NP-MRD: Showing NP-Card for Verrol 4-acetate (NP0003192)

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Record Information

Version

2.0

Created at

2020-12-09 00:31:42 UTC

Updated at

2021-07-15 16:45:45 UTC

NP-MRD ID

NP0003192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Verrol 4-acetate

Provided By

NPAtlas

Description

[(1'S,9'R,11'R)-11'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-2'-yl]methyl (2E)-5-hydroxy-3-methylpent-2-enoate 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. Verrol 4-acetate is found in Acremonium. Verrol 4-acetate was first documented in 2000 (PMID: 10705737). Based on a literature review very few articles have been published on [(1'S,9'R,11'R)-11'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-2'-yl]methyl (2E)-5-hydroxy-3-methylpent-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 62 65  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117463D          

 62 65  0  0  0  0            999 V2000
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  1  2  1  0  0  0  0
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  4  5  1  0  0  0  0
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  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
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 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
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 15 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
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 29 30  1  0  0  0  0
 26  5  1  0  0  0  0
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 15  9  1  0  0  0  0
  1 31  1  0  0  0  0
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 27 60  1  0  0  0  0
 29 61  1  0  0  0  0
 29 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C([H])([H])C(=C(/[H])C(=O)OC([H])([H])[C@@]12C([H])([H])C([H])([H])C(=C([H])[C@]1([H])O[C@]1([H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]2(C([H])([H])[H])[C@]11OC1([H])[H])C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O7/c1-14-5-7-22(12-27-20(26)10-15(2)6-8-24)18(9-14)30-19-11-17(29-16(3)25)21(22,4)23(19)13-28-23/h9-10,17-19,24H,5-8,11-13H2,1-4H3/b15-10+/t17-,18+,19-,21-,22+,23-/m1/s1

> <INCHI_KEY>
RMSNSMQSVVPVHV-NCIZUERJSA-N

> <FORMULA>
C23H32O7

> <MOLECULAR_WEIGHT>
420.502

> <EXACT_MASS>
420.21480337

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.154718451611814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1'S,2R,2'S,7'S,9'R,11'R)-11'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl (2E)-5-hydroxy-3-methylpent-2-enoate

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
1.694806941333331

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.107593224301187

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8730354854160614

> <JCHEM_POLAR_SURFACE_AREA>
94.59

> <JCHEM_REFRACTIVITY>
109.13549999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'S,7'S,9'R,11'R)-11'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl (2E)-5-hydroxy-3-methylpent-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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  9 10  1  0
 10 11  2  0
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 26  5  1  0
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 28  7  1  0
 15  9  1  0
  1 31  1  0
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  1 33  1  0
  5 34  1  1
  6 35  1  0
  6 36  1  0
  7 37  1  6
  9 38  1  6
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 27 58  1  0
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 27 60  1  0
 29 61  1  0
 29 62  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      -5.059  -3.699   1.516  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.293  -2.429   1.648  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.814  -2.123   2.772  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.114  -1.603   0.547  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.385  -0.380   0.639  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.259   0.739   0.146  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.565   1.290  -1.112  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.553   2.155  -0.793  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.266   1.654  -0.954  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.341   2.748  -0.563  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.226   2.868   0.613  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.156   4.019   0.920  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.044   1.865   1.659  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.145   0.914   1.336  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.108   0.415  -0.090  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.150  -0.339  -0.406  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.325   0.381  -0.226  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.549  -0.251  -0.500  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.460  -1.440  -0.893  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.823   0.409  -0.345  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.919  -0.262  -0.628  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.880  -1.665  -1.097  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.244   0.438  -0.467  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.027  -0.341   0.554  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.291  -0.335   1.737  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.268  -0.479  -0.377  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.913  -1.919  -0.582  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.997  -0.015  -1.624  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.753  -0.821  -2.490  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.511  -0.178  -2.865  0.00  0.00           O+0
HETATM   31  H   UNK     0      -4.527  -4.561   1.945  0.00  0.00           H+0
HETATM   32  H   UNK     0      -6.000  -3.563   2.083  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.231  -3.899   0.457  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.053  -0.282   1.665  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.452   1.523   0.879  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.237   0.349  -0.204  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.319   1.693  -1.812  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.039   1.425  -2.022  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.115   3.509  -1.302  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.599   4.816   1.456  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.990   3.672   1.562  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.544   4.474  -0.015  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.382   2.451   2.567  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.893   1.379   1.982  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.085   1.498   1.441  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.080   0.061   2.042  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.123  -1.278   0.190  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.089  -0.598  -1.502  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.928   1.436  -0.006  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.939  -2.009  -1.297  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.393  -1.772  -2.098  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.509  -2.383  -0.342  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.753   0.302  -1.457  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.094   1.486  -0.214  0.00  0.00           H+0
HETATM   55  H   UNK     0       8.039   0.094   0.695  0.00  0.00           H+0
HETATM   56  H   UNK     0       7.145  -1.377   0.185  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.835  -0.772   2.446  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.559  -2.419   0.362  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.266  -2.121  -1.437  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.888  -2.446  -0.804  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.668  -1.912  -2.663  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.633  -0.389  -3.036  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26   34                                             
CONECT    6    5    7   35   36                                             
CONECT    7    6    8   28   37                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   15   38                                             
CONECT   10    9   11   39                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   40   41   42                                             
CONECT   13   11   14   43   44                                             
CONECT   14   13   15   45   46                                             
CONECT   15   14   16   26    9                                             
CONECT   16   15   17   47   48                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   49                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   50   51   52                                             
CONECT   23   21   24   53   54                                             
CONECT   24   23   25   55   56                                             
CONECT   25   24   57                                                       
CONECT   26   15   27   28    5                                             
CONECT   27   26   58   59   60                                             
CONECT   28   26   29   30    7                                             
CONECT   29   28   30   61   62                                             
CONECT   30   29   28                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   20                                                            
CONECT   50   22                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
CONECT   60   27                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
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   -4.2926   -2.4294    1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8136   -2.1229    2.7719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1135   -1.6032    0.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3849   -0.3798    0.6388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2588    0.7390    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5649    1.2895   -1.1116 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.2662    1.6541   -0.9539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3414    2.7481   -0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260    2.8681    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556    4.0186    0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5109   -0.1784   -2.8647 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4522    1.5226    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2368    0.3490   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3186    1.6932   -1.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392    1.4251   -2.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153    3.5090   -1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9895    3.6717    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442    4.4737   -0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3818    2.4509    2.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    1.3785    1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0850    1.4981    1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    0.0614    2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1228   -1.2785    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0892   -0.5984   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9275    1.4360   -0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3932   -1.7720   -2.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7534    0.3022   -1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0936    1.4864   -0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0387    0.0943    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449   -1.3767    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8349   -0.7722    2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -2.4193    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2662   -2.1206   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8882   -2.4456   -0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681   -1.9122   -2.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6328   -0.3888   -3.0358 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 15 26  1  0
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 26  5  1  0
 28 30  1  6
 28  7  1  0
 15  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  1
  6 35  1  0
  6 36  1  0
  7 37  1  6
  9 38  1  6
 10 39  1  0
 12 40  1  0
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 12 42  1  0
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 27 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 29 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
[(1's,9'r,11'r)-11'-(Acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0,]dodecan]-5'-en-2'-yl]methyl (2E)-5-hydroxy-3-methylpent-2-enoic acid	Generator
Verrol 4-acetic acid	Generator

Chemical Formula

C₂₃H₃₂O₇

Average Mass

420.5020 Da

Monoisotopic Mass

420.21480 Da

IUPAC Name

[(1'S,2R,2'S,7'S,9'R,11'R)-11'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl (2E)-5-hydroxy-3-methylpent-2-enoate

Traditional Name

(1'S,2R,2'S,7'S,9'R,11'R)-11'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl (2E)-5-hydroxy-3-methylpent-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H]2OC3C=C(C)CCC3(COC(=O)\C=C(/C)CCO)[C@]1(C)C21CO1

InChI Identifier

InChI=1S/C23H32O7/c1-14-5-7-22(12-27-20(26)10-15(2)6-8-24)18(9-14)30-19-11-17(29-16(3)25)21(22,4)23(19)13-28-23/h9-10,17-19,24H,5-8,11-13H2,1-4H3/b15-10+/t17-,18?,19-,21-,22?,23?/m1/s1

InChI Key

RMSNSMQSVVPVHV-NCIZUERJSA-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
Acremonium	NPAtlas	10705737

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
Fatty acid ester
Oxepane
Dicarboxylic acid or derivatives
Oxane
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.06	ALOGPS
logP	1.69	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	17.11	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	109.14 m³·mol⁻¹	ChemAxon
Polarizability	45.15 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	Yes	ChemAxon

External Links

NPAtlas ID

NPA006871

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10478913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21776401

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Laurent D, Guella G, Roquebert MF, Farinole F, Mancini I, Pietra F: Cytotoxins, mycotoxins and drugs from a new deuteromycete, Acremonium neo-caledoniae, from the southwestern lagoon of New Caledonia. Planta Med. 2000 Feb;66(1):63-6. doi: 10.1055/s-2000-11110. [PubMed:10705737 ]

Showing NP-Card for Verrol 4-acetate (NP0003192)

MOL for NP0003192 (Verrol 4-acetate)

3D MOL for NP0003192 (Verrol 4-acetate)

3D SDF for NP0003192 (Verrol 4-acetate)

3D-SDF for NP0003192 (Verrol 4-acetate)

PDB for NP0003192 (Verrol 4-acetate)

3D PDB for NP0003192 (Verrol 4-acetate)

SMILES for NP0003192 (Verrol 4-acetate)

INCHI for NP0003192 (Verrol 4-acetate)

Structure for NP0003192 (Verrol 4-acetate)

3D Structure for NP0003192 (Verrol 4-acetate)