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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:37:33 UTC

Update Date

2022-03-07 02:54:13 UTC

HMDB ID

HMDB0034723

Secondary Accession Numbers

HMDB34723

Metabolite Identification

Common Name

Encelin

Description

Encelin belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a small amount of articles have been published on Encelin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0034723
     RDKit          3D
Encelin
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.6467    0.1872   -1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023    0.0304   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3818    0.2025    1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158    0.5444    1.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109   -0.0917    1.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630   -0.8605    1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0194   -0.7012    1.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723   -0.3665    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021    0.0163    1.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -1.5887    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8706   -1.6240   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0356   -0.3691   -1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4529   -0.3653   -3.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6919    0.8595   -1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2253    2.0028   -1.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585    0.8183   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    0.8980   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660   -0.3410   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2255    0.0433   -2.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6910    0.4606   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215   -1.9100    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393    0.0624    2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2569   -1.6643    2.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9335    0.7278    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429    0.5622    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145   -0.8571    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188   -2.5280    0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1149   -2.5701   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9045    2.0370   -2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    2.9352   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    1.7287    0.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    1.7730   -0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719    1.0704   -1.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963   -1.1222   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  3
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 16  8  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
M  END


  Mrv0541 05061308022D          

 18 20  0  0  0  0            999 V2000
    3.1830    0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2380    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  2  0  0  0  0
  9  2  2  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 15  3  1  0  0  0  0
 15  5  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  2  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034723

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CC3OC(=O)C(=C)C3CC1C(=C)C(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O3/c1-8-10-6-11-9(2)12(16)4-5-15(11,3)7-13(10)18-14(8)17/h4-5,10-11,13H,1-2,6-7H2,3H3

> <INCHI_KEY>
LXMUZMFQJGRVFW-UHFFFAOYSA-N

> <FORMULA>
C15H16O3

> <MOLECULAR_WEIGHT>
244.2857

> <EXACT_MASS>
244.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.937422194496797

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8a-methyl-3,5-dimethylidene-2H,3H,3aH,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2,6-dione

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
2.688515450333333

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.895243095468358

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
67.9839

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8a-methyl-3,5-dimethylidene-3aH,4H,4aH,9H,9aH-naphtho[2,3-b]furan-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034723
     RDKit          3D
Encelin
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.6467    0.1872   -1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023    0.0304   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3818    0.2025    1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158    0.5444    1.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109   -0.0917    1.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630   -0.8605    1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0194   -0.7012    1.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723   -0.3665    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021    0.0163    1.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -1.5887    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8706   -1.6240   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0356   -0.3691   -1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4529   -0.3653   -3.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6919    0.8595   -1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2253    2.0028   -1.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585    0.8183   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    0.8980   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660   -0.3410   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2255    0.0433   -2.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6910    0.4606   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215   -1.9100    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393    0.0624    2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2569   -1.6643    2.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9335    0.7278    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429    0.5622    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145   -0.8571    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188   -2.5280    0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1149   -2.5701   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9045    2.0370   -2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    2.9352   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    1.7287    0.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    1.7730   -0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719    1.0704   -1.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963   -1.1222   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  3
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 16  8  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.942   0.369   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.466   1.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.371   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.911   3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.466   4.326   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4    5   12                                                       
CONECT    5    4   15                                                       
CONECT    6   10   11                                                       
CONECT    7   13   15                                                       
CONECT    8    1   10   14                                                  
CONECT    9    2   11   12                                                  
CONECT   10    6    8   13                                                  
CONECT   11    6    9   15                                                  
CONECT   12    4    9   16                                                  
CONECT   13    7   10   18                                                  
CONECT   14    8   17   18                                                  
CONECT   15    3    5    7   11                                             
CONECT   16   12                                                            
CONECT   17   14                                                            
CONECT   18   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0034723
HETATM    1  C1  UNL     1       3.647   0.187  -1.380  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.902   0.030  -0.307  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.382   0.202   1.058  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.516   0.544   1.483  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.311  -0.092   1.894  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.363  -0.861   1.176  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.019  -0.701   1.797  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.072  -0.367   0.825  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.302   0.016   1.652  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.429  -1.589   0.075  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.871  -1.624  -1.167  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.036  -0.369  -1.901  1.00  0.00           C  
HETATM   13  O3  UNL     1      -2.453  -0.365  -3.084  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.692   0.860  -1.190  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.225   2.003  -1.591  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.758   0.818  -0.038  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.662   0.898  -0.479  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.466  -0.341  -0.227  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.226   0.043  -2.367  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.691   0.461  -1.337  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.721  -1.910   1.183  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.039   0.062   2.606  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.257  -1.664   2.285  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.933   0.728   2.437  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.043   0.562   1.058  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.715  -0.857   2.184  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.319  -2.528   0.590  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.115  -2.570  -1.657  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.905   2.037  -2.429  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.999   2.935  -1.094  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.978   1.729   0.574  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.188   1.773  -0.043  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.672   1.070  -1.586  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.296  -1.122  -1.002  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3   18
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   21
CONECT    7    8   22   23
CONECT    8    9   10   16
CONECT    9   24   25   26
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   14
CONECT   14   15   15   16
CONECT   15   29   30
CONECT   16   17   31
CONECT   17   18   32   33
CONECT   18   34
END

