NP-MRD: Showing NP-Card for (1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate (NP0330137)

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Record Information

Version

2.0

Created at

2022-09-12 15:12:06 UTC

Updated at

2022-09-12 15:12:07 UTC

NP-MRD ID

NP0330137

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate

Description

Calonectrin 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. (1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate is found in Fusarium culmorum and Fusarium sporotrichioides. (1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate was first documented in 2004 (PMID: 15066795). Based on a literature review a small amount of articles have been published on Calonectrin (PMID: 16604118) (PMID: 27120196) (PMID: 24434906) (PMID: 22095495).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122217122D          

 25 28  0  0  1  0            999 V2000
    3.9220   -1.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216   -0.2774    0.0000 O   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
    2.7212    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3584    0.4952    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
    4.2661    1.5988    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
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   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  0  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1923    1.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0974    2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267    3.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113    2.7658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  2  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
    1.5184    1.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    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
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    3.7095    3.6860    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005    2.8623   -0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3847    3.2534    0.1830 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5668    1.7738   -0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025    0.8549   -1.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0017   -0.1113   -0.6090 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1135   -0.8796    0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4314   -2.2163   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2289   -3.0498   -0.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435   -4.4679   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1712   -2.4258   -1.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032   -1.0134   -1.5628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1155   -0.5675   -1.6933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411   -0.7728   -0.5220 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3529    0.6126   -0.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1240    1.2128   -1.1003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3778    1.7203   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2305    2.3688   -1.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8025    1.6155    0.3408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0135    1.2987    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189    0.3010    0.4057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6235    0.6728    1.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8647   -0.9559    0.6092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9012   -1.8284    1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6111   -0.6812    1.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6354    3.2364   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247    3.8268    1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5744    4.6586   -0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3450    0.1815   -2.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0086    1.2874   -2.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8618   -1.0969    1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0675   -0.3119    0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814   -2.0476   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1336   -2.7163    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972   -5.0001   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -4.5182    0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482   -5.0059   -0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439   -3.0272   -1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6359   -0.9270   -2.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6213   -1.5166   -0.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8206    0.5754    0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2782    2.3591   -1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1751    1.8442   -2.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9383    3.4285   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8416    1.8417   -0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1246    2.0929    0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3379   -0.0887    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7026    0.8559    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1677    1.6325    2.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0160   -2.0797    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550   -2.7477    1.5503 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
  6  5  1  6
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 12  6  1  0
 23 14  1  0
 23 25  1  6
 21  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  6
 14 40  1  6
 15 41  1  1
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 24 50  1  0
 24 51  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
M  END


  Mrv1652309122217122D          

 25 28  0  0  1  0            999 V2000
    3.9220   -1.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216   -0.2774    0.0000 O   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
    2.7212    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3584    0.4952    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
    4.2661    1.5988    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
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   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  0  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1923    1.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0974    2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267    3.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113    2.7658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  2  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
    1.5184    1.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    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
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330137

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]12CCC(C)=CC1OC1[C@@H](C[C@@]2(C)C11CO1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-14(24-13(3)21)8-17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3/t14-,15?,16?,17-,18-,19?/m1/s1

> <INCHI_KEY>
IGDIDZAQDRAJRB-GRGGRPSZSA-N

> <FORMULA>
C19H26O6

> <MOLECULAR_WEIGHT>
350.411

> <EXACT_MASS>
350.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.36942820715533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1'R,2'R,10'R)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

> <JCHEM_LOGP>
1.295995752333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.930401673270809

> <JCHEM_POLAR_SURFACE_AREA>
74.36

> <JCHEM_REFRACTIVITY>
87.89219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2'R,10'R)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       7.321  -2.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.062  -2.052   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.665  -2.699   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.200  -0.518   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.941   0.369   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.080   1.903   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.269   0.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.711   1.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.963   2.984   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.405   3.525   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.774   3.963   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.332   3.422   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.302   4.567   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.765   4.475   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.878   3.216   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.359   3.468   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.182   4.910   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.796   6.099   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.701   5.163   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.310   1.737   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.734   1.153   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.826  -0.384   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.834   2.693   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.770   1.580   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.338   3.058   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                                                       
CONECT    6    5    7   12   21                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20    6   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   14   24   25                                             
CONECT   24   23   25                                                       
CONECT   25   24   23                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₆

Average Mass

350.4110 Da

Monoisotopic Mass

350.17294 Da

IUPAC Name

[(1'R,2'R,10'R)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

Traditional Name

(1'R,2'R,10'R)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]12CCC(C)=CC1OC1[C@@H](C[C@@]2(C)C11CO1)OC(C)=O

InChI Identifier

InChI=1S/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-14(24-13(3)21)8-17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3/t14-,15?,16?,17-,18-,19?/m1/s1

InChI Key

IGDIDZAQDRAJRB-GRGGRPSZSA-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

Species Name	Source	Reference
Fusarium culmorum	LOTUS Database	35616633
Fusarium sporotrichioides	LOTUS Database	35616633

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
Oxepane
Oxane
Dicarboxylic acid or derivatives
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	1.3	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.89 m³·mol⁻¹	ChemAxon
Polarizability	36.37 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00012629

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

102515046

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

McCormick SP, Alexander NJ, Proctor RH: Heterologous expression of two trichothecene P450 genes in Fusarium verticillioides. Can J Microbiol. 2006 Mar;52(3):220-6. doi: 10.1139/w05-124. [PubMed:16604118 ]
Maeda K, Tanaka A, Sugiura R, Koshino H, Tokai T, Sato M, Nakajima Y, Tanahashi Y, Kanamaru K, Kobayashi T, Nishiuchi T, Fujimura M, Takahashi-Ando N, Kimura M: Hydroxylations of trichothecene rings in the biosynthesis of Fusarium trichothecenes: evolution of alternative pathways in the nivalenol chemotype. Environ Microbiol. 2016 Nov;18(11):3798-3811. doi: 10.1111/1462-2920.13338. Epub 2016 Jun 27. [PubMed:27120196 ]
Fruhmann P, Hametner C, Mikula H, Adam G, Krska R, Frohlich J: Stereoselective Luche reduction of deoxynivalenol and three of its acetylated derivatives at C8. Toxins (Basel). 2014 Jan 10;6(1):325-36. doi: 10.3390/toxins6010325. [PubMed:24434906 ]
Kadota T, Kimura M, Hirano S, Tajima O, Nakajima T, Kamata Y, Sugita-Konishi Y: Development of a simultaneous liquid chromatography/tandem mass spectrometric method for the determination of type B trichothecenes, their derivatives, and precursors in wheat. Rapid Commun Mass Spectrom. 2011 Dec 15;25(23):3481-90. doi: 10.1002/rcm.5250. [PubMed:22095495 ]
McCormick SP, Harris LJ, Alexander NJ, Ouellet T, Saparno A, Allard S, Desjardins AE: Tri1 in Fusarium graminearum encodes a P450 oxygenase. Appl Environ Microbiol. 2004 Apr;70(4):2044-51. doi: 10.1128/AEM.70.4.2044-2051.2004. [PubMed:15066795 ]
LOTUS database [Link]

Showing NP-Card for (1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate (NP0330137)

MOL for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D MOL for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D SDF for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D-SDF for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

PDB for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D PDB for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

SMILES for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

INCHI for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

Structure for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)

3D Structure for NP0330137 ((1'r,2'r,10'r)-10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate)