NP-MRD: Showing NP-Card for 52-Epiciguatoxin (NP0335231)

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Record Information

Version

2.0

Created at

2024-09-11 00:39:30 UTC

Updated at

2024-09-11 00:39:30 UTC

NP-MRD ID

NP0335231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

52-Epiciguatoxin

Description

52-Epiciguatoxin was first documented in 1996 (PMID: 9026141). Based on a literature review very few articles have been published on 52-Epiciguatoxin.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262303112D          

 79 91  0  0  0  0            999 V2000
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M  END


  Mrv2104 05262303112D          

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  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 25  1  0  0  0  0
  3 56  1  0  0  0  0
  4  5  1  0  0  0  0
  4 19  1  0  0  0  0
  4 47  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
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 24  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  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
 21 46  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 56  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 53  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 59  1  0  0  0  0
 35 36  1  0  0  0  0
 35 52  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 60  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 63  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 58  1  0  0  0  0
 43 44  1  0  0  0  0
 43 64  1  0  0  0  0
 44 45  1  0  0  0  0
 44 66  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 51  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 77  1  0  0  0  0
 50 51  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 76  1  0  0  0  0
 56 57  1  0  0  0  0
 58 67  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
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 65 66  1  0  0  0  0
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 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
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 70 71  1  0  0  0  0
 71 72  1  0  0  0  0
 72 73  2  0  0  0  0
 73 74  1  0  0  0  0
 74 75  1  0  0  0  0
 74 79  1  0  0  0  0
 75 78  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335231

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(C)C2(CC(O)CO2)OC2C1OC1CC3OC4CC5OC6C\C=C/CC7OC8C=CC9OC%10C(CC9OC8C=CC7OC6CC(O)C5(C)OC4CC(C)CC3OC1C(C)C2O)OC1CC=CC(OC1C%10O)\C=C/C(O)CO

> <INCHI_IDENTIFIER>
InChI=1/C60H86O19/c1-28-19-42-44(22-48-54(76-42)30(3)52(65)58-55(77-48)29(2)31(4)60(79-58)25-33(63)27-67-60)73-46-24-51-59(5,78-47(46)20-28)50(64)23-45-36(74-51)11-7-6-10-35-37(71-45)15-16-39-38(69-35)17-18-40-43(70-39)21-49-57(75-40)53(66)56-41(72-49)12-8-9-34(68-56)14-13-32(62)26-61/h6-9,13-18,28-58,61-66H,10-12,19-27H2,1-5H3/b7-6-,14-13-

> <INCHI_KEY>
VYVRIXWNTVOIRD-ZBXVJARNNA-N

> <FORMULA>
C60H86O19

> <MOLECULAR_WEIGHT>
1111.329

> <EXACT_MASS>
1110.576330549

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
165

> <JCHEM_AVERAGE_POLARIZABILITY>
120.60871171703772

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(29Z)-16-[(1Z)-3,4-dihydroxybut-1-en-1-yl]-43,44,49,54,58-pentamethyl-2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxaspiro[dodecacyclo[30.28.0.0^{3,27}.0^{6,25}.0^{8,22}.0^{10,20}.0^{12,18}.0^{34,58}.0^{36,56}.0^{38,52}.0^{40,50}.0^{42,47}]hexacontane-45,2'-oxolane]-4,14,23,29-tetraene-4',19,48,59-tetrol

> <JCHEM_LOGP>
2.757961526333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
13

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.441243696762005

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.867226674722946

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9539993342725523

> <JCHEM_POLAR_SURFACE_AREA>
241.36999999999995

> <JCHEM_REFRACTIVITY>
284.1614999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(29Z)-16-[(1Z)-3,4-dihydroxybut-1-en-1-yl]-43,44,49,54,58-pentamethyl-2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxaspiro[dodecacyclo[30.28.0.0^{3,27}.0^{6,25}.0^{8,22}.0^{10,20}.0^{12,18}.0^{34,58}.0^{36,56}.0^{38,52}.0^{40,50}.0^{42,47}]hexacontane-45,2'-oxolane]-4,14,23,29-tetraene-4',19,48,59-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       6.500   6.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.299   5.733   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.949   6.331   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.649  -3.563   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.200  -5.060   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.595   8.279   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.997   6.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.898   5.733   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.052   4.231   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.997   3.034   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.446   1.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.951   1.081   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.100  -0.416   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.247   3.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.495   1.982   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.998   2.282   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.549   3.633   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.100  -3.409   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.448  -2.811   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.448  -1.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.944  -0.865   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.247   0.631   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.898   0.934   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.500   3.183   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.453   4.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.103   3.484   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.755   4.231   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.275   2.636   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.801   1.982   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.250   0.631   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.652  -0.711   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.696  -1.314   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.046  -1.160   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.240  -0.262   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.240   1.235   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.441   2.136   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.792   1.833   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.544   0.485   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -8.040   0.785   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -9.242  -0.113   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -10.593   0.631   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -11.941  -0.113   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -11.941  -1.610   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -13.291  -2.510   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0     -12.988  -4.012   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      13.992  -1.912   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      14.295  -3.409   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      15.799  -3.263   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      16.698  -4.465   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      15.645  -5.658   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      14.295  -4.914   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -1.892   2.136   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -0.696   2.734   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -0.549   4.231   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.652   5.283   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       2.600   5.733   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       2.600   7.273   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0     -13.291   0.631   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      -4.441  -1.160   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -5.946  -0.865   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -6.544  -2.215   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -8.040  -2.665   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -9.242  -1.610   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0     -10.593  -2.510   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0     -15.835  -2.510   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0     -14.639  -1.763   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0     -14.639  -0.113   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0     -15.835   0.785   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0     -17.339   0.336   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0     -18.084  -1.014   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0     -17.339  -2.362   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0     -18.238  -3.563   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0     -17.635  -5.060   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0     -15.386  -5.658   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0     -15.237  -7.612   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0       0.652   7.232   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      18.238  -4.526   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0     -13.848  -8.279   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0     -14.202  -4.672   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2   56                                                       
CONECT    4    5   19   47                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    1    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   20                                                       
CONECT   14   15                                                            
CONECT   15   14   16   22                                                  
CONECT   16   12   15   17                                                  
CONECT   17    9   16                                                       
CONECT   18   19                                                            
CONECT   19    4   18   20                                                  
CONECT   20   13   19   21                                                  
CONECT   21   20   22   46                                                  
CONECT   22   15   21   23                                                  
CONECT   23   22                                                            
CONECT   24   10   25                                                       
CONECT   25    2   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   56                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   53                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   59                                                  
CONECT   35   34   36   52                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   60                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   63                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   58                                                  
CONECT   43   42   44   64                                                  
CONECT   44   43   45   66                                                  
CONECT   45   44                                                            
CONECT   46   21   47                                                       
CONECT   47    4   46   48   51                                             
CONECT   48   47   49                                                       
CONECT   49   48   50   77                                                  
CONECT   50   49   51                                                       
CONECT   51   47   50                                                       
CONECT   52   35   53                                                       
CONECT   53   29   52   54                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56   76                                                  
CONECT   56    3   27   55   57                                             
CONECT   57   56                                                            
CONECT   58   42   67                                                       
CONECT   59   34   60                                                       
CONECT   60   38   59   61                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   40   62   64                                                  
CONECT   64   43   63                                                       
CONECT   65   66   71                                                       
CONECT   66   44   65   67                                                  
CONECT   67   58   66   68                                                  
CONECT   68   67   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   65   70   72                                                  
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75   79                                                  
CONECT   75   74   78                                                       
CONECT   76   55                                                            
CONECT   77   49                                                            
CONECT   78   75                                                            
CONECT   79   74                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  182    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₆₀H₈₆O₁₉

Average Mass

1111.3290 Da

Monoisotopic Mass

1110.57633 Da

IUPAC Name

(29Z)-16-[(1Z)-3,4-dihydroxybut-1-en-1-yl]-43,44,49,54,58-pentamethyl-2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxaspiro[dodecacyclo[30.28.0.0^{3,27}.0^{6,25}.0^{8,22}.0^{10,20}.0^{12,18}.0^{34,58}.0^{36,56}.0^{38,52}.0^{40,50}.0^{42,47}]hexacontane-45,2'-oxolane]-4,14,23,29-tetraene-4',19,48,59-tetrol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1C(C)C2(CC(O)CO2)OC2C1OC1CC3OC4CC5OC6C\C=C/CC7OC8C=CC9OC%10C(CC9OC8C=CC7OC6CC(O)C5(C)OC4CC(C)CC3OC1C(C)C2O)OC1CC=CC(OC1C%10O)\C=C/C(O)CO

InChI Identifier

InChI=1/C60H86O19/c1-28-19-42-44(22-48-54(76-42)30(3)52(65)58-55(77-48)29(2)31(4)60(79-58)25-33(63)27-67-60)73-46-24-51-59(5,78-47(46)20-28)50(64)23-45-36(74-51)11-7-6-10-35-37(71-45)15-16-39-38(69-35)17-18-40-43(70-39)21-49-57(75-40)53(66)56-41(72-49)12-8-9-34(68-56)14-13-32(62)26-61/h6-9,13-18,28-58,61-66H,10-12,19-27H2,1-5H3/b7-6-,14-13-

InChI Key

VYVRIXWNTVOIRD-ZBXVJARNNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	2.76	ChemAxon
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	241.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	284.16 m³·mol⁻¹	ChemAxon
Polarizability	120.61 Å³	ChemAxon
Number of Rings	13	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Satake M, Ishibashi Y, Legrand AM, Yasumoto T: Isolation and structure of ciguatoxin-4A, a new ciguatoxin precursor, from cultures of dinoflagellate Gambierdiscus toxicus and parrotfish Scarus gibbus. Biosci Biotechnol Biochem. 1996 Dec;60(12):2103-5. doi: 10.1271/bbb.60.2103. [PubMed:9026141 ]

Showing NP-Card for 52-Epiciguatoxin (NP0335231)

MOL for NP0335231 (52-Epiciguatoxin)

3D MOL for NP0335231 (52-Epiciguatoxin)

3D SDF for NP0335231 (52-Epiciguatoxin)

3D-SDF for NP0335231 (52-Epiciguatoxin)

PDB for NP0335231 (52-Epiciguatoxin)

3D PDB for NP0335231 (52-Epiciguatoxin)

SMILES for NP0335231 (52-Epiciguatoxin)

INCHI for NP0335231 (52-Epiciguatoxin)

Structure for NP0335231 (52-Epiciguatoxin)

3D Structure for NP0335231 (52-Epiciguatoxin)