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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 16:31:39 UTC

Update Date

2021-10-13 04:43:34 UTC

HMDB ID

HMDB0004304

Secondary Accession Numbers

HMDB04304

Metabolite Identification

Common Name

Nivalenol

Description

Nivalenol is a trichothecene produced by Fusaria, Stachybotrys, Trichoderma and other fungi, and some higher plants. They may contaminate food or feed grains, induce emesis and hemorrhage in lungs and brain, and damage bone marrow due to protein and DNA synthesis inhibition.(PubChem). It has been reported in the urine of patients suffering chronic idiopathic spastic paraparesis. These patients are usually found in hot and humid regions, most of which have heavy rains, and these conditions allow foods to be polluted by fungi some of which become toxigenic (PubMed ID 8855894 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0004304
     RDKit          3D
Nivalenol
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.5054    0.4841   -0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0283    0.2658   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581    1.2474   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6971    1.0114   -0.3244 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2393    0.8808   -1.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    0.5979   -1.7762 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9745    1.5030   -0.9082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5734    2.8056   -0.9139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9176    0.8340    0.4483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2593    0.4502    0.7244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1120   -0.4356    0.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6899   -1.5510    1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095   -0.7118   -1.1574 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7406   -1.3220   -1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297   -1.8980   -1.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659   -0.2441    0.4992 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7716    0.0330    1.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544    1.1093    2.5194 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1090   -1.4305   -0.0787 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0753   -2.5555    0.6673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5452   -1.0862   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302   -2.0491   -0.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8172    0.1266   -1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665    1.5560   -0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -0.1433    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5728    2.2623   -0.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457    1.8567    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    0.6872   -2.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9764    1.4486   -1.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958    3.4656   -0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6428    1.4949    1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8988    0.9444    0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763   -2.5112    0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7669   -1.3210    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -1.7041    2.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3102   -0.9019   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462   -1.7615   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8748    0.2879    1.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864   -0.8392    2.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6484    1.3188    3.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719   -1.6459   -1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5761   -2.5597    1.5067 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
  9 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 11 16  1  0
 16 17  1  1
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21  2  1  0
 16  4  1  0
 13  6  1  0
 13 15  1  6
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  1
  6 28  1  6
  7 29  1  6
  8 30  1  0
  9 31  1  1
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  6
 20 42  1  0
M  END

  Mrv0541 02231219552D          

 24 27  0  0  1  0            999 V2000
   25.4722  -11.0285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.7604  -11.4428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.4759  -10.2035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.6144  -11.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8548  -10.4757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0442  -11.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.3043  -11.4356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.7533  -12.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7640   -9.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2971  -10.2035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.0478  -10.2000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.3282  -11.4392    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.2475  -11.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0131  -11.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0061   -9.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3282   -9.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6084  -11.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8917  -12.0752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0370  -12.6061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6084  -10.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8958  -11.4320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8958   -9.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4687   -9.3824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.0422   -9.3379    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  6  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  1  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  6  0  0  0
  7 14  1  1  0  0  0
 10 15  1  6  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  6  0  0  0
 13 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 21  2  0  0  0  0
 20 22  1  0  0  0  0
  4  5  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 17 20  1  0  0  0  0
  3 23  1  1  0  0  0
 11 24  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0004304

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O7/c1-6-3-7-14(4-16,11(20)8(6)17)13(2)10(19)9(18)12(22-7)15(13)5-21-15/h3,7,9-12,16,18-20H,4-5H2,1-2H3/t7-,9-,10-,11-,12-,13-,14-,15-/m1/s1

> <INCHI_KEY>
UKOTXHQERFPCBU-YQPARWETSA-N

> <FORMULA>
C15H20O7

> <MOLECULAR_WEIGHT>
312.3151

> <EXACT_MASS>
312.120902994

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
30.13974975121178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2R,2'R,3'S,7'R,9'R,10'R,11'S)-3',10',11'-trihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-1.8876930373333338

> <ALOGPS_LOGS>
-0.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.123225225237078

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.232938883651498

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8436561041865334

> <JCHEM_POLAR_SURFACE_AREA>
119.75

> <JCHEM_REFRACTIVITY>
72.82809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nivalenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004304
     RDKit          3D
Nivalenol
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.5054    0.4841   -0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0283    0.2658   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581    1.2474   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6971    1.0114   -0.3244 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2393    0.8808   -1.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    0.5979   -1.7762 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9745    1.5030   -0.9082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5734    2.8056   -0.9139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9176    0.8340    0.4483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2593    0.4502    0.7244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1120   -0.4356    0.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6899   -1.5510    1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095   -0.7118   -1.1574 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7406   -1.3220   -1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297   -1.8980   -1.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659   -0.2441    0.4992 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7716    0.0330    1.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544    1.1093    2.5194 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1090   -1.4305   -0.0787 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0753   -2.5555    0.6673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5452   -1.0862   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302   -2.0491   -0.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8172    0.1266   -1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665    1.5560   -0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -0.1433    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5728    2.2623   -0.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457    1.8567    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    0.6872   -2.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9764    1.4486   -1.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958    3.4656   -0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6428    1.4949    1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8988    0.9444    0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763   -2.5112    0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7669   -1.3210    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -1.7041    2.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3102   -0.9019   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462   -1.7615   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8748    0.2879    1.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864   -0.8392    2.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6484    1.3188    3.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719   -1.6459   -1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5761   -2.5597    1.5067 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
  9 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 11 16  1  0
 16 17  1  1
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21  2  1  0
 16  4  1  0
 13  6  1  0
 13 15  1  6
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  1
  6 28  1  6
  7 29  1  6
  8 30  1  0
  9 31  1  1
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  6
 20 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      47.548 -20.587   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      46.219 -21.360   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      47.555 -19.047   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      45.947 -20.579   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      46.396 -19.555   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      44.883 -20.580   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.101 -21.346   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      46.206 -22.893   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      46.226 -18.280   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      49.088 -19.047   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      44.889 -19.040   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      43.546 -21.353   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      45.262 -22.053   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      50.424 -22.120   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      50.411 -18.274   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      43.546 -18.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.202 -20.580   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      42.731 -22.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      44.869 -23.531   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      42.202 -19.040   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      40.872 -21.340   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      40.872 -18.274   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      47.542 -17.514   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      44.879 -17.431   0.000  0.00  0.00           H+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7    8                                             
CONECT    3    1    9   10   23                                             
CONECT    4    1    5                                                       
CONECT    5    1    4                                                       
CONECT    6    2   11   12   13                                             
CONECT    7    2   14   10                                                  
CONECT    8    2                                                            
CONECT    9    3   11                                                       
CONECT   10    3   15    7                                                  
CONECT   11    6   16    9   24                                             
CONECT   12    6   17   18                                                  
CONECT   13    6   19                                                       
CONECT   14    7                                                            
CONECT   15   10                                                            
CONECT   16   11   20                                                       
CONECT   17   12   21   20                                                  
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   16   22   17                                                  
CONECT   21   17                                                            
CONECT   22   20                                                            
CONECT   23    3                                                            
CONECT   24   11                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0004304
HETATM    1  C1  UNL     1       4.505   0.484  -0.457  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.028   0.266  -0.395  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.158   1.247  -0.386  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.697   1.011  -0.324  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.239   0.881  -1.625  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.086   0.598  -1.776  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.974   1.503  -0.908  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.573   2.806  -0.914  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.918   0.834   0.448  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.259   0.450   0.724  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.112  -0.436   0.299  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.690  -1.551   1.115  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.409  -0.712  -1.157  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.741  -1.322  -1.444  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.530  -1.898  -1.742  1.00  0.00           O  
HETATM   16  C12 UNL     1       0.366  -0.244   0.499  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.772   0.033   1.909  1.00  0.00           C  
HETATM   18  O5  UNL     1       0.154   1.109   2.519  1.00  0.00           O  
HETATM   19  C14 UNL     1       1.109  -1.431  -0.079  1.00  0.00           C  
HETATM   20  O6  UNL     1       1.075  -2.556   0.667  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.545  -1.086  -0.343  1.00  0.00           C  
HETATM   22  O7  UNL     1       3.330  -2.049  -0.521  1.00  0.00           O  
HETATM   23  H1  UNL     1       4.817   0.127  -1.474  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.766   1.556  -0.396  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.036  -0.143   0.274  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.573   2.262  -0.427  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.246   1.857   0.196  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.352   0.687  -2.836  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.976   1.449  -1.380  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.296   3.466  -0.871  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.643   1.495   1.250  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.899   0.944   0.187  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.676  -2.511   0.540  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.767  -1.321   1.313  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.217  -1.704   2.085  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.310  -0.902  -2.277  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.346  -1.761  -0.630  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.875   0.288   1.980  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.586  -0.839   2.586  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.648   1.319   3.333  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.672  -1.646  -1.071  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.576  -2.560   1.507  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   21
CONECT    3    4   26
CONECT    4    5   16   27
CONECT    5    6
CONECT    6    7   13   28
CONECT    7    8    9   29
CONECT    8   30
CONECT    9   10   11   31
CONECT   10   32
CONECT   11   12   13   16
CONECT   12   33   34   35
CONECT   13   14   15
CONECT   14   15   36   37
CONECT   16   17   19
CONECT   17   18   38   39
CONECT   18   40
CONECT   19   20   21   41
CONECT   20   42
CONECT   21   22   22
END

HMDB0004304
     RDKit          3D
Nivalenol
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.5054    0.4841   -0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0283    0.2658   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581    1.2474   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6971    1.0114   -0.3244 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2393    0.8808   -1.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859    0.5979   -1.7762 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9745    1.5030   -0.9082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5734    2.8056   -0.9139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9176    0.8340    0.4483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2593    0.4502    0.7244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1120   -0.4356    0.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6899   -1.5510    1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095   -0.7118   -1.1574 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7406   -1.3220   -1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297   -1.8980   -1.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659   -0.2441    0.4992 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7716    0.0330    1.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544    1.1093    2.5194 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1090   -1.4305   -0.0787 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0753   -2.5555    0.6673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5452   -1.0862   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302   -2.0491   -0.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8172    0.1266   -1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665    1.5560   -0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -0.1433    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5728    2.2623   -0.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457    1.8567    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    0.6872   -2.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9764    1.4486   -1.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958    3.4656   -0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6428    1.4949    1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8988    0.9444    0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763   -2.5112    0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7669   -1.3210    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -1.7041    2.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3102   -0.9019   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462   -1.7615   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8748    0.2879    1.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864   -0.8392    2.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6484    1.3188    3.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719   -1.6459   -1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5761   -2.5597    1.5067 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
  9 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 11 16  1  0
 16 17  1  1
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21  2  1  0
 16  4  1  0
 13  6  1  0
 13 15  1  6
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  1
  6 28  1  6
  7 29  1  6
  8 30  1  0
  9 31  1  1
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  6
 20 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₇

Average Molecular Weight

312.3151

Monoisotopic Molecular Weight

312.120902994

IUPAC Name

(1'S,2R,2'R,3'S,7'R,9'R,10'R,11'S)-3',10',11'-trihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one

Traditional Name

nivalenol

CAS Registry Number

23282-20-4

SMILES

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

InChI Identifier

InChI=1S/C15H20O7/c1-6-3-7-14(4-16,11(20)8(6)17)13(2)10(19)9(18)12(22-7)15(13)5-21-15/h3,7,9-12,16,18-20H,4-5H2,1-2H3/t7-,9-,10-,11-,12-,13-,14-,15-/m1/s1

InChI Key

UKOTXHQERFPCBU-YQPARWETSA-N

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
Ketone
Secondary alcohol
Cyclic ketone
Dialkyl ether
Oxirane
Ether
Oxacycle
Polyol
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

trichothecene (CHEBI:7599 )
Trichothecenes (C06080 )

Ontology

Not Available

Kidney (HMDB: HMDB0004304)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004304)

Source

Endogenous

Endogenous (HMDB: HMDB0004304)

Animal

Animal (HMDB: HMDB0004304)

Exogenous

Food

Food (HMDB: HMDB0004304)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0004304)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0004304)

Lipid metabolism pathway (HMDB: HMDB0004304)

Cellular process

Cell signaling (HMDB: HMDB0004304)

Biochemical process

Lipid transport (HMDB: HMDB0004304)

Role

Biological role

Energy source (HMDB: HMDB0004304)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	222 °C	Not Available
Boiling Point	585.09 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	858900 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-1.558 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	64.6 g/L	ALOGPS
logP	-0.79	ALOGPS
logP	-1.9	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	12.23	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.83 m³·mol⁻¹	ChemAxon
Polarizability	30.14 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.045	31661259
DarkChem	[M-H]-	168.725	31661259
DeepCCS	[M-2H]-	202.926	30932474
DeepCCS	[M+Na]+	177.957	30932474
AllCCS	[M+H]+	171.2	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	174.2	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	174.7	32859911
AllCCS	[M+Na-2H]-	174.3	32859911
AllCCS	[M+HCOO]-	173.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nivalenol	[H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)([C@H](O)[C@H]1O)[C@@]21CO1	3898.6	Standard polar	33892256
Nivalenol	[H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)([C@H](O)[C@H]1O)[C@@]21CO1	2463.1	Standard non polar	33892256
Nivalenol	[H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)([C@H](O)[C@H]1O)[C@@]21CO1	2450.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nivalenol,1TMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO)[C@H](O[Si](C)(C)C)C1=O)[C@@]31CO1	2570.8	Semi standard non polar	33892256
Nivalenol,1TMS,isomer #2	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@@](C)([C@@]34CO4)[C@@]2(CO[Si](C)(C)C)[C@H](O)C1=O	2538.2	Semi standard non polar	33892256
Nivalenol,1TMS,isomer #3	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C)[C@@](C)([C@@]34CO4)[C@@]2(CO)[C@H](O)C1=O	2561.0	Semi standard non polar	33892256
Nivalenol,1TMS,isomer #4	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O)[C@@](C)([C@@]34CO4)[C@@]2(CO)[C@H](O)C1=O	2575.4	Semi standard non polar	33892256
Nivalenol,1TMS,isomer #5	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO)C(O)=C1O[Si](C)(C)C)[C@@]31CO1	2561.4	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO)[C@H](O[Si](C)(C)C)C1=O)[C@@]31CO1	2580.3	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #10	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO)C(O)=C1O[Si](C)(C)C)[C@@]31CO1	2569.9	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #2	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO)[C@H](O[Si](C)(C)C)C1=O)[C@@]31CO1	2568.9	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #3	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1=O)[C@@]31CO1	2547.2	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #4	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2514.9	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #5	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O)[C@@](C)([C@@]34CO4)[C@@]2(CO[Si](C)(C)C)[C@H](O)C1=O	2559.1	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #6	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C)[C@@](C)([C@@]34CO4)[C@@]2(CO[Si](C)(C)C)[C@H](O)C1=O	2547.1	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #7	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O)=C1O[Si](C)(C)C)[C@@]31CO1	2545.3	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #8	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@](C)([C@@]34CO4)[C@@]2(CO)[C@H](O)C1=O	2564.1	Semi standard non polar	33892256
Nivalenol,2TMS,isomer #9	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO)C(O)=C1O[Si](C)(C)C)[C@@]31CO1	2573.7	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO)[C@H](O[Si](C)(C)C)C1=O)[C@@]31CO1	2561.0	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #10	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO)C(O)=C1O[Si](C)(C)C)[C@@]31CO1	2557.4	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #2	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1=O)[C@@]31CO1	2555.0	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #3	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2510.2	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #4	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1=O)[C@@]31CO1	2554.8	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #5	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2513.2	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #6	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2508.4	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #7	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@](C)([C@@]34CO4)[C@@]2(CO[Si](C)(C)C)[C@H](O)C1=O	2523.1	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #8	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O)=C1O[Si](C)(C)C)[C@@]31CO1	2529.4	Semi standard non polar	33892256
Nivalenol,3TMS,isomer #9	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O)=C1O[Si](C)(C)C)[C@@]31CO1	2532.1	Semi standard non polar	33892256
Nivalenol,4TMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1=O)[C@@]31CO1	2535.7	Semi standard non polar	33892256
Nivalenol,4TMS,isomer #2	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2488.8	Semi standard non polar	33892256
Nivalenol,4TMS,isomer #3	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2494.9	Semi standard non polar	33892256
Nivalenol,4TMS,isomer #4	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2496.7	Semi standard non polar	33892256
Nivalenol,4TMS,isomer #5	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O)=C1O[Si](C)(C)C)[C@@]31CO1	2503.4	Semi standard non polar	33892256
Nivalenol,5TMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2488.9	Semi standard non polar	33892256
Nivalenol,5TMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2747.8	Standard non polar	33892256
Nivalenol,5TMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]31CO1	2610.0	Standard polar	33892256