HMDB0034723
     RDKit          3D
Encelin
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.6467    0.1872   -1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023    0.0304   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3818    0.2025    1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158    0.5444    1.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109   -0.0917    1.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630   -0.8605    1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0194   -0.7012    1.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723   -0.3665    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021    0.0163    1.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -1.5887    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8706   -1.6240   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0356   -0.3691   -1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4529   -0.3653   -3.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6919    0.8595   -1.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2253    2.0028   -1.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585    0.8183   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    0.8980   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660   -0.3410   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2255    0.0433   -2.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6910    0.4606   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215   -1.9100    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393    0.0624    2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2569   -1.6643    2.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9335    0.7278    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429    0.5622    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145   -0.8571    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188   -2.5280    0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1149   -2.5701   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9045    2.0370   -2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    2.9352   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    1.7287    0.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    1.7730   -0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719    1.0704   -1.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963   -1.1222   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  3
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 16  8  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
dehydro-Farinosin	HMDB
Dehydrofarinosin	HMDB

Chemical Formula

C₁₅H₁₆O₃

Average Molecular Weight

244.2857

Monoisotopic Molecular Weight

244.109944378

IUPAC Name

8a-methyl-3,5-dimethylidene-2H,3H,3aH,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2,6-dione

Traditional Name

8a-methyl-3,5-dimethylidene-3aH,4H,4aH,9H,9aH-naphtho[2,3-b]furan-2,6-dione

CAS Registry Number

15569-50-3

SMILES

CC12CC3OC(=O)C(=C)C3CC1C(=C)C(=O)C=C2

InChI Identifier

InChI=1S/C15H16O3/c1-8-10-6-11-9(2)12(16)4-5-15(11,3)7-13(10)18-14(8)17/h4-5,10-11,13H,1-2,6-7H2,3H3

InChI Key

LXMUZMFQJGRVFW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
O-quinomethane
Quinomethane
Cyclohexenone
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034723)

Source

Endogenous

Endogenous (HMDB: HMDB0034723)

Plant

Plant (HMDB: HMDB0034723)

Animal

Animal (HMDB: HMDB0034723)

Exogenous

Food

Food (HMDB: HMDB0034723)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0034723)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034723)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034723)

Lipid metabolism pathway (HMDB: HMDB0034723)

Cellular process

Cell signaling (HMDB: HMDB0034723)

Biochemical process

Lipid transport (HMDB: HMDB0034723)

Role

Biological role

Energy source (HMDB: HMDB0034723)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0034723)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034723)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 - 196 °C	Not Available
Boiling Point	432.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	865.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.480 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	1.29	ALOGPS
logP	2.69	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.98 m³·mol⁻¹	ChemAxon
Polarizability	25.94 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.745	31661259
DarkChem	[M-H]-	154.435	31661259
DeepCCS	[M-2H]-	193.658	30932474
DeepCCS	[M+Na]+	169.223	30932474
AllCCS	[M+H]+	156.6	32859911
AllCCS	[M+H-H2O]+	152.8	32859911
AllCCS	[M+NH4]+	160.1	32859911
AllCCS	[M+Na]+	161.2	32859911
AllCCS	[M-H]-	161.5	32859911
AllCCS	[M+Na-2H]-	161.3	32859911
AllCCS	[M+HCOO]-	161.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.71 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1395 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2340.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	400.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	174.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	207.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	474.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	635.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1187.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	420.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1419.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	361.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	400.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	412.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	398.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	30.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Encelin	CC12CC3OC(=O)C(=C)C3CC1C(=C)C(=O)C=C2	2916.8	Standard polar	33892256
Encelin	CC12CC3OC(=O)C(=C)C3CC1C(=C)C(=O)C=C2	2033.3	Standard non polar	33892256
Encelin	CC12CC3OC(=O)C(=C)C3CC1C(=C)C(=O)C=C2	2239.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Encelin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gcc-2940000000-129d6f7caf64571182fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Encelin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 10V, Positive-QTOF	splash10-0002-0290000000-0faead28f8296e8308cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 20V, Positive-QTOF	splash10-002b-1970000000-1747138bc0de4219f15d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 40V, Positive-QTOF	splash10-0gbc-9710000000-501609c74aca0f85de52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 10V, Negative-QTOF	splash10-0006-0290000000-570b03562448ef1057a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 20V, Negative-QTOF	splash10-0007-0690000000-2f3935f01e4e2fab4631	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 40V, Negative-QTOF	splash10-0002-2900000000-29ab1418b26b9c129fca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 10V, Negative-QTOF	splash10-0006-0190000000-4f2bad47bfeafa166b15	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 20V, Negative-QTOF	splash10-00di-0900000000-71f2b48d57f6d43a3f9e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 40V, Negative-QTOF	splash10-00e9-1920000000-baa0319e59a7d48799a7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 10V, Positive-QTOF	splash10-0002-0090000000-5953db200ad25139a014	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 20V, Positive-QTOF	splash10-002b-0960000000-5a06caa064a181963282	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encelin 40V, Positive-QTOF	splash10-014r-1910000000-8c82d513a62040969aed	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

329302

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1434971

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yang ZD, Gao K, Jia ZJ: Eudesmane derivatives and other constituents from Saussurea parviflora. Phytochemistry. 2003 Apr;62(8):1195-9. [PubMed:12648535 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Encelin (HMDB0034723)

MOL for HMDB0034723 (Encelin)

3D MOL for HMDB0034723 (Encelin)

3D SDF for HMDB0034723 (Encelin)

3D-SDF for HMDB0034723 (Encelin)

PDB for HMDB0034723 (Encelin)

3D PDB for HMDB0034723 (Encelin)

SMILES for HMDB0034723 (Encelin)

INCHI for HMDB0034723 (Encelin)

Structure for HMDB0034723 (Encelin)

3D Structure for HMDB0034723 (Encelin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra