NP-MRD: Showing NP-Card for Brevetoxin A (NP0078348)

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Record Information

Version

2.0

Created at

2022-04-28 23:26:43 UTC

Updated at

2022-04-28 23:26:44 UTC

NP-MRD ID

NP0078348

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brevetoxin A

Description

2-{[(1R,3S,4R,6S,8S,10R,12S,16R,18R,20R,22R,24Z,27R,29R,33S,35R,37R,39S,41R,42S,44R,46S,48R)-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 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). Brevetoxin A is found in Apis cerana and Karenia brevis. Based on a literature review very few articles have been published on 2-{[(1R,3S,4R,6S,8S,10R,12S,16R,18R,20R,22R,24Z,27R,29R,33S,35R,37R,39S,41R,42S,44R,46S,48R)-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


  Mrv1652304292201262D          

 62 71  0  0  1  0            999 V2000
   16.1037    1.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3600    1.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5816    1.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2246    0.6758    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4980   -0.1026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2418   -0.4596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0201   -0.1862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3772    0.5576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1555    0.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8993    0.4740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1727   -0.3044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8157   -1.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0373   -1.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2936   -0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9835   -0.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5209    0.1692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.2474    0.9476    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.4366    1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7848    1.5736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5956    1.4212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.8691    0.6429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.3317    0.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6799    0.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2172    1.1165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.9438    1.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1330    2.0472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8595    2.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0280    0.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.3762    1.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9136    2.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7298    1.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1541   -0.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1634    0.3361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.7008    0.9621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5148    1.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5464    1.7725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8165    2.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0607    1.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8482    1.0291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3389    0.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0516    0.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4675    1.3972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6800    2.1944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4767    2.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2666    2.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4695    3.1209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.4051    0.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6510    0.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9371    0.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7362    1.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9948    2.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2096    2.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  4  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 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
  7 14  1  0  0  0  0
 11 15  1  1  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 17 19  1  1  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  6  0  0  0
 24 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 10 33  1  6  0  0  0
  5 34  1  0  0  0  0
 34 35  1  0  0  0  0
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 53 59  1  1  0  0  0
 51 60  1  1  0  0  0
 48 61  1  1  0  0  0
 41 62  1  1  0  0  0
M  END

     RDKit          3D

132141  0  0  0  0  0  0  0  0999 V2000
   13.1051   -1.6070   -1.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4389   -1.3536   -0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6115   -2.4078   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1629   -2.0015   -0.1382 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.9101   -2.6779    0.6503 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.8737   -1.3270    1.3308 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.4052    0.3525    1.9529 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.4540    1.5240    0.8417 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292201262D          

 62 71  0  0  1  0            999 V2000
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   11.8165    2.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0607    1.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8482    1.0291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3389    0.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0516    0.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6800    2.1944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4767    2.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2666    2.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4695    3.1209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7555    2.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7535    0.9839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6510    0.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9948    2.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2096    2.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  4  0  0  0
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  4  5  1  0  0  0  0
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  7  6  1  1  0  0  0
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 11 12  1  0  0  0  0
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  7 14  1  0  0  0  0
 11 15  1  1  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
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 31 32  2  0  0  0  0
 10 33  1  6  0  0  0
  5 34  1  0  0  0  0
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 35 36  2  0  0  0  0
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 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
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  4 40  1  0  0  0  0
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 41 42  1  0  0  0  0
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 43 44  1  0  0  0  0
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 57 58  2  0  0  0  0
 57 59  1  0  0  0  0
 53 59  1  1  0  0  0
 51 60  1  1  0  0  0
 48 61  1  1  0  0  0
 41 62  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2O[C@@]3(C)C[C@H](C)C[C@@H]4OC(=O)C[C@H]4O[C@@H]3C[C@H]2O[C@@H]2C\C=C/C[C@H]3O[C@@H]4CCC[C@@H]5O[C@@H]6C[C@H]7O[C@@H](CC(=C)C=O)C[C@@H](O)[C@@H]7O[C@@H]6C[C@]5(C)O[C@@H]4C=CC[C@H]3O[C@@H]12

> <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?/t26-,28-,29+,30-,31-,32-,33-,34-,35-,36+,37-,38-,39-,40+,41-,42-,43+,44-,46+,47+,48+,49+/m1/s1

> <INCHI_KEY>
MGVIMUPHKPHTKF-QGYNCCGGSA-N

> <FORMULA>
C49H70O13

> <MOLECULAR_WEIGHT>
867.086

> <EXACT_MASS>
866.481642314

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
95.78796699931021

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(1R,3S,4R,6S,8S,10R,12S,16R,18R,20R,22R,24Z,27R,29R,33S,35R,37R,39S,41R,42S,44R,46S,48R)-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>
146.67000000000002

