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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:48 UTC

Update Date

2022-03-07 02:52:45 UTC

HMDB ID

HMDB0030911

Secondary Accession Numbers

HMDB30911

Metabolite Identification

Common Name

2-Oxo-5,11(13)-eudesmadien-12,8-olide

Description

2-Oxo-5,11(13)-eudesmadien-12,8-olide 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 2-Oxo-5,11(13)-eudesmadien-12,8-olide.

Structure

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

HMDB0030911
     RDKit          3D
2-Oxo-5,11(13)-eudesmadien-12,8-olide
 36 38  0  0  0  0  0  0  0  0999 V2000
    2.5164    2.9666   -0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.6394   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    0.9162    0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7216    1.4416    0.9389 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -0.4397    0.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910   -0.4298    0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209   -1.6767    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -1.4360   -0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246   -2.4542   -1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996   -1.6987    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.5447    1.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5516   -0.1608    2.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5960    0.1728    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553    0.2849   -0.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133    1.6910   -0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -0.0488   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    0.8847   -0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6871    0.5884   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6849    3.4021   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3005    3.5816    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4729   -0.0430    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5523   -1.9219   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130   -2.5537    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9120   -2.3573   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2526   -2.3453   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5268   -3.4530   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6022   -2.5664    1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -1.9582    2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5695   -0.3654    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7975    1.1809    1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750   -0.4276   -1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792    1.9010   -1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8889    2.4131   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4135    1.8200   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0828    1.8598   -0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199    0.1370   -1.5757 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  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  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
 10 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv0541 05061305352D          

 18 20  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    0.1979    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    1.2375    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
    0.0000    2.4750    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
    0.0000    0.8250    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
   -0.7145    2.0625    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
    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    2.4750    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
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  2  2  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  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>
HMDB0030911

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC(=O)CC2(C)CC3OC(=O)C(=C)C3C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h5,8,11,13H,2,4,6-7H2,1,3H3

> <INCHI_KEY>
DSTJGYCTYZXZNH-UHFFFAOYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.3016

> <EXACT_MASS>
246.125594442

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.389626484796015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2,7-dione

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
2.1208239263333333

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.755951278835116

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
67.9113

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,8a-dimethyl-3-methylidene-3aH,5H,6H,8H,9H,9aH-naphtho[2,3-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030911
     RDKit          3D
2-Oxo-5,11(13)-eudesmadien-12,8-olide
 36 38  0  0  0  0  0  0  0  0999 V2000
    2.5164    2.9666   -0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.6394   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    0.9162    0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7216    1.4416    0.9389 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -0.4397    0.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910   -0.4298    0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209   -1.6767    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -1.4360   -0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246   -2.4542   -1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996   -1.6987    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.5447    1.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5516   -0.1608    2.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5960    0.1728    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553    0.2849   -0.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133    1.6910   -0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -0.0488   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    0.8847   -0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6871    0.5884   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6849    3.4021   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3005    3.5816    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4729   -0.0430    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5523   -1.9219   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130   -2.5537    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9120   -2.3573   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2526   -2.3453   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5268   -3.4530   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6022   -2.5664    1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -1.9582    2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5695   -0.3654    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7975    1.1809    1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750   -0.4276   -1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792    1.9010   -1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8889    2.4131   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4135    1.8200   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0828    1.8598   -0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199    0.1370   -1.5757 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  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  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
 10 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.942   0.369   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   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.466   1.834   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   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   4.620   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    8   10                                                       
CONECT    5   11   12                                                       
CONECT    6   10   15                                                       
CONECT    7   13   15                                                       
CONECT    8    1    4   12                                                  
CONECT    9    2   11   14                                                  
CONECT   10    4    6   16                                                  
CONECT   11    5    9   13                                                  
CONECT   12    5    8   15                                                  
CONECT   13    7   11   18                                                  
CONECT   14    9   17   18                                                  
CONECT   15    3    6    7   12                                             
CONECT   16   10                                                            
CONECT   17   14                                                            
CONECT   18   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0030911
HETATM    1  C1  UNL     1       2.516   2.967  -0.359  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.597   1.639  -0.203  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.663   0.916   0.498  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.722   1.442   0.939  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.274  -0.440   0.573  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.891  -0.430   0.471  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.221  -1.677   0.049  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.261  -1.436  -0.028  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.825  -2.454  -1.026  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.900  -1.699   1.312  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.662  -0.545   1.834  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.552  -0.161   2.976  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.596   0.173   0.937  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.055   0.285  -0.470  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.313   1.691  -0.964  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.614  -0.049  -0.417  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.278   0.885  -0.711  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.687   0.588  -0.665  1.00  0.00           C  
HETATM   19  H1  UNL     1       1.685   3.402  -0.895  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.301   3.582   0.063  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.473  -0.043   1.418  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.552  -1.922  -1.002  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.413  -2.554   0.697  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.912  -2.357  -1.143  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.253  -2.345  -1.964  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.527  -3.453  -0.609  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.602  -2.566   1.273  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.115  -1.958   2.080  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.569  -0.365   0.877  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.798   1.181   1.350  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.575  -0.428  -1.146  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.879   1.901  -1.944  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.889   2.413  -0.213  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.414   1.820  -1.030  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.083   1.860  -0.981  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.120   0.137  -1.576  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   27   28
CONECT   11   12   12   13
CONECT   13   14   29   30
CONECT   14   15   16   31
CONECT   15   32   33   34
CONECT   16   17   17
CONECT   17   18   35
CONECT   18   36
END

