NP-MRD: Showing NP-Card for 13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid (NP0307047)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 23:54:43 UTC

Updated at

2022-09-10 23:54:43 UTC

NP-MRD ID

NP0307047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid

Description

13',25'-Dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]Heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid 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. 13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid is found in Paramyrothecium roridum. Based on a literature review very few articles have been published on 13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]Heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201542D          

 37 41  0  0  0  0            999 V2000
    5.1122    0.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435    1.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084    0.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771   -0.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -0.2891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1319    0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358    0.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2249   -0.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -1.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2933   -1.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568   -0.9704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -2.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517    0.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0992    0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101    1.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4410    1.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    2.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8021    1.8141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4666    3.2031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373    2.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704    3.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724    3.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411    3.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430    3.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4762    4.1718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8118    2.7828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5786    1.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767    1.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7670    0.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0046    0.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0307    1.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3721    2.2626    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
  3  4  1  4  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  4  0  0  0
 24 25  2  0  0  0  0
 26 25  1  4  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 20 33  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 18 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 37  1  0  0  0  0
M  END

     RDKit          3D

 67 71  0  0  0  0  0  0  0  0999 V2000
    3.9329    2.9299    1.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9325    2.5000    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0265    3.3767    0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9811    3.1202   -0.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341    3.9515   -1.6895 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1872    2.0264   -0.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4608    1.5207    0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020    0.5935    0.1241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8737    1.2225    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8671    1.4991   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136    2.1971   -1.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7716    3.4284   -2.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2416    4.0249   -3.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9419    3.9091   -1.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944    1.6552   -2.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256    0.3987   -1.3742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4536   -0.6229   -1.7738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2221   -1.8296   -1.1678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7606   -2.1945   -1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -1.5015    0.1776 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2139   -2.3367    1.1702 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282   -3.0016    1.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632   -2.6323    2.5764 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9575   -4.1245    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337   -4.1741   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597   -3.1122   -1.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1798   -2.0231   -1.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601   -1.5514   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4086   -1.5906   -0.8534 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9479   -1.0593    0.7885 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875    0.0921    1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225    1.1057    0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4483   -0.7597    0.7454 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2649   -0.6710    2.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406   -1.6649    0.3171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0142   -2.8133    1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8205   -1.6006    0.7631 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987    2.3574    1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5666    2.8894    2.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2420    4.0023    1.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824    4.3882    0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024    2.3493    1.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2928    0.9793    1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838    0.6016    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745    2.2013    1.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344    0.5679   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6469    2.2079   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9332    4.3906   -0.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925    2.1253   -2.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831    0.2424   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8262   -2.6069   -1.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585   -3.2810   -0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1973   -1.9395   -1.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202   -0.7756   -0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0693   -5.0821    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8553   -5.1832   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -3.2669   -2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540   -1.3459   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9760    0.5912    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -0.0706    1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057    0.8485   -0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9466    1.0619   -0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1704   -0.5334    2.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    0.2216    2.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -1.5770    2.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4661   -3.6544    0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780   -2.9977    2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  8  7  1  6
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 20 33  1  0
 33 34  1  1
 33 35  1  0
 35 36  1  0
 36 37  1  0
 11 12  1  0
 12 14  1  0
 12 13  2  0
 32  2  1  0
 35 37  1  6
 16  8  1  0
 35 18  1  0
 33  8  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  7 42  1  0
  7 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 15 49  1  0
 16 50  1  6
 18 51  1  6
 19 52  1  0
 19 53  1  0
 20 54  1  6
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
 31 59  1  0
 31 60  1  0
 32 61  1  0
 32 62  1  0
 34 63  1  0
 34 64  1  0
 34 65  1  0
 36 66  1  0
 36 67  1  0
 14 48  1  0
M  END


  Mrv1652309112201542D          

 37 41  0  0  0  0            999 V2000
    5.1122    0.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435    1.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084    0.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771   -0.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -0.2891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1319    0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358    0.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2249   -0.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -1.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2933   -1.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568   -0.9704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -2.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517    0.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0992    0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101    1.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4410    1.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    2.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8021    1.8141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4666    3.2031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373    2.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704    3.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724    3.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411    3.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430    3.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4762    4.1718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8118    2.7828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5786    1.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767    1.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7670    0.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0046    0.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0307    1.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3721    2.2626    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
  3  4  1  4  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  4  0  0  0
 24 25  2  0  0  0  0
 26 25  1  4  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 20 33  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 18 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)OCC23CCC(=CC2OC2CC(OC(=O)C=CC=CC(=O)OCC1)C3(C)C21CO1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O10/c1-16-8-10-33-21(28)5-3-4-6-22(29)37-18-13-20-27(15-35-27)25(18,2)26(14-34-23(30)11-16)9-7-17(24(31)32)12-19(26)36-20/h3-6,11-12,18-20H,7-10,13-15H2,1-2H3,(H,31,32)

> <INCHI_KEY>
ZVTFIUWWSHNKFE-UHFFFAOYSA-N

> <FORMULA>
C27H30O10

> <MOLECULAR_WEIGHT>
514.527

> <EXACT_MASS>
514.183897166

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.702620847197785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid

> <JCHEM_LOGP>
2.7272843879999984

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.476469397653233

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.014160802066531

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9206370136983097

> <JCHEM_POLAR_SURFACE_AREA>
137.96

> <JCHEM_REFRACTIVITY>
129.64239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       9.543   0.763   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.481   1.878   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.984   1.517   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.549   0.040   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.611  -1.076   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.047  -0.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.980   0.358   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.493   0.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.286  -1.094   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.504  -2.036   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.930  -1.453   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.148  -2.395   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.573  -1.811   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.941  -3.921   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.137   0.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.919   1.016   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.126   2.542   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.690   3.489   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.793   5.020   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.085   3.019   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.364   3.386   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.799   4.864   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.738   5.979   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.296   5.225   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.731   6.702   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.228   7.064   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.290   5.948   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.787   6.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.222   7.787   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.849   5.195   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.413   3.717   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.916   3.356   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.432   1.547   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.009   1.003   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.482   2.900   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.057   2.880   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.695   4.223   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16   33                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    2                                                       
CONECT   33   20    8   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   18   36   37                                             
CONECT   36   35   37                                                       
CONECT   37   36   35                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
13',25'-Dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0,.0,]heptacosane]-4',12',18',20'-tetraene-5'-carboxylate	Generator

Chemical Formula

C₂₇H₃₀O₁₀

Average Mass

514.5270 Da

Monoisotopic Mass

514.18390 Da

IUPAC Name

13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid

Traditional Name

13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)OCC23CCC(=CC2OC2CC(OC(=O)C=CC=CC(=O)OCC1)C3(C)C21CO1)C(O)=O

InChI Identifier

InChI=1S/C27H30O10/c1-16-8-10-33-21(28)5-3-4-6-22(29)37-18-13-20-27(15-35-27)25(18,2)26(14-34-23(30)11-16)9-7-17(24(31)32)12-19(26)36-20/h3-6,11-12,18-20H,7-10,13-15H2,1-2H3,(H,31,32)

InChI Key

ZVTFIUWWSHNKFE-UHFFFAOYSA-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
Myrothecium roridum	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
Tetracarboxylic acid or derivatives
Oxepane
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid
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	2.73	ChemAxon
pKa (Strongest Acidic)	4.01	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.96 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	129.64 m³·mol⁻¹	ChemAxon
Polarizability	50.7 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

163064912

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid (NP0307047)

MOL for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)

3D MOL for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)

3D SDF for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)

3D-SDF for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)

PDB for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)

3D PDB for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)

SMILES for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)

INCHI for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)

Structure for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)

3D Structure for NP0307047 (13',25'-dimethyl-11',17',22'-trioxo-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-5'-carboxylic acid)