NP-MRD: Showing NP-Card for (1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one (NP0231842)

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Record Information

Version

2.0

Created at

2022-09-06 12:52:10 UTC

Updated at

2022-09-06 12:52:10 UTC

NP-MRD ID

NP0231842

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one

Description

Vomitoxin, also known as deoxynivalenol or 3-epi-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. (1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one is found in Fusarium culmorum and Fusarium graminearum. (1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one was first documented in 2021 (PMID: 34437383). Based on a literature review a small amount of articles have been published on Vomitoxin (PMID: 35998355) (PMID: 35324714) (PMID: 35307023) (PMID: 33890134).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    4.4016   -0.5368   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9107   -0.4048   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0696   -0.8081   -1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -0.6993   -0.8682 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1520   -1.8299   -0.2230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1679   -1.8348    0.1334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0130   -1.4566   -1.0963 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5729   -2.0573   -2.2414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796    0.0547   -1.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763    0.4899    0.1663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8289    1.7908    0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5688   -0.6939    1.0228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9276   -0.8894    1.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350   -0.7208    2.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261    0.5200   -0.0178 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7248    1.7905   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138    2.0210   -1.8811 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003    0.2750    1.3182 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6255    1.2393    2.2596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3600    0.1703    1.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157    0.5821    2.0514 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180   -0.6658   -1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035   -1.4718    0.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417    0.2997    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5119   -1.2401   -1.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2027   -0.5816   -1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4367   -2.8187    0.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561   -1.7867   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219   -2.7759   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    0.4557   -1.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5307    0.4785   -2.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7938    1.7208    1.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1602    2.3767    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0008    2.4285   -0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6438   -0.0888    1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -1.9203    1.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8416    1.8063   -0.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4300    2.6215    0.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2999    2.8583   -1.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5268   -0.7125    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216    2.0143    2.1664 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  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  6
 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  1
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  6
  6 27  1  1
  7 28  1  1
  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  1
 19 41  1  0
M  END


  Mrv1652309062214522D          

 21 24  0  0  1  0            999 V2000
    5.6625    1.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900    1.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    1.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286    1.9488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050    1.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300    1.2251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8162    1.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8612    0.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245    0.1202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6736   -0.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423    0.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5721    0.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409    1.1407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451    0.5218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2710   -0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455   -0.7749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9823   -0.0023    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3511   -0.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    0.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3919   -0.2367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  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
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
  4 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  1  0  0  0
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0231842

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2OC3[C@H](O)C[C@@](C)(C33CO3)[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-GPBIUMILSA-N

> <FORMULA>
C15H20O6

> <MOLECULAR_WEIGHT>
296.319

> <EXACT_MASS>
296.125988364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.32794622041883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2'R,3'S,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_LOGP>
-0.9686968903333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.057467154231482

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.679137950165813

> <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

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2'R,3'S,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

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      10.570   2.596   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.128   2.056   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.939   3.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.497   2.493   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.467   3.638   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.929   3.546   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.043   2.287   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.524   2.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.474   0.809   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.899   0.224   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.991  -1.313   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.999   1.764   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.935   0.651   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.503   2.129   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.244   0.974   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.106  -0.560   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.365  -1.447   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.434  -0.004   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.122  -1.382   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.875   0.536   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.065  -0.442   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   15                                             
CONECT   11   10                                                            
CONECT   12   10    6   13   14                                             
CONECT   13   12   14                                                       
CONECT   14   13   12                                                       
CONECT   15   10    4   16   18                                             
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₅H₂₀O₆

Average Mass

296.3190 Da

Monoisotopic Mass

296.12599 Da

IUPAC Name

(1'R,2'R,3'S,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'R,2'R,3'S,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=CC2OC3[C@H](O)C[C@@](C)(C33CO3)[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-GPBIUMILSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusarium culmorum	LOTUS Database	35616633
Fusarium graminearum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.97	ChemAxon
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	29.33 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

C00003201

Chemspider ID

23550500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vomitoxin

METLIN ID

Not Available

PubChem Compound

44715213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shi D, Cui C, Wang S, Wang X, Gao N, Guan H, Zeng L, Zhang X, Zhao J: Tetrazole-Containing Triphenylamine-Based MOF as a Sensitive Sensor for Food Inspection. Inorg Chem. 2022 Sep 5;61(35):13768-13774. doi: 10.1021/acs.inorgchem.2c01456. Epub 2022 Aug 23. [PubMed:35998355 ]
Evans NM, Shao S: Mycotoxin Metabolism by Edible Insects. Toxins (Basel). 2022 Mar 17;14(3):217. doi: 10.3390/toxins14030217. [PubMed:35324714 ]
Ruckner A, Plagge L, Heenemann K, Harzer M, Thaa B, Winkler J, Danicke S, Kauffold J, Vahlenkamp TW: The mycotoxin deoxynivalenol (DON) can deteriorate vaccination efficacy against porcine reproductive and respiratory syndrome virus (PRRSV) at subtoxic levels. Porcine Health Manag. 2022 Mar 20;8(1):13. doi: 10.1186/s40813-022-00254-1. [PubMed:35307023 ]
Yue J, Guo D, Gao X, Wang J, Nepovimova E, Wu W, Kuca K: Deoxynivalenol (Vomitoxin)-Induced Anorexia Is Induced by the Release of Intestinal Hormones in Mice. Toxins (Basel). 2021 Jul 22;13(8):512. doi: 10.3390/toxins13080512. [PubMed:34437383 ]
Del Favero G, Janker L, Neuditschko B, Hohenbichler J, Kiss E, Woelflingseder L, Gerner C, Marko D: Exploring the dermotoxicity of the mycotoxin deoxynivalenol: combined morphologic and proteomic profiling of human epidermal cells reveals alteration of lipid biosynthesis machinery and membrane structural integrity relevant for skin barrier function. Arch Toxicol. 2021 Jun;95(6):2201-2221. doi: 10.1007/s00204-021-03042-y. Epub 2021 Apr 23. [PubMed:33890134 ]
LOTUS database [Link]

Showing NP-Card for (1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one (NP0231842)

MOL for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)

3D MOL for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)

3D SDF for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)

3D-SDF for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)

PDB for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)

3D PDB for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)

SMILES for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)

INCHI for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)

Structure for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)

3D Structure for NP0231842 ((1'r,2'r,3's,10'r)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-one)