Nivalenol,1TBDMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO)[C@H](O[Si](C)(C)C(C)(C)C)C1=O)[C@@]31CO1	2802.0	Semi standard non polar	33892256
Nivalenol,1TBDMS,isomer #2	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@@](C)([C@@]34CO4)[C@@]2(CO[Si](C)(C)C(C)(C)C)[C@H](O)C1=O	2793.8	Semi standard non polar	33892256
Nivalenol,1TBDMS,isomer #3	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@](C)([C@@]34CO4)[C@@]2(CO)[C@H](O)C1=O	2816.5	Semi standard non polar	33892256
Nivalenol,1TBDMS,isomer #4	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@](C)([C@@]34CO4)[C@@]2(CO)[C@H](O)C1=O	2817.2	Semi standard non polar	33892256
Nivalenol,1TBDMS,isomer #5	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO)C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	2828.1	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO)[C@H](O[Si](C)(C)C(C)(C)C)C1=O)[C@@]31CO1	3049.6	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #10	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO)C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3052.7	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #2	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO)[C@H](O[Si](C)(C)C(C)(C)C)C1=O)[C@@]31CO1	3052.4	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #3	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1=O)[C@@]31CO1	3030.5	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #4	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3016.7	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #5	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@](C)([C@@]34CO4)[C@@]2(CO[Si](C)(C)C(C)(C)C)[C@H](O)C1=O	3042.9	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #6	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@](C)([C@@]34CO4)[C@@]2(CO[Si](C)(C)C(C)(C)C)[C@H](O)C1=O	3048.4	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #7	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3034.5	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #8	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@](C)([C@@]34CO4)[C@@]2(CO)[C@H](O)C1=O	3049.4	Semi standard non polar	33892256
Nivalenol,2TBDMS,isomer #9	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO)C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3057.6	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO)[C@H](O[Si](C)(C)C(C)(C)C)C1=O)[C@@]31CO1	3247.2	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #10	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO)C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3260.1	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #2	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1=O)[C@@]31CO1	3245.5	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #3	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3222.6	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #4	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1=O)[C@@]31CO1	3249.5	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #5	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3223.4	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #6	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3240.4	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #7	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@](C)([C@@]34CO4)[C@@]2(CO[Si](C)(C)C(C)(C)C)[C@H](O)C1=O	3240.4	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #8	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3254.2	Semi standard non polar	33892256
Nivalenol,3TBDMS,isomer #9	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3260.4	Semi standard non polar	33892256
Nivalenol,4TBDMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1=O)[C@@]31CO1	3456.3	Semi standard non polar	33892256
Nivalenol,4TBDMS,isomer #2	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3386.2	Semi standard non polar	33892256
Nivalenol,4TBDMS,isomer #3	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3421.5	Semi standard non polar	33892256
Nivalenol,4TBDMS,isomer #4	CC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3410.1	Semi standard non polar	33892256
Nivalenol,4TBDMS,isomer #5	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3442.5	Semi standard non polar	33892256
Nivalenol,5TBDMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3530.4	Semi standard non polar	33892256
Nivalenol,5TBDMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3663.9	Standard non polar	33892256
Nivalenol,5TBDMS,isomer #1	CC1=C[C@H]2O[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)([C@@]2(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]31CO1	3099.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kai-6290000000-2911fd296ba057ae09a6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (4 TMS) - 70eV, Positive	splash10-000i-1022190000-2a675063c4f13c2c2f00	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (TBDMS_3_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (TBDMS_3_5) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (TBDMS_3_6) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (TBDMS_4_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (TBDMS_4_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS (TBDMS_4_4) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nivalenol GC-MS ("Nivalenol,2TBDMS,#4" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 10V, Positive-QTOF	splash10-01ot-0095000000-1a5c96aabc3407c96a58	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 20V, Positive-QTOF	splash10-054t-0691000000-27d03079b4a3017e4ae6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 40V, Positive-QTOF	splash10-004i-4690000000-0e33ef132bad47787225	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 10V, Negative-QTOF	splash10-03di-0059000000-ff9e3108776ac7ec47e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 20V, Negative-QTOF	splash10-03ec-0291000000-e9bacc0055cfdbc1ce73	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 40V, Negative-QTOF	splash10-0v0a-7900000000-3fed75622c3dfbbf2ace	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 10V, Negative-QTOF	splash10-03di-0009000000-8c08f5008f04459cecc5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 20V, Negative-QTOF	splash10-03di-0069000000-31d25081330244050f03	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 40V, Negative-QTOF	splash10-001l-4970000000-17c950a72b871800b391	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 10V, Positive-QTOF	splash10-03di-0009000000-77331bab21c19de7c6e5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 20V, Positive-QTOF	splash10-03e9-0097000000-b75a12b7a67f62d1c60b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nivalenol 40V, Positive-QTOF	splash10-0w30-3292000000-d226ebdf00fdf68ba374	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Kidney

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nivalenol

METLIN ID

7047

PubChem Compound

440908

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1669701

References

Synthesis Reference

Konishi, Ryoko; Sakai, Ayako; Takatori, Kosuke; Yamasaki, Hiroyuki; Kurihara, Makoto. Easy preparation of nivalenol from fusarenone X-producing Fusarium. Jpn. Kokai Tokkyo Koho (2007), 8pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Black RM, Clarke RJ, Read RW: Detection of trace levels of trichothecene mycotoxins in human urine by gas chromatography-mass spectrometry. J Chromatogr. 1986 Sep 26;367(1):103-15. [PubMed:3782332 ]
Bretz M, Knecht A, Gockler S, Humpf HU: Structural elucidation and analysis of thermal degradation products of the Fusarium mycotoxin nivalenol. Mol Nutr Food Res. 2005 Apr;49(4):309-16. [PubMed:15744714 ]

Showing metabocard for Nivalenol (HMDB0004304)

MOL for HMDB0004304 (Nivalenol)

3D MOL for HMDB0004304 (Nivalenol)

3D SDF for HMDB0004304 (Nivalenol)

3D-SDF for HMDB0004304 (Nivalenol)

PDB for HMDB0004304 (Nivalenol)

3D PDB for HMDB0004304 (Nivalenol)

SMILES for HMDB0004304 (Nivalenol)

INCHI for HMDB0004304 (Nivalenol)

Structure for HMDB0004304 (Nivalenol)

3D Structure for HMDB0004304 (Nivalenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra