NP-MRD: Showing NP-Card for Azaspiracid (NP0337588)

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Record Information

Version

2.0

Created at

2024-09-11 11:30:25 UTC

Updated at

2024-09-11 11:30:26 UTC

NP-MRD ID

NP0337588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Azaspiracid

Description

Azaspiracid was first documented in 2023 (PMID: 37999505). Based on a literature review a small amount of articles have been published on Azaspiracid (PMID: 39029196) (PMID: 38741723) (PMID: 38490144) (PMID: 38460449).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262314022D          

 60 68  0  0  0  0            999 V2000
    0.4708    2.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4708    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845    1.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967    2.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845    2.9787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870    3.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199    3.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8352    2.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2853    2.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150    3.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1372    3.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782    2.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9984    2.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1789    2.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    1.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630    2.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    2.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393    1.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643    1.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4017    0.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8142   -0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6392   -0.1671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4017   -0.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879    2.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4017    2.8714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6392    2.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6392   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4017   -1.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7518   -1.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269   -1.4168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -2.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269   -2.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7518   -2.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630   -2.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689   -0.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2440    1.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2 60  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  5 18  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 11  1  0  0  0  0
  9 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 26  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
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 22 23  1  0  0  0  0
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 54 55  1  0  0  0  0
 55 57  1  0  0  0  0
M  END


  Mrv2104 05262314022D          

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    1.8967    2.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0337588

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CNC2(CC3OC4(CC(=C)C5OC(O)(C(O)C6CC7OC8(CCC9(CC=CC(O9)\C=C\CCC(O)=O)O8)C(C)CC7O6)C(C)CC5C)CC(C)CC(O4)C3O2)C(C)C1

> <INCHI_IDENTIFIER>
InChI=1/C47H71NO12/c1-26-18-36-41-38(24-45(58-41)30(5)17-27(2)25-48-45)56-44(22-26,55-36)23-29(4)40-28(3)19-32(7)47(52,59-40)42(51)37-21-35-34(53-37)20-31(6)46(57-35)16-15-43(60-46)14-10-12-33(54-43)11-8-9-13-39(49)50/h8,10-12,26-28,30-38,40-42,48,51-52H,4,9,13-25H2,1-3,5-7H3,(H,49,50)/b11-8+

> <INCHI_KEY>
BVZWTQCTAVYACS-DHZHZOJONA-N

> <FORMULA>
C47H71NO12

> <MOLECULAR_WEIGHT>
842.08

> <EXACT_MASS>
841.49762673

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
131

> <JCHEM_AVERAGE_POLARIZABILITY>
94.18809142414193

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0^{2,6}]dodecan]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-6-methyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoic acid

> <JCHEM_LOGP>
4.724207758980684

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.868226798339737

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9547511647299527

> <JCHEM_PKA_STRONGEST_BASIC>
9.319417479833279

> <JCHEM_POLAR_SURFACE_AREA>
163.63

> <JCHEM_REFRACTIVITY>
221.91650000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0^{2,6}]dodecan]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-6-methyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoic 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       0.879   4.793   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.879   3.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.211   2.483   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.541   3.253   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.541   4.793   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.211   5.560   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.722   6.325   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.784   6.649   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.559   5.314   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.533   4.164   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.455   6.566   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.989   6.415   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.626   5.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.730   3.759   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.201   3.907   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.003   2.778   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.904   4.023   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.003   5.263   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.367   2.357   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.907   2.357   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.677   1.023   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.217   1.023   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.987  -0.312   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -10.527  -0.312   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -8.217  -1.646   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.444   4.023   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.217   2.693   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.217   5.360   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.444   1.359   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.217   0.024   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.757   0.024   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.527   1.359   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.757   2.693   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.527   4.023   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.527  -1.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.444  -1.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.217  -2.645   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.904  -1.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.137  -2.645   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.597  -2.645   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.827  -3.979   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.597  -5.314   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.137  -5.314   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.904  -3.979   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       4.049  -1.556   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       1.739  -2.891   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.509  -1.556   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.474  -0.412   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.063  -1.043   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       0.224  -2.583   0.000  0.00  0.00           O+0
HETATM   51  N   UNK     0       0.063   0.497   0.000  0.00  0.00           N+0
HETATM   52  C   UNK     0      -1.271   1.266   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -2.606   0.497   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -2.606  -1.043   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -1.271  -1.813   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       5.904  -6.649   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -1.271  -3.353   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -3.941   1.266   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       6.728   2.296   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -0.455   2.483   0.000  0.00  0.00           C+0
CONECT    1    2    6    7   10                                             
CONECT    2    1    3   60                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   18                                                  
CONECT    6    1    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   15                                             
CONECT   10    1    9                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15    9   14                                                       
CONECT   16    4   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18    5   17                                                       
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   17   27   28                                                  
CONECT   27   26   29   33   59                                             
CONECT   28   26                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   27   32   34                                                  
CONECT   34   33                                                            
CONECT   35   31                                                            
CONECT   36   30   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   44   45                                             
CONECT   40   39   41                                                       
CONECT   41   40   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   56                                                  
CONECT   44   39   43                                                       
CONECT   45   39   47                                                       
CONECT   46   41   47   50                                                  
CONECT   47   45   46   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51   55                                             
CONECT   50   46   49                                                       
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   58                                                  
CONECT   54   53   55                                                       
CONECT   55   49   54   57                                                  
CONECT   56   43                                                            
CONECT   57   55                                                            
CONECT   58   53                                                            
CONECT   59   27                                                            
CONECT   60    2                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  136    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₇₁NO₁₂

Average Mass

842.0800 Da

Monoisotopic Mass

841.49763 Da

IUPAC Name

(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0^{2,6}]dodecan]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-6-methyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1CNC2(CC3OC4(CC(=C)C5OC(O)(C(O)C6CC7OC8(CCC9(CC=CC(O9)\C=C\CCC(O)=O)O8)C(C)CC7O6)C(C)CC5C)CC(C)CC(O4)C3O2)C(C)C1

InChI Identifier

InChI=1/C47H71NO12/c1-26-18-36-41-38(24-45(58-41)30(5)17-27(2)25-48-45)56-44(22-26,55-36)23-29(4)40-28(3)19-32(7)47(52,59-40)42(51)37-21-35-34(53-37)20-31(6)46(57-35)16-15-43(60-46)14-10-12-33(54-43)11-8-9-13-39(49)50/h8,10-12,26-28,30-38,40-42,48,51-52H,4,9,13-25H2,1-3,5-7H3,(H,49,50)/b11-8+

InChI Key

BVZWTQCTAVYACS-DHZHZOJONA-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	4.72	ChemAxon
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	163.63 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	221.92 m³·mol⁻¹	ChemAxon
Polarizability	94.19 Å³	ChemAxon
Number of Rings	9	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

Azaspiracid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sibat M, Mai T, Tanniou S, Biegala I, Hess P, Jauffrais T: Seasonal Single-Site Sampling Reveals Large Diversity of Marine Algal Toxins in Coastal Waters and Shellfish of New Caledonia (Southwestern Pacific). Toxins (Basel). 2023 Nov 3;15(11):642. doi: 10.3390/toxins15110642. [PubMed:37999505 ]
Wu H, Zhang Q, Dong C, Zheng G, Tan Z, Gu H: Coordination regulation of enhanced performance reveals the tolerance mechanism of Chlamys farreri to azaspiracid toxicity. J Hazard Mater. 2024 Sep 5;476:135247. doi: 10.1016/j.jhazmat.2024.135247. Epub 2024 Jul 17. [PubMed:39029196 ]
Alarcan J, Braeuning A: Effects of okadaic acid, azaspiracid-1, yessotoxin and their binary mixtures on human intestinal Caco-2 cells. EXCLI J. 2024 Apr 22;23:509-522. doi: 10.17179/excli2023-6884. eCollection 2024. [PubMed:38741723 ]
Ochi N, Suzuki T: Determination of lipophilic marine biotoxins (azaspiracids, brevetoxins, and okadaic acid group) and domoic acid in mussels by solid-phase extraction and reversed-phase liquid chromatography with tandem mass spectrometry. J Chromatogr A. 2024 Apr 12;1720:464795. doi: 10.1016/j.chroma.2024.464795. Epub 2024 Mar 5. [PubMed:38490144 ]
Ozawa M, Uchida H, Watanabe R, Numano S, Matsushima R, Oikawa H, Takahashi K, Lum WM, Benico G, Iwataki M, Suzuki T: New azaspiracid analogues detected as bi-charged ions in Azadinium poporum (Amphidomataceae, Dinophyceae) isolated from Japanese coastal waters. J Chromatogr B Analyt Technol Biomed Life Sci. 2024 Apr 1;1236:124065. doi: 10.1016/j.jchromb.2024.124065. Epub 2024 Mar 2. [PubMed:38460449 ]

Showing NP-Card for Azaspiracid (NP0337588)

MOL for NP0337588 (Azaspiracid)

3D MOL for NP0337588 (Azaspiracid)

3D SDF for NP0337588 (Azaspiracid)

3D-SDF for NP0337588 (Azaspiracid)

PDB for NP0337588 (Azaspiracid)

3D PDB for NP0337588 (Azaspiracid)

SMILES for NP0337588 (Azaspiracid)

INCHI for NP0337588 (Azaspiracid)

Structure for NP0337588 (Azaspiracid)

3D Structure for NP0337588 (Azaspiracid)