NP-MRD: Showing NP-Card for Acetyl-T2 Toxin (NP0084642)

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Record Information

Version

2.0

Created at

2022-04-29 05:19:27 UTC

Updated at

2022-04-29 05:19:27 UTC

NP-MRD ID

NP0084642

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acetyl-T2 Toxin

Description

Acetyl T-2 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. Acetyl-T2 Toxin is found in Fusarium graminearum, Fusarium poae and Fusarium sporotrichioides. Acetyl-T2 Toxin was first documented in 2002 (PMID: 12236496). Based on a literature review a small amount of articles have been published on Acetyl T-2 (PMID: 32016569) (PMID: 23042183).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207192D          

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M  END

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 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 12 23  1  1  0  0  0
 12 24  1  0  0  0  0
  4 24  1  0  0  0  0
  6 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 33 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084642

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O10/c1-13(2)8-20(30)35-18-10-25(11-31-15(4)27)19(9-14(18)3)36-23-21(33-16(5)28)22(34-17(6)29)24(25,7)26(23)12-32-26/h9,13,18-19,21-23H,8,10-12H2,1-7H3/t18-,19+,21+,22+,23+,24+,25+,26-/m0/s1

> <INCHI_KEY>
NOTOVTQRFFVBSB-VZPCOZJFSA-N

> <FORMULA>
C26H36O10

> <MOLECULAR_WEIGHT>
508.564

> <EXACT_MASS>
508.230847359

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.548531811661135

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-10',11'-bis(acetyloxy)-2'-[(acetyloxy)methyl]-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-methylbutanoate

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
1.4605629673333345

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9304723956594096

> <JCHEM_POLAR_SURFACE_AREA>
126.96000000000001

> <JCHEM_REFRACTIVITY>
122.69469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-10',11'-bis(acetyloxy)-2'-[(acetyloxy)methyl]-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      10.570   0.433   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.128   0.974   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.939  -0.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.497   0.536   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       5.019   0.968   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       6.244   2.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.899   2.805   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.991   4.343   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.999   1.266   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.503   0.900   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.935   2.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.929  -0.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.043   0.743   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.524   0.490   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.983  -0.952   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.536  -1.204   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.961  -2.141   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.474   2.221   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.330   3.251   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.865   2.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.545   1.269   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.280   3.805   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       3.180  -1.862   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0       5.467  -0.608   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.106   3.589   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.365   4.476   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.227   6.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.829   6.657   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.486   6.897   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.434   3.034   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.875   2.493   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.065   3.471   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.507   2.931   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.696   3.909   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.138   3.368   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.327   4.346   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.391   1.849   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.759   1.411   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   24                                             
CONECT    5    4                                                            
CONECT    6    4    7   25   30                                             
CONECT    7    6    8    9   18                                             
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9   11                                                       
CONECT   11   10    9                                                       
CONECT   12    9   13   23   24                                             
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   12                                                            
CONECT   24   12    4                                                       
CONECT   25    6   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    6   31                                                       
CONECT   31   30    2   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
3-Acetyl T-2 toxin	MeSH

Chemical Formula

C₂₆H₃₆O₁₀

Average Mass

508.5640 Da

Monoisotopic Mass

508.23085 Da

IUPAC Name

(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-10',11'-bis(acetyloxy)-2'-[(acetyloxy)methyl]-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-methylbutanoate

Traditional Name

(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-10',11'-bis(acetyloxy)-2'-[(acetyloxy)methyl]-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H36O10/c1-13(2)8-20(30)35-18-10-25(11-31-15(4)27)19(9-14(18)3)36-23-21(33-16(5)28)22(34-17(6)29)24(25,7)26(23)12-32-26/h9,13,18-19,21-23H,8,10-12H2,1-7H3/t18-,19+,21+,22+,23+,24+,25+,26-/m0/s1

InChI Key

NOTOVTQRFFVBSB-VZPCOZJFSA-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	Fungi	KNApSAcK
Fusarium poae	Fungi	KNApSAcK
Fusarium sporotrichioides	Fungi	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Tetracarboxylic acid or derivatives
Fatty acid ester
Oxepane
Oxane
Fatty acyl
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.51	ALOGPS
logP	1.46	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	126.96 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	122.69 m³·mol⁻¹	ChemAxon
Polarizability	52.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054164

Chemspider ID

10216228

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49796734

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abreu DCP, da Silva Oliveira FA, Vargas EA, Madureira FD, Magalhaes EJ, da Silva LP, Saczk AA: Methodology development based on "dilute and shoot" and QuEChERS for determination of multiple mycotoxins in cocoa by LC-MS/MS. Anal Bioanal Chem. 2020 Mar;412(8):1757-1767. doi: 10.1007/s00216-020-02390-5. Epub 2020 Feb 3. [PubMed:32016569 ]
McCormick SP, Price NP, Kurtzman CP: Glucosylation and other biotransformations of T-2 toxin by yeasts of the trichomonascus clade. Appl Environ Microbiol. 2012 Dec;78(24):8694-702. doi: 10.1128/AEM.02391-12. Epub 2012 Oct 5. [PubMed:23042183 ]
Razzazi-Fazeli E, Rabus B, Cecon B, Bohm J: Simultaneous quantification of A-trichothecene mycotoxins in grains using liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2002 Aug 30;968(1-2):129-42. doi: 10.1016/s0021-9673(02)00957-3. [PubMed:12236496 ]

Showing NP-Card for Acetyl-T2 Toxin (NP0084642)

MOL for NP0084642 (Acetyl-T2 Toxin)

3D MOL for NP0084642 (Acetyl-T2 Toxin)

3D SDF for NP0084642 (Acetyl-T2 Toxin)

3D-SDF for NP0084642 (Acetyl-T2 Toxin)

PDB for NP0084642 (Acetyl-T2 Toxin)

3D PDB for NP0084642 (Acetyl-T2 Toxin)

SMILES for NP0084642 (Acetyl-T2 Toxin)

INCHI for NP0084642 (Acetyl-T2 Toxin)

Structure for NP0084642 (Acetyl-T2 Toxin)

3D Structure for NP0084642 (Acetyl-T2 Toxin)