NP-MRD: Showing NP-Card for Monoacetoxyscirpenol (NP0023604)

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Record Information

Version

2.0

Created at

2021-01-06 08:39:53 UTC

Updated at

2021-07-15 17:42:12 UTC

NP-MRD ID

NP0023604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monoacetoxyscirpenol

Provided By

NPAtlas

Description

Monoacetoxyscirpenol belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. Monoacetoxyscirpenol is found in Fusarium, Fusarium roseum and Fusarium sulphureum. Monoacetoxyscirpenol was first documented in 1976 (PMID: 946065). Based on a literature review a small amount of articles have been published on Monoacetoxyscirpenol (PMID: 33615927) (PMID: 32604961) (PMID: 31382481) (PMID: 31232057).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120433D          

 47 50  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242120433D          

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  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  0  0  0  0
 12 37  1  1  0  0  0
 14 38  1  6  0  0  0
 15 39  1  6  0  0  0
 16 40  1  0  0  0  0
 17 41  1  1  0  0  0
 18 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]([H])(O[H])[C@@]2(C([H])([H])[H])[C@@]3(OC3([H])[H])[C@]1([H])O[C@]1([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])[C@]21C([H])([H])OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O6/c1-9-4-5-16(7-21-10(2)18)11(6-9)23-14-12(19)13(20)15(16,3)17(14)8-22-17/h6,11-14,19-20H,4-5,7-8H2,1-3H3/t11-,12-,13-,14-,15-,16-,17+/m1/s1

> <INCHI_KEY>
IRXDUBNENLKYTC-OINWIYPRSA-N

> <FORMULA>
C17H24O6

> <MOLECULAR_WEIGHT>
324.373

> <EXACT_MASS>
324.157288493

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
40.05801759450332

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1'R,2S,2'R,7'R,9'R,10'R,11'S)-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
-0.06412580500000041

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.505241415439805

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.975677325389725

> <JCHEM_PKA_STRONGEST_BASIC>
-3.427785626626804

> <JCHEM_POLAR_SURFACE_AREA>
88.52000000000001

> <JCHEM_REFRACTIVITY>
79.9482

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,2'R,7'R,9'R,10'R,11'S)-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    4.0745    2.1079    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684    1.9906    0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9903    2.7582   -0.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9409    1.1148    1.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6376    0.7847    1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1529    0.1322    0.2062 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3567    0.8898   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1307    2.1601   -0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1184    2.1136    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613    3.3342    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3065    1.0744    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5131   -0.1820    0.7831 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2537   -1.0582    0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807   -2.1375   -0.4638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9218   -2.9819    0.6183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7280   -3.1207    1.7305 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3442   -2.1967    0.9013 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4339   -3.1014    0.9194 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5105   -1.1906   -0.2031 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9307   -1.0392   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3594   -1.7816   -1.2870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1908   -1.8369   -2.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264   -2.9501   -1.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839    1.7578   -0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4649    1.5415    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811    3.1610    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0261    1.6853    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048    0.1293    2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5164    1.0297   -1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0244    0.2013   -1.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368    2.2552   -1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    3.0934   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6085    3.8817    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011    3.9867   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0293    3.0451    0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695    1.1470    1.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793   -0.5668    1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -2.7176   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6748   -3.9585    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687   -3.5097    2.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2202   -1.7725    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238   -2.6797    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2368   -2.0148   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1244   -0.2776   -1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6129   -0.9315    0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6518   -1.3135   -3.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -2.0567   -3.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 12  6  1  0
 21 14  1  0
 19  6  1  0
 21 23  1  1
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  1
 14 38  1  6
 15 39  1  6
 16 40  1  0
 17 41  1  1
 18 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.074   2.108   0.391  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.568   1.991   0.362  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.990   2.758  -0.413  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.941   1.115   1.125  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.638   0.785   1.298  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.153   0.132   0.206  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.357   0.890  -1.055  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.131   2.160  -0.975  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.118   2.114   0.132  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.961   3.334   0.355  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.307   1.074   0.932  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.513  -0.182   0.783  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.254  -1.058   0.049  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.581  -2.138  -0.464  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.922  -2.982   0.618  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.728  -3.121   1.730  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.344  -2.197   0.901  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.434  -3.101   0.919  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.510  -1.191  -0.203  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.931  -1.039  -0.615  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.359  -1.782  -1.287  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.191  -1.837  -2.627  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.226  -2.950  -1.835  0.00  0.00           O+0
HETATM   24  H   UNK     0       4.484   1.758  -0.577  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.465   1.542   1.254  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.381   3.161   0.505  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.026   1.685   1.694  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.605   0.129   2.237  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.516   1.030  -1.700  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.024   0.201  -1.694  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.737   2.255  -1.942  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.546   3.093  -0.966  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.608   3.882   1.264  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.001   3.987  -0.528  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.029   3.045   0.570  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.070   1.147   1.724  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.379  -0.567   1.810  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.276  -2.718  -1.088  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.675  -3.958   0.131  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.169  -3.510   2.449  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.220  -1.773   1.906  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.124  -2.680   1.507  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.237  -2.015  -1.101  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.124  -0.278  -1.363  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.613  -0.932   0.248  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.652  -1.313  -3.147  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.016  -2.057  -3.332  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   27   28                                             
CONECT    6    5    7   12   19                                             
CONECT    7    6    8   29   30                                             
CONECT    8    7    9   31   32                                             
CONECT    9    8   10   11                                                  
CONECT   10    9   33   34   35                                             
CONECT   11    9   12   36                                                  
CONECT   12   11   13    6   37                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   21   38                                             
CONECT   15   14   16   17   39                                             
CONECT   16   15   40                                                       
CONECT   17   15   18   19   41                                             
CONECT   18   17   42                                                       
CONECT   19   17   20   21    6                                             
CONECT   20   19   43   44   45                                             
CONECT   21   19   22   14   23                                             
CONECT   22   21   23   46   47                                             
CONECT   23   22   21                                                       
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29    7                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   18                                                            
CONECT   43   20                                                            
CONECT   44   20                                                            
CONECT   45   20                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

RDKit          3D

47 50  0  0  0  0  0  0  0  0999 V2000
    4.0745    2.1079    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684    1.9906    0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9903    2.7582   -0.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9409    1.1148    1.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6376    0.7847    1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1529    0.1322    0.2062 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3567    0.8898   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1307    2.1601   -0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1184    2.1136    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613    3.3342    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3065    1.0744    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5131   -0.1820    0.7831 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2537   -1.0582    0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807   -2.1375   -0.4638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9218   -2.9819    0.6183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7280   -3.1207    1.7305 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3442   -2.1967    0.9013 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4339   -3.1014    0.9194 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5105   -1.1906   -0.2031 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9307   -1.0392   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3594   -1.7816   -1.2870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1908   -1.8369   -2.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264   -2.9501   -1.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839    1.7578   -0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4649    1.5415    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811    3.1610    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0261    1.6853    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048    0.1293    2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5164    1.0297   -1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0244    0.2013   -1.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368    2.2552   -1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    3.0934   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6085    3.8817    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011    3.9867   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0293    3.0451    0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695    1.1470    1.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793   -0.5668    1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -2.7176   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6748   -3.9585    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687   -3.5097    2.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2202   -1.7725    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238   -2.6797    1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2368   -2.0148   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1244   -0.2776   -1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6129   -0.9315    0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6518   -1.3135   -3.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -2.0567   -3.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 12  6  1  0
 21 14  1  0
 19  6  1  0
 21 23  1  1
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  1
 14 38  1  6
 15 39  1  6
 16 40  1  0
 17 41  1  1
 18 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
[(1's,2S,2'r,7'r,9'r,10'r,11's)-10',11'-Dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0,]dodecan]-5'-en-2'-yl]methyl acetic acid	Generator

Chemical Formula

C₁₇H₂₄O₆

Average Mass

324.3730 Da

Monoisotopic Mass

324.15729 Da

IUPAC Name

[(1'R,2S,2'R,7'R,9'R,10'R,11'S)-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

Traditional Name

(1'R,2S,2'R,7'R,9'R,10'R,11'S)-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]12CCC(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@]2(C)[C@]11CO1

InChI Identifier

InChI=1S/C17H24O6/c1-9-4-5-16(7-21-10(2)18)11(6-9)23-14-12(19)13(20)15(16,3)17(14)8-22-17/h6,11-14,19-20H,4-5,7-8H2,1-3H3/t11-,12-,13-,14-,15-,16-,17+/m1/s1

InChI Key

IRXDUBNENLKYTC-OINWIYPRSA-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
Fusarium	NPAtlas	946065
Fusarium sambucinum	Fungi	KNApSAcK
Fusarium sulphureum	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Oxepane
Oxane
Cyclic alcohol
1,2-diol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
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	0.57	ALOGPS
logP	-0.064	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.98	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.95 m³·mol⁻¹	ChemAxon
Polarizability	40.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA013367

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

19975982

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21117975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pathre SV, Mirocha CJ, Christensen CM, Behrens J: Monoacetoxyscirpenol. A new mycotoxin produced by Fusarium roseum Gibbosum. J Agric Food Chem. 1976 Jan-Feb;24(1):97-103. doi: 10.1021/jf60203a053. [PubMed:946065 ]
Ulrich S, Gottschalk C, Biermaier B, Bahlinger E, Twaruzek M, Asmussen S, Schollenberger M, Valenta H, Ebel F, Danicke S: Occurrence of type A, B and D trichothecenes, zearalenone and stachybotrylactam in straw. Arch Anim Nutr. 2021 Apr;75(2):105-120. doi: 10.1080/1745039X.2021.1877075. Epub 2021 Feb 21. [PubMed:33615927 ]
Kosicki R, Twaruzek M, Dopierala P, Rudzki B, Grajewski J: Occurrence of Mycotoxins in Winter Rye Varieties Cultivated in Poland (2017-2019). Toxins (Basel). 2020 Jun 26;12(6). pii: toxins12060423. doi: 10.3390/toxins12060423. [PubMed:32604961 ]
Viegas C, Faria T, Caetano LA, Carolino E, Quintal-Gomes A, Twaruzek M, Kosicki R, Viegas S: Characterization of Occupational Exposure To Fungal Burden in Portuguese Bakeries. Microorganisms. 2019 Aug 2;7(8). pii: microorganisms7080234. doi: 10.3390/microorganisms7080234. [PubMed:31382481 ]
Pokrzywa P, Cieslik E, Surma M: Effect of storage conditions on the formation of type A and B trichothecenes in cereal products. Ann Agric Environ Med. 2019 Jun 17;26(2):260-265. doi: 10.26444/aaem/103398. Epub 2019 Mar 18. [PubMed:31232057 ]

Showing NP-Card for Monoacetoxyscirpenol (NP0023604)

MOL for NP0023604 (Monoacetoxyscirpenol)

3D MOL for NP0023604 (Monoacetoxyscirpenol)

3D SDF for NP0023604 (Monoacetoxyscirpenol)

3D-SDF for NP0023604 (Monoacetoxyscirpenol)

PDB for NP0023604 (Monoacetoxyscirpenol)

3D PDB for NP0023604 (Monoacetoxyscirpenol)

SMILES for NP0023604 (Monoacetoxyscirpenol)

INCHI for NP0023604 (Monoacetoxyscirpenol)

Structure for NP0023604 (Monoacetoxyscirpenol)

3D Structure for NP0023604 (Monoacetoxyscirpenol)