NP-MRD: Showing NP-Card for Vomitoxin (NP0021450)

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Record Information

Version

2.0

Created at

2021-01-06 06:41:48 UTC

Updated at

2021-08-20 00:00:00 UTC

NP-MRD ID

NP0021450

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vomitoxin

Provided By

NPAtlas

Description

Vomitoxin is also known as deoxynivalenol or DON. Vomitoxin is found in Fusarium graminearum and Fusarium roseum. Vomitoxin was first documented in 1973 (PMID: 4767291). Based on a literature review very few articles have been published on Vomitoxin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105153D          

 41 44  0  0  0  0            999 V2000
    4.2174    0.9650    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416    0.7230    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066    0.8585    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537    0.6136    0.9680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1089    1.8044    0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3364    1.7768    0.0402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3708    1.2378    1.0291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0686    1.7309    2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1387   -0.2515    0.9241 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2837   -0.5025   -0.2954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7387   -1.7473   -0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033    0.7531   -1.0675 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4967    0.9358   -2.0661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0979    0.9807   -2.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -0.5530    0.0955 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3683   -1.8638    0.8676 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6478   -2.0063    1.3555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631   -0.6725   -1.1189 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7115   -1.9338   -1.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1663    0.3182   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6012    0.7983   -2.2137 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4128    1.5683    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125    1.5993   -0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7871    0.0371    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328    1.1583    2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848    0.3477    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058    2.7632   -0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.5290    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707    2.7178    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1283   -0.7758    0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -0.5745    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391   -2.5098   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7110   -1.5569   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.1820   -1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0580    0.1296   -2.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    1.9383   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725   -2.6668    0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -2.0210    1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922   -2.9488    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813   -0.6610   -2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964   -1.8572   -0.7692 H   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  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20  2  1  0  0  0  0
 15  4  1  0  0  0  0
 12  6  1  0  0  0  0
 12 14  1  6  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4 26  1  1  0  0  0
  6 27  1  6  0  0  0
  7 28  1  6  0  0  0
  8 29  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 17 39  1  0  0  0  0
 18 40  1  6  0  0  0
 19 41  1  0  0  0  0
M  END

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    4.2174    0.9650    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416    0.7230    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066    0.8585    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537    0.6136    0.9680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1089    1.8044    0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3364    1.7768    0.0402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3708    1.2378    1.0291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0686    1.7309    2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1387   -0.2515    0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -0.5025   -0.2954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7387   -1.7473   -0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033    0.7531   -1.0675 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4967    0.9358   -2.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0979    0.9807   -2.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -0.5530    0.0955 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3683   -1.8638    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478   -2.0063    1.3555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631   -0.6725   -1.1189 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7115   -1.9338   -1.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1663    0.3182   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6012    0.7983   -2.2137 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4128    1.5683    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125    1.5993   -0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7871    0.0371    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328    1.1583    2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848    0.3477    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058    2.7632   -0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.5290    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707    2.7178    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1283   -0.7758    0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -0.5745    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391   -2.5098   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7110   -1.5569   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.1820   -1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0580    0.1296   -2.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    1.9383   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725   -2.6668    0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -2.0210    1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922   -2.9488    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813   -0.6610   -2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964   -1.8572   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  1
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  2  1  0
 15  4  1  0
 12  6  1  0
 12 14  1  6
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  1
  6 27  1  6
  7 28  1  6
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  6
 19 41  1  0
M  END


  Mrv1652306242105153D          

 41 44  0  0  0  0            999 V2000
    4.2174    0.9650    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416    0.7230    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066    0.8585    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537    0.6136    0.9680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1089    1.8044    0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3364    1.7768    0.0402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3708    1.2378    1.0291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0686    1.7309    2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1387   -0.2515    0.9241 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2837   -0.5025   -0.2954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7387   -1.7473   -0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033    0.7531   -1.0675 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4967    0.9358   -2.0661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0979    0.9807   -2.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -0.5530    0.0955 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3683   -1.8638    0.8676 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6478   -2.0063    1.3555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631   -0.6725   -1.1189 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7115   -1.9338   -1.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1663    0.3182   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6012    0.7983   -2.2137 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4128    1.5683    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125    1.5993   -0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7871    0.0371    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328    1.1583    2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848    0.3477    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058    2.7632   -0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.5290    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707    2.7178    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1283   -0.7758    0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -0.5745    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391   -2.5098   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7110   -1.5569   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.1820   -1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0580    0.1296   -2.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    1.9383   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725   -2.6668    0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -2.0210    1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922   -2.9488    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813   -0.6610   -2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964   -1.8572   -0.7692 H   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  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20  2  1  0  0  0  0
 15  4  1  0  0  0  0
 12  6  1  0  0  0  0
 12 14  1  6  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4 26  1  1  0  0  0
  6 27  1  6  0  0  0
  7 28  1  6  0  0  0
  8 29  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 17 39  1  0  0  0  0
 18 40  1  6  0  0  0
 19 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021450

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3/t8-,9-,11-,12-,13-,14-,15-/m1/s1

> <INCHI_KEY>
LINOMUASTDIRTM-LZTLOYDTSA-N

> <FORMULA>
C15H20O6

> <MOLECULAR_WEIGHT>
296.319

> <EXACT_MASS>
296.125988364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
50.56386714621672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.76

> <JCHEM_LOGP>
-0.9686968903333336

> <ALOGPS_LOGS>
-0.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.057467154231485

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.679137950165817

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8416551078886947

> <JCHEM_POLAR_SURFACE_AREA>
99.52000000000001

> <JCHEM_REFRACTIVITY>
71.6206

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.60e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    4.2174    0.9650    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416    0.7230    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066    0.8585    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537    0.6136    0.9680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1089    1.8044    0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3364    1.7768    0.0402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3708    1.2378    1.0291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0686    1.7309    2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1387   -0.2515    0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -0.5025   -0.2954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7387   -1.7473   -0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033    0.7531   -1.0675 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4967    0.9358   -2.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0979    0.9807   -2.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -0.5530    0.0955 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3683   -1.8638    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478   -2.0063    1.3555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631   -0.6725   -1.1189 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7115   -1.9338   -1.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1663    0.3182   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6012    0.7983   -2.2137 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4128    1.5683    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125    1.5993   -0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7871    0.0371    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328    1.1583    2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848    0.3477    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058    2.7632   -0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.5290    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707    2.7178    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1283   -0.7758    0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -0.5745    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391   -2.5098   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7110   -1.5569   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.1820   -1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0580    0.1296   -2.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    1.9383   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725   -2.6668    0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -2.0210    1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922   -2.9488    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813   -0.6610   -2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964   -1.8572   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  1
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  2  1  0
 15  4  1  0
 12  6  1  0
 12 14  1  6
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  1
  6 27  1  6
  7 28  1  6
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  6
 19 41  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       4.217   0.965   0.262  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.742   0.723   0.124  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.907   0.859   1.137  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.454   0.614   0.968  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.109   1.804   0.594  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.336   1.777   0.040  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.371   1.238   1.029  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.069   1.731   2.288  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.139  -0.252   0.924  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.284  -0.502  -0.295  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.739  -1.747  -0.984  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.503   0.753  -1.067  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.497   0.936  -2.066  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.098   0.981  -2.340  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.181  -0.553   0.096  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.368  -1.864   0.868  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.648  -2.006   1.355  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.063  -0.673  -1.119  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.712  -1.934  -1.175  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.166   0.318  -1.152  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.601   0.798  -2.214  0.00  0.00           O+0
HETATM   22  H   UNK     0       4.413   1.568   1.166  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.513   1.599  -0.614  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.787   0.037   0.335  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.333   1.158   2.103  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.085   0.348   2.005  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.606   2.763  -0.338  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.387   1.529   0.679  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.171   2.718   2.237  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.128  -0.776   0.795  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.723  -0.575   1.870  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.939  -2.510  -0.175  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.711  -1.557  -1.465  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.998  -2.182  -1.661  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.058   0.130  -2.559  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.012   1.938  -2.134  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.173  -2.667   0.097  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.354  -2.021   1.659  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.792  -2.949   1.579  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.481  -0.661  -2.084  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.596  -1.857  -0.769  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3   20                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5   15   26                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   12   27                                             
CONECT    7    6    8    9   28                                             
CONECT    8    7   29                                                       
CONECT    9    7   10   30   31                                             
CONECT   10    9   11   12   15                                             
CONECT   11   10   32   33   34                                             
CONECT   12   10   13    6   14                                             
CONECT   13   12   14   35   36                                             
CONECT   14   13   12                                                       
CONECT   15   10   16   18    4                                             
CONECT   16   15   17   37   38                                             
CONECT   17   16   39                                                       
CONECT   18   15   19   20   40                                             
CONECT   19   18   41                                                       
CONECT   20   18   21    2                                                  
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   19                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

