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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:56:57 UTC

Update Date

2022-03-07 02:53:38 UTC

HMDB ID

HMDB0033235

Secondary Accession Numbers

HMDB33235

Metabolite Identification

Common Name

8,12-Epoxy-4(15),7,11-eudesmatrien-1-one

Description

8,12-Epoxy-4(15),7,11-eudesmatrien-1-one belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a small amount of articles have been published on 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one.

Structure

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

HMDB0033235
     RDKit          3D
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.4705    2.2183   -1.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2480    1.2912   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811    1.5316    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9455    0.2824    1.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330   -0.8355    0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1786   -1.4294    0.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9856   -1.1438   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110   -2.0574   -1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -2.0086    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106   -1.3300    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -1.5841    1.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893   -0.6889    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438    0.2256    1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080    1.4316    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -0.1823    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698    0.4050   -0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780    0.0642   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    3.1131   -1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0960    2.0788   -2.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7730    2.0386    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    2.2417    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150    0.4090    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650    0.1077    2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604   -3.0085   -1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -1.5012   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -2.2887   -2.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676   -2.5376    1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405   -2.8553   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5482   -0.6534    2.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    1.1073    0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606    1.9199   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171    2.0791    1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6007    0.0672   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375    1.5022   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047   -0.0095   -2.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  7  1  0
 15 10  2  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
M  END


  Mrv0541 05061307002D          

 17 19  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
   -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 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
    3.4130    1.6500    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
    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
    0.0000    2.4750    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    3.3000    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  1  0  0  0  0
  9  1  2  0  0  0  0
  9  4  1  0  0  0  0
 10  2  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  5  1  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033235

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=COC2=C1CC1C(=C)CCC(=O)C1(C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-9-4-5-14(16)15(3)7-13-11(6-12(9)15)10(2)8-17-13/h8,12H,1,4-7H2,2-3H3

> <INCHI_KEY>
AKNPMCISDQNRFC-UHFFFAOYSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.3022

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.831942664784766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8a-dimethyl-5-methylidene-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-one

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
3.4148472593333326

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6131706840606013

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
67.1177

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8a-dimethyl-5-methylidene-4H,4aH,6H,7H,9H-naphtho[2,3-b]furan-8-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033235
     RDKit          3D
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.4705    2.2183   -1.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2480    1.2912   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811    1.5316    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9455    0.2824    1.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330   -0.8355    0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1786   -1.4294    0.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9856   -1.1438   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110   -2.0574   -1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -2.0086    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106   -1.3300    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -1.5841    1.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893   -0.6889    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438    0.2256    1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080    1.4316    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -0.1823    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698    0.4050   -0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780    0.0642   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    3.1131   -1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0960    2.0788   -2.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7730    2.0386    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    2.2417    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150    0.4090    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650    0.1077    2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604   -3.0085   -1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -1.5012   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -2.2887   -2.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676   -2.5376    1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405   -2.8553   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5482   -0.6534    2.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    1.1073    0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606    1.9199   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171    2.0791    1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6007    0.0672   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375    1.5022   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047   -0.0095   -2.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  7  1  0
 15 10  2  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  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      -1.334   3.850   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       6.371   3.080   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       5.466   1.834   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       0.000   4.620   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       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.466   4.326   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5    9                                                       
CONECT    5    4   14                                                       
CONECT    6   11   12                                                       
CONECT    7   13   15                                                       
CONECT    8   10   17                                                       
CONECT    9    1    4   12                                                  
CONECT   10    2    8   11                                                  
CONECT   11    6   10   13                                                  
CONECT   12    6    9   15                                                  
CONECT   13    7   11   17                                                  
CONECT   14    5   15   16                                                  
CONECT   15    3    7   12   14                                             
CONECT   16   14                                                            
CONECT   17    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0033235
HETATM    1  C1  UNL     1      -1.471   2.218  -1.685  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.248   1.291  -0.772  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.781   1.532   0.585  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.945   0.282   1.393  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.133  -0.836   0.431  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.179  -1.429   0.441  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.986  -1.144  -0.496  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.611  -2.057  -1.566  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.040  -2.009   0.261  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.111  -1.330   0.841  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.849  -1.584   1.863  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.789  -0.689   2.016  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.644   0.226   1.001  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.508   1.432   0.781  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.571  -0.182   0.248  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.970   0.405  -0.943  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.478   0.064  -1.143  1.00  0.00           C  
HETATM   18  H1  UNL     1      -2.021   3.113  -1.438  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.096   2.079  -2.690  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.773   2.039   0.468  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.154   2.242   1.159  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.815   0.409   2.049  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.065   0.108   2.043  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.960  -3.008  -1.085  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.449  -1.501  -2.026  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.816  -2.289  -2.300  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.568  -2.538   1.086  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.340  -2.855  -0.388  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.548  -0.653   2.786  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.548   1.107   0.578  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.161   1.920  -0.170  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.417   2.079   1.657  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.601   0.067  -1.822  1.00  0.00           H  
HETATM   34  H17 UNL     1       1.138   1.502  -0.902  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.605  -0.010  -2.259  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   17
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6    6    7
CONECT    7    8    9   17
CONECT    8   24   25   26
CONECT    9   10   27   28
CONECT   10   11   15   15
CONECT   11   12
CONECT   12   13   13   29
CONECT   13   14   15
CONECT   14   30   31   32
CONECT   15   16
CONECT   16   17   33   34
CONECT   17   35
END

HMDB0033235
     RDKit          3D
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.4705    2.2183   -1.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2480    1.2912   -0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811    1.5316    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9455    0.2824    1.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330   -0.8355    0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1786   -1.4294    0.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9856   -1.1438   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110   -2.0574   -1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -2.0086    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106   -1.3300    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -1.5841    1.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893   -0.6889    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438    0.2256    1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080    1.4316    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -0.1823    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698    0.4050   -0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780    0.0642   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    3.1131   -1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0960    2.0788   -2.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7730    2.0386    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    2.2417    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150    0.4090    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650    0.1077    2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604   -3.0085   -1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -1.5012   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -2.2887   -2.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676   -2.5376    1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405   -2.8553   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5482   -0.6534    2.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    1.1073    0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606    1.9199   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171    2.0791    1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6007    0.0672   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375    1.5022   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047   -0.0095   -2.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  7  1  0
 15 10  2  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₂

Average Molecular Weight

230.3022

Monoisotopic Molecular Weight

230.13067982

IUPAC Name

3,8a-dimethyl-5-methylidene-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-one

Traditional Name

3,8a-dimethyl-5-methylidene-4H,4aH,6H,7H,9H-naphtho[2,3-b]furan-8-one

CAS Registry Number

220289-78-1

SMILES

CC1=COC2=C1CC1C(=C)CCC(=O)C1(C)C2

InChI Identifier

InChI=1S/C15H18O2/c1-9-4-5-14(16)15(3)7-13-11(6-12(9)15)10(2)8-17-13/h8,12H,1,4-7H2,2-3H3

InChI Key

AKNPMCISDQNRFC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Heteroaromatic compound
Furan
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033235)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033235)

Source

Endogenous

Endogenous (HMDB: HMDB0033235)

Plant

Plant (HMDB: HMDB0033235)

Animal

Animal (HMDB: HMDB0033235)

Exogenous

Food

Food (HMDB: HMDB0033235)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033235)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033235)

Cellular process

Cell signaling (HMDB: HMDB0033235)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033235)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033235)

Nutrient

Nutrient (HMDB: HMDB0033235)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	3.02	ALOGPS
logP	3.41	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.12 m³·mol⁻¹	ChemAxon
Polarizability	25.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.165	31661259
DarkChem	[M-H]-	152.283	31661259
DeepCCS	[M+H]+	158.72	30932474
DeepCCS	[M-H]-	156.362	30932474
DeepCCS	[M-2H]-	189.907	30932474
DeepCCS	[M+Na]+	164.98	30932474
AllCCS	[M+H]+	152.6	32859911
AllCCS	[M+H-H2O]+	148.6	32859911
AllCCS	[M+NH4]+	156.2	32859911
AllCCS	[M+Na]+	157.3	32859911
AllCCS	[M-H]-	160.1	32859911
AllCCS	[M+Na-2H]-	159.9	32859911
AllCCS	[M+HCOO]-	159.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one	CC1=COC2=C1CC1C(=C)CCC(=O)C1(C)C2	2612.0	Standard polar	33892256
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one	CC1=COC2=C1CC1C(=C)CCC(=O)C1(C)C2	1787.5	Standard non polar	33892256
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one	CC1=COC2=C1CC1C(=C)CCC(=O)C1(C)C2	1861.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one,1TMS,isomer #1	C=C1CC=C(O[Si](C)(C)C)C2(C)CC3=C(CC12)C(C)=CO3	2076.5	Semi standard non polar	33892256
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one,1TMS,isomer #1	C=C1CC=C(O[Si](C)(C)C)C2(C)CC3=C(CC12)C(C)=CO3	1870.4	Standard non polar	33892256
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one,1TBDMS,isomer #1	C=C1CC=C(O[Si](C)(C)C(C)(C)C)C2(C)CC3=C(CC12)C(C)=CO3	2331.9	Semi standard non polar	33892256
8,12-Epoxy-4(15),7,11-eudesmatrien-1-one,1TBDMS,isomer #1	C=C1CC=C(O[Si](C)(C)C(C)(C)C)C2(C)CC3=C(CC12)C(C)=CO3	2061.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2940000000-2de24f393878a1a7ee73	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 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 - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 10V, Positive-QTOF	splash10-001i-0190000000-3c708dee7fd9331e177d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 20V, Positive-QTOF	splash10-053r-4970000000-c78cd4979ec31a25dc6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 40V, Positive-QTOF	splash10-0udj-9400000000-eb8dddf4fcb118be5151	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 10V, Negative-QTOF	splash10-004i-0090000000-3b78861975a0159c8ef3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 20V, Negative-QTOF	splash10-004i-0190000000-f365ffd4b6549c3955b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 40V, Negative-QTOF	splash10-01pn-3920000000-107ce0e0b7eba32f8872	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 10V, Negative-QTOF	splash10-004i-0090000000-fb2ff0c6ce4213f1f376	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 20V, Negative-QTOF	splash10-004i-0290000000-945b9d7a1e9186467701	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 40V, Negative-QTOF	splash10-001i-1920000000-c873164cf20a91401281	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 10V, Positive-QTOF	splash10-001i-0090000000-b1296a20086cd9a33ddb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 20V, Positive-QTOF	splash10-007k-2950000000-4686c763adfbeee5db86	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one 40V, Positive-QTOF	splash10-014m-7900000000-608652cbea9fcaa2a0f5	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB011250

KNApSAcK ID

Not Available

Chemspider ID

35013563

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751397

PDB ID

Not Available

ChEBI ID

Not Available

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 8,12-Epoxy-4(15),7,11-eudesmatrien-1-one (HMDB0033235)

MOL for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

3D MOL for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

3D SDF for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

3D-SDF for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

PDB for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

3D PDB for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

SMILES for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

INCHI for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

Structure for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

3D Structure for HMDB0033235 (8,12-Epoxy-4(15),7,11-eudesmatrien-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra