NP-MRD: Showing NP-Card for 15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one. (NP0084889)

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Record Information

Version

2.0

Created at

2022-04-29 05:30:24 UTC

Updated at

2022-04-29 05:30:24 UTC

NP-MRD ID

NP0084889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.

Description

15-Acetyldeoxynivalenol, also known as 15-ADON or 15-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. 15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one. is found in Fusarium culmorum and Fusarium graminearum. 15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one. was first documented in 2021 (PMID: 34666620). Based on a literature review a small amount of articles have been published on 15-acetyldeoxynivalenol (PMID: 35448850) (PMID: 35051496) (PMID: 35001349) (PMID: 34564663).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207302D          

 26 29  0  0  1  0            999 V2000
    5.3919    1.8597    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
    4.8900    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625    0.2321    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  1  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
    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
    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
    2.1423    0.6780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3409    0.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5721    1.2742    0.0000 O   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
    3.8714    3.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228    3.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459    3.6946    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 18  1  6  0  0  0
 14 19  1  0  0  0  0
  6 19  1  0  0  0  0
  8 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
  8 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  6  0  0  0
M  END

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    3.4455    2.5005   -2.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9791    2.3085   -2.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1971    3.0322   -2.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886    1.3341   -1.2097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    1.0982   -1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1742   -0.0081   -0.0469 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4100   -1.2793   -0.6659 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7669   -1.0399   -0.9887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2540   -1.5988   -1.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264   -2.1104   -2.9032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6644   -1.3282   -2.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833   -1.8431   -3.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998   -0.6537   -1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6775   -0.1249    0.0299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1668   -0.8019    1.0994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -0.8089    2.2526 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4842    0.6010    2.8120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7148    1.1981    2.5428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3730    1.2634    2.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3932    0.1700    1.3089 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8532    0.3388    1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0014   -1.0474    2.1262 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7186   -2.1479    2.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6340   -1.0449    3.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976    1.4725   -2.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8548    2.9235   -1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119    3.0770   -3.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3842    0.8926   -1.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    2.0511   -0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -2.1171    0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523   -1.6418   -1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6918   -1.7266   -4.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2393   -1.1542   -3.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7366   -2.8700   -3.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3644   -0.4761   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1029    0.9249    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9196   -1.4703    3.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2212    0.6396    3.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953    1.9205    3.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3028    1.8398    2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8201    2.0001    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2997    1.2182    0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3948   -0.6167    1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536    0.4825    2.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471   -3.0883    2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -2.2886    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  2  0
 11 12  1  0
 11  9  1  0
  9 10  2  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  1  6
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6 20  1  0
 20 21  1  6
 20 19  1  0
 19 17  1  0
 17 18  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 17 16  1  0
 22 24  1  1
 22 16  1  0
  6 14  1  0
 16 37  1  1
 14 36  1  1
 13 35  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
  7 30  1  1
  8 31  1  0
  5 28  1  0
  5 29  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 19 40  1  0
 19 41  1  0
 17 38  1  1
 18 39  1  0
 23 45  1  0
 23 46  1  0
M  END


  Mrv1652304292207302D          

 26 29  0  0  1  0            999 V2000
    5.3919    1.8597    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
    4.8900    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625    0.2321    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  1  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
    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
    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
    2.1423    0.6780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3409    0.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5721    1.2742    0.0000 O   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
    3.8714    3.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228    3.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459    3.6946    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 18  1  6  0  0  0
 14 19  1  0  0  0  0
  6 19  1  0  0  0  0
  8 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
  8 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0084889

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
IDGRYIRJIFKTAN-HTJQZXIKSA-N

> <FORMULA>
C17H22O7

> <MOLECULAR_WEIGHT>
338.356

> <EXACT_MASS>
338.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.326556668288795

> <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',10'-dihydroxy-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

> <ALOGPS_LOGP>
-0.54

> <JCHEM_LOGP>
-0.5275714799999995

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.098462112239151

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.742955454554497

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2026020401789026

> <JCHEM_POLAR_SURFACE_AREA>
105.59000000000002

> <JCHEM_REFRACTIVITY>
80.77210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      10.065   3.471   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.875   2.493   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.128   0.974   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.570   0.433   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.939  -0.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.497   0.536   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       5.019   0.968   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0       6.244   2.056   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.899   2.805   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.991   4.343   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.474   2.221   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.043   0.743   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.524   0.490   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.929  -0.516   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       3.180  -1.862   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       3.999   1.266   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.503   0.900   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.935   2.379   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.467  -0.608   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.106   3.589   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.365   4.476   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.227   6.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.829   6.657   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.486   6.897   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.434   3.034   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.122   4.411   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8   19                                             
CONECT    7    6                                                            
CONECT    8    6    9   20   25                                             
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   19                                             
CONECT   15   14                                                            
CONECT   16   14    9   17   18                                             
CONECT   17   16   18                                                       
CONECT   18   17   16                                                       
CONECT   19   14    6                                                       
CONECT   20    8   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    8    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)-15-(Acetyloxy)-12,13-epoxy-3,7-dihydroxytrichothec-9-en-8-one	ChEBI
15-(Acetyloxy)-12,13-epoxy-3alpha,7alpha-dihydroxytrichothec-9-en-8-one	ChEBI
15-AcDON	ChEBI
15-Acetyl-deoxynivalenol	ChEBI
15-Acetyl-DON	ChEBI
15-ADON	ChEBI
(3a,7a)-15-(Acetyloxy)-12,13-epoxy-3,7-dihydroxytrichothec-9-en-8-one	Generator
(3Α,7α)-15-(acetyloxy)-12,13-epoxy-3,7-dihydroxytrichothec-9-en-8-one	Generator
15-(Acetyloxy)-12,13-epoxy-3a,7a-dihydroxytrichothec-9-en-8-one	Generator
15-(Acetyloxy)-12,13-epoxy-3α,7α-dihydroxytrichothec-9-en-8-one	Generator
15-Monoacetyldeoxynivalenol	MeSH
15ADON	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',10'-dihydroxy-1',5'-dimethyl-4'-oxo-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,3'S,7'R,9'R,10'R)-3',10'-dihydroxy-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

IDGRYIRJIFKTAN-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, 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 culmorum	LOTUS Database	35616633
Fusarium graminearum	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
Cyclohexenone
Oxepane
Oxane
Cyclic alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Oxacycle
Carboxylic acid derivative
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	-0.54	ALOGPS
logP	-0.53	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3.2	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	33.33 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

C00054510

Chemspider ID

8557926

KEGG Compound ID

Not Available

BioCyc ID

CPD-18420

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10382483

PDB ID

Not Available

ChEBI ID

146194

Good Scents ID

rw1680891

References

General References

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 ]
Wang L, Yan Z, Zhou H, Fan Y, Wang C, Zhang J, Liao Y, Wu A: Validation of LC-MS/MS Coupled with a Chiral Column for the Determination of 3- or 15-Acetyl Deoxynivalenol Mycotoxins from Fusarium graminearum in Wheat. Toxins (Basel). 2021 Sep 16;13(9). pii: toxins13090659. doi: 10.3390/toxins13090659. [PubMed:34564663 ]

Showing NP-Card for 15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one. (NP0084889)

MOL for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)

3D MOL for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)

3D SDF for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)

3D-SDF for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)

PDB for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)

3D PDB for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)

SMILES for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)

INCHI for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)

Structure for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)

3D Structure for NP0084889 (15-Acetoxy-12,13-epoxy-3,7-dihydroxy-9-trichothecen-8-one.)