HMDB0030911
     RDKit          3D
2-Oxo-5,11(13)-eudesmadien-12,8-olide
 36 38  0  0  0  0  0  0  0  0999 V2000
    2.5164    2.9666   -0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.6394   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    0.9162    0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7216    1.4416    0.9389 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -0.4397    0.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910   -0.4298    0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209   -1.6767    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -1.4360   -0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246   -2.4542   -1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996   -1.6987    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.5447    1.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5516   -0.1608    2.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5960    0.1728    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553    0.2849   -0.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133    1.6910   -0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -0.0488   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    0.8847   -0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6871    0.5884   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6849    3.4021   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3005    3.5816    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4729   -0.0430    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5523   -1.9219   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130   -2.5537    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9120   -2.3573   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2526   -2.3453   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5268   -3.4530   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6022   -2.5664    1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -1.9582    2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5695   -0.3654    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7975    1.1809    1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750   -0.4276   -1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792    1.9010   -1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8889    2.4131   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4135    1.8200   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0828    1.8598   -0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199    0.1370   -1.5757 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  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  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
 10 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Oxoalantolactone	HMDB
[3AR-(3aalpha,5beta,8abeta,9aalpha)]-3,3a,5,6,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2,7-dione	HMDB

Chemical Formula

C₁₅H₁₈O₃

Average Molecular Weight

246.3016

Monoisotopic Molecular Weight

246.125594442

IUPAC Name

5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2,7-dione

Traditional Name

5,8a-dimethyl-3-methylidene-3aH,5H,6H,8H,9H,9aH-naphtho[2,3-b]furan-2,7-dione

CAS Registry Number

68776-46-5

SMILES

CC1CC(=O)CC2(C)CC3OC(=O)C(=C)C3C=C12

InChI Identifier

InChI=1S/C15H18O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h5,8,11,13H,2,4,6-7H2,1,3H3

InChI Key

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 - 153 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	1.63	ALOGPS
logP	2.12	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	-6.8	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	67.91 m³·mol⁻¹	ChemAxon
Polarizability	26.39 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]+	158.299	31661259
DarkChem	[M-H]-	157.255	31661259
DeepCCS	[M-2H]-	195.813	30932474
DeepCCS	[M+Na]+	171.379	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Oxo-5,11(13)-eudesmadien-12,8-olide	CC1CC(=O)CC2(C)CC3OC(=O)C(=C)C3C=C12	2887.2	Standard polar	33892256
2-Oxo-5,11(13)-eudesmadien-12,8-olide	CC1CC(=O)CC2(C)CC3OC(=O)C(=C)C3C=C12	2001.1	Standard non polar	33892256
2-Oxo-5,11(13)-eudesmadien-12,8-olide	CC1CC(=O)CC2(C)CC3OC(=O)C(=C)C3C=C12	2140.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Oxo-5,11(13)-eudesmadien-12,8-olide,1TMS,isomer #1	C=C1C(=O)OC2CC3(C)C=C(O[Si](C)(C)C)CC(C)C3=CC12	2224.9	Semi standard non polar	33892256
2-Oxo-5,11(13)-eudesmadien-12,8-olide,1TMS,isomer #1	C=C1C(=O)OC2CC3(C)C=C(O[Si](C)(C)C)CC(C)C3=CC12	1977.8	Standard non polar	33892256
2-Oxo-5,11(13)-eudesmadien-12,8-olide,1TMS,isomer #2	C=C1C(=O)OC2CC3(C)CC(O[Si](C)(C)C)=CC(C)C3=CC12	2260.6	Semi standard non polar	33892256
2-Oxo-5,11(13)-eudesmadien-12,8-olide,1TMS,isomer #2	C=C1C(=O)OC2CC3(C)CC(O[Si](C)(C)C)=CC(C)C3=CC12	1988.0	Standard non polar	33892256
2-Oxo-5,11(13)-eudesmadien-12,8-olide,1TBDMS,isomer #1	C=C1C(=O)OC2CC3(C)C=C(O[Si](C)(C)C(C)(C)C)CC(C)C3=CC12	2450.0	Semi standard non polar	33892256
2-Oxo-5,11(13)-eudesmadien-12,8-olide,1TBDMS,isomer #1	C=C1C(=O)OC2CC3(C)C=C(O[Si](C)(C)C(C)(C)C)CC(C)C3=CC12	2212.8	Standard non polar	33892256
2-Oxo-5,11(13)-eudesmadien-12,8-olide,1TBDMS,isomer #2	C=C1C(=O)OC2CC3(C)CC(O[Si](C)(C)C(C)(C)C)=CC(C)C3=CC12	2492.2	Semi standard non polar	33892256
2-Oxo-5,11(13)-eudesmadien-12,8-olide,1TBDMS,isomer #2	C=C1C(=O)OC2CC3(C)CC(O[Si](C)(C)C(C)(C)C)=CC(C)C3=CC12	2224.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fw9-4980000000-5ef1d3cbf76bcb4798f0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 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 - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 10V, Positive-QTOF	splash10-0002-0290000000-cdb9b5e8cf30e623b30c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 20V, Positive-QTOF	splash10-002b-1790000000-4dbd01ab92119b22e468	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 40V, Positive-QTOF	splash10-0fsi-7920000000-77f7a97d3cdfe27d756d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-3168613a3e3818afdbff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 20V, Negative-QTOF	splash10-0f6t-0190000000-ce177ebfc06b42b5c440	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 40V, Negative-QTOF	splash10-0udm-5920000000-2b1bd39342493d60805f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-851e47b490f6973ef9e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 20V, Negative-QTOF	splash10-0f6t-0290000000-87552303eb275cb126a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 40V, Negative-QTOF	splash10-0fgx-2930000000-7898beaf2d69f595b704	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 10V, Positive-QTOF	splash10-0002-0190000000-3153d4463cc9ee7ceb86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 20V, Positive-QTOF	splash10-00or-0950000000-90a29d93b5002aac0b2e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxo-5,11(13)-eudesmadien-12,8-olide 40V, Positive-QTOF	splash10-008i-1910000000-3922cb51a6026d512e66	2021-09-22	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

FDB002877

KNApSAcK ID

C00012896

Chemspider ID

35013285

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751096

PDB ID

Not Available

ChEBI ID

172485

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 2-Oxo-5,11(13)-eudesmadien-12,8-olide (HMDB0030911)

MOL for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

3D MOL for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

3D SDF for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

3D-SDF for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

PDB for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

3D PDB for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

SMILES for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

INCHI for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

Structure for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

3D Structure for HMDB0030911 (2-Oxo-5,11(13)-eudesmadien-12,8-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra