NP-MRD: Showing NP-Card for 2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal (NP0153027)

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Record Information

Version

2.0

Created at

2022-09-02 09:36:54 UTC

Updated at

2022-09-02 09:36:54 UTC

NP-MRD ID

NP0153027

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal

Description

2-[[(24Z,49Z)-41-Hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.03,22.06,20.08,18.012,16.029,48.033,46.035,44.037,42]Henpentaconta-24,49-dien-39-yl]methyl]prop-2-enal, also known as brevetoxin a or GB-1 toxin, 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-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal is found in Garcinia kola and Karenia brevis. Based on a literature review very few articles have been published on 2-[[(24Z,49Z)-41-Hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.03,22.06,20.08,18.012,16.029,48.033,46.035,44.037,42]Henpentaconta-24,49-dien-39-yl]methyl]prop-2-enal.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211362D          

 62 71  0  0  0  0            999 V2000
   -0.2450   -9.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7823   -8.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931   -9.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8666   -9.8285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089   -8.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -7.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754   -7.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3862   -7.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596   -6.2580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -7.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -7.5100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2717   -8.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0825   -7.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6199   -8.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7894   -7.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3636   -8.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1420   -8.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4154   -7.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1592   -7.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9376   -7.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2946   -8.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0044   -7.9873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8184   -8.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9728   -7.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3096   -6.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7027   -6.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4584   -7.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0425   -6.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8391   -6.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5244   -6.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2525   -6.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0497   -5.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.7636   -6.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.7829   -7.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8681   -8.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5821   -8.5797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1140   -8.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5628   -7.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7656   -8.0997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0517   -7.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4676   -8.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6709   -8.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1802   -8.7176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3558   -8.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3650   -9.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8418  -10.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0310  -10.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3120   -9.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0211   -9.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2774   -9.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -9.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2256  -10.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4818  -10.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035  -10.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464   -9.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -9.5403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9983   -8.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875   -9.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -8.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -8.5931    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
 11 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
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 39 40  1  0  0  0  0
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 27 44  1  0  0  0  0
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 49 50  1  0  0  0  0
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 21 51  1  0  0  0  0
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 17 53  1  0  0  0  0
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 55 56  1  0  0  0  0
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 14 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 12 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 10 61  1  0  0  0  0
 61 62  1  0  0  0  0
  6 62  1  0  0  0  0
M  END

     RDKit          3D

132141  0  0  0  0  0  0  0  0999 V2000
   14.0239    2.6489    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7587    1.4540   -0.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7629    0.4099   -0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5355   -0.7210   -0.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4554    1.2204   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7137    0.1567   -0.2863 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5593    0.4286    1.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1242    0.8183    1.5441 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0535    0.8468    2.9432 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1579   -0.2824    1.0828 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9626    0.2949    0.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9152   -0.5451   -0.2443 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6272   -0.9413   -1.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2187    2.0926   -0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.8315    0.0463    1.0281 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022211362D          

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M  END
> <DATABASE_ID>
NP0153027

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2OC3(C)CC(C)CC4OC(=O)CC4OC3CC2OC2C\C=C/CC3OC4CCCC5OC6CC7OC(CC(=C)C=O)CC(O)C7OC6CC5(C)OC4\C=C/CC3OC12

> <INCHI_IDENTIFIER>
InChI=1S/C49H70O13/c1-26-17-36-39(22-45(52)58-36)57-44-21-38-40(62-48(44,4)23-26)18-28(3)46-35(55-38)11-7-6-10-31-32(59-46)12-8-14-34-33(54-31)13-9-15-43-49(5,61-34)24-42-37(56-43)20-41-47(60-42)30(51)19-29(53-41)16-27(2)25-50/h6-8,14,25-26,28-44,46-47,51H,2,9-13,15-24H2,1,3-5H3/b7-6-,14-8-

> <INCHI_KEY>
MGVIMUPHKPHTKF-PMAMELDRSA-N

> <FORMULA>
C49H70O13

> <MOLECULAR_WEIGHT>
867.086

> <EXACT_MASS>
866.481642314

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
96.04391770676075

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(24Z,49Z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0^{3,22}.0^{6,20}.0^{8,18}.0^{12,16}.0^{29,48}.0^{33,46}.0^{35,44}.0^{37,42}]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
4.690477807333332

> <ALOGPS_LOGS>
-5.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.03147921731022

> <JCHEM_PKA_STRONGEST_BASIC>
-3.222430990348509

> <JCHEM_POLAR_SURFACE_AREA>
146.67

> <JCHEM_REFRACTIVITY>
226.30379999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(24Z,49Z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0^{3,22}.0^{6,20}.0^{8,18}.0^{12,16}.0^{29,48}.0^{33,46}.0^{35,44}.0^{37,42}]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.457 -17.778   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.460 -16.609   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.974 -16.894   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.484 -18.347   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.950 -15.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564 -14.872   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.074 -13.419   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.588 -13.134   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.098 -11.682   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.591 -14.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.104 -14.019   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.107 -15.187   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.621 -14.903   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.624 -16.071   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.940 -14.564   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.012 -15.405   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.465 -15.915   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.975 -14.462   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.364 -13.796   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.817 -14.306   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.483 -15.695   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.808 -14.910   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      18.328 -15.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.616 -13.647   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.378 -12.731   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.978 -12.929   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.389 -13.547   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      22.479 -12.459   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      23.966 -12.860   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.379 -11.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.738 -11.527   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.226 -11.130   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      26.429  -9.604   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      27.559 -11.902   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      27.955 -13.390   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      29.461 -13.712   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      29.621 -15.244   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      30.953 -16.016   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      28.213 -15.868   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      27.184 -14.723   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      25.696 -15.119   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      24.363 -14.348   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      23.273 -15.435   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      21.786 -15.035   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      20.870 -16.273   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      19.331 -16.329   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      19.348 -17.868   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      18.371 -19.059   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      16.858 -19.344   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      15.516 -18.589   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      14.973 -17.148   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      13.584 -17.814   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      12.132 -17.304   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      11.621 -18.756   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      10.233 -19.423   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.780 -18.912   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       8.113 -17.524   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       6.600 -17.809   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       5.597 -16.640   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       4.083 -16.924   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       3.080 -15.756   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       1.567 -16.040   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   62                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   61                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   59                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   57                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   53                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   51                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   46                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   44                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31   42                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   35   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   29   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   27   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45   23   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   21   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   17   54                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   14   58                                                  
CONECT   58   57   59                                                       
CONECT   59   58   12   60                                                  
CONECT   60   59   61                                                       
CONECT   61   60   10   62                                                  
CONECT   62   61    6                                                       
MASTER        0    0    0    0    0    0    0    0   62    0  142    0
END

View in JSmol

Synonyms

Value	Source
Brevetoxin a	MeSH
GB-1 Toxin	MeSH

Chemical Formula

C₄₉H₇₀O₁₃

Average Mass

867.0860 Da

Monoisotopic Mass

866.48164 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1CC2OC3(C)CC(C)CC4OC(=O)CC4OC3CC2OC2C\C=C/CC3OC4CCCC5OC6CC7OC(CC(=C)C=O)CC(O)C7OC6CC5(C)OC4\C=C/CC3OC12

InChI Identifier

InChI=1S/C49H70O13/c1-26-17-36-39(22-45(52)58-36)57-44-21-38-40(62-48(44,4)23-26)18-28(3)46-35(55-38)11-7-6-10-31-32(59-46)12-8-14-34-33(54-31)13-9-15-43-49(5,61-34)24-42-37(56-43)20-41-47(60-42)30(51)19-29(53-41)16-27(2)25-50/h6-8,14,25-26,28-44,46-47,51H,2,9-13,15-24H2,1,3-5H3/b7-6-,14-8-

InChI Key

MGVIMUPHKPHTKF-PMAMELDRSA-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
Garcinia kola	LOTUS Database	35616633
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 a fragment
Oxepane
Gamma butyrolactone
Monosaccharide
Oxane
Alpha,beta-unsaturated aldehyde
Enal
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Aldehyde
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
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	3.97	ALOGPS
logS	-5.7	ALOGPS

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

4941677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6437089

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal (NP0153027)

MOL for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)

3D MOL for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)

3D SDF for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)

3D-SDF for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)

PDB for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)

3D PDB for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)

SMILES for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)

INCHI for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)

Structure for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)

3D Structure for NP0153027 (2-{[(24z,49z)-41-hydroxy-4,8,10,46-tetramethyl-14-oxo-2,7,13,17,21,28,34,38,43,47-decaoxadecacyclo[25.24.0.0³,²².0⁶,²⁰.0⁸,¹⁸.0¹²,¹⁶.0²⁹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]henpentaconta-24,49-dien-39-yl]methyl}prop-2-enal)