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Showing NP-Card for Acetyldeoxynivalenol (NP0333978)

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Record Information
Version2.0
Created at2024-09-09 21:31:31 UTC
Updated at2024-09-09 21:31:31 UTC
NP-MRD IDNP0333978
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetyldeoxynivalenol
DescriptionToxin from infected barley. Acetyldeoxynivalenol is found in cereals and cereal products.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333978 (Acetyldeoxynivalenol)


  Mrv2104 05252300032D          

 24 27  0  0  0  0            999 V2000
    4.0536   -0.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446   -1.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2208    1.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6309   -0.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    1.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3036   -0.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222   -0.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8809   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264    0.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4764    0.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690   -0.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037    0.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084   -0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4945    1.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9436   -1.0590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991    1.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967    1.6129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217    0.0659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784   -0.2318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2869   -0.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3 15  1  0  0  0  0
  4  8  2  0  0  0  0
  4 11  1  0  0  0  0
  5 10  1  0  0  0  0
  5 15  1  0  0  0  0
  6 16  1  0  0  0  0
  6 18  1  0  0  0  0
  7 17  1  0  0  0  0
  7 22  1  0  0  0  0
  8 12  1  0  0  0  0
  9 19  2  0  0  0  0
  9 23  1  0  0  0  0
 10 14  1  0  0  0  0
 10 23  1  0  0  0  0
 11 16  1  0  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 20  2  0  0  0  0
 13 16  1  0  0  0  0
 13 21  1  0  0  0  0
 14 17  1  0  0  0  0
 14 24  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
Download

3D MOL for NP0333978 (Acetyldeoxynivalenol)

Download
3D SDF for NP0333978 (Acetyldeoxynivalenol)

  Mrv2104 05252300032D          

 24 27  0  0  0  0            999 V2000
    4.0536   -0.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446   -1.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2208    1.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6309   -0.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    1.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3036   -0.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222   -0.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8809   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264    0.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4764    0.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690   -0.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037    0.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084   -0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4945    1.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9436   -1.0590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991    1.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967    1.6129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217    0.0659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784   -0.2318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2869   -0.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3 15  1  0  0  0  0
  4  8  2  0  0  0  0
  4 11  1  0  0  0  0
  5 10  1  0  0  0  0
  5 15  1  0  0  0  0
  6 16  1  0  0  0  0
  6 18  1  0  0  0  0
  7 17  1  0  0  0  0
  7 22  1  0  0  0  0
  8 12  1  0  0  0  0
  9 19  2  0  0  0  0
  9 23  1  0  0  0  0
 10 14  1  0  0  0  0
 10 23  1  0  0  0  0
 11 16  1  0  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 20  2  0  0  0  0
 13 16  1  0  0  0  0
 13 21  1  0  0  0  0
 14 17  1  0  0  0  0
 14 24  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)C(=O)C(O)C21CO

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

> <INCHI_KEY>
ADFIQZBYNGPCGY-UHFFFAOYNA-N

> <FORMULA>
C17H22O7

> <MOLECULAR_WEIGHT>
338.356

> <EXACT_MASS>
338.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.56223705093681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.5275714799999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.000602125233748

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.770683306761702

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8416553622596945

> <JCHEM_POLAR_SURFACE_AREA>
105.59

> <JCHEM_REFRACTIVITY>
80.7721

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333978 (Acetyldeoxynivalenol)
Download
PDB for NP0333978 (Acetyldeoxynivalenol)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0       7.567  -1.131   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.203  -3.088   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.279   3.164   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.911  -1.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.616   1.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.338   2.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.865  -1.321   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.167  -0.489   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.095  -1.833   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.080  -0.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.511  -0.739   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.023   1.044   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.623   1.686   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.875  -1.607   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.078   1.637   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.367   0.794   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.882  -0.135   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.656   3.129   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.628  -1.977   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.278   1.935   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.407   3.011   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.401   0.123   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.453  -0.433   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.402  -1.808   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4    8   11                                                       
CONECT    5   10   15                                                       
CONECT    6   16   18                                                       
CONECT    7   17   22                                                       
CONECT    8    1    4   12                                                  
CONECT    9    2   19   23                                                  
CONECT   10    5   14   23                                                  
CONECT   11    4   16   24                                                  
CONECT   12    8   13   20                                                  
CONECT   13   12   16   21                                                  
CONECT   14   10   17   24                                                  
CONECT   15    3    5   16   17                                             
CONECT   16    6   11   13   15                                             
CONECT   17    7   14   15   22                                             
CONECT   18    6                                                            
CONECT   19    9                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22    7   17                                                       
CONECT   23    9   10                                                       
CONECT   24   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

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3D PDB for NP0333978 (Acetyldeoxynivalenol)
Download
SMILES for NP0333978 (Acetyldeoxynivalenol)
CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)C(=O)C(O)C21CO
Download
INCHI for NP0333978 (Acetyldeoxynivalenol)
InChI=1/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC17H22O7
Average Mass338.3560 Da
Monoisotopic Mass338.13655 Da
IUPAC Name3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate
Traditional Name3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)C(=O)C(O)C21CO
InChI Identifier
InChI=1/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3
InChI KeyADFIQZBYNGPCGY-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentTrichothecenes  
Alternative Parents
Substituents
  • Trichothecene skeleton
    • 

  • Oxepane
    • 

  • Cyclohexenone
    • 

  • Oxane
    • 

  • Carboxylic acid ester
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Cyclic ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Carbonyl group
    • 

  • Primary alcohol
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.53ChemAxon
pKa (Strongest Acidic)12.77ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.59 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity80.77 m³·mol⁻¹ChemAxon
Polarizability33.56 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ji X, He Y, Xiao Y, Liang Y, Yang W, Xiong L, Guo C, Zhang J, Wang X, Yang H: Distribution and safety evaluation of deoxynivalenol and its derivatives throughout the wheat product processing chain. Food Res Int. 2024 Sep;192:114784. doi: 10.1016/j.foodres.2024.114784. Epub 2024  Jul 17. [PubMed:39147488  ] 
  2. Ma Z, He Y, Li Y, Wang Q, Fang M, Yang Q, Gong Z, Xu L: Effects of Deoxynivalenol and Its Acetylated Derivatives on Lipid Metabolism in Human Normal Hepatocytes. Toxins (Basel). 2024 Jun 26;16(7):294. doi: 10.3390/toxins16070294. [PubMed:39057934  ] 
  3. Yulfo-Soto G, McCormick S, Chen H, Bai G, Trick HN, Hao G: Reduction of Fusarium head blight and trichothecene contamination in transgenic wheat expressing Fusarium graminearum trichothecene 3-O-acetyltransferase. Front Plant Sci. 2024 Apr 8;15:1389605. doi: 10.3389/fpls.2024.1389605.  eCollection 2024. [PubMed:38650698  ] 
  4. Cervini C, Naz N, Verheecke-Vaessen C, Medina A: Impact of predicted climate change environmental conditions on the growth of Fusarium asiaticum strains and mycotoxins production on a wheat-based matrix. Int J Food Microbiol. 2024 May 2;416:110658. doi:  10.1016/j.ijfoodmicro.2024.110658. Epub 2024 Mar 7. [PubMed:38484608  ] 
  5. Odukoya JO, De Saeger S, De Boevre M, Adegoke GO, Devlieghere F, Croubels S, Antonissen G, Odukoya JO, Njobeh PB: Influence of traditional dehulling on mycotoxin reduction and GC-HRTOF-MS metabolites profile of fermented maize products. Heliyon. 2023 Dec 7;10(1):e23025. doi: 10.1016/j.heliyon.2023.e23025. eCollection  2024 Jan 15. [PubMed:38205294  ]