NP-MRD: Showing NP-Card for gelomulide K (NP0025251)

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Record Information

Version

2.0

Created at

2021-06-19 17:25:28 UTC

Updated at

2021-06-29 23:50:05 UTC

NP-MRD ID

NP0025251

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gelomulide K

Provided By

JEOL Database JEOL Logo

Description

Gelomulide K is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. gelomulide K is found in Gelonium aequoreum. gelomulide K was first documented in 2011 (PMID: 21641992). Based on a literature review very few articles have been published on gelomulide K.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119253D          

 55 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192119253D          

 55 59  0  0  0  0            999 V2000
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   -2.5574    3.4453    1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1408    4.4552    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760    2.2138    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572    2.3987   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    3.7741   -0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    3.0080   -2.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    2.9617   -2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7469    1.0816   -3.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -1.7728   -6.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -1.8931   -6.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302   -0.3402   -6.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580   -1.6947   -1.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -2.0759   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774   -1.5773   -2.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8679    0.3711   -1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -1.2942    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    0.1884   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    0.0020    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 11  1  0  0  0  0
 26 27  1  1  0  0  0
 23 17  1  0  0  0  0
 26 11  1  0  0  0  0
 26  5  1  0  0  0  0
 24 25  1  0  0  0  0
 24 23  1  0  0  0  0
 17 18  2  0  0  0  0
 18 20  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 16  1  0  0  0  0
 20 21  2  0  0  0  0
 11 12  1  0  0  0  0
 18 19  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  6  0  0  0
 16 15  1  0  0  0  0
 13 14  1  0  0  0  0
 25 52  1  1  0  0  0
 14 25  1  0  0  0  0
  8  9  1  1  0  0  0
  5  6  1  0  0  0  0
  5  4  1  0  0  0  0
 25 26  1  0  0  0  0
  8 10  1  0  0  0  0
  6  7  2  0  0  0  0
 23 49  1  1  0  0  0
 11 40  1  6  0  0  0
  4  2  1  0  0  0  0
 17 16  1  0  0  0  0
  2  3  2  0  0  0  0
  7  8  1  0  0  0  0
  2  1  1  0  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
  5 31  1  1  0  0  0
  6 32  1  0  0  0  0
  7 33  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 16 45  1  6  0  0  0
 27 53  1  0  0  0  0
 27 54  1  0  0  0  0
 27 55  1  0  0  0  0
 19 46  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
 10 37  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025251

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]34O[C@]3([H])C3=C(C(=O)O[C@]3([H])C([H])([H])[C@@]4([H])[C@]2(C([H])([H])[H])[C@]1([H])OC(=O)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O5/c1-11-17-13(26-19(11)24)10-15-21(5)14(6-9-22(15)18(17)27-22)20(3,4)8-7-16(21)25-12(2)23/h7-8,13-16,18H,6,9-10H2,1-5H3/t13-,14-,15+,16-,18-,21-,22+/m1/s1

> <INCHI_KEY>
IWHCUIYQYFOMEF-FBERYXRISA-N

> <FORMULA>
C22H28O5

> <MOLECULAR_WEIGHT>
372.461

> <EXACT_MASS>
372.193674002

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.42957377141201

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,8R,10S,11R,12R,16R)-5,11,15,15-tetramethyl-6-oxo-2,7-dioxapentacyclo[8.8.0.0^{1,3}.0^{4,8}.0^{11,16}]octadeca-4,13-dien-12-yl acetate

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
2.991234184999999

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.079093702023115

> <JCHEM_PKA_STRONGEST_BASIC>
-4.259613141713822

> <JCHEM_POLAR_SURFACE_AREA>
65.13

> <JCHEM_REFRACTIVITY>
99.05299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,8R,10S,11R,12R,16R)-5,11,15,15-tetramethyl-6-oxo-2,7-dioxapentacyclo[8.8.0.0^{1,3}.0^{4,8}.0^{11,16}]octadeca-4,13-dien-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -5.2089   -0.5929   -0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -1.0496    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433   -2.1558    0.9756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961   -0.0560    0.4091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6979   -0.3417    0.9625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7302    0.1247    2.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510    1.3036    2.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6477    2.3578    1.9006 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7601    2.7121    2.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    3.6306    2.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792    1.9229    0.3817 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3291    2.6996   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551    2.4883   -1.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039    1.0342   -2.3431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4025    0.9471   -3.7305 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9091    0.4685   -3.4356 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1437   -0.9646   -3.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -1.7452   -4.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9482   -1.4190   -5.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3330   -3.1290   -4.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6012   -4.1242   -4.6830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -3.1224   -2.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7262   -1.7794   -2.3175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6834   -1.3925   -1.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8225    0.1003   -1.4389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5822    0.3700    0.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7838   -0.2023    0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0532   -0.3575   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9497   -1.3942   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864    0.2803    0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5030   -1.4208    0.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -0.5546    3.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3241    1.5416    3.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    3.5971    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    2.9463    3.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4801    1.9019    2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292    3.9795    3.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5574    3.4453    1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1408    4.4552    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760    2.2138    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572    2.3987   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    3.7741   -0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    3.0080   -2.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    2.9617   -2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7469    1.0816   -3.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -1.7728   -6.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -1.8931   -6.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302   -0.3402   -6.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580   -1.6947   -1.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -2.0759   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774   -1.5773   -2.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8679    0.3711   -1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -1.2942    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    0.1884   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    0.0020    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 11  1  0
 26 27  1  1
 23 17  1  0
 26 11  1  0
 26  5  1  0
 24 25  1  0
 24 23  1  0
 17 18  2  0
 18 20  1  0
 20 22  1  0
 22 23  1  0
 14 16  1  0
 20 21  2  0
 11 12  1  0
 18 19  1  0
 12 13  1  0
 14 15  1  6
 16 15  1  0
 13 14  1  0
 25 52  1  1
 14 25  1  0
  8  9  1  1
  5  6  1  0
  5  4  1  0
 25 26  1  0
  8 10  1  0
  6  7  2  0
 23 49  1  1
 11 40  1  6
  4  2  1  0
 17 16  1  0
  2  3  2  0
  7  8  1  0
  2  1  1  0
 24 50  1  0
 24 51  1  0
  5 31  1  1
  6 32  1  0
  7 33  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 16 45  1  6
 27 53  1  0
 27 54  1  0
 27 55  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.209  -0.593  -0.126  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.921  -1.050   0.487  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.743  -2.156   0.976  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.996  -0.056   0.409  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.698  -0.342   0.963  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.730   0.125   2.390  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.251   1.304   2.809  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.648   2.358   1.901  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.760   2.712   2.427  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.517   3.631   2.062  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.679   1.923   0.382  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.329   2.700  -0.484  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.055   2.488  -1.961  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.004   1.034  -2.343  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.403   0.947  -3.731  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.909   0.469  -3.436  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.144  -0.965  -3.477  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.527  -1.745  -4.487  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.948  -1.419  -5.866  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.333  -3.129  -4.035  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.601  -4.124  -4.683  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.775  -3.122  -2.792  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.726  -1.779  -2.317  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.683  -1.393  -1.863  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.823   0.100  -1.439  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.582   0.370   0.111  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.784  -0.202   0.560  0.00  0.00           C+0
HETATM   28  H   UNK     0      -5.053  -0.358  -1.182  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.950  -1.394  -0.053  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.586   0.280   0.412  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.503  -1.421   0.959  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.183  -0.555   3.109  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.324   1.542   3.870  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.168   3.597   1.926  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.735   2.946   3.499  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.480   1.902   2.297  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.529   3.979   3.102  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.557   3.445   1.770  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.141   4.455   1.447  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.676   2.214   0.012  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.357   2.399  -0.256  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.263   3.774  -0.279  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.825   3.008  -2.543  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.902   2.962  -2.218  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.747   1.082  -3.752  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.968  -1.773  -6.047  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.283  -1.893  -6.595  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.930  -0.340  -6.050  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.458  -1.695  -1.512  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.023  -2.076  -1.079  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.377  -1.577  -2.697  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.868   0.371  -1.643  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.798  -1.294   0.483  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.612   0.188  -0.038  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.002   0.002   1.609  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5   26    6    4   31                                             
CONECT    6    5    7   32                                                  
CONECT    7    6    8   33                                                  
CONECT    8   11    9   10    7                                             
CONECT    9    8   34   35   36                                             
CONECT   10    8   37   38   39                                             
CONECT   11    8   26   12   40                                             
CONECT   12   11   13   41   42                                             
CONECT   13   12   14   43   44                                             
CONECT   14   16   15   13   25                                             
CONECT   15   14   16                                                       
CONECT   16   14   15   17   45                                             
CONECT   17   23   18   16                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   46   47   48                                             
CONECT   20   18   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   17   24   22   49                                             
CONECT   24   25   23   50   51                                             
CONECT   25   24   52   14   26                                             
CONECT   26   27   11    5   25                                             
CONECT   27   26   53   54   55                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   16                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   27                                                            
CONECT   54   27                                                            
CONECT   55   27                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

RDKit          3D

55 59  0  0  0  0  0  0  0  0999 V2000
   -5.2089   -0.5929   -0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -1.0496    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433   -2.1558    0.9756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961   -0.0560    0.4091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6979   -0.3417    0.9625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7302    0.1247    2.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510    1.3036    2.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6477    2.3578    1.9006 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7601    2.7121    2.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    3.6306    2.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792    1.9229    0.3817 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3291    2.6996   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551    2.4883   -1.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039    1.0342   -2.3431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4025    0.9471   -3.7305 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9091    0.4685   -3.4356 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1437   -0.9646   -3.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -1.7452   -4.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9482   -1.4190   -5.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3330   -3.1290   -4.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6012   -4.1242   -4.6830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -3.1224   -2.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7262   -1.7794   -2.3175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6834   -1.3925   -1.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8225    0.1003   -1.4389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5822    0.3700    0.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7838   -0.2023    0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0532   -0.3575   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9497   -1.3942   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864    0.2803    0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5030   -1.4208    0.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -0.5546    3.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3241    1.5416    3.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    3.5971    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    2.9463    3.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4801    1.9019    2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292    3.9795    3.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5574    3.4453    1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1408    4.4552    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760    2.2138    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572    2.3987   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    3.7741   -0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    3.0080   -2.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    2.9617   -2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7469    1.0816   -3.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -1.7728   -6.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -1.8931   -6.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302   -0.3402   -6.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580   -1.6947   -1.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -2.0759   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774   -1.5773   -2.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8679    0.3711   -1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -1.2942    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    0.1884   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    0.0020    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 11  1  0
 26 27  1  1
 23 17  1  0
 26 11  1  0
 26  5  1  0
 24 25  1  0
 24 23  1  0
 17 18  2  0
 18 20  1  0
 20 22  1  0
 22 23  1  0
 14 16  1  0
 20 21  2  0
 11 12  1  0
 18 19  1  0
 12 13  1  0
 14 15  1  6
 16 15  1  0
 13 14  1  0
 25 52  1  1
 14 25  1  0
  8  9  1  1
  5  6  1  0
  5  4  1  0
 25 26  1  0
  8 10  1  0
  6  7  2  0
 23 49  1  1
 11 40  1  6
  4  2  1  0
 17 16  1  0
  2  3  2  0
  7  8  1  0
  2  1  1  0
 24 50  1  0
 24 51  1  0
  5 31  1  1
  6 32  1  0
  7 33  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 16 45  1  6
 27 53  1  0
 27 54  1  0
 27 55  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
1beta-Acetoxy-8beta,14beta-epoxy-ent-abieta-2(3),13(15)-diene-16,12-olide	ChEBI
1b-Acetoxy-8b,14b-epoxy-ent-abieta-2(3),13(15)-diene-16,12-olide	Generator
1Β-acetoxy-8β,14β-epoxy-ent-abieta-2(3),13(15)-diene-16,12-olide	Generator

Chemical Formula

C₂₂H₂₈O₅

Average Mass

372.4610 Da

Monoisotopic Mass

372.19367 Da

IUPAC Name

(1S,3R,8R,10S,11R,12R,16R)-5,11,15,15-tetramethyl-6-oxo-2,7-dioxapentacyclo[8.8.0.0^{1,3}.0^{4,8}.0^{11,16}]octadeca-4,13-dien-12-yl acetate

Traditional Name

(1S,3R,8R,10S,11R,12R,16R)-5,11,15,15-tetramethyl-6-oxo-2,7-dioxapentacyclo[8.8.0.0^{1,3}.0^{4,8}.0^{11,16}]octadeca-4,13-dien-12-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]34O[C@]3([H])C3=C(C(=O)O[C@]3([H])C([H])([H])[C@@]4([H])[C@]2(C([H])([H])[H])[C@]1([H])OC(=O)C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H28O5/c1-11-17-13(26-19(11)24)10-15-21(5)14(6-9-22(15)18(17)27-22)20(3,4)8-7-16(21)25-12(2)23/h7-8,13-16,18H,6,9-10H2,1-5H3/t13-,14-,15+,16-,18-,21-,22+/m1/s1

InChI Key

IWHCUIYQYFOMEF-FBERYXRISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gelonium aequoreum	KNApSAcK Database	22123792
Suregada aequorea	JEOL database	Lee, C.-L., et al, Phytochem. 69, 276 (2008)

Chemical Taxonomy

Classification

Not classified

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	3.77	ALOGPS
logP	2.99	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.05 m³·mol⁻¹	ChemAxon
Polarizability	40.43 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00033860

Chemspider ID

28284865

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

65955

Good Scents ID

Not Available

References

General References

Yang JC, Lu MC, Lee CL, Chen GY, Lin YY, Chang FR, Wu YC: Selective targeting of breast cancer cells through ROS-mediated mechanisms potentiates the lethality of paclitaxel by a novel diterpene, gelomulide K. Free Radic Biol Med. 2011 Aug 1;51(3):641-57. doi: 10.1016/j.freeradbiomed.2011.05.012. Epub 2011 May 15. [PubMed:21641992 ]
Lee, C.-L., et al. (2008). Lee, C.-L., et al, Phytochem. 69, 276 (2008). Phytochem..

Showing NP-Card for gelomulide K (NP0025251)

MOL for NP0025251 (gelomulide K)

3D MOL for NP0025251 (gelomulide K)

3D SDF for NP0025251 (gelomulide K)

3D-SDF for NP0025251 (gelomulide K)

PDB for NP0025251 (gelomulide K)

3D PDB for NP0025251 (gelomulide K)

SMILES for NP0025251 (gelomulide K)

INCHI for NP0025251 (gelomulide K)

Structure for NP0025251 (gelomulide K)

3D Structure for NP0025251 (gelomulide K)