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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:48:34 UTC

Update Date

2022-03-07 02:55:23 UTC

HMDB ID

HMDB0037558

Secondary Accession Numbers

HMDB37558

Metabolite Identification

Common Name

3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid

Description

3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review a small amount of articles have been published on 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid.

Structure

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

HMDB0037558
     RDKit          3D
3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
    0.6115    1.7641   -3.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515    0.7812   -2.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.2187   -3.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0075   -0.1086   -4.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2627   -1.2980   -2.6676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5080    0.6695   -1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157   -0.5773   -1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7165   -0.7715    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4435   -0.9731    1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710   -2.1851    0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7835   -1.3521    2.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829   -0.6646    3.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4254    0.5232    3.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208    1.1939    4.3464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751    0.9287    1.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044    2.1708    1.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    0.2378    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141    0.7326   -0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604    2.5427   -3.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403    1.8032   -4.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762   -2.2605   -2.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    1.5283   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -1.4480   -1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2838   -0.3948   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089    0.1857    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428   -1.6457    0.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1585   -1.7875   -0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -2.7447   -0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538   -2.7944    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030   -2.2469    2.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -1.0053    4.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0561    2.9698    1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5626    1.9925    1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8582    2.5931    2.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0798    1.7697   -0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222    0.0902   -0.7840 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
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18  6  1  0
 17  9  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
M  END


  Mrv0541 05061309512D          

 18 19  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    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
    4.2868    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  4  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 13 10  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 13  2  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037558

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2CC(CCC2(C)C=CC1=O)C(=C)C(O)=O

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

> <INCHI_KEY>
FPCQVGOUFYTXFX-UHFFFAOYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.3016

> <EXACT_MASS>
246.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.604051859274463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4a,8-dimethyl-7-oxo-1,2,3,4,4a,7-hexahydronaphthalen-2-yl)prop-2-enoic acid

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
2.997884294333333

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.717650731251788

> <JCHEM_PKA_STRONGEST_BASIC>
-4.971967553214556

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
70.6895

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4a,8-dimethyl-7-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037558
     RDKit          3D
3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
    0.6115    1.7641   -3.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515    0.7812   -2.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.2187   -3.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0075   -0.1086   -4.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2627   -1.2980   -2.6676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5080    0.6695   -1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157   -0.5773   -1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7165   -0.7715    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4435   -0.9731    1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710   -2.1851    0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7835   -1.3521    2.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829   -0.6646    3.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4254    0.5232    3.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208    1.1939    4.3464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751    0.9287    1.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044    2.1708    1.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    0.2378    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141    0.7326   -0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604    2.5427   -3.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403    1.8032   -4.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762   -2.2605   -2.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    1.5283   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -1.4480   -1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2838   -0.3948   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089    0.1857    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428   -1.6457    0.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1585   -1.7875   -0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -2.7447   -0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538   -2.7944    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030   -2.2469    2.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -1.0053    4.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0561    2.9698    1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5626    1.9925    1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8582    2.5931    2.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0798    1.7697   -0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222    0.0902   -0.7840 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
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18  6  1  0
 17  9  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    6   11                                                       
CONECT    5    7   13                                                       
CONECT    6    4   15                                                       
CONECT    7    5   15                                                       
CONECT    8   11   12                                                       
CONECT    9    1   11   14                                                  
CONECT   10    2   12   13                                                  
CONECT   11    4    8    9                                                  
CONECT   12    8   10   15                                                  
CONECT   13    5   10   16                                                  
CONECT   14    9   17   18                                                  
CONECT   15    3    6    7   12                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0037558
HETATM    1  C1  UNL     1       0.612   1.764  -3.471  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.151   0.781  -2.726  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.715  -0.219  -3.323  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.008  -0.109  -4.566  1.00  0.00           O  
HETATM    5  O2  UNL     1      -1.263  -1.298  -2.668  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.508   0.669  -1.289  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.316  -0.577  -1.120  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.716  -0.771   0.299  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.443  -0.973   1.133  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.271  -2.185   0.525  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.784  -1.352   2.496  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.383  -0.665   3.539  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.425   0.523   3.357  1.00  0.00           C  
HETATM   14  O3  UNL     1      -0.821   1.194   4.346  1.00  0.00           O  
HETATM   15  C12 UNL     1      -0.775   0.929   1.983  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.604   2.171   1.869  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.370   0.238   0.966  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.714   0.733  -0.408  1.00  0.00           C  
HETATM   19  H1  UNL     1       1.260   2.543  -3.088  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.340   1.803  -4.506  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.976  -2.261  -2.901  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.180   1.528  -1.045  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.879  -1.448  -1.625  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.284  -0.395  -1.688  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.209   0.186   0.625  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.343  -1.646   0.482  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.158  -1.788  -0.001  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.356  -2.745  -0.178  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.654  -2.794   1.354  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.403  -2.247   2.674  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.667  -1.005   4.557  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.056   2.970   1.333  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.563   1.993   1.343  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.858   2.593   2.861  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.080   1.770  -0.357  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.522   0.090  -0.784  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    6
CONECT    3    4    4    5
CONECT    5   21
CONECT    6    7   18   22
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   11   17
CONECT   10   27   28   29
CONECT   11   12   12   30
CONECT   12   13   31
CONECT   13   14   14   15
CONECT   15   16   17   17
CONECT   16   32   33   34
CONECT   17   18
CONECT   18   35   36
END

HMDB0037558
     RDKit          3D
3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
    0.6115    1.7641   -3.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515    0.7812   -2.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.2187   -3.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0075   -0.1086   -4.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2627   -1.2980   -2.6676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5080    0.6695   -1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157   -0.5773   -1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7165   -0.7715    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4435   -0.9731    1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710   -2.1851    0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7835   -1.3521    2.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829   -0.6646    3.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4254    0.5232    3.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208    1.1939    4.3464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751    0.9287    1.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044    2.1708    1.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    0.2378    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141    0.7326   -0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604    2.5427   -3.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403    1.8032   -4.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762   -2.2605   -2.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    1.5283   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -1.4480   -1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2838   -0.3948   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089    0.1857    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428   -1.6457    0.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1585   -1.7875   -0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -2.7447   -0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538   -2.7944    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030   -2.2469    2.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -1.0053    4.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0561    2.9698    1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5626    1.9925    1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8582    2.5931    2.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0798    1.7697   -0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222    0.0902   -0.7840 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
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18  6  1  0
 17  9  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-oxo-1,4,11(13)-Eudesmatrien-12-Oate	Generator
2-(4a,8-Dimethyl-7-oxo-1,2,3,4,4a,7-hexahydronaphthalen-2-yl)prop-2-enoate	HMDB

Chemical Formula

C₁₅H₁₈O₃

Average Molecular Weight

246.3016

Monoisotopic Molecular Weight

246.125594442

IUPAC Name

2-(4a,8-dimethyl-7-oxo-1,2,3,4,4a,7-hexahydronaphthalen-2-yl)prop-2-enoic acid

Traditional Name

2-(4a,8-dimethyl-7-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)prop-2-enoic acid

CAS Registry Number

135594-80-8

SMILES

CC1=C2CC(CCC2(C)C=CC1=O)C(=C)C(O)=O

InChI Identifier

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

InChI Key

FPCQVGOUFYTXFX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0037558)
Cell membrane (HMDB: HMDB0037558)

Cellular substructure

Extracellular (HMDB: HMDB0037558)
Membrane (HMDB: HMDB0037558)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037558)

Source

Endogenous

Endogenous (HMDB: HMDB0037558)

Animal

Animal (HMDB: HMDB0037558)

Exogenous

Food

Food (HMDB: HMDB0037558)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037558)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037558)

Cellular process

Cell signaling (HMDB: HMDB0037558)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037558)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037558)

Nutrient

Nutrient (HMDB: HMDB0037558)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037558)

Emulsifier (HMDB: HMDB0037558)

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	0.14 g/L	ALOGPS
logP	2.8	ALOGPS
logP	3	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.69 m³·mol⁻¹	ChemAxon
Polarizability	26.6 Å³	ChemAxon
Number of Rings	2	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]+	156.477	31661259
DarkChem	[M-H]-	154.391	31661259
DeepCCS	[M+H]+	161.017	30932474
DeepCCS	[M-H]-	158.659	30932474
DeepCCS	[M-2H]-	191.672	30932474
DeepCCS	[M+Na]+	167.11	30932474
AllCCS	[M+H]+	156.9	32859911
AllCCS	[M+H-H2O]+	153.2	32859911
AllCCS	[M+NH4]+	160.4	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	161.9	32859911
AllCCS	[M+HCOO]-	162.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid	CC1=C2CC(CCC2(C)C=CC1=O)C(=C)C(O)=O	3333.3	Standard polar	33892256
3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid	CC1=C2CC(CCC2(C)C=CC1=O)C(=C)C(O)=O	1824.3	Standard non polar	33892256
3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid	CC1=C2CC(CCC2(C)C=CC1=O)C(=C)C(O)=O	2150.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid,1TMS,isomer #1	C=C(C(=O)O[Si](C)(C)C)C1CCC2(C)C=CC(=O)C(C)=C2C1	2174.2	Semi standard non polar	33892256
3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid,1TBDMS,isomer #1	C=C(C(=O)O[Si](C)(C)C(C)(C)C)C1CCC2(C)C=CC(=O)C(C)=C2C1	2419.3	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 - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0950000000-6a4e4c8eb69c9811f23a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0udi-3973000000-ed66a8391adbcc128f8a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 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 - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 10V, Positive-QTOF	splash10-002b-0290000000-3473d0350b4a265533ae	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 20V, Positive-QTOF	splash10-0fb9-1970000000-80da5a295b4459fa520e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 40V, Positive-QTOF	splash10-0uxs-4900000000-ff55f9e677e2634552be	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 10V, Negative-QTOF	splash10-0002-0090000000-ab0bde6a032886fce25b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 20V, Negative-QTOF	splash10-0udj-0190000000-2ad0debb242a961a3f42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 40V, Negative-QTOF	splash10-0g29-5920000000-6137c2857b401009b54e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 10V, Positive-QTOF	splash10-0fb9-0950000000-cea9f17e25eb57afcff7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 20V, Positive-QTOF	splash10-0040-1920000000-fb9f7491a0338aa3f238	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 40V, Positive-QTOF	splash10-014i-7900000000-3952661ff4e332b98d63	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 10V, Negative-QTOF	splash10-0udi-0090000000-667b165b22b6e86fb11b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 20V, Negative-QTOF	splash10-0udi-0790000000-fd79b540f1b9982ce3c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid 40V, Negative-QTOF	splash10-000i-0900000000-f772b27b5c4bedcbb04a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB016640

KNApSAcK ID

C00057035

Chemspider ID

35014431

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14864220

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 3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid (HMDB0037558)

MOL for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

3D MOL for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

3D SDF for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

3D-SDF for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

PDB for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

3D PDB for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

SMILES for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

INCHI for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

Structure for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

3D Structure for HMDB0037558 (3-Oxo-1,4,11(13)-eudesmatrien-12-oic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra