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Showing NP-Card for Deoxynivalenol 3-glucoside (NP0337719)

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Record Information
Version2.0
Created at2024-09-11 12:05:12 UTC
Updated at2024-09-11 12:05:12 UTC
NP-MRD IDNP0337719
Secondary Accession NumbersNone
Natural Product Identification
Common NameDeoxynivalenol 3-glucoside
DescriptionDeoxynivalenol 3-glucoside 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. Based on a literature review very few articles have been published on Deoxynivalenol 3-glucoside.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337719 (Deoxynivalenol 3-glucoside)


  Mrv2104 05262314372D          

 32 36  0  0  0  0            999 V2000
   -3.5243    1.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243    0.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    0.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    1.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    2.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    0.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    1.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    2.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384    2.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384    0.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101   -0.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0352   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    0.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2580    0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548    0.9335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4757    1.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835   -0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847   -0.6074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0589    0.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8499   -0.2112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4373   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2326   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4418    0.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8556    0.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0675    1.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2384    0.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -1.1550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2281   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8158   -2.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  2  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 31  1  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
 27 28  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
Download

3D MOL for NP0337719 (Deoxynivalenol 3-glucoside)

Download
3D SDF for NP0337719 (Deoxynivalenol 3-glucoside)

  Mrv2104 05262314372D          

 32 36  0  0  0  0            999 V2000
   -3.5243    1.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243    0.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    0.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    1.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    2.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    0.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    1.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    2.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384    2.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384    0.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101   -0.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0352   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    0.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2580    0.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548    0.9335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4757    1.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835   -0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847   -0.6074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0589    0.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8499   -0.2112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4373   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2326   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4418    0.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8556    0.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0675    1.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2384    0.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -1.1550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2281   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8158   -2.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  2  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 31  1  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
 27 28  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337719

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2OC3C(CC(C)(C33CO3)C2(CO)C(O)C1=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C21H30O11/c1-8-3-11-20(6-23,16(28)12(8)24)19(2)4-9(17(32-11)21(19)7-29-21)30-18-15(27)14(26)13(25)10(5-22)31-18/h3,9-11,13-18,22-23,25-28H,4-7H2,1-2H3

> <INCHI_KEY>
PUMXWMGECQIOGB-UHFFFAOYNA-N

> <FORMULA>
C21H30O11

> <MOLECULAR_WEIGHT>
458.46

> <EXACT_MASS>
458.178811786

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.68157699546582

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-10'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-one

> <JCHEM_LOGP>
-2.7395325359999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.73839330464673

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.104842069693778

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8416551967185324

> <JCHEM_POLAR_SURFACE_AREA>
178.67

> <JCHEM_REFRACTIVITY>
104.03389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-10'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0337719 (Deoxynivalenol 3-glucoside)
Download
PDB for NP0337719 (Deoxynivalenol 3-glucoside)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -6.579   3.284   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.579   1.743   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.245   0.972   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.915   1.743   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.915   3.284   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.245   4.051   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.583   0.972   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.252   1.743   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.252   3.284   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.583   4.051   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -7.912   4.051   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.912   0.972   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.245  -0.569   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.915   0.202   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.066  -0.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.265   1.794   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.482   0.407   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.289   1.743   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.755   2.187   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.583  -0.569   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.145  -1.134   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.843   1.098   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.453  -0.394   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.550  -1.478   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.034  -1.072   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.425   0.415   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.330   1.496   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.726   2.986   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.912   0.821   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.128  -2.156   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.159  -2.968   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.256  -4.051   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5    7   14                                             
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   15   20                                             
CONECT    8    7    9   17   18                                             
CONECT    9    8   10   16                                                  
CONECT   10    5    9                                                       
CONECT   11    1                                                            
CONECT   12    2                                                            
CONECT   13    3                                                            
CONECT   14    4   21                                                       
CONECT   15    7   16                                                       
CONECT   16    9   15   19                                                  
CONECT   17    8   18                                                       
CONECT   18    8   17                                                       
CONECT   19   16   22                                                       
CONECT   20    7                                                            
CONECT   21   14                                                            
CONECT   22   19   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27   29                                                  
CONECT   27   22   26   28                                                  
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30   25                                                            
CONECT   31   24   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

Download
3D PDB for NP0337719 (Deoxynivalenol 3-glucoside)
Download
SMILES for NP0337719 (Deoxynivalenol 3-glucoside)
CC1=CC2OC3C(CC(C)(C33CO3)C2(CO)C(O)C1=O)OC1OC(CO)C(O)C(O)C1O
Download
INCHI for NP0337719 (Deoxynivalenol 3-glucoside)
InChI=1/C21H30O11/c1-8-3-11-20(6-23,16(28)12(8)24)19(2)4-9(17(32-11)21(19)7-29-21)30-18-15(27)14(26)13(25)10(5-22)31-18/h3,9-11,13-18,22-23,25-28H,4-7H2,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC21H30O11
Average Mass458.4600 Da
Monoisotopic Mass458.17881 Da
IUPAC Name3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-10'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-one
Traditional Name3'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-10'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-one
CAS Registry NumberNot Available
SMILES
CC1=CC2OC3C(CC(C)(C33CO3)C2(CO)C(O)C1=O)OC1OC(CO)C(O)C(O)C1O
InChI Identifier
InChI=1/C21H30O11/c1-8-3-11-20(6-23,16(28)12(8)24)19(2)4-9(17(32-11)21(19)7-29-21)30-18-15(27)14(26)13(25)10(5-22)31-18/h3,9-11,13-18,22-23,25-28H,4-7H2,1-2H3
InChI KeyPUMXWMGECQIOGB-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
    • 

  • Hexose monosaccharide
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Cyclohexenone
    • 

  • Oxepane
    • 

  • Monosaccharide
    • 

  • Oxane
    • 

  • Ketone
    • 

  • Cyclic ketone
    • 

  • Secondary alcohol
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Polyol
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Primary alcohol
    • 

  • 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-2.7ChemAxon
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area178.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.03 m³·mol⁻¹ChemAxon
Polarizability44.68 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
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