NP-MRD: Showing NP-Card for 13-epi-9-deacetylxenicin (NP0028504)

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Record Information

Version

2.0

Created at

2021-06-19 20:22:39 UTC

Updated at

2021-06-29 23:55:20 UTC

NP-MRD ID

NP0028504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-epi-9-deacetylxenicin

Provided By

JEOL Database JEOL Logo

Description

13-epi-9-deacetylxenicin is found in Xenia blumi and Xenia plicata. 13-epi-9-deacetylxenicin was first documented in 2005 (El-Gamal, A.A.H., et al.). Based on a literature review very few articles have been published on CHEMBL442990.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122223D          

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     RDKit          3D

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  Mrv1652306192122223D          

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   -3.2714    0.8445   -3.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274    2.3932   -4.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934    0.1799   -3.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536    1.0239    4.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    1.5067    2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -0.2529    3.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0  0  0  0
 22 23  1  0  0  0  0
 14 15  2  0  0  0  0
 23 24  1  0  0  0  0
 15 16  1  0  0  0  0
 11 12  1  0  0  0  0
 16 17  1  0  0  0  0
  3  2  1  0  0  0  0
 16 18  1  0  0  0  0
  2 24  1  0  0  0  0
 16 19  1  1  0  0  0
 24 11  1  0  0  0  0
  2  1  2  3  0  0  0
 11 10  1  0  0  0  0
 24 52  1  1  0  0  0
 10  9  1  0  0  0  0
 11 39  1  6  0  0  0
  9  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 20 21  2  0  0  0  0
  7  5  1  0  0  0  0
  6  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  1  0  0  0
 20 22  1  0  0  0  0
 12 13  2  0  0  0  0
 20 12  1  0  0  0  0
  5 31  1  6  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
 10 37  1  0  0  0  0
 10 38  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
 13 40  1  0  0  0  0
 14 41  1  0  0  0  0
 15 42  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
 19 49  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(\C([H])=C(/[H])\C(\[H])=C1\C(=O)OC([H])([H])[C@@]2([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@]3([H])O[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]12[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-13-7-8-17-20(4,24-17)11-9-14-15(6-5-10-19(2,3)22)18(21)23-12-16(13)14/h5-6,10,14,16-17,22H,1,7-9,11-12H2,2-4H3/b10-5+,15-6+/t14-,16+,17+,20+/m1/s1

> <INCHI_KEY>
YXTOBXGODMEKLL-GQSXVQPESA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.77084706727306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,6S,10R,14E)-14-[(2E)-4-hydroxy-4-methylpent-2-en-1-ylidene]-4-methyl-9-methylidene-5,12-dioxatricyclo[8.4.0.0^{4,6}]tetradecan-13-one

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
2.9401328946666663

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.911528583100132

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5244281170855096

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
94.819

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6S,10R,14E)-14-[(2E)-4-hydroxy-4-methylpent-2-en-1-ylidene]-4-methyl-9-methylidene-5,12-dioxatricyclo[8.4.0.0^{4,6}]tetradecan-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
   -2.2705   -1.0883    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1297   -1.1462    2.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7531   -2.4163    3.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0507   -3.4842    2.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836   -2.8887    1.2349 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1531   -3.5079    1.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721   -2.2002    1.6493 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7587   -2.2687    3.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6328   -1.0797    0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0799    0.2993    1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5277    0.4398    1.1095 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1839    1.8729    0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2573    2.3661   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5028    1.6101   -1.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754    2.1762   -2.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2663    1.4688   -4.0519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5813    2.1881   -5.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755    1.3973   -4.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7773    0.1292   -4.0066 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3671    2.8603    1.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260    3.9793    1.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117    2.3927    3.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8447    1.2414    3.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    0.0351    2.4527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5650   -0.1998    1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9423   -1.9407    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1150   -2.1568    3.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.8628    3.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8098   -4.0574    1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -4.2022    2.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653   -2.5665    0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325   -3.1585    3.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855   -1.3931    3.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8519   -2.3050    2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7289   -1.0381    0.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590   -1.2792   -0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    1.0188    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526    0.5761    2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -0.2186    0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4493    3.4390   -0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065    0.5418   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959    3.2435   -2.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7464    1.6492   -6.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5048    2.2291   -5.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493    3.2129   -5.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016    0.8565   -5.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2714    0.8445   -3.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274    2.3932   -4.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934    0.1799   -3.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536    1.0239    4.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    1.5067    2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -0.2529    3.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 22 23  1  0
 14 15  2  0
 23 24  1  0
 15 16  1  0
 11 12  1  0
 16 17  1  0
  3  2  1  0
 16 18  1  0
  2 24  1  0
 16 19  1  1
 24 11  1  0
  2  1  2  3
 11 10  1  0
 24 52  1  1
 10  9  1  0
 11 39  1  6
  9  7  1  0
  3  4  1  0
  4  5  1  0
 20 21  2  0
  7  5  1  0
  6  7  1  0
  5  6  1  0
  7  8  1  1
 20 22  1  0
 12 13  2  0
 20 12  1  0
  5 31  1  6
 23 50  1  0
 23 51  1  0
  3 27  1  0
  3 28  1  0
 10 37  1  0
 10 38  1  0
  9 35  1  0
  9 36  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
  1 25  1  0
  1 26  1  0
  4 29  1  0
  4 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      -2.271  -1.088   1.625  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.130  -1.146   2.335  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.753  -2.416   3.084  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.051  -3.484   2.228  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.884  -2.889   1.235  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.153  -3.508   1.038  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.172  -2.200   1.649  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.759  -2.269   3.029  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.633  -1.080   0.761  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.080   0.299   1.161  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.528   0.440   1.109  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.184   1.873   0.759  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.257   2.366  -0.414  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.503   1.610  -1.623  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.975   2.176  -2.747  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.266   1.469  -4.052  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.581   2.188  -5.217  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.776   1.397  -4.284  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.777   0.129  -4.007  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.367   2.860   1.855  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.826   3.979   1.679  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.012   2.393   3.078  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.845   1.241   3.116  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.162   0.035   2.453  0.00  0.00           C+0
HETATM   25  H   UNK     0      -2.565  -0.200   1.073  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.942  -1.941   1.562  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.115  -2.157   3.937  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.650  -2.863   3.533  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.810  -4.057   1.681  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.456  -4.202   2.883  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.365  -2.567   0.339  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.433  -3.159   3.576  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.486  -1.393   3.623  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.852  -2.305   2.971  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.729  -1.038   0.781  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.359  -1.279  -0.283  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.533   1.019   0.464  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.453   0.576   2.155  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.168  -0.219   0.313  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.449   3.439  -0.485  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.307   0.542  -1.615  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.196   3.244  -2.748  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.746   1.649  -6.157  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.505   2.229  -5.071  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.949   3.213  -5.337  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.002   0.857  -5.210  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.271   0.845  -3.477  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.227   2.393  -4.347  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.193   0.180  -3.979  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.054   1.024   4.170  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.803   1.507   2.652  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.632  -0.253   3.151  0.00  0.00           H+0
CONECT    1    2   25   26                                                  
CONECT    2    3   24    1                                                  
CONECT    3    2    4   27   28                                             
CONECT    4    3    5   29   30                                             
CONECT    5    4    7    6   31                                             
CONECT    6    7    5                                                       
CONECT    7    9    5    6    8                                             
CONECT    8    7   32   33   34                                             
CONECT    9   10    7   35   36                                             
CONECT   10   11    9   37   38                                             
CONECT   11   12   24   10   39                                             
CONECT   12   11   13   20                                                  
CONECT   13   14   12   40                                                  
CONECT   14   13   15   41                                                  
CONECT   15   14   16   42                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16   43   44   45                                             
CONECT   18   16   46   47   48                                             
CONECT   19   16   49                                                       
CONECT   20   21   22   12                                                  
CONECT   21   20                                                            
CONECT   22   23   20                                                       
CONECT   23   22   24   50   51                                             
CONECT   24   23    2   11   52                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

RDKit          3D

52 54  0  0  0  0  0  0  0  0999 V2000
   -2.2705   -1.0883    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1297   -1.1462    2.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7531   -2.4163    3.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0507   -3.4842    2.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836   -2.8887    1.2349 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1531   -3.5079    1.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721   -2.2002    1.6493 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7587   -2.2687    3.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6328   -1.0797    0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0799    0.2993    1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5277    0.4398    1.1095 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1839    1.8729    0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2573    2.3661   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5028    1.6101   -1.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754    2.1762   -2.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2663    1.4688   -4.0519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5813    2.1881   -5.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755    1.3973   -4.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7773    0.1292   -4.0066 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3671    2.8603    1.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260    3.9793    1.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117    2.3927    3.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8447    1.2414    3.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    0.0351    2.4527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5650   -0.1998    1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9423   -1.9407    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1150   -2.1568    3.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.8628    3.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8098   -4.0574    1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -4.2022    2.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653   -2.5665    0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325   -3.1585    3.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855   -1.3931    3.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8519   -2.3050    2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7289   -1.0381    0.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590   -1.2792   -0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    1.0188    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526    0.5761    2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -0.2186    0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4493    3.4390   -0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065    0.5418   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959    3.2435   -2.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7464    1.6492   -6.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5048    2.2291   -5.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493    3.2129   -5.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016    0.8565   -5.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2714    0.8445   -3.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274    2.3932   -4.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934    0.1799   -3.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536    1.0239    4.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    1.5067    2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -0.2529    3.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 22 23  1  0
 14 15  2  0
 23 24  1  0
 15 16  1  0
 11 12  1  0
 16 17  1  0
  3  2  1  0
 16 18  1  0
  2 24  1  0
 16 19  1  1
 24 11  1  0
  2  1  2  3
 11 10  1  0
 24 52  1  1
 10  9  1  0
 11 39  1  6
  9  7  1  0
  3  4  1  0
  4  5  1  0
 20 21  2  0
  7  5  1  0
  6  7  1  0
  5  6  1  0
  7  8  1  1
 20 22  1  0
 12 13  2  0
 20 12  1  0
  5 31  1  6
 23 50  1  0
 23 51  1  0
  3 27  1  0
  3 28  1  0
 10 37  1  0
 10 38  1  0
  9 35  1  0
  9 36  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
  1 25  1  0
  1 26  1  0
  4 29  1  0
  4 30  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

(1S,4S,6S,10R,14E)-14-[(2E)-4-hydroxy-4-methylpent-2-en-1-ylidene]-4-methyl-9-methylidene-5,12-dioxatricyclo[8.4.0.0^{4,6}]tetradecan-13-one

Traditional Name

(1S,4S,6S,10R,14E)-14-[(2E)-4-hydroxy-4-methylpent-2-en-1-ylidene]-4-methyl-9-methylidene-5,12-dioxatricyclo[8.4.0.0^{4,6}]tetradecan-13-one

CAS Registry Number

Not Available

SMILES

[H]OC(\C([H])=C(/[H])\C(\[H])=C1\C(=O)OC([H])([H])[C@@]2([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@]3([H])O[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]12[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H28O4/c1-13-7-8-17-20(4,24-17)11-9-14-15(6-5-10-19(2,3)22)18(21)23-12-16(13)14/h5-6,10,14,16-17,22H,1,7-9,11-12H2,2-4H3/b10-5+,15-6+/t14-,16+,17+,20+/m1/s1

InChI Key

YXTOBXGODMEKLL-GQSXVQPESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Xenia blumi	JEOL database	El-Gamal, A.A.H., et al, J. Nat. Prod. 68, 1336 (2005)
Xenia plicata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta valerolactone
Delta_valerolactone
Oxane
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.99	ALOGPS
logP	2.94	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	17.91	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.82 m³·mol⁻¹	ChemAxon
Polarizability	36.77 Å³	ChemAxon
Number of Rings	3	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

Not Available

Chemspider ID

9488539

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11313572

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

El-Gamal, A.A.H., et al. (2005). El-Gamal, A.A.H., et al, J. Nat. Prod. 68, 1336 (2005). J. Nat. Prod..

Showing NP-Card for 13-epi-9-deacetylxenicin (NP0028504)

MOL for NP0028504 (13-epi-9-deacetylxenicin)

3D MOL for NP0028504 (13-epi-9-deacetylxenicin)

3D SDF for NP0028504 (13-epi-9-deacetylxenicin)

3D-SDF for NP0028504 (13-epi-9-deacetylxenicin)

PDB for NP0028504 (13-epi-9-deacetylxenicin)

3D PDB for NP0028504 (13-epi-9-deacetylxenicin)

SMILES for NP0028504 (13-epi-9-deacetylxenicin)

INCHI for NP0028504 (13-epi-9-deacetylxenicin)

Structure for NP0028504 (13-epi-9-deacetylxenicin)

3D Structure for NP0028504 (13-epi-9-deacetylxenicin)