NP-MRD: Showing NP-Card for (1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione (NP0220363)

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Record Information

Version

2.0

Created at

2022-09-05 21:39:20 UTC

Updated at

2024-09-12 20:33:07 UTC

NP-MRD ID

NP0220363

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione

Description

16-Hydroxyroridin E 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,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione is found in Paramyrothecium roridum. (1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione was first documented in 2013 (PMID: 24152038). Based on a literature review very few articles have been published on 16-hydroxyroridin E.

Structure

MOL SDF PDB SMILES InChI

NP0004179
  Mrv2104 05272322233D          

 76 80  0  0  0  0            999 V2000
   -2.2636    3.5463    2.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    3.0725    1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1534    2.5864    0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2086    2.4655    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6577    3.0921    2.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8776    1.5452    0.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2184    1.2989    0.7706 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8354   -0.0015    0.1567 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3194   -0.0035    0.6619 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3278    0.8838   -0.0954 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8875    1.4365   -1.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8319    2.4039   -2.0762 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0192    1.7092   -2.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7423    1.0456   -2.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7930    0.0590   -1.4054 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1040   -1.1956   -2.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192   -2.3466   -1.5234 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9011   -2.1386   -1.4741 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6457   -1.4631   -0.1059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4308   -2.0238    0.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -3.3448    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198   -4.2687    0.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8812   -3.6081    1.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -2.9427    1.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4061   -1.7420    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6808   -1.3299    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1703   -0.1223    0.0312 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6345   -0.5008   -1.3984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2842    0.6784   -2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -0.9445   -2.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1626    0.8982   -0.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5470    2.0793    0.6988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5557    3.2077    0.4130 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0566   -1.3502    0.6177 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -1.5092    2.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7965   -2.4835   -0.0895 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.6521   -3.7948    0.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550    3.1722    3.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3988    3.2715    3.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2345    2.2485   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2558    1.2444    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8158    2.1697    0.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3430    0.2885    1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7467   -1.0111    0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2263    0.2522   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6631    1.7059    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0733    3.2376   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4211    2.8300   -2.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7510    1.0543   -3.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4754    1.4130   -2.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922    0.3603   -1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887   -3.2143   -2.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -3.0907   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -1.4867   -2.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534   -0.4720   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8063   -4.5473    2.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8313   -3.3854    2.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -1.1593    0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4613   -1.9334    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0484    0.2380    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3556   -1.3234   -1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5546    1.4770   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1140    1.0764   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6624    0.3817   -3.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8995   -1.2444   -3.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5428    2.4015    0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6110    1.8525    1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038    4.1657    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3818    3.2591   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697   -1.5069    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3945   -0.7063    2.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -2.4560    2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458   -3.0781    1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6510   -3.7223   -0.3290 H   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  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  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  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 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  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 19 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 33  2  1  0  0  0  0
 36 38  1  1  0  0  0
 15  8  1  0  0  0  0
 36 17  1  0  0  0  0
 34  8  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  3 42  1  0  0  0  0
  7 43  1  0  0  0  0
  7 44  1  0  0  0  0
  9 45  1  0  0  0  0
  9 46  1  0  0  0  0
 10 47  1  0  0  0  0
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 12 49  1  0  0  0  0
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 13 51  1  0  0  0  0
 14 52  1  0  0  0  0
 15 53  1  1  0  0  0
 17 54  1  6  0  0  0
 18 55  1  0  0  0  0
 18 56  1  0  0  0  0
 19 57  1  6  0  0  0
 23 58  1  0  0  0  0
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 29 64  1  0  0  0  0
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 33 70  1  0  0  0  0
 33 71  1  0  0  0  0
 35 72  1  0  0  0  0
 35 73  1  0  0  0  0
 35 74  1  0  0  0  0
 37 75  1  0  0  0  0
 37 76  1  0  0  0  0
M  END

NP0004179
  Mrv2104 05272322233D          

 76 80  0  0  0  0            999 V2000
   -2.2636    3.5463    2.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    3.0725    1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1534    2.5864    0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2086    2.4655    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6577    3.0921    2.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8776    1.5452    0.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2184    1.2989    0.7706 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8354   -0.0015    0.1567 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3194   -0.0035    0.6619 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3278    0.8838   -0.0954 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8875    1.4365   -1.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8319    2.4039   -2.0762 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0192    1.7092   -2.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7423    1.0456   -2.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7930    0.0590   -1.4054 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1040   -1.1956   -2.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192   -2.3466   -1.5234 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9011   -2.1386   -1.4741 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6457   -1.4631   -0.1059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4308   -2.0238    0.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -3.3448    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198   -4.2687    0.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8812   -3.6081    1.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -2.9427    1.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4061   -1.7420    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6808   -1.3299    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1703   -0.1223    0.0312 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6345   -0.5008   -1.3984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2842    0.6784   -2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -0.9445   -2.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1626    0.8982   -0.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5470    2.0793    0.6988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5557    3.2077    0.4130 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0566   -1.3502    0.6177 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -1.5092    2.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7965   -2.4835   -0.0895 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9843   -3.2945    0.4072 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6521   -3.7948    0.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550    3.1722    3.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3988    3.2715    3.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3298    4.6378    2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345    2.2485   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2558    1.2444    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8158    2.1697    0.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3430    0.2885    1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7467   -1.0111    0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2263    0.2522   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6631    1.7059    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0733    3.2376   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6887   -3.2143   -2.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -3.0907   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -1.4867   -2.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534   -0.4720   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8063   -4.5473    2.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8313   -3.3854    2.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -1.1593    0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4613   -1.9334    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0484    0.2380    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3556   -1.3234   -1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5546    1.4770   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1140    1.0764   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6624    0.3817   -3.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8995   -1.2444   -3.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5428    2.4015    0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6110    1.8525    1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038    4.1657    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3818    3.2591   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697   -1.5069    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3945   -0.7063    2.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -2.4560    2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458   -3.0781    1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6510   -3.7223   -0.3290 H   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  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  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  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 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  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 19 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 33  2  1  0  0  0  0
 36 38  1  1  0  0  0
 15  8  1  0  0  0  0
 36 17  1  0  0  0  0
 34  8  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  3 42  1  0  0  0  0
  7 43  1  0  0  0  0
  7 44  1  0  0  0  0
  9 45  1  0  0  0  0
  9 46  1  0  0  0  0
 10 47  1  0  0  0  0
 10 48  1  0  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 13 51  1  0  0  0  0
 14 52  1  0  0  0  0
 15 53  1  1  0  0  0
 17 54  1  6  0  0  0
 18 55  1  0  0  0  0
 18 56  1  0  0  0  0
 19 57  1  6  0  0  0
 23 58  1  0  0  0  0
 24 59  1  0  0  0  0
 25 60  1  0  0  0  0
 26 61  1  0  0  0  0
 27 62  1  1  0  0  0
 28 63  1  1  0  0  0
 29 64  1  0  0  0  0
 29 65  1  0  0  0  0
 29 66  1  0  0  0  0
 30 67  1  0  0  0  0
 32 68  1  0  0  0  0
 32 69  1  0  0  0  0
 33 70  1  0  0  0  0
 33 71  1  0  0  0  0
 35 72  1  0  0  0  0
 35 73  1  0  0  0  0
 35 74  1  0  0  0  0
 37 75  1  0  0  0  0
 37 76  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220363

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])[C@@]2([H])O[C@]3([H])C([H])([H])[C@@]4([H])OC(=O)\C([H])=C(\[H])/C(/[H])=C([H])/[C@@]([H])(OC([H])([H])C([H])([H])\C(=C([H])\C(=O)OC([H])([H])[C@@]2(C([H])([H])C1([H])[H])[C@]4(C([H])([H])[H])[C@@]31OC1([H])[H])C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1/C29H38O9/c1-18-9-11-34-21(19(2)31)6-4-5-7-25(32)38-22-14-24-29(17-36-29)27(22,3)28(16-35-26(33)12-18)10-8-20(15-30)13-23(28)37-24/h4-7,12-13,19,21-24,30-31H,8-11,14-17H2,1-3H3/b6-4+,7-5-,18-12+/t19-,21-,22-,23-,24-,27-,28-,29+/s2

> <INCHI_KEY>
DUKCZSLAWRKJBB-CAKQYEDVNA-N

> <FORMULA>
C29H38O9

> <MOLECULAR_WEIGHT>
530.614

> <EXACT_MASS>
530.251582804

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.15105379704861

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2S,3'R,8'R,12'E,17'R,18'E,20'Z,24'R,25'S)-17'-[(1R)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',12',18',20'-tetraene-11',22'-dione

> <JCHEM_LOGP>
1.9846852913333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.226820384986231

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.371944572632234

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7344927114403603

> <JCHEM_POLAR_SURFACE_AREA>
124.05000000000001

> <JCHEM_REFRACTIVITY>
140.19590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,3'R,8'R,12'E,17'R,18'E,20'Z,24'R,25'S)-17'-[(1R)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',12',18',20'-tetraene-11',22'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0004179                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0      -2.264   3.546   2.586  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.234   3.072   1.151  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.153   2.586   0.511  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.209   2.466   1.082  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.658   3.092   2.021  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.878   1.545   0.345  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.218   1.299   0.771  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.835  -0.002   0.157  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.319  -0.004   0.662  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.328   0.884  -0.095  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.888   1.437  -1.421  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.832   2.404  -2.076  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.019   1.709  -2.422  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.742   1.046  -2.006  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.793   0.059  -1.405  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.104  -1.196  -2.044  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.419  -2.347  -1.523  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.901  -2.139  -1.474  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.646  -1.463  -0.106  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.431  -2.024   0.680  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.658  -3.345   0.813  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.020  -4.269   0.399  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.881  -3.608   1.594  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.045  -2.943   1.628  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.406  -1.742   0.906  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.681  -1.330   0.797  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.170  -0.122   0.031  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.635  -0.501  -1.398  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.284   0.678  -2.111  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.533  -0.945  -2.200  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.163   0.898  -0.028  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.547   2.079   0.699  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.556   3.208   0.413  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.057  -1.350   0.618  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.976  -1.509   2.138  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.797  -2.483  -0.090  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.984  -3.295   0.407  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.652  -3.795   0.462  0.00  0.00           O+0
HETATM   39  H   UNK     0      -3.155   3.172   3.097  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.399   3.272   3.176  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.330   4.638   2.601  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.234   2.248  -0.526  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.256   1.244   1.865  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.816   2.170   0.484  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.343   0.289   1.729  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.747  -1.011   0.665  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.226   0.252  -0.275  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.663   1.706   0.564  0.00  0.00           H+0
HETATM   49  H   UNK     0       6.073   3.238  -1.407  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.421   2.830  -2.997  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.751   1.054  -3.085  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.475   1.413  -2.993  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.792   0.360  -1.736  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.689  -3.214  -2.134  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.377  -3.091  -1.586  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.554  -1.487  -2.281  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.253  -0.472  -0.332  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.806  -4.547   2.133  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.831  -3.385   2.237  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.644  -1.159   0.401  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.461  -1.933   1.245  0.00  0.00           H+0
HETATM   62  H   UNK     0      -6.048   0.238   0.582  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.356  -1.323  -1.336  0.00  0.00           H+0
HETATM   64  H   UNK     0      -5.555   1.477  -2.285  0.00  0.00           H+0
HETATM   65  H   UNK     0      -7.114   1.076  -1.519  0.00  0.00           H+0
HETATM   66  H   UNK     0      -6.662   0.382  -3.098  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.899  -1.244  -3.048  0.00  0.00           H+0
HETATM   68  H   UNK     0      -5.543   2.401   0.361  0.00  0.00           H+0
HETATM   69  H   UNK     0      -4.611   1.853   1.774  0.00  0.00           H+0
HETATM   70  H   UNK     0      -4.004   4.166   0.699  0.00  0.00           H+0
HETATM   71  H   UNK     0      -3.382   3.259  -0.667  0.00  0.00           H+0
HETATM   72  H   UNK     0       2.970  -1.507   2.595  0.00  0.00           H+0
HETATM   73  H   UNK     0       1.395  -0.706   2.597  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.503  -2.456   2.422  0.00  0.00           H+0
HETATM   75  H   UNK     0       4.446  -3.078   1.360  0.00  0.00           H+0
HETATM   76  H   UNK     0       4.651  -3.722  -0.329  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    1    3   33                                                  
CONECT    3    2    4   42                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   43   44                                             
CONECT    8    7    9   15   34                                             
CONECT    9    8   10   45   46                                             
CONECT   10    9   11   47   48                                             
CONECT   11   10   12   14                                                  
CONECT   12   11   13   49   50                                             
CONECT   13   12   51                                                       
CONECT   14   11   15   52                                                  
CONECT   15   14   16    8   53                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   36   54                                             
CONECT   18   17   19   55   56                                             
CONECT   19   18   20   34   57                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   58                                                  
CONECT   24   23   25   59                                                  
CONECT   25   24   26   60                                                  
CONECT   26   25   27   61                                                  
CONECT   27   26   28   31   62                                             
CONECT   28   27   29   30   63                                             
CONECT   29   28   64   65   66                                             
CONECT   30   28   67                                                       
CONECT   31   27   32                                                       
CONECT   32   31   33   68   69                                             
CONECT   33   32    2   70   71                                             
CONECT   34   19   35   36    8                                             
CONECT   35   34   72   73   74                                             
CONECT   36   34   37   38   17                                             
CONECT   37   36   38   75   76                                             
CONECT   38   37   36                                                       
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    3                                                            
CONECT   43    7                                                            
CONECT   44    7                                                            
CONECT   45    9                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   17                                                            
CONECT   55   18                                                            
CONECT   56   18                                                            
CONECT   57   19                                                            
CONECT   58   23                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   29                                                            
CONECT   66   29                                                            
CONECT   67   30                                                            
CONECT   68   32                                                            
CONECT   69   32                                                            
CONECT   70   33                                                            
CONECT   71   33                                                            
CONECT   72   35                                                            
CONECT   73   35                                                            
CONECT   74   35                                                            
CONECT   75   37                                                            
CONECT   76   37                                                            
MASTER        0    0    0    0    0    0    0    0   76    0  160    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₈O₉

Average Mass

530.6140 Da

Monoisotopic Mass

530.25158 Da

IUPAC Name

(1'R,2S,3'R,8'R,12'E,17'R,18'E,20'Z,24'R,25'S)-17'-[(1R)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',12',18',20'-tetraene-11',22'-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C([H])[C@@]2([H])O[C@]3([H])C([H])([H])[C@@]4([H])OC(=O)\C([H])=C(\[H])/C(/[H])=C([H])/[C@@]([H])(OC([H])([H])C([H])([H])\C(=C([H])\C(=O)OC([H])([H])[C@@]2(C([H])([H])C1([H])[H])[C@]4(C([H])([H])[H])[C@@]31OC1([H])[H])C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[H]

InChI Identifier

InChI=1/C29H38O9/c1-18-9-11-34-21(19(2)31)6-4-5-7-25(32)38-22-14-24-29(17-36-29)27(22,3)28(16-35-26(33)12-18)10-8-20(15-30)13-23(28)37-24/h4-7,12-13,19,21-24,30-31H,8-11,14-17H2,1-3H3/b6-4+,7-5-,18-12+/t19-,21-,22-,23-,24-,27-,28-,29+/s2

InChI Key

DUKCZSLAWRKJBB-CAKQYEDVNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Myrothecium roridum	LOTUS Database	35616633

Chemical Taxonomy

Description

This 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.

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
Dicarboxylic acid or derivatives
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Primary 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	1.98	ChemAxon
pKa (Strongest Acidic)	14.37	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	124.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	140.2 m³·mol⁻¹	ChemAxon
Polarizability	56.15 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Piao MZ, Shen L, Wang FW: A new trichothecene from Myrothecium roridum QDFE005, a symbiotic fungus isolated from Mactra chinensis. J Asian Nat Prod Res. 2013;15(12):1284-9. doi: 10.1080/10286020.2013.841141. Epub 2013 Oct 24. [PubMed:24152038 ]
LOTUS database [Link]

Showing NP-Card for (1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione (NP0220363)

MOL for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)

3D MOL for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)

3D SDF for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)

3D-SDF for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)

PDB for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)

3D PDB for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)

SMILES for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)

INCHI for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)

Structure for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)

3D Structure for NP0220363 ((1'r,2s,3'r,8'r,12'e,17'r,18'e,20'z,24'r,25's)-17'-[(1r)-1-hydroxyethyl]-5'-(hydroxymethyl)-13',25'-dimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',12',18',20'-tetraene-11',22'-dione)