NP-MRD: Showing NP-Card for Xeniolide H (NP0026123)

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Record Information

Version

2.0

Created at

2021-06-19 18:03:54 UTC

Updated at

2021-06-29 23:51:28 UTC

NP-MRD ID

NP0026123

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xeniolide H

Provided By

JEOL Database JEOL Logo

Description

Xeniolide H is found in Xenia umbellata. Xeniolide H was first documented in 2002 (PMID: 12502332). Based on a literature review very few articles have been published on xeniolide-H (PMID: 16562830).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120033D          

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     RDKit          3D

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    2.4735    0.6460    4.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202   -3.4817    2.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -3.2602    0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3699   -4.5249    1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  2  0  0  0  0
 12 11  1  0  0  0  0
 20 21  1  0  0  0  0
  5  4  1  0  0  0  0
 20 22  1  0  0  0  0
  7  9  1  0  0  0  0
 13 14  2  0  0  0  0
  9 10  1  0  0  0  0
  2  1  2  3  0  0  0
 12 13  1  0  0  0  0
 12 40  1  6  0  0  0
 11 16  1  0  0  0  0
 11 39  1  6  0  0  0
  5  7  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
 15 13  1  0  0  0  0
 10 11  1  0  0  0  0
  7  8  1  1  0  0  0
  3  4  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  6  0  0  0
 16 23  1  0  0  0  0
  3  2  1  0  0  0  0
 23 24  1  0  0  0  0
 17 18  2  0  0  0  0
  5 31  1  1  0  0  0
  4 29  1  0  0  0  0
  4 30  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
  3 27  1  0  0  0  0
  3 28  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
 17 41  1  0  0  0  0
 18 42  1  0  0  0  0
 19 43  1  0  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 24 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026123

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1(OC(=O)[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])=C(/[H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-13(2)6-5-10-20(12-21)15-9-11-19(4)16(23-19)8-7-14(3)17(15)18(22)24-20/h5-6,10,15-17,21H,3,7-9,11-12H2,1-2,4H3/b10-5+/t15-,16-,17-,19-,20-/m0/s1

> <INCHI_KEY>
JYBJATPZXXGWRQ-JFJONPEWSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.08291708760141

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,6S,10R,13R)-13-(hydroxymethyl)-4-methyl-9-methylidene-13-[(1E)-4-methylpenta-1,3-dien-1-yl]-5,12-dioxatricyclo[8.3.0.0^{4,6}]tridecan-11-one

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
2.918554759333334

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.288696116482985

> <JCHEM_PKA_STRONGEST_BASIC>
-3.109924318650342

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
94.33109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6S,10R,13R)-13-(hydroxymethyl)-4-methyl-9-methylidene-13-[(1E)-4-methylpenta-1,3-dien-1-yl]-5,12-dioxatricyclo[8.3.0.0^{4,6}]tridecan-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
   -5.8009   -0.0367    2.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004    0.3073    2.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1115    1.7698    2.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3950    2.6175    1.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5190    2.1771    0.0713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8741    2.4271   -1.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557    1.0518   -0.8547 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3607    0.5472   -1.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551    0.1233   -1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6717   -1.0478   -0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026   -0.6321    1.1612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4263   -0.7727    2.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6263   -0.9018    3.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -0.7539    4.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277   -1.2207    3.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1634   -1.4581    1.8016 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1877   -0.9263    1.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -0.3588    2.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810    0.1288    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3740    0.7100    2.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6297    1.1653    1.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798    0.9744    3.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1822   -2.9946    1.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798   -3.5572    1.7480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1250   -1.0727    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5806    0.7104    2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531    1.8514    2.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6661    2.2064    3.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672    3.6656    1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576    2.5842    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4724    2.3347    0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5277   -0.3660   -0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1120    1.2830   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5469    0.3099   -2.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036    0.6617   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0776   -0.2816   -2.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5750   -1.6687   -0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8780   -1.6723   -0.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9596    0.4077    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300   -1.7365    2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3860   -1.0243    0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9308   -0.2569    3.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5207    0.0044    0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7675    2.2436    1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5025    0.6492    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6044    0.9640    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2235    0.4569    4.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4882    2.0480    3.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    0.6460    4.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202   -3.4817    2.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -3.2602    0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3699   -4.5249    1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
 18 19  1  0
 20 19  2  0
 12 11  1  0
 20 21  1  0
  5  4  1  0
 20 22  1  0
  7  9  1  0
 13 14  2  0
  9 10  1  0
  2  1  2  3
 12 13  1  0
 12 40  1  6
 11 16  1  0
 11 39  1  6
  5  7  1  0
  6  5  1  0
  7  6  1  0
 15 13  1  0
 10 11  1  0
  7  8  1  1
  3  4  1  0
 16 15  1  0
 16 17  1  6
 16 23  1  0
  3  2  1  0
 23 24  1  0
 17 18  2  0
  5 31  1  1
  4 29  1  0
  4 30  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
  3 27  1  0
  3 28  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
  1 25  1  0
  1 26  1  0
 23 50  1  0
 23 51  1  0
 24 52  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      -5.801  -0.037   2.384  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.500   0.307   2.310  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.112   1.770   2.442  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.395   2.618   1.186  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.519   2.177   0.071  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.874   2.427  -1.284  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.956   1.052  -0.855  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.361   0.547  -1.020  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.855   0.123  -1.270  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.672  -1.048  -0.283  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.303  -0.632   1.161  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.426  -0.773   2.205  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.626  -0.902   3.492  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.042  -0.754   4.631  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.328  -1.221   3.212  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.163  -1.458   1.802  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.188  -0.926   1.345  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.121  -0.359   2.127  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.381   0.129   1.610  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.374   0.710   2.311  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.630   1.165   1.610  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.380   0.974   3.793  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.182  -2.995   1.579  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.480  -3.557   1.748  0.00  0.00           O+0
HETATM   25  H   UNK     0      -6.125  -1.073   2.342  0.00  0.00           H+0
HETATM   26  H   UNK     0      -6.581   0.710   2.504  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.053   1.851   2.719  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.666   2.206   3.284  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.167   3.666   1.414  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.458   2.584   0.927  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.472   2.335   0.303  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.528  -0.366  -0.445  0.00  0.00           H+0
HETATM   33  H   UNK     0      -6.112   1.283  -0.720  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.547   0.310  -2.074  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.904   0.662  -1.366  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.078  -0.282  -2.265  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.575  -1.669  -0.275  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.878  -1.672  -0.708  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.960   0.408   1.161  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.930  -1.736   2.068  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.386  -1.024   0.278  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.931  -0.257   3.192  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.521   0.004   0.535  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.768   2.244   1.743  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.503   0.649   2.024  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.604   0.964   0.534  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.223   0.457   4.262  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.488   2.048   3.981  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.474   0.646   4.305  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.520  -3.482   2.306  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.839  -3.260   0.574  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.370  -4.525   1.776  0.00  0.00           H+0
CONECT    1    2   25   26                                                  
CONECT    2   12    1    3                                                  
CONECT    3    4    2   27   28                                             
CONECT    4    5    3   29   30                                             
CONECT    5    4    7    6   31                                             
CONECT    6    5    7                                                       
CONECT    7    9    5    6    8                                             
CONECT    8    7   32   33   34                                             
CONECT    9    7   10   35   36                                             
CONECT   10    9   11   37   38                                             
CONECT   11   12   16   39   10                                             
CONECT   12    2   11   13   40                                             
CONECT   13   14   12   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   11   15   17   23                                             
CONECT   17   16   18   41                                                  
CONECT   18   19   17   42                                                  
CONECT   19   18   20   43                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   44   45   46                                             
CONECT   22   20   47   48   49                                             
CONECT   23   16   24   50   51                                             
CONECT   24   23   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   12                                                            
CONECT   41   17                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   21                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
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
   -5.8009   -0.0367    2.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004    0.3073    2.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1115    1.7698    2.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3950    2.6175    1.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5190    2.1771    0.0713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8741    2.4271   -1.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557    1.0518   -0.8547 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3607    0.5472   -1.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551    0.1233   -1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6717   -1.0478   -0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026   -0.6321    1.1612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4263   -0.7727    2.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6263   -0.9018    3.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -0.7539    4.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277   -1.2207    3.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1634   -1.4581    1.8016 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1877   -0.9263    1.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -0.3588    2.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810    0.1288    1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3740    0.7100    2.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6297    1.1653    1.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798    0.9744    3.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1822   -2.9946    1.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798   -3.5572    1.7480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1250   -1.0727    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5806    0.7104    2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531    1.8514    2.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6661    2.2064    3.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672    3.6656    1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576    2.5842    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4724    2.3347    0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5277   -0.3660   -0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1120    1.2830   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5469    0.3099   -2.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036    0.6617   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0776   -0.2816   -2.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5750   -1.6687   -0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8780   -1.6723   -0.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9596    0.4077    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300   -1.7365    2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3860   -1.0243    0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9308   -0.2569    3.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5207    0.0044    0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7675    2.2436    1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5025    0.6492    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6044    0.9640    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2235    0.4569    4.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4882    2.0480    3.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    0.6460    4.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202   -3.4817    2.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -3.2602    0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3699   -4.5249    1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
 18 19  1  0
 20 19  2  0
 12 11  1  0
 20 21  1  0
  5  4  1  0
 20 22  1  0
  7  9  1  0
 13 14  2  0
  9 10  1  0
  2  1  2  3
 12 13  1  0
 12 40  1  6
 11 16  1  0
 11 39  1  6
  5  7  1  0
  6  5  1  0
  7  6  1  0
 15 13  1  0
 10 11  1  0
  7  8  1  1
  3  4  1  0
 16 15  1  0
 16 17  1  6
 16 23  1  0
  3  2  1  0
 23 24  1  0
 17 18  2  0
  5 31  1  1
  4 29  1  0
  4 30  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
  3 27  1  0
  3 28  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
  1 25  1  0
  1 26  1  0
 23 50  1  0
 23 51  1  0
 24 52  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,13R)-13-(hydroxymethyl)-4-methyl-9-methylidene-13-[(1E)-4-methylpenta-1,3-dien-1-yl]-5,12-dioxatricyclo[8.3.0.0^{4,6}]tridecan-11-one

Traditional Name

(1S,4S,6S,10R,13R)-13-(hydroxymethyl)-4-methyl-9-methylidene-13-[(1E)-4-methylpenta-1,3-dien-1-yl]-5,12-dioxatricyclo[8.3.0.0^{4,6}]tridecan-11-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1(OC(=O)[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])=C(/[H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H28O4/c1-13(2)6-5-10-20(12-21)15-9-11-19(4)16(23-19)8-7-14(3)17(15)18(22)24-20/h5-6,10,15-17,21H,3,7-9,11-12H2,1-2,4H3/b10-5+/t15-,16-,17-,19-,20-/m0/s1

InChI Key

JYBJATPZXXGWRQ-JFJONPEWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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 umbellata	JEOL database	Duh, C.-Y., et al, J. Nat. Prod. 65, 1882 (2002)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.95	ALOGPS
logP	2.92	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.29	ChemAxon
pKa (Strongest Basic)	-3.1	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	3	ChemAxon
Refractivity	94.33 m³·mol⁻¹	ChemAxon
Polarizability	37.08 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

9177287

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11002095

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

El-Gamal AA, Wang SK, Duh CY: Cytotoxic xenia diterpenoids from the soft coral Xenia umbellata. J Nat Prod. 2006 Mar;69(3):338-41. doi: 10.1021/np058093r. [PubMed:16562830 ]
Duh CY, El-Gamal AA, Chiang CY, Chu CJ, Wang SK, Dai CF: New cytotoxic xenia diterpenoids from the Formosan soft coral Xenia umbellata. J Nat Prod. 2002 Dec;65(12):1882-5. doi: 10.1021/np020268z. [PubMed:12502332 ]
Duh, C.-Y., et al. (2002). Duh, C.-Y., et al, J. Nat. Prod. 65, 1882 (2002). J. Nat. Prod..

Showing NP-Card for Xeniolide H (NP0026123)

MOL for NP0026123 (Xeniolide H)

3D MOL for NP0026123 (Xeniolide H)

3D SDF for NP0026123 (Xeniolide H)

3D-SDF for NP0026123 (Xeniolide H)

PDB for NP0026123 (Xeniolide H)

3D PDB for NP0026123 (Xeniolide H)

SMILES for NP0026123 (Xeniolide H)

INCHI for NP0026123 (Xeniolide H)

Structure for NP0026123 (Xeniolide H)

3D Structure for NP0026123 (Xeniolide H)