NP-MRD: Showing NP-Card for Verrucarin M (NP0004020)

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Record Information

Version

2.0

Created at

2020-12-09 01:32:12 UTC

Updated at

2021-07-15 16:48:01 UTC

NP-MRD ID

NP0004020

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Verrucarin M

Provided By

NPAtlas

Description

(1'R,3'R,18'E,20'E)-27'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]Heptacosane]-4',12',18',20'-tetraene-11',17',22'-trione 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. Verrucarin M is found in Albifimbria verrucaria and Myrothecium. Verrucarin M was first documented in 2001 (PMID: 11827043). Based on a literature review very few articles have been published on (1'R,3'R,18'E,20'E)-27'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]Heptacosane]-4',12',18',20'-tetraene-11',17',22'-trione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118033D          

 68 72  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242118033D          

 68 72  0  0  0  0            999 V2000
   -2.9592   -3.9856   -1.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839   -2.6540   -1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727   -1.5436   -1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073   -0.1710   -1.2759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5997    0.4924   -1.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188    1.7241   -0.7097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4571    2.6182   -1.1016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8523    3.9313   -0.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153    2.1915   -0.1590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8228    3.3455    0.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4284    3.4036    1.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7811    4.5147    1.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    2.2340    1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343    1.5791    0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838    1.7720   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678    2.0268   -1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334    2.1538   -0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197    3.0987   -0.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1564    1.0956    0.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0333   -0.2572   -0.1844 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5213   -1.2072    0.8544 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6964   -2.2309    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5262   -3.0084   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -2.5768    0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287   -2.1376    1.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1309   -2.8404    2.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -1.1088    0.8644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793   -0.7596   -0.1645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7467   -0.2345    0.0914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5376   -1.2669    0.8828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4100   -2.6366    0.2940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8554    1.1193    0.7138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5006    1.1643    2.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442    1.5190    0.7265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8713    2.3879    1.7870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1999    1.0602    1.6608 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8698   -1.5808   -2.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7187    0.3121   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952    2.2006   -0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9554    4.0645    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182    1.8429   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    1.8271    2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069    0.5848    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109    1.6289   -1.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6582    2.1987   -2.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4647   -0.3511   -1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767   -0.5780   -0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0289   -0.6885    1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4132   -1.7248    1.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630   -3.5606   -1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1865   -2.3283   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1295   -3.4864   -0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5382   -1.6621   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2126   -3.2689    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4598   -3.1424    0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972    0.8409    2.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918    0.5383    2.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
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 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
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 35 36  1  0  0  0  0
 31  2  1  0  0  0  0
 34 36  1  1  0  0  0
 29  4  1  0  0  0  0
 34  6  1  0  0  0  0
 32  9  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  3 40  1  0  0  0  0
  4 41  1  6  0  0  0
  6 42  1  1  0  0  0
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  8 44  1  0  0  0  0
  9 45  1  6  0  0  0
 13 46  1  0  0  0  0
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 15 48  1  0  0  0  0
 16 49  1  0  0  0  0
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 23 56  1  0  0  0  0
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 31 62  1  0  0  0  0
 31 63  1  0  0  0  0
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 33 65  1  0  0  0  0
 33 66  1  0  0  0  0
 35 67  1  0  0  0  0
 35 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004020

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]2([H])O[C@]3([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]33C([H])([H])OC(=O)\C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])OC(=O)\C([H])=C(\[H])/C(/[H])=C([H])\C(=O)O[C@@]1([H])[C@@]3(C([H])([H])[H])[C@]21OC1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O9/c1-16-8-10-26-14-33-21(30)13-17(2)9-11-32-19(28)6-4-5-7-20(29)36-23-22(31)24(35-18(26)12-16)27(15-34-27)25(23,26)3/h4-7,12-13,18,22-24,31H,8-11,14-15H2,1-3H3/b6-4-,7-5-,17-13-/t18-,22+,23-,24-,25-,26-,27-/m1/s1

> <INCHI_KEY>
SBDCDLYTQBGFRK-KUPGYVKFSA-N

> <FORMULA>
C27H32O9

> <MOLECULAR_WEIGHT>
500.544

> <EXACT_MASS>
500.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.420297065442725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,3'R,8'R,12'Z,18'Z,20'Z,24'S,25'S,27'S)-27'-hydroxy-5',13',25'-trimethyl-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',17',22'-trione

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
2.8452971080000005

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.476486498361165

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.071671506384007

> <JCHEM_PKA_STRONGEST_BASIC>
-3.642243403587079

> <JCHEM_POLAR_SURFACE_AREA>
120.89

> <JCHEM_REFRACTIVITY>
129.02229999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,3'R,8'R,12'Z,18'Z,20'Z,24'S,25'S,27'S)-27'-hydroxy-5',13',25'-trimethyl-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',17',22'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
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   -2.6839   -2.6540   -1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4073   -0.1710   -1.2759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5997    0.4924   -1.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188    1.7241   -0.7097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4571    2.6182   -1.1016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8523    3.9313   -0.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153    2.1915   -0.1590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8228    3.3455    0.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4284    3.4036    1.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0343    1.5791    0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838    1.7720   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6918    0.5383    2.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    2.2070    2.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2851    2.7311    2.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    3.0831    1.5329 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 29 28  1  6
 29 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  1  1
 32 34  1  0
 34 35  1  0
 35 36  1  0
 31  2  1  0
 34 36  1  1
 29  4  1  0
 34  6  1  0
 32  9  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  4 41  1  6
  6 42  1  1
  7 43  1  6
  8 44  1  0
  9 45  1  6
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 31 63  1  0
 33 64  1  0
 33 65  1  0
 33 66  1  0
 35 67  1  0
 35 68  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.959  -3.986  -1.793  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.684  -2.654  -1.157  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.673  -1.544  -1.836  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.407  -0.171  -1.276  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.600   0.492  -1.324  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.619   1.724  -0.710  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.457   2.618  -1.102  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.852   3.931  -0.794  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.315   2.192  -0.159  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.823   3.345   0.451  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.428   3.404   1.124  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.781   4.515   1.552  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.251   2.234   1.307  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.034   1.579   0.465  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.384   1.772  -0.913  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.568   2.027  -1.473  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.833   2.154  -0.733  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.620   3.099  -0.856  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.156   1.096   0.188  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.033  -0.257  -0.184  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.521  -1.207   0.854  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.696  -2.231   0.182  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.526  -3.008  -0.862  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.452  -2.577   0.287  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.329  -2.138   1.078  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.131  -2.840   2.171  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.439  -1.109   0.864  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.379  -0.760  -0.165  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.747  -0.235   0.091  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.538  -1.267   0.883  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.410  -2.637   0.294  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.855   1.119   0.714  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.501   1.164   2.163  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.344   1.519   0.727  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.871   2.388   1.787  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.200   1.060   1.661  0.00  0.00           O+0
HETATM   37  H   UNK     0      -2.716  -3.951  -2.886  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.291  -4.760  -1.358  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.005  -4.286  -1.706  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.870  -1.581  -2.900  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.719   0.312  -2.021  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.595   2.201  -0.931  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.190   2.561  -2.153  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.955   4.064   0.177  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.518   1.843  -0.849  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.295   1.827   2.384  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.407   0.585   0.910  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.611   1.629  -1.716  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.658   2.199  -2.564  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.465  -0.351  -1.138  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.077  -0.578  -0.465  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.029  -0.689   1.659  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.413  -1.725   1.353  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.863  -3.561  -1.535  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.133  -3.706  -0.249  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.186  -2.328  -1.401  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.130  -3.486  -0.365  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.176  -0.070  -0.872  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.538  -1.662  -0.852  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.276  -1.280   1.940  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.634  -1.010   0.777  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.213  -3.269   0.776  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.460  -3.142   0.545  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.397   0.841   2.781  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.692   0.538   2.499  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.333   2.207   2.467  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.285   2.731   2.653  0.00  0.00           H+0
HETATM   68  H   UNK     0      -4.707   3.083   1.533  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    1    3   31                                                  
CONECT    3    2    4   40                                                  
CONECT    4    3    5   29   41                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   34   42                                             
CONECT    7    6    8    9   43                                             
CONECT    8    7   44                                                       
CONECT    9    7   10   32   45                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   46                                                  
CONECT   14   13   15   47                                                  
CONECT   15   14   16   48                                                  
CONECT   16   15   17   49                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   50   51                                             
CONECT   21   20   22   52   53                                             
CONECT   22   21   23   24                                                  
CONECT   23   22   54   55   56                                             
CONECT   24   22   25   57                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   58   59                                             
CONECT   29   28   30   32    4                                             
CONECT   30   29   31   60   61                                             
CONECT   31   30    2   62   63                                             
CONECT   32   29   33   34    9                                             
CONECT   33   32   64   65   66                                             
CONECT   34   32   35   36    6                                             
CONECT   35   34   36   67   68                                             
CONECT   36   35   34                                                       
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   30                                                            
CONECT   61   30                                                            
CONECT   62   31                                                            
CONECT   63   31                                                            
CONECT   64   33                                                            
CONECT   65   33                                                            
CONECT   66   33                                                            
CONECT   67   35                                                            
CONECT   68   35                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  144    0
END

RDKit          3D

68 72  0  0  0  0  0  0  0  0999 V2000
   -2.9592   -3.9856   -1.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839   -2.6540   -1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727   -1.5436   -1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073   -0.1710   -1.2759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5997    0.4924   -1.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188    1.7241   -0.7097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4571    2.6182   -1.1016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8523    3.9313   -0.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153    2.1915   -0.1590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8228    3.3455    0.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4284    3.4036    1.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7811    4.5147    1.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    2.2340    1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343    1.5791    0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838    1.7720   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678    2.0268   -1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334    2.1538   -0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197    3.0987   -0.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1564    1.0956    0.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0333   -0.2572   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -1.2072    0.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964   -2.2309    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5262   -3.0084   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -2.5768    0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287   -2.1376    1.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1309   -2.8404    2.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -1.1088    0.8644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793   -0.7596   -0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7467   -0.2345    0.0914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5376   -1.2669    0.8828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4100   -2.6366    0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554    1.1193    0.7138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5006    1.1643    2.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442    1.5190    0.7265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8713    2.3879    1.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1999    1.0602    1.6608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7156   -3.9506   -2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2907   -4.7603   -1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0047   -4.2857   -1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8698   -1.5808   -2.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7187    0.3121   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952    2.2006   -0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1902    2.5611   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9554    4.0645    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182    1.8429   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    1.8271    2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069    0.5848    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109    1.6289   -1.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6582    2.1987   -2.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4647   -0.3511   -1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767   -0.5780   -0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0289   -0.6885    1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4132   -1.7248    1.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630   -3.5606   -1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1333   -3.7057   -0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1865   -2.3283   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1295   -3.4864   -0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762   -0.0700   -0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382   -1.6621   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2765   -1.2804    1.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6340   -1.0098    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2126   -3.2689    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4598   -3.1424    0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972    0.8409    2.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918    0.5383    2.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    2.2070    2.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2851    2.7311    2.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    3.0831    1.5329 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 29 28  1  6
 29 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  1  1
 32 34  1  0
 34 35  1  0
 35 36  1  0
 31  2  1  0
 34 36  1  1
 29  4  1  0
 34  6  1  0
 32  9  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  4 41  1  6
  6 42  1  1
  7 43  1  6
  8 44  1  0
  9 45  1  6
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 31 63  1  0
 33 64  1  0
 33 65  1  0
 33 66  1  0
 35 67  1  0
 35 68  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₉

Average Mass

500.5440 Da

Monoisotopic Mass

500.20463 Da

IUPAC Name

(1'R,2R,3'R,8'R,12'Z,18'Z,20'Z,24'S,25'S,27'S)-27'-hydroxy-5',13',25'-trimethyl-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',17',22'-trione

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1=C[C@H]2O[C@@H]3C(O)C4OC(=O)\C=C\C=C\C(=O)OCCC(C)=CC(=O)OCC2(CC1)C4(C)C31CO1

InChI Identifier

InChI=1S/C27H32O9/c1-16-8-10-26-14-33-21(30)13-17(2)9-11-32-19(28)6-4-5-7-20(29)36-23-22(31)24(35-18(26)12-16)27(15-34-27)25(23,26)3/h4-7,12-13,18,22-24,31H,8-11,14-15H2,1-3H3/b6-4+,7-5+,17-13?/t18-,22?,23?,24-,25?,26?,27?/m1/s1

InChI Key

SBDCDLYTQBGFRK-KUPGYVKFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Albifimbria verrucaria	LOTUS Database	35616633
Myrothecium	NPAtlas	11827043

Species Where Detected

Species Name	Source	Reference
Myrothecium verrucaria	KNApSAcK Database	22123792

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
Tricarboxylic acid or derivatives
Oxepane
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.72	ALOGPS
logP	2.85	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	129.02 m³·mol⁻¹	ChemAxon
Polarizability	50.42 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

NPAtlas ID

NPA005413

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

139584609

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Murakami Y, Okuda T, Shindo K: Roridin L, M and verrucarin M, new macrocyclic trichothecene group antitumor antibiotics, from Myrothecium verrucaria. J Antibiot (Tokyo). 2001 Nov;54(11):980-3. doi: 10.7164/antibiotics.54.980. [PubMed:11827043 ]

Showing NP-Card for Verrucarin M (NP0004020)

MOL for NP0004020 (Verrucarin M)

3D MOL for NP0004020 (Verrucarin M)

3D SDF for NP0004020 (Verrucarin M)

3D-SDF for NP0004020 (Verrucarin M)

PDB for NP0004020 (Verrucarin M)

3D PDB for NP0004020 (Verrucarin M)

SMILES for NP0004020 (Verrucarin M)

INCHI for NP0004020 (Verrucarin M)

Structure for NP0004020 (Verrucarin M)

3D Structure for NP0004020 (Verrucarin M)