NP-MRD: Showing NP-Card for Epipolone (NP0025516)

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Record Information

Version

1.0

Created at

2021-06-19 17:37:17 UTC

Updated at

2021-06-29 23:50:32 UTC

NP-MRD ID

NP0025516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epipolone

Provided By

JEOL Database JEOL Logo

Description

Epipolone is found in Epipolasis reiswigi and Myrmekioderma gyroderma. It was first documented in 2001 (PMID: 11559187). Based on a literature review very few articles have been published on Epipolone (PMID: 33651529) (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454) (PMID: 26389451).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119373D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192119373D          

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   -5.1690    3.8928    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2200    2.5599    2.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    0.9911    2.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    1.7385    2.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956    0.7980    0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017   -0.2524    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1569    1.0894    1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4356   -0.0869   -1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0  0  0  0
 14 15  1  0  0  0  0
 19 17  1  0  0  0  0
 15 17  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
  7  9  1  0  0  0  0
 22  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  6  0  0  0
  6  7  1  0  0  0  0
 12 13  1  6  0  0  0
  7 22  1  0  0  0  0
 15 43  1  6  0  0  0
 17 18  1  6  0  0  0
 12 21  1  0  0  0  0
 22 52  1  6  0  0  0
 11 12  1  0  0  0  0
  4  2  1  0  0  0  0
 21 20  1  0  0  0  0
  2  1  1  0  0  0  0
 11  9  1  0  0  0  0
  2  3  1  0  0  0  0
 12 14  1  0  0  0  0
 21 51  1  1  0  0  0
 21 22  1  0  0  0  0
  9 10  2  0  0  0  0
 11 36  1  0  0  0  0
 11 37  1  0  0  0  0
  5 30  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
 13 38  1  0  0  0  0
 13 39  1  0  0  0  0
 13 40  1  0  0  0  0
 18 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
  2 26  1  1  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025516

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-12(2)13-6-8-19(4)15(21)10-18(3)11-16-20(5,22-16)9-7-14(18)17(13)19/h6,12,14,16-17H,7-11H2,1-5H3/t14-,16-,17-,18+,19+,20+/m0/s1

> <INCHI_KEY>
QHNAUKRTMMVXFK-DAJYORATSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.47045125013102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,6S,9S,11S,13R)-6,9,13-trimethyl-3-(propan-2-yl)-12-oxatetracyclo[7.6.0.0^{2,6}.0^{11,13}]pentadec-3-en-7-one

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
4.192807591666667

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.224285496245096

> <JCHEM_POLAR_SURFACE_AREA>
29.6

> <JCHEM_REFRACTIVITY>
88.95069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,9S,11S,13R)-3-isopropyl-6,9,13-trimethyl-12-oxatetracyclo[7.6.0.0^{2,6}.0^{11,13}]pentadec-3-en-7-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -0.9178   -2.8727    1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1302   -2.3595    0.2753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0589   -3.5217   -0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -1.2747   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1905   -1.3848   -0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8545   -0.2225   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6959    0.3755   -1.5483 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5864   -0.3269   -2.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    1.8504   -1.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5787    2.2461   -2.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    2.8315   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719    2.6002   -0.2042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8742    2.8024   -1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802    3.7008    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    3.9289    1.2652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7340    4.0174    2.6777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874    2.8781    1.9998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7809    2.8914    1.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180    1.5840    2.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2707    0.7766    1.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9303    1.1450    0.3884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5729    0.0634   -0.6989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7071   -3.5815    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9419   -2.0524    2.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0423   -3.3894    1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1475   -1.9587    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -3.1730   -1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202   -4.2746   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821   -4.0177   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390   -2.2452    0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2561    0.4642    0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793   -0.5509   -1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208    0.1158   -3.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127   -0.2204   -3.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830   -1.3990   -2.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963    2.7594    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513    3.8386   -1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8153    3.8259   -1.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820    2.1294   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079    2.6298   -1.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    4.6627    0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4678    3.4700    1.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0213    4.6286    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1259    2.2205    1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1690    3.8928    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2200    2.5599    2.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    0.9911    2.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    1.7385    2.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956    0.7980    0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017   -0.2524    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1569    1.0894    1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4356   -0.0869   -1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 14 15  1  0
 19 17  1  0
 15 17  1  0
 15 16  1  0
 17 16  1  0
  7  9  1  0
 22  4  1  0
  4  5  2  0
  5  6  1  0
  7  8  1  6
  6  7  1  0
 12 13  1  6
  7 22  1  0
 15 43  1  6
 17 18  1  6
 12 21  1  0
 22 52  1  6
 11 12  1  0
  4  2  1  0
 21 20  1  0
  2  1  1  0
 11  9  1  0
  2  3  1  0
 12 14  1  0
 21 51  1  1
 21 22  1  0
  9 10  2  0
 11 36  1  0
 11 37  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
 20 49  1  0
 20 50  1  0
 14 41  1  0
 14 42  1  0
 19 47  1  0
 19 48  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
  2 26  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 27  1  0
  3 28  1  0
  3 29  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      -0.918  -2.873   1.702  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.130  -2.360   0.275  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.059  -3.522  -0.721  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.148  -1.275  -0.093  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.190  -1.385  -0.066  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.855  -0.223  -0.728  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.696   0.376  -1.548  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.586  -0.327  -2.926  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.961   1.850  -1.794  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.579   2.246  -2.785  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.562   2.832  -0.728  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.872   2.600  -0.204  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.874   2.802  -1.364  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.080   3.701   0.880  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.504   3.929   1.265  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.734   4.017   2.678  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.287   2.878   2.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.781   2.891   1.919  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.618   1.584   2.336  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.271   0.777   1.085  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.930   1.145   0.388  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.573   0.063  -0.699  0.00  0.00           C+0
HETATM   23  H   UNK     0      -1.707  -3.582   1.975  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.942  -2.052   2.427  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.042  -3.389   1.810  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.147  -1.959   0.207  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.239  -3.173  -1.744  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.820  -4.275  -0.489  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.082  -4.018  -0.699  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.739  -2.245   0.294  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.256   0.464   0.025  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.679  -0.551  -1.369  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.221   0.116  -3.521  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.513  -0.220  -3.503  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.383  -1.399  -2.837  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.296   2.759   0.083  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.651   3.839  -1.156  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.815   3.826  -1.753  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.682   2.129  -2.205  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.908   2.630  -1.050  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.702   4.663   0.507  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.468   3.470   1.761  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.021   4.629   0.622  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.126   2.220   1.126  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.169   3.893   1.703  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.220   2.560   2.865  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.300   0.991   2.959  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.720   1.738   2.948  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.096   0.798   0.364  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.202  -0.252   1.440  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.157   1.089   1.170  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.436  -0.087  -1.361  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    4    1    3   26                                             
CONECT    3    2   27   28   29                                             
CONECT    4   22    5    2                                                  
CONECT    5    4    6   30                                                  
CONECT    6    5    7   31   32                                             
CONECT    7    9    8    6   22                                             
CONECT    8    7   33   34   35                                             
CONECT    9    7   11   10                                                  
CONECT   10    9                                                            
CONECT   11   12    9   36   37                                             
CONECT   12   13   21   11   14                                             
CONECT   13   12   38   39   40                                             
CONECT   14   15   12   41   42                                             
CONECT   15   14   17   16   43                                             
CONECT   16   15   17                                                       
CONECT   17   19   15   16   18                                             
CONECT   18   17   44   45   46                                             
CONECT   19   20   17   47   48                                             
CONECT   20   19   21   49   50                                             
CONECT   21   12   20   51   22                                             
CONECT   22    4    7   52   21                                             
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36   11                                                            
CONECT   37   11                                                            
CONECT   38   13                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  110    0
END

RDKit          3D

52 55  0  0  0  0  0  0  0  0999 V2000
   -0.9178   -2.8727    1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1302   -2.3595    0.2753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0589   -3.5217   -0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -1.2747   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1905   -1.3848   -0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8545   -0.2225   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6959    0.3755   -1.5483 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5864   -0.3269   -2.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    1.8504   -1.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5787    2.2461   -2.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    2.8315   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719    2.6002   -0.2042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8742    2.8024   -1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802    3.7008    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    3.9289    1.2652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7340    4.0174    2.6777 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7809    2.8914    1.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180    1.5840    2.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2707    0.7766    1.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9303    1.1450    0.3884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5729    0.0634   -0.6989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7071   -3.5815    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9419   -2.0524    2.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0423   -3.3894    1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1475   -1.9587    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -3.1730   -1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202   -4.2746   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821   -4.0177   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390   -2.2452    0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2561    0.4642    0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793   -0.5509   -1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208    0.1158   -3.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127   -0.2204   -3.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830   -1.3990   -2.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963    2.7594    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513    3.8386   -1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8153    3.8259   -1.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820    2.1294   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079    2.6298   -1.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    4.6627    0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4678    3.4700    1.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0213    4.6286    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1259    2.2205    1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1690    3.8928    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2200    2.5599    2.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    0.9911    2.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    1.7385    2.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956    0.7980    0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017   -0.2524    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1569    1.0894    1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4356   -0.0869   -1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 14 15  1  0
 19 17  1  0
 15 17  1  0
 15 16  1  0
 17 16  1  0
  7  9  1  0
 22  4  1  0
  4  5  2  0
  5  6  1  0
  7  8  1  6
  6  7  1  0
 12 13  1  6
  7 22  1  0
 15 43  1  6
 17 18  1  6
 12 21  1  0
 22 52  1  6
 11 12  1  0
  4  2  1  0
 21 20  1  0
  2  1  1  0
 11  9  1  0
  2  3  1  0
 12 14  1  0
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 21 22  1  0
  9 10  2  0
 11 36  1  0
 11 37  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
 20 49  1  0
 20 50  1  0
 14 41  1  0
 14 42  1  0
 19 47  1  0
 19 48  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
  2 26  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(1S,2R,6S,9S,11S,13R)-6,9,13-trimethyl-3-(propan-2-yl)-12-oxatetracyclo[7.6.0.0^{2,6}.0^{11,13}]pentadec-3-en-7-one

Traditional Name

(1S,2R,6S,9S,11S,13R)-3-isopropyl-6,9,13-trimethyl-12-oxatetracyclo[7.6.0.0^{2,6}.0^{11,13}]pentadec-3-en-7-one

CAS Registry Number

Not Available

SMILES

[H]C1=C(C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])([H])[C@]4(O[C@@]4([H])C([H])([H])[C@@]3(C([H])([H])[H])C([H])([H])C(=O)[C@@]2(C([H])([H])[H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H30O2/c1-12(2)13-6-8-19(4)15(21)10-18(3)11-16-20(5,22-16)9-7-14(18)17(13)19/h6,12,14,16-17H,7-11H2,1-5H3/t14-,16-,17-,18+,19+,20+/m0/s1

InChI Key

QHNAUKRTMMVXFK-DAJYORATSA-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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Epipolasis reiswigi	JEOL database	Rodriguez, A. D., et al, J. Org. Chem. 66, 6364 (2001)
Myrmekioderma gyroderma	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	4.54	ALOGPS
logP	4.19	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.95 m³·mol⁻¹	ChemAxon
Polarizability	35.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

8239050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10063509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
Authors unspecified: Cancer Prevention Overview (PDQ(R)): Health Professional Version. 2002. [PubMed:26389451 ]
Authors unspecified: Spirituality in Cancer Care (PDQ(R)): Health Professional Version. 2002. [PubMed:26389436 ]
Authors unspecified: Oral Cavity, Oropharyngeal, Hypopharyngeal, and Laryngeal Cancer Prevention (PDQ(R)): Health Professional Version. 2002. [PubMed:26389416 ]
Authors unspecified: Adjustment to Cancer: Anxiety and Distress (PDQ(R)): Health Professional Version. 2002. [PubMed:26389397 ]
Rodriguez AD, Vera B: New diterpenes from the Caribbean sponge Epipolasis reiswigi. J Org Chem. 2001 Sep 21;66(19):6364-8. doi: 10.1021/jo0104734. [PubMed:11559187 ]
Rodriguez, A. D., et al. (2001). Rodriguez, A. D., et al, J. Org. Chem. 66, 6364 (2001). J. Org. Chem..

Showing NP-Card for Epipolone (NP0025516)

MOL for NP0025516 (Epipolone)

3D MOL for NP0025516 (Epipolone)

3D SDF for NP0025516 (Epipolone)

3D-SDF for NP0025516 (Epipolone)

PDB for NP0025516 (Epipolone)

3D PDB for NP0025516 (Epipolone)

SMILES for NP0025516 (Epipolone)

INCHI for NP0025516 (Epipolone)

Structure for NP0025516 (Epipolone)

3D Structure for NP0025516 (Epipolone)