NP-MRD: Showing NP-Card for 1-Desulfoyessotoxin (NP0335350)

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Record Information

Version

2.0

Created at

2024-09-11 01:11:54 UTC

Updated at

2024-09-11 01:11:54 UTC

NP-MRD ID

NP0335350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Desulfoyessotoxin

Description

1-Desulfoyessotoxin was first documented in 2013 (PMID: 23851005). Based on a literature review very few articles have been published on 1-Desulfoyessotoxin.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262303442D          

 74 84  0  0  0  0            999 V2000
   -3.0409   10.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5868   10.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1107    1.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6402    6.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1247    8.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0367    7.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0135    1.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2628    1.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9454    4.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2229   10.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9064    9.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6959    2.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv2104 05262303442D          

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 53 16  1  0  0  0  0
 53 44  1  0  0  0  0
 54  8  1  0  0  0  0
 54 17  1  0  0  0  0
 54 43  1  0  0  0  0
 55  9  1  0  0  0  0
 55 46  1  0  0  0  0
 55 49  1  0  0  0  0
 56 19  1  0  0  0  0
 57 49  1  0  0  0  0
 58 51  1  0  0  0  0
 62 31  1  0  0  0  0
 62 33  1  0  0  0  0
 63 34  1  0  0  0  0
 63 36  1  0  0  0  0
 64 35  1  0  0  0  0
 64 37  1  0  0  0  0
 65 32  1  0  0  0  0
 65 43  1  0  0  0  0
 66 41  1  0  0  0  0
 66 44  1  0  0  0  0
 67 42  1  0  0  0  0
 67 46  1  0  0  0  0
 68 38  1  0  0  0  0
 68 50  1  0  0  0  0
 69 47  1  0  0  0  0
 69 48  1  0  0  0  0
 70 40  1  0  0  0  0
 70 52  1  0  0  0  0
 71 39  1  0  0  0  0
 71 55  1  0  0  0  0
 72 45  1  0  0  0  0
 73 53  1  0  0  0  0
 73 54  1  0  0  0  0
 74 59  1  0  0  0  0
 74 60  2  0  0  0  0
 74 61  2  0  0  0  0
 74 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(C)OC3(C)CCC4OC5CC6OC7CC(OS(O)(=O)=O)C(C)(CCO)OC7CC6OC5CC4OC3CC2OC2CC3OC4CC5OC(C(=C)CC5OC4(C)C(O)C3OC12)C(C)(O)\C=C\C(=C)CC=C

> <INCHI_IDENTIFIER>
InChI=1/C55H82O18S/c1-10-11-28(2)12-15-51(5,58)50-30(4)20-39-38(68-50)26-46-55(9,71-39)49(57)48-42(67-46)24-41-47(69-48)29(3)13-16-53(7)44(66-41)27-43-54(8,73-53)17-14-31-32(65-43)21-34-33(62-31)22-35-36(63-34)23-40-37(64-35)25-45(72-74(59,60)61)52(6,70-40)18-19-56/h10,12,15,29,31-50,56-58H,1-2,4,11,13-14,16-27H2,3,5-9H3,(H,59,60,61)/b15-12+

> <INCHI_KEY>
STPLAPGVFWFJCX-NTCAYCPXNA-N

> <FORMULA>
C55H82O18S

> <MOLECULAR_WEIGHT>
1063.3

> <EXACT_MASS>
1062.522186974

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
156

> <JCHEM_AVERAGE_POLARIZABILITY>
115.95729358653625

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13-(2-hydroxyethyl)-13,25,27,30,35-pentamethyl-39-methylidene-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0^{3,25}.0^{5,22}.0^{7,20}.0^{9,18}.0^{11,16}.0^{31,48}.0^{33,46}.0^{35,44}.0^{37,42}]nonatetracontan-14-yl}oxidanesulfonic acid

> <JCHEM_LOGP>
1.5473312299386863

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.820609561234589

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.682174796241954

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4154211715669334

> <JCHEM_POLAR_SURFACE_AREA>
225.8199999999999

> <JCHEM_REFRACTIVITY>
265.6027999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13-(2-hydroxyethyl)-13,25,27,30,35-pentamethyl-39-methylidene-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0^{3,25}.0^{5,22}.0^{7,20}.0^{9,18}.0^{11,16}.0^{31,48}.0^{33,46}.0^{35,44}.0^{37,42}]nonatetracontan-14-yl}oxidanesulfonic acid

> <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      -5.676  19.674   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.095  19.075   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.673   3.380   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.195  12.363   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.099  15.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.069  13.949   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.092   3.154   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.424   3.454   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.631   7.698   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.149  19.474   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.559  18.052   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.441  16.431   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.229   3.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.099   4.735   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.086  16.231   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.756   3.418   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.656   4.198   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.300  14.839   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.825  15.282   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.923  10.742   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.426   8.862   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.346   7.750   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.886  11.789   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.149   8.323   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.806  10.677   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.913  11.566   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.710   7.106   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.031  17.853   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.006   4.151   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.332  12.164   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.579   6.199   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.734   7.486   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      20.809   7.662   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.964   8.950   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      23.039   9.126   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      22.194  10.413   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      25.269  10.589   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.386  11.765   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.450  10.543   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      24.424  11.877   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.740   6.901   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.622   8.522   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.133   6.518   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.489   6.167   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      27.499  12.053   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.504  10.144   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       8.803   5.678   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.686   7.299   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       5.159   7.499   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       1.268  13.387   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.677  14.809   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      26.654  13.340   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      12.692   4.641   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      15.336   4.991   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.568   8.921   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      24.472  16.781   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       4.222   6.276   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      -0.745  14.218   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      28.594  10.008   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      31.169  11.698   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      30.726   9.566   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      20.116   6.287   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      20.656  10.325   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      24.576   9.214   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      16.200   7.628   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      11.266   7.103   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0       7.031   9.944   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0       2.795  13.187   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0       7.276   5.877   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0      25.116  13.252   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0       3.041   9.120   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      29.036  12.141   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      14.115   4.053   0.000  0.00  0.00           O+0
HETATM   74  S   UNK     0      29.881  10.853   0.000  0.00  0.00           S+0
CONECT    1   10                                                            
CONECT    2   28                                                            
CONECT    3   29                                                            
CONECT    4   30                                                            
CONECT    5   51                                                            
CONECT    6   52                                                            
CONECT    7   53                                                            
CONECT    8   54                                                            
CONECT    9   55                                                            
CONECT   10    1   11                                                       
CONECT   11   10   28                                                       
CONECT   12   15   28                                                       
CONECT   13   16   29                                                       
CONECT   14   17   31                                                       
CONECT   15   12   51                                                       
CONECT   16   13   53                                                       
CONECT   17   14   54                                                       
CONECT   18   19   52                                                       
CONECT   19   18   56                                                       
CONECT   20   30   39                                                       
CONECT   21   32   34                                                       
CONECT   22   33   35                                                       
CONECT   23   36   40                                                       
CONECT   24   41   42                                                       
CONECT   25   37   45                                                       
CONECT   26   38   46                                                       
CONECT   27   43   44                                                       
CONECT   28    2   11   12                                                  
CONECT   29    3   13   47                                                  
CONECT   30    4   20   50                                                  
CONECT   31   14   32   62                                                  
CONECT   32   21   31   65                                                  
CONECT   33   22   34   62                                                  
CONECT   34   21   33   63                                                  
CONECT   35   22   36   64                                                  
CONECT   36   23   35   63                                                  
CONECT   37   25   40   64                                                  
CONECT   38   26   39   68                                                  
CONECT   39   20   38   71                                                  
CONECT   40   23   37   70                                                  
CONECT   41   24   47   66                                                  
CONECT   42   24   48   67                                                  
CONECT   43   27   54   65                                                  
CONECT   44   27   53   66                                                  
CONECT   45   25   52   72                                                  
CONECT   46   26   55   67                                                  
CONECT   47   29   41   69                                                  
CONECT   48   42   49   69                                                  
CONECT   49   48   55   57                                                  
CONECT   50   30   51   68                                                  
CONECT   51    5   15   50   58                                             
CONECT   52    6   18   45   70                                             
CONECT   53    7   16   44   73                                             
CONECT   54    8   17   43   73                                             
CONECT   55    9   46   49   71                                             
CONECT   56   19                                                            
CONECT   57   49                                                            
CONECT   58   51                                                            
CONECT   59   74                                                            
CONECT   60   74                                                            
CONECT   61   74                                                            
CONECT   62   31   33                                                       
CONECT   63   34   36                                                       
CONECT   64   35   37                                                       
CONECT   65   32   43                                                       
CONECT   66   41   44                                                       
CONECT   67   42   46                                                       
CONECT   68   38   50                                                       
CONECT   69   47   48                                                       
CONECT   70   40   52                                                       
CONECT   71   39   55                                                       
CONECT   72   45   74                                                       
CONECT   73   53   54                                                       
CONECT   74   59   60   61   72                                             
MASTER        0    0    0    0    0    0    0    0   74    0  168    0
END

View in JSmol

Synonyms

Value	Source
1-Desulphoyessotoxin	Generator

Chemical Formula

C₅₅H₈₂O₁₈S

Average Mass

1063.3000 Da

Monoisotopic Mass

1062.52219 Da

IUPAC Name

{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13-(2-hydroxyethyl)-13,25,27,30,35-pentamethyl-39-methylidene-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0^{3,25}.0^{5,22}.0^{7,20}.0^{9,18}.0^{11,16}.0^{31,48}.0^{33,46}.0^{35,44}.0^{37,42}]nonatetracontan-14-yl}oxidanesulfonic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)OC3(C)CCC4OC5CC6OC7CC(OS(O)(=O)=O)C(C)(CCO)OC7CC6OC5CC4OC3CC2OC2CC3OC4CC5OC(C(=C)CC5OC4(C)C(O)C3OC12)C(C)(O)\C=C\C(=C)CC=C

InChI Identifier

InChI=1/C55H82O18S/c1-10-11-28(2)12-15-51(5,58)50-30(4)20-39-38(68-50)26-46-55(9,71-39)49(57)48-42(67-46)24-41-47(69-48)29(3)13-16-53(7)44(66-41)27-43-54(8,73-53)17-14-31-32(65-43)21-34-33(62-31)22-35-36(63-34)23-40-37(64-35)25-45(72-74(59,60)61)52(6,70-40)18-19-56/h10,12,15,29,31-50,56-58H,1-2,4,11,13-14,16-27H2,3,5-9H3,(H,59,60,61)/b15-12+

InChI Key

STPLAPGVFWFJCX-NTCAYCPXNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as ciguatera toxins. These are lipid-soluble polyether compounds consisting of 13 to 14 rings fused by ether linkages into a most rigid ladder-like structure.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Ciguatera toxins

Sub Class

Not Available

Direct Parent

Ciguatera toxins

Alternative Parents

Substituents

Ciguatera toxin fragment
Oxepane
Monosaccharide
Oxane
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Organic sulfuric acid or derivatives
Tertiary alcohol
Secondary alcohol
Dialkyl ether
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Primary alcohol
Organic oxide
Organooxygen compound
Alcohol
Hydrocarbon derivative
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	1.55	ChemAxon
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	225.82 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	265.6 m³·mol⁻¹	ChemAxon
Polarizability	115.96 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	Yes	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

Korsnes MS, Espenes A, Hermansen LC, Loader JI, Miles CO: Cytotoxic responses in BC3H1 myoblast cell lines exposed to 1-desulfoyessotoxin. Toxicol In Vitro. 2013 Sep;27(6):1962-9. doi: 10.1016/j.tiv.2013.06.012. Epub 2013 Jul 11. [PubMed:23851005 ]

Showing NP-Card for 1-Desulfoyessotoxin (NP0335350)

MOL for NP0335350 (1-Desulfoyessotoxin)

3D MOL for NP0335350 (1-Desulfoyessotoxin)

3D SDF for NP0335350 (1-Desulfoyessotoxin)

3D-SDF for NP0335350 (1-Desulfoyessotoxin)

PDB for NP0335350 (1-Desulfoyessotoxin)

3D PDB for NP0335350 (1-Desulfoyessotoxin)

SMILES for NP0335350 (1-Desulfoyessotoxin)

INCHI for NP0335350 (1-Desulfoyessotoxin)

Structure for NP0335350 (1-Desulfoyessotoxin)

3D Structure for NP0335350 (1-Desulfoyessotoxin)