NP-MRD: Showing NP-Card for [4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate) (NP0059167)

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Record Information

Version

2.0

Created at

2022-04-28 04:27:14 UTC

Updated at

2022-04-28 04:27:14 UTC

NP-MRD ID

NP0059167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate)

Description

(1'R,2R,2'R,7'R,9'S,11'S)-5'-(hydroxymethyl)-1',2'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-11'-yl (2E,4E,6S,7R)-6,7-dihydroxyocta-2,4-dienoate 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. [4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate) is found in Myrothecium verrucaria. Based on a literature review very few articles have been published on (1'R,2R,2'R,7'R,9'S,11'S)-5'-(hydroxymethyl)-1',2'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-11'-yl (2E,4E,6S,7R)-6,7-dihydroxyocta-2,4-dienoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206272D          

 30 33  0  0  1  0            999 V2000
    3.3584    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6757    1.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.3972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5184    1.4425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    0.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3319    1.4409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    0.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715   -0.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9561    0.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5693   -0.5116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3979   -1.3186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -0.2565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9670   -0.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5252    0.5505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
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 28 29  1  0  0  0  0
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  2 30  1  1  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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    7.7122   -0.8754   -0.0822 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9535   -0.7892   -0.6651 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7511   -1.4350   -1.1315 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1562   -2.6900   -1.5575 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3712   -1.4515   -0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5329   -0.4728   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9809    2.8754    0.8025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9977    2.1460    1.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0871    0.8305    0.9599 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5846    0.0379    2.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4675   -1.2618    1.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9799   -2.1318    3.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9388   -3.0776    3.4296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8425   -1.8312    0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0900   -1.0275   -0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5205    0.4229   -0.3415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6270    0.5589   -1.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3778    1.3386   -0.8088 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8734    0.9732   -2.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511    2.7215   -0.7024 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9197    3.3283   -1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5943    3.7361   -1.5234 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1849   -2.8559    0.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4747   -1.6191    1.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7855   -2.2003    1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6385    1.2364   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5679    2.1409    2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9011    3.2894    1.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1235    3.9353    1.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1939    0.5827    0.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3204    0.4870    3.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0673   -2.6465    2.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221   -1.4911    3.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7814   -2.8929    2.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206   -1.5999    0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3682   -1.5078   -1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988   -1.1510   -0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3466    1.3526   -1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2240   -0.3997   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263    0.6205   -2.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771    0.0374   -2.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
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 29 61  1  0
 29 62  1  0
M  END


  Mrv1652304282206272D          

 30 33  0  0  1  0            999 V2000
    3.3584    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6757    1.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.3972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5184    1.4425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5693   -0.5116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3979   -1.3186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5252    0.5505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0059167

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O7/c1-14(25)16(26)6-4-5-7-20(27)30-18-11-19-23(13-28-23)22(18,3)21(2)9-8-15(12-24)10-17(21)29-19/h4-7,10,14,16-19,24-26H,8-9,11-13H2,1-3H3/b6-4+,7-5+/t14-,16+,17-,18+,19+,21+,22+,23-/m1/s1

> <INCHI_KEY>
VOMLNLQETZSQIE-HXKBPVKASA-N

> <FORMULA>
C23H32O7

> <MOLECULAR_WEIGHT>
420.502

> <EXACT_MASS>
420.21480337

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.278930232343185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2R,2'R,7'R,9'S,11'S)-5'-(hydroxymethyl)-1',2'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2E,4E,6S,7R)-6,7-dihydroxyocta-2,4-dienoate

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
1.035114810333332

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.97360849885337

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.726206521800012

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7344759990357552

> <JCHEM_POLAR_SURFACE_AREA>
108.75

> <JCHEM_REFRACTIVITY>
111.6469

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'R,7'R,9'S,11'S)-5'-(hydroxymethyl)-1',2'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2E,4E,6S,7R)-6,7-dihydroxyocta-2,4-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.269   0.924   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.080   1.903   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.332   3.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.774   3.963   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.963   2.984   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.711   1.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.405   3.525   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.595   2.547   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.302   4.567   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.765   4.475   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.834   2.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.734   1.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   1.737   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.878   3.216   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.165   0.707   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.300   1.183   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.619   2.690   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.444   0.153   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.909   0.629   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.053  -0.401   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.518   0.075   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.663  -0.955   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.343  -2.461   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.127  -0.479   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.272  -1.509   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -8.447   1.028   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.826  -0.384   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.770   1.580   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.338   3.058   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.941   0.369   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12   30                                             
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   28   29                                             
CONECT   12   11    2   13   27                                             
CONECT   13   12   14   15                                                  
CONECT   14   13   10                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   12                                                            
CONECT   28   11   29                                                       
CONECT   29   28   11                                                       
CONECT   30    2                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
(1'r,2R,2'r,7'r,9's,11's)-5'-(Hydroxymethyl)-1',2'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0,]dodecan]-5'-en-11'-yl (2E,4E,6S,7R)-6,7-dihydroxyocta-2,4-dienoic acid	Generator

Chemical Formula

C₂₃H₃₂O₇

Average Mass

420.5020 Da

Monoisotopic Mass

420.21480 Da

IUPAC Name

(1'R,2R,2'R,7'R,9'S,11'S)-5'-(hydroxymethyl)-1',2'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2E,4E,6S,7R)-6,7-dihydroxyocta-2,4-dienoate

Traditional Name

(1'R,2R,2'R,7'R,9'S,11'S)-5'-(hydroxymethyl)-1',2'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2E,4E,6S,7R)-6,7-dihydroxyocta-2,4-dienoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H32O7/c1-14(25)16(26)6-4-5-7-20(27)30-18-11-19-23(13-28-23)22(18,3)21(2)9-8-15(12-24)10-17(21)29-19/h4-7,10,14,16-19,24-26H,8-9,11-13H2,1-3H3/b6-4+,7-5+/t14-,16+,17-,18+,19+,21+,22+,23-/m1/s1

InChI Key

VOMLNLQETZSQIE-HXKBPVKASA-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
Myrothecium verrucaria	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
Fatty alcohol
Oxepane
Fatty acid ester
Fatty acyl
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
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	2.39	ALOGPS
logP	1.04	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.73	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	111.65 m³·mol⁻¹	ChemAxon
Polarizability	44.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162844424

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for [4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate) (NP0059167)

MOL for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))

3D MOL for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))

3D SDF for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))

3D-SDF for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))

PDB for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))

3D PDB for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))

SMILES for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))

INCHI for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))

Structure for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))

3D Structure for NP0059167 ([4beta(2Z,4E,6S,7S)]- 12,13-Epoxytrichothec-9-ene-4,16-diol 4-(6,7-dihydroxy-2,4-octadienoate))