NP-MRD: Showing NP-Card for 3-Acetyldeoxy Nivalenol (NP0139351)

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Record Information

Version

2.0

Created at

2022-06-29 19:50:33 UTC

Updated at

2022-06-29 19:50:33 UTC

NP-MRD ID

NP0139351

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Acetyldeoxy Nivalenol

Description

3-Acetyldeoxynivalenol, also known as 15-ADON or 3-acetyl DON, 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. 3-Acetyldeoxy Nivalenol is found in Fusarium culmorum and Fusarium graminearum. 3-Acetyldeoxy Nivalenol was first documented in 2001 (PMID: 11510664). Based on a literature review a significant number of articles have been published on 3-acetyldeoxynivalenol (PMID: 34199242) (PMID: 35448850) (PMID: 35051496) (PMID: 35001349) (PMID: 34666620) (PMID: 34597541).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221502D          

 26 29  0  0  1  0            999 V2000
    5.6625    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529   -0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    0.2874    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6885    0.5186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451    1.1012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6245    1.5028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8612    1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300    0.3979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8162    0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5264   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505   -1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2874   -0.6452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6736    2.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423    0.6780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3409    0.4823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5721    1.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050   -0.2767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7034   -0.9973    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    1.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455    2.3979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9823    1.6253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3511    2.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    1.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3919    1.8597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  7 14  1  1  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  4 20  1  0  0  0  0
  6 21  1  6  0  0  0
 21 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    3.8457    0.7262   -3.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -0.3314   -2.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232   -1.5343   -2.9762 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0524   -0.0688   -2.0922 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269   -1.0850   -1.3875 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0409   -1.2188   -1.6253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7186   -1.2811   -0.2534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8876   -2.1932   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4285   -1.8033    0.5806 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3843   -2.7693    1.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6903   -3.2054    0.2321 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -0.9256    0.1299 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3199    0.3787    0.5218 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    0.9515   -0.0428 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0316    2.2966    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000    2.4563    1.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7319    3.7992    2.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837    1.3235    2.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943    1.4647    3.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0516   -0.0112    1.8081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0721   -0.8062    2.2605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0275    0.0933    0.2791 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2898    0.6936   -0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    0.8459   -1.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7839    1.7217   -3.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5111    0.7867   -4.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296    0.4714   -3.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9481   -2.0614   -1.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694   -0.4756   -2.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2446   -2.2215   -2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -2.6825    0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180   -3.0355   -1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304   -1.6775   -0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5864   -3.1180    1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -2.8902    2.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5414   -1.2177    0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094    1.1367   -1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    3.1862    0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5576    4.6224    1.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    3.8333    2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375    3.9291    3.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469   -0.4005    2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6913   -0.3117    2.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800    1.7079    0.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627    0.1270    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914    0.7736   -1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  6
 23 24  1  0
 22  7  1  0
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  5 12  1  0
  9 11  1  6
  9 12  1  0
 22 14  1  0
 12 36  1  1
 14 37  1  6
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 20 42  1  1
 21 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  6 29  1  0
  6 30  1  0
  5 28  1  6
  1 25  1  0
  1 26  1  0
  1 27  1  0
 10 34  1  0
 10 35  1  0
M  END


  Mrv1652306292221502D          

 26 29  0  0  1  0            999 V2000
    5.6625    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529   -0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    0.2874    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6885    0.5186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451    1.1012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6245    1.5028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8612    1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300    0.3979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8162    0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5264   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505   -1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2874   -0.6452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6736    2.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423    0.6780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3409    0.4823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5721    1.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050   -0.2767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7034   -0.9973    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    1.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455    2.3979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9823    1.6253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3511    2.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    1.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3919    1.8597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  7 14  1  1  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  4 20  1  0  0  0  0
  6 21  1  6  0  0  0
 21 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0139351

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)(C[C@H]1OC(C)=O)[C@]21CO1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3/t10-,11-,13-,14-,15-,16-,17+/m1/s1

> <INCHI_KEY>
ADFIQZBYNGPCGY-HTJQZXIKSA-N

> <FORMULA>
C17H22O7

> <MOLECULAR_WEIGHT>
338.356

> <EXACT_MASS>
338.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.5258091359703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2S,2'R,3'S,7'R,9'R,10'R)-3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
-0.5275714799999995

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.017315545011694

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.749202780547702

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8416553622596945

> <JCHEM_POLAR_SURFACE_AREA>
105.59

> <JCHEM_REFRACTIVITY>
80.7721

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,2'R,3'S,7'R,9'R,10'R)-3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      10.570   0.433   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.128   0.974   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.939  -0.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.497   0.536   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       5.019   0.968   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       6.244   2.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.899   2.805   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.474   2.221   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.043   0.743   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.524   0.490   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.983  -0.952   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.961  -2.141   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.536  -1.204   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.991   4.343   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.999   1.266   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.503   0.900   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.935   2.379   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.929  -0.516   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       3.180  -1.862   0.000  0.00  0.00           H+0
HETATM   20  O   UNK     0       5.467  -0.608   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.106   3.589   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.365   4.476   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.434   3.034   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.122   4.411   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.875   2.493   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.065   3.471   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   20                                             
CONECT    5    4                                                            
CONECT    6    4    7   21   23                                             
CONECT    7    6    8   14   15                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7                                                            
CONECT   15    7   16   17   18                                             
CONECT   16   15   17                                                       
CONECT   17   16   15                                                       
CONECT   18   15    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    4                                                       
CONECT   21    6   22                                                       
CONECT   22   21                                                            
CONECT   23    6   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    2   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
(3alpha,7alpha)-3-(Acetyloxy)-12,13-epoxy-7,15-dihydroxytrichothec-9-en-8-one	ChEBI
15-ADON	ChEBI
3-(Acetyloxy)-12,13-epoxy-7alpha,15alpha-dihydroxytrichothec-9-en-8-one	ChEBI
3-Acetyl DON	ChEBI
3-Acetyl-deoxynivalenol	ChEBI
3-Acetyl-DON	ChEBI
(3a,7a)-3-(Acetyloxy)-12,13-epoxy-7,15-dihydroxytrichothec-9-en-8-one	Generator
(3Α,7α)-3-(acetyloxy)-12,13-epoxy-7,15-dihydroxytrichothec-9-en-8-one	Generator
3-(Acetyloxy)-12,13-epoxy-7a,15a-dihydroxytrichothec-9-en-8-one	Generator
3-(Acetyloxy)-12,13-epoxy-7α,15α-dihydroxytrichothec-9-en-8-one	Generator
3-ADON	MeSH
AcetylDON	MeSH

Chemical Formula

C₁₇H₂₂O₇

Average Mass

338.3560 Da

Monoisotopic Mass

338.13655 Da

IUPAC Name

(1'R,2S,2'R,3'S,7'R,9'R,10'R)-3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate

Traditional Name

(1'R,2S,2'R,3'S,7'R,9'R,10'R)-3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)(C[C@H]1OC(C)=O)[C@]21CO1

InChI Identifier

InChI=1S/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3/t10-,11-,13-,14-,15-,16-,17+/m1/s1

InChI Key

ADFIQZBYNGPCGY-HTJQZXIKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 culmorum	LOTUS Database	35616633
Fusarium graminearum	LOTUS Database	35616633

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
Cyclohexenone
Oxane
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Primary alcohol
Organic oxide
Organic oxygen compound
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	-0.61	ALOGPS
logP	-0.53	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.75	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.77 m³·mol⁻¹	ChemAxon
Polarizability	33.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4572447

KEGG Compound ID

Not Available

BioCyc ID

CPD-18419

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5458510

PDB ID

Not Available

ChEBI ID

146195

Good Scents ID

rw1680881

References

General References

Tarazona A, Gomez JV, Mateo F, Jimenez M, Mateo EM: Potential Health Risk Associated with Mycotoxins in Oat Grains Consumed in Spain. Toxins (Basel). 2021 Jun 13;13(6). pii: toxins13060421. doi: 10.3390/toxins13060421. [PubMed:34199242 ]
Zhang D, Zhao L, Chen Y, Gao H, Hua Y, Yuan X, Yang H: Mycotoxins in Maize Silage from China in 2019. Toxins (Basel). 2022 Mar 27;14(4). pii: toxins14040241. doi: 10.3390/toxins14040241. [PubMed:35448850 ]
Hu Y, Li H, Min J, Yu Y, Liu W, Huang JW, Zhang L, Yang Y, Dai L, Chen CC, Guo RT: Crystal structure and biochemical analysis of the specialized deoxynivalenol-detoxifying glyoxalase SPG from Gossypium hirsutum. Int J Biol Macromol. 2022 Mar 1;200:388-396. doi: 10.1016/j.ijbiomac.2022.01.055. Epub 2022 Jan 18. [PubMed:35051496 ]
de Arruda MHM, Schwab EDP, Zchonski FL, da Cruz JF, Tessmann DJ, Da-Silva PR: Production of type-B trichothecenes by Fusarium meridionale, F. graminearum, and F. austroamericanum in wheat plants and rice medium. Mycotoxin Res. 2022 Feb;38(1):1-11. doi: 10.1007/s12550-021-00445-9. Epub 2022 Jan 10. [PubMed:35001349 ]
Liang J, Ning M, Guan S, Fang L, Chen X, Dong Z, Fan L: Risk assessment of multiple-mycotoxin exposure for consumers of chestnuts in Shandong Province markets in China. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2021 Dec;38(12):2137-2150. doi: 10.1080/19440049.2021.1970240. Epub 2021 Oct 19. [PubMed:34666620 ]
Goessens T, De Baere S, Deknock A, De Troyer N, Van Leeuwenberg R, Martel A, Pasmans F, Goethals P, Lens L, Spanoghe P, Vanhaecke L, Croubels S: Agricultural contaminants in amphibian breeding ponds: Occurrence, risk and correlation with agricultural land use. Sci Total Environ. 2022 Feb 1;806(Pt 2):150661. doi: 10.1016/j.scitotenv.2021.150661. Epub 2021 Sep 29. [PubMed:34597541 ]
Arce-Lopez B, Alvarez-Erviti L, De Santis B, Izco M, Lopez-Calvo S, Marzo-Sola ME, Debegnach F, Lizarraga E, Lopez de Cerain A, Gonzalez-Penas E, Vettorazzi A: Biomonitoring of Mycotoxins in Plasma of Patients with Alzheimer's and Parkinson's Disease. Toxins (Basel). 2021 Jul 10;13(7):477. doi: 10.3390/toxins13070477. [PubMed:34357949 ]
Alonso-Jauregui M, Gonzalez-Penas E, Lopez de Cerain A, Vettorazzi A: Genotoxicity of 12 Mycotoxins by the SOS/umu Test: Comparison of Liver and Kidney S9 Fraction. Toxins (Basel). 2022 Jun 10;14(6):400. doi: 10.3390/toxins14060400. [PubMed:35737061 ]
Kudupoje MB, Malathi V, Yiannikouris A: Impact of a Natural Fusarial Multi-Mycotoxin Challenge on Broiler Chickens and Mitigation Properties Provided by a Yeast Cell Wall Extract and a Postbiotic Yeast Cell Wall-Based Blend. Toxins (Basel). 2022 Apr 28;14(5):315. doi: 10.3390/toxins14050315. [PubMed:35622561 ]
Jia H, Zhang T, Liu N, Si X, Bai J, Yang Y, Chen Z, Wu Z: 4-Phenylbutyric acid alleviates 3-acetyldeoxynivalenol-induced immune cells response by inhibiting endoplasmic reticulum stress in mouse spleen. Food Chem Toxicol. 2022 Jun;164:113002. doi: 10.1016/j.fct.2022.113002. Epub 2022 Apr 9. [PubMed:35413383 ]
Tretiakova P, Voegele RT, Soloviev A, Link TI: Successful Silencing of the Mycotoxin Synthesis Gene TRI5 in Fusarium culmorum and Observation of Reduced Virulence in VIGS and SIGS Experiments. Genes (Basel). 2022 Feb 23;13(3):395. doi: 10.3390/genes13030395. [PubMed:35327949 ]
Pack ED, Weiland S, Musser R, Schmale DG: Survey of zearalenone and type-B trichothecene mycotoxins in swine feed in the USA. Mycotoxin Res. 2021 Nov;37(4):297-313. doi: 10.1007/s12550-021-00442-y. Epub 2021 Sep 18. [PubMed:34537950 ]
Wang SS, Cui H, Chen MZ, Li L, Wu Y, Wang SX: Simultaneous quantitation of 3ADON and 15ADON chemotypes of DON-producing Fusarium species in Chinese wheat based on duplex droplet digital PCR assay. J Microbiol Methods. 2021 Nov;190:106319. doi: 10.1016/j.mimet.2021.106319. Epub 2021 Sep 2. [PubMed:34480973 ]
Jorquera-Pereira D, Pavon-Perez J, Rios-Gajardo G: Identification of type B trichothecenes and zearalenone in Chilean cereals by planar chromatography coupled to mass spectroscopy. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2021 Oct;38(10):1778-1787. doi: 10.1080/19440049.2021.1948618. Epub 2021 Jul 13. [PubMed:34254899 ]
Zhu T, Li L, Petridis A, Xydis G, Ren M: First Report of Fusarium asiaticum Causing Stem Rot of Ligusticum chuanxiong in China. Plant Dis. 2021 Jul 2. doi: 10.1094/PDIS-05-21-1026-PDN. [PubMed:34213965 ]
Jia H, Liu N, Zhang Y, Wang C, Yang Y, Wu Z: 3-Acetyldeoxynivalenol induces cell death through endoplasmic reticulum stress in mouse liver. Environ Pollut. 2021 Oct 1;286:117238. doi: 10.1016/j.envpol.2021.117238. Epub 2021 Apr 27. [PubMed:33984781 ]
Xu F, Liu W, Song Y, Zhou Y, Xu X, Yang G, Wang J, Zhang J, Liu L: The Distribution of Fusarium graminearum and Fusarium asiaticum Causing Fusarium Head Blight of Wheat in Relation to Climate and Cropping System. Plant Dis. 2021 Oct;105(10):2830-2835. doi: 10.1094/PDIS-01-21-0013-RE. Epub 2021 Nov 1. [PubMed:33881919 ]
Dong F, Li Y, Chen X, Wu J, Wang S, Zhang X, Ma G, Lee YW, Mokoena MP, Olaniran AO, Xu JH, Shi JR: Analysis of the Fusarium graminearum Species Complex from Gramineous Weeds Near Wheat Fields in Jiangsu Province, China. Plant Dis. 2021 Oct;105(10):3269-3275. doi: 10.1094/PDIS-11-20-2376-RE. Epub 2021 Nov 9. [PubMed:33847508 ]
Niknejad F, Escriva L, Adel Rad KB, Khoshnia M, Barba FJ, Berrada H: Biomonitoring of Multiple Mycotoxins in Urine by GC-MS/MS: A Pilot Study on Patients with Esophageal Cancer in Golestan Province, Northeastern Iran. Toxins (Basel). 2021 Mar 29;13(4):243. doi: 10.3390/toxins13040243. [PubMed:33805401 ]
Arce-Lopez B, Lizarraga E, Lopez de Mesa R, Gonzalez-Penas E: Assessment of Exposure to Mycotoxins in Spanish Children through the Analysis of Their Levels in Plasma Samples. Toxins (Basel). 2021 Feb 15;13(2):150. doi: 10.3390/toxins13020150. [PubMed:33672088 ]
Abramson D, Clear RM, Gaba D, Smith DM, Patrick SK, Saydak D: Trichothecene and moniliformin production by Fusarium species from western Canadian wheat. J Food Prot. 2001 Aug;64(8):1220-5. doi: 10.4315/0362-028x-64.8.1220. [PubMed:11510664 ]
Eriksen GS, Pettersson H, Lindberg JE: Absorption, metabolism and excretion of 3-acetyl DON in pigs. Arch Tierernahr. 2003 Oct;57(5):335-45. doi: 10.1080/00039420310001607699. [PubMed:14620907 ]
Bretz M, Beyer M, Cramer B, Humpf HU: Stable isotope dilution analysis of the Fusarium mycotoxins deoxynivalenol and 3-acetyldeoxynivalenol. Mol Nutr Food Res. 2006 Mar;50(3):251-60. doi: 10.1002/mnfr.200500230. [PubMed:16521158 ]
Vujanovic V, Goh YK: Sphaerodes mycoparasitica biotrophic mycoparasite of 3-acetyldeoxynivalenol- and 15-acetyldeoxynivalenol-producing toxigenic Fusarium graminearum chemotypes. FEMS Microbiol Lett. 2011 Mar;316(2):136-43. doi: 10.1111/j.1574-6968.2010.02201.x. Epub 2011 Jan 19. [PubMed:21204935 ]
Amarasinghe C, Wang JH, Liao YC, Fernando WG: Difference in TRI13 gene sequences between the 3-acetyldeoxynivalenol producing Fusarium graminearum chemotypes from Canada and China. Int J Mol Sci. 2011;12(9):6164-75. doi: 10.3390/ijms12096164. Epub 2011 Sep 20. [PubMed:22016651 ]

Showing NP-Card for 3-Acetyldeoxy Nivalenol (NP0139351)

MOL for NP0139351 (3-Acetyldeoxy Nivalenol)

3D MOL for NP0139351 (3-Acetyldeoxy Nivalenol)

3D SDF for NP0139351 (3-Acetyldeoxy Nivalenol)

3D-SDF for NP0139351 (3-Acetyldeoxy Nivalenol)

PDB for NP0139351 (3-Acetyldeoxy Nivalenol)

3D PDB for NP0139351 (3-Acetyldeoxy Nivalenol)

SMILES for NP0139351 (3-Acetyldeoxy Nivalenol)

INCHI for NP0139351 (3-Acetyldeoxy Nivalenol)

Structure for NP0139351 (3-Acetyldeoxy Nivalenol)

3D Structure for NP0139351 (3-Acetyldeoxy Nivalenol)