> <JCHEM_REFRACTIVITY>
226.30379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(1R,3S,4R,6S,8S,10R,12S,16R,18R,20R,22R,24Z,27R,29R,33S,35R,37R,39S,41R,42S,44R,46S,48R)-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                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      30.060   2.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.672   3.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.219   2.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.553   1.261   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.063  -0.192   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      28.451  -0.858   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      29.904  -0.348   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.571   1.041   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      32.024   1.551   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      33.412   0.885   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.922  -0.568   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.256  -1.957   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.803  -2.467   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.415  -1.800   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      35.436  -0.853   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      36.439   0.316   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.929   1.769   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.415   2.053   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      36.932   2.937   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      38.445   2.653   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.956   1.200   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.953   0.032   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      40.469   0.916   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      41.472   2.084   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      40.962   3.537   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      39.448   3.822   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      38.938   5.274   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      42.986   1.800   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      43.989   2.968   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      43.478   4.421   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      45.502   2.684   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      46.505   3.852   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      33.096   2.392   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      26.520  -1.633   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      25.178  -2.388   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      23.664  -2.103   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      22.688  -0.912   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      22.705   0.627   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.708   1.796   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      25.228   2.046   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      23.420   3.309   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      22.057   4.027   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      20.647   3.409   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      20.250   1.921   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      21.166   0.683   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      18.763   1.521   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      17.673   2.608   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      18.069   4.096   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      19.556   4.497   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      17.298   5.429   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      15.810   5.826   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      14.477   5.054   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      14.080   3.566   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      14.852   2.233   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      16.340   1.837   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      13.823   1.088   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      12.415   1.712   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      11.083   0.940   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      12.574   3.244   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      15.607   7.352   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      18.657   5.520   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      24.658   4.225   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   40                                                  
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    1    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18   33                                             
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   10                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   16                                                       
CONECT   23   21   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26                                                            
CONECT   28   24   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   10                                                            
CONECT   34    5   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   45                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39    4                                                       
CONECT   41   39   42   62                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   49                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44   38                                                       
CONECT   46   44   47                                                       
CONECT   47   46   48   55                                                  
CONECT   48   47   49   50   61                                             
CONECT   49   48   43                                                       
CONECT   50   48   51                                                       
CONECT   51   50   52   60                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   59                                                  
CONECT   54   53   55   56                                                  
CONECT   55   54   47                                                       
CONECT   56   54   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   53                                                       
CONECT   60   51                                                            
CONECT   61   48                                                            
CONECT   62   41                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  142    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₉H₇₀O₁₃

Average Mass

867.0860 Da

Monoisotopic Mass

866.48164 Da

IUPAC Name

2-{[(1R,3S,4R,6S,8S,10R,12S,16R,18R,20R,22R,24Z,27R,29R,33S,35R,37R,39S,41R,42S,44R,46S,48R)-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

Traditional Name

2-{[(1R,3S,4R,6S,8S,10R,12S,16R,18R,20R,22R,24Z,27R,29R,33S,35R,37R,39S,41R,42S,44R,46S,48R)-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

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2O[C@@]3(C)C[C@H](C)C[C@@H]4OC(=O)C[C@H]4O[C@@H]3C[C@H]2O[C@@H]2C\C=C/C[C@H]3O[C@@H]4CCC[C@@H]5O[C@@H]6C[C@H]7O[C@@H](CC(=C)C=O)C[C@@H](O)[C@@H]7O[C@@H]6C[C@]5(C)O[C@@H]4C=CC[C@H]3O[C@@H]12

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?/t26-,28-,29+,30-,31-,32-,33-,34-,35-,36+,37-,38-,39-,40+,41-,42-,43+,44-,46+,47+,48+,49+/m1/s1

InChI Key

MGVIMUPHKPHTKF-QGYNCCGGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Apis cerana	LOTUS Database	35616633
Karenia brevis	-	KNApSAcK

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
Oxane
Monosaccharide
Gamma butyrolactone
Tetrahydrofuran
Enal
Alpha,beta-unsaturated aldehyde
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
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
logP	4.69	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	14.03	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	146.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	226.3 m³·mol⁻¹	ChemAxon
Polarizability	95.79 Å³	ChemAxon
Number of Rings	10	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162889171

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Brevetoxin A (NP0078348)

MOL for NP0078348 (Brevetoxin A)

3D MOL for NP0078348 (Brevetoxin A)

3D SDF for NP0078348 (Brevetoxin A)

3D-SDF for NP0078348 (Brevetoxin A)

PDB for NP0078348 (Brevetoxin A)

3D PDB for NP0078348 (Brevetoxin A)

SMILES for NP0078348 (Brevetoxin A)

INCHI for NP0078348 (Brevetoxin A)

Structure for NP0078348 (Brevetoxin A)

3D Structure for NP0078348 (Brevetoxin A)