NP-MRD: Showing NP-Card for trichothecolone acetate (NP0228244)

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Record Information

Version

2.0

Created at

2022-09-06 07:49:17 UTC

Updated at

2022-09-06 07:49:17 UTC

NP-MRD ID

NP0228244

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trichothecolone acetate

Description

Trichothecolone acetate 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. trichothecolone acetate was first documented in 2014 (PMID: 24697667). Based on a literature review very few articles have been published on Trichothecolone acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
    5.0520    0.9971    0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6358    0.8224    1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620    1.5048    2.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8624   -0.1054    0.4275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -0.3211    0.7746 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2861   -1.7798    1.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1376   -2.2022    0.1856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0900   -1.8429    0.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094   -0.5086    1.0127 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6378   -0.2164    1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4778    0.2681    0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8962    0.5460    0.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0324    0.5436   -0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799    1.1022   -1.7924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328    0.1274   -1.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431    0.4096   -0.0959 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8195    1.8275    0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6598   -0.0349   -0.4706 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3575    0.9077   -1.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064   -1.4318   -1.0393 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4421   -1.7716   -2.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -1.9810   -1.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7196    1.0731    1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4335    0.1609    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2002    1.9754    0.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2369    0.3508    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1673   -2.3688    0.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0447   -1.9528    2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -3.2823    0.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6542   -0.3289    1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330   -0.4044    2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2622   -0.0863    1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5272    0.4234   -0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9647    1.6053    1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6798   -0.9942   -1.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2808    0.6013   -2.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760    1.9761    1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606    2.4025   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063    2.3150   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003    0.3509   -1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614    1.7052   -0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923    1.3213   -2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016   -1.0113   -3.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967   -2.6927   -2.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 18  5  1  0
 20 22  1  1
 20  7  1  0
 16  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  7 29  1  6
  9 30  1  1
 10 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
M  END


  Mrv1652309062209492D          

 22 25  0  0  1  0            999 V2000
   -1.6160    1.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434    1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716    0.2214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2428    1.2130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298    0.6190    0.0000 C   0  0  2  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
    0.4690   -0.8610    0.0000 C   0  0  1  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
    1.8809   -0.3960    0.0000 C   0  0  2  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
    3.3036   -0.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536   -0.6059    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
    3.8991    1.0368    0.0000 O   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
    1.8037    0.4254    0.0000 C   0  0  1  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
    1.1133    0.8771    0.0000 C   0  0  1  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
    1.0084   -0.0725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8217    0.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.7076    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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0228244

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)C(=O)C[C@]3(C)[C@]1(C)[C@]21CO1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-9-5-12-15(3,7-11(9)19)16(4)13(21-10(2)18)6-14(22-12)17(16)8-20-17/h5,12-14H,6-8H2,1-4H3/t12-,13-,14-,15+,16-,17+/m1/s1

> <INCHI_KEY>
UGISZOXYFHGCSR-IKIFYQGPSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.753333524863677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,2'R,7'R,9'R,11'R)-1',2',5'-trimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl acetate

> <JCHEM_LOGP>
1.2396566713333317

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.612266169521146

> <JCHEM_PKA_STRONGEST_BASIC>
-3.914532120915005

> <JCHEM_POLAR_SURFACE_AREA>
65.13000000000001

> <JCHEM_REFRACTIVITY>
77.7696

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,2'R,7'R,9'R,11'R)-1',2',5'-trimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl acetate

> <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      -3.016   3.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.948   1.893   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.374   0.413   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.453   2.264   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.616   1.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.080  -0.288   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.875  -1.607   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.402  -1.808   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.511  -0.739   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.911  -1.381   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.167  -0.489   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.567  -1.131   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.023   1.044   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.278   1.935   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.623   1.686   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       3.338   2.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.078   1.637   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.279   3.164   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.882  -0.135   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.401   0.123   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.865  -1.321   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17   18                                             
CONECT   17   16                                                            
CONECT   18   16    5   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    7   21   22                                             
CONECT   21   20   22                                                       
CONECT   22   21   20                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
Trichothecolone acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)C(=O)C[C@]3(C)[C@]1(C)[C@]21CO1

InChI Identifier

InChI=1S/C17H22O5/c1-9-5-12-15(3,7-11(9)19)16(4)13(21-10(2)18)6-14(22-12)17(16)8-20-17/h5,12-14H,6-8H2,1-4H3/t12-,13-,14-,15+,16-,17+/m1/s1

InChI Key

UGISZOXYFHGCSR-IKIFYQGPSA-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

Not Available

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
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20147984

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20841657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Surup F, Medjedovic A, Szczygielski M, Schroers HJ, Stadler M: Production of Trichothecenes by the apple sooty blotch fungus Microcyclospora tardicrescens. J Agric Food Chem. 2014 Apr 23;62(16):3525-30. doi: 10.1021/jf500153d. Epub 2014 Apr 14. [PubMed:24697667 ]
LOTUS database [Link]

Showing NP-Card for trichothecolone acetate (NP0228244)

MOL for NP0228244 (trichothecolone acetate)

3D MOL for NP0228244 (trichothecolone acetate)

3D SDF for NP0228244 (trichothecolone acetate)

3D-SDF for NP0228244 (trichothecolone acetate)

PDB for NP0228244 (trichothecolone acetate)

3D PDB for NP0228244 (trichothecolone acetate)

SMILES for NP0228244 (trichothecolone acetate)

INCHI for NP0228244 (trichothecolone acetate)

Structure for NP0228244 (trichothecolone acetate)

3D Structure for NP0228244 (trichothecolone acetate)