-48(6)38(57-31)20-35-45(63-48)27(3)16-43(53)59-35/h9-10,16,24,26,28-42,44-45,52H,1,11-15,17-23H2,2-8H3/b10-9-

InChI Key

LYTCVQQGCSNFJU-KTKRTIGZSA-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
Karenia brevis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as brevetoxins and derivatives. These are a group of cyclic polyether compounds produced naturally by a species of dinoflagellate known as Karenia brevis. They contain a Pentaoxapentacycloheptacos- 23-en-7-one derivative (type a brevetoxin) or a pentaoxapentacyclotetracosa- 8,23-dien-7-one derivative (type b brevetoxin).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Brevetoxins and derivatives

Sub Class

Not Available

Direct Parent

Brevetoxins and derivatives

Alternative Parents

Substituents

Brevetoxin type b fragment
Dihydropyranone
Oxepane
Pyran
Oxane
Monosaccharide
Alpha,beta-unsaturated aldehyde
Enal
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Aldehyde
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.41	ALOGPS
logP	3.67	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	155.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	230.12 m³·mol⁻¹	ChemAxon
Polarizability	98.58 Å³	ChemAxon
Number of Rings	11	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

4510092

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5353447

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang X, Ding M, Zhang C, Mao Y, Wang Y, Li P, Jiang H, Wang Z, Yu X: Development of a New Monoclonal Antibody against Brevetoxins in Oyster Samples Based on the Indirect Competitive Enzyme-Linked Immunosorbent Assay. Foods. 2021 Oct 9;10(10):2398. doi: 10.3390/foods10102398. [PubMed:34681447 ]
Estrada N, Nunez-Vazquez EJ, Palacios A, Ascencio F, Guzman-Villanueva L, Contreras RG: In vitro Evaluation of Programmed Cell Death in the Immune System of Pacific Oyster Crassostrea gigas by the Effect of Marine Toxins. Front Immunol. 2021 Apr 1;12:634497. doi: 10.3389/fimmu.2021.634497. eCollection 2021. [PubMed:33868255 ]
LOTUS database [Link]

MOL for NP0170997 (2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal)

3D MOL for NP0170997 (2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal)

3D SDF for NP0170997 (2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal)

3D-SDF for NP0170997 (2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal)

PDB for NP0170997 (2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal)

3D PDB for NP0170997 (2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal)

SMILES for NP0170997 (2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal)

INCHI for NP0170997 (2-{[(21z)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-14-yl]methyl}prop-2-enal)