RDKit          3D

41 44  0  0  0  0  0  0  0  0999 V2000
    4.2174    0.9650    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416    0.7230    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066    0.8585    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537    0.6136    0.9680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1089    1.8044    0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3364    1.7768    0.0402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3708    1.2378    1.0291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0686    1.7309    2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1387   -0.2515    0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -0.5025   -0.2954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7387   -1.7473   -0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033    0.7531   -1.0675 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4967    0.9358   -2.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0979    0.9807   -2.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -0.5530    0.0955 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3683   -1.8638    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478   -2.0063    1.3555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0631   -0.6725   -1.1189 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7115   -1.9338   -1.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1663    0.3182   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6012    0.7983   -2.2137 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4128    1.5683    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125    1.5993   -0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7871    0.0371    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328    1.1583    2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848    0.3477    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058    2.7632   -0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    1.5290    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707    2.7178    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1283   -0.7758    0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -0.5745    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391   -2.5098   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7110   -1.5569   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.1820   -1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0580    0.1296   -2.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    1.9383   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725   -2.6668    0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -2.0210    1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922   -2.9488    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813   -0.6610   -2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964   -1.8572   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  1
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  2  1  0
 15  4  1  0
 12  6  1  0
 12 14  1  6
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  1
  6 27  1  6
  7 28  1  6
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  6
 19 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Deoxynivalenol	Kegg
DON	Kegg
3-Epi-DON	MeSH
3-Epi-deoxynivalenol	MeSH

Chemical Formula

C₁₅H₂₀O₆

Average Mass

296.3190 Da

Monoisotopic Mass

296.12599 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1=C[C@H]2O[C@@H]3[C@H](O)C[C@](C)([C@@]33CO3)[C@@]2(CO)[C@H](O)C1=O

InChI Identifier

InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3/t8-,9-,11-,12-,13-,14-,15-/m1/s1

InChI Key

LINOMUASTDIRTM-LZTLOYDTSA-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 graminearum	NPAtlas	4767291
Fusarium sambucinum	Fungi	KNApSAcK

Species Where Detected

Species Name	Source	Reference
Fusarium roseum	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	152.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	543.88 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	51750 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-1.250 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	-0.76	ALOGPS
logP	-0.97	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	12.68	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.62 m³·mol⁻¹	ChemAxon
Polarizability	50.56 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

NPAtlas ID

NPA005872

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003201

Chemspider ID

390849

KEGG Compound ID

C09747

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vomitoxin

METLIN ID

Not Available

PubChem Compound

442408

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1680861

References

General References

Vesonder RF, Ciegler A, Jensen AH: Isolation of the emetic principle from Fusarium-infected corn. Appl Microbiol. 1973 Dec;26(6):1008-10. [PubMed:4767291 ]

Showing NP-Card for Vomitoxin (NP0021450)

MOL for NP0021450 (Vomitoxin)

3D MOL for NP0021450 (Vomitoxin)

3D SDF for NP0021450 (Vomitoxin)

3D-SDF for NP0021450 (Vomitoxin)

PDB for NP0021450 (Vomitoxin)

3D PDB for NP0021450 (Vomitoxin)

SMILES for NP0021450 (Vomitoxin)

INCHI for NP0021450 (Vomitoxin)

Structure for NP0021450 (Vomitoxin)

3D Structure for NP0021450 (Vomitoxin)