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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:48:31 UTC

Update Date

2022-03-07 02:55:23 UTC

HMDB ID

HMDB0037557

Secondary Accession Numbers

HMDB37557

Metabolite Identification

Common Name

1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid

Description

1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid.

Structure

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

HMDB0037557
     RDKit          3D
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.6189   -0.9201   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159   -0.0482    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636    0.7404    1.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    1.5740    1.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8982    0.6127    1.4901 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4759    0.1156   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246   -0.7378   -1.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357   -0.5818   -1.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    0.4001   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    1.7906   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393    0.1299   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8681   -0.0291   -2.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0308   -1.1249   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817   -1.3424    1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7305   -0.3137    1.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -0.0173    2.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7717    0.4018    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895   -0.1830    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601   -1.0484   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -1.5128   -1.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5742    1.2011    1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    1.1976   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6482   -0.5617   -2.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871   -1.8098   -1.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9788   -1.5497   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387   -0.2085   -2.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513    2.5027   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8519    2.2064   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897    1.7524   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543    0.9925   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398   -0.0571   -2.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6598   -1.8804   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144   -2.2264    1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621   -0.5175    3.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458    0.7474    3.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489    1.4525    1.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -1.2928    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310    0.1457    1.9171 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  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  3
 15 17  1  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
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
M  END


  Mrv0541 05061309512D          

 18 19  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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    0.0000    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
    3.5724    1.2375    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.8579    0.0000    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
    5.0013   -1.2375    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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  1  0  0  0  0
  9  1  2  0  0  0  0
  9  4  1  0  0  0  0
 10  2  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 14 10  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 13  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037557

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC(CC1C(=C)C=CC2O)C(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-4-5-13(16)15(3)7-6-11(8-12(9)15)10(2)14(17)18/h4-5,11-13,16H,1-2,6-8H2,3H3,(H,17,18)

> <INCHI_KEY>
GQPOONXHFROSAO-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.110955962225905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-hydroxy-4a-methyl-8-methylidene-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-yl)prop-2-enoic acid

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
2.3321103973333335

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.03732962987642

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.830428166569463

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0328726806449775

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
70.5752

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(5-hydroxy-4a-methyl-8-methylidene-1,2,3,4,5,8a-hexahydronaphthalen-2-yl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037557
     RDKit          3D
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.6189   -0.9201   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159   -0.0482    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636    0.7404    1.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    1.5740    1.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8982    0.6127    1.4901 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4759    0.1156   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246   -0.7378   -1.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357   -0.5818   -1.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    0.4001   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    1.7906   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393    0.1299   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8681   -0.0291   -2.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0308   -1.1249   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817   -1.3424    1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7305   -0.3137    1.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -0.0173    2.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7717    0.4018    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895   -0.1830    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601   -1.0484   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -1.5128   -1.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5742    1.2011    1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    1.1976   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6482   -0.5617   -2.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871   -1.8098   -1.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9788   -1.5497   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387   -0.2085   -2.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513    2.5027   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8519    2.2064   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897    1.7524   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543    0.9925   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398   -0.0571   -2.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6598   -1.8804   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144   -2.2264    1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621   -0.5175    3.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458    0.7474    3.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489    1.4525    1.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -1.2928    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310    0.1457    1.9171 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  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  3
 15 17  1  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
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   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   0.000   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       8.002   1.540   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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   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       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5    9                                                       
CONECT    5    4   13                                                       
CONECT    6    7   11                                                       
CONECT    7    6   15                                                       
CONECT    8   11   12                                                       
CONECT    9    1    4   12                                                  
CONECT   10    2   11   14                                                  
CONECT   11    6    8   10                                                  
CONECT   12    8    9   15                                                  
CONECT   13    5   15   16                                                  
CONECT   14   10   17   18                                                  
CONECT   15    3    7   12   13                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0037557
HETATM    1  C1  UNL     1       3.619  -0.920  -0.541  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.916  -0.048   0.127  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.564   0.740   1.167  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.868   1.574   1.797  1.00  0.00           O  
HETATM    5  O2  UNL     1       4.898   0.613   1.490  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.476   0.116  -0.197  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.025  -0.738  -1.335  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.436  -0.582  -1.594  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.157   0.400  -0.729  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.911   1.791  -1.332  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.639   0.130  -0.876  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.868  -0.029  -2.259  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.031  -1.125  -0.218  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.582  -1.342   1.006  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.730  -0.314   1.602  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.790  -0.017   2.889  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.772   0.402   0.698  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.590  -0.183   0.979  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.660  -1.048  -0.319  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.173  -1.513  -1.309  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.574   1.201   1.035  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.352   1.198  -0.426  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.648  -0.562  -2.238  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.187  -1.810  -1.047  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.979  -1.550  -1.589  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.539  -0.208  -2.655  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.651   2.503  -0.534  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.852   2.206  -1.792  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.190   1.752  -2.169  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.254   0.992  -0.550  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.840  -0.057  -2.449  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.660  -1.880  -0.665  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.814  -2.226   1.572  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.462  -0.517   3.541  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.146   0.747   3.288  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.749   1.453   1.066  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.471  -1.293   1.038  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.031   0.146   1.917  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   13   30
CONECT   12   31
CONECT   13   14   14   32
CONECT   14   15   33
CONECT   15   16   16   17
CONECT   16   34   35
CONECT   17   18   36
CONECT   18   37   38
END

HMDB0037557
     RDKit          3D
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.6189   -0.9201   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159   -0.0482    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636    0.7404    1.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    1.5740    1.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8982    0.6127    1.4901 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4759    0.1156   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246   -0.7378   -1.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357   -0.5818   -1.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    0.4001   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    1.7906   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393    0.1299   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8681   -0.0291   -2.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0308   -1.1249   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817   -1.3424    1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7305   -0.3137    1.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -0.0173    2.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7717    0.4018    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895   -0.1830    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601   -1.0484   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -1.5128   -1.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5742    1.2011    1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    1.1976   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6482   -0.5617   -2.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871   -1.8098   -1.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9788   -1.5497   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387   -0.2085   -2.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513    2.5027   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8519    2.2064   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897    1.7524   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543    0.9925   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398   -0.0571   -2.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6598   -1.8804   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144   -2.2264    1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621   -0.5175    3.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458    0.7474    3.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489    1.4525    1.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -1.2928    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0310    0.1457    1.9171 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  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  3
 15 17  1  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
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1a-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-Oate	Generator
1a-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-Oic acid	Generator
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-Oate	Generator
1Α-1-hydroxy-2,4(18),11(13)-eudesmatrien-12-Oate	Generator
1Α-1-hydroxy-2,4(18),11(13)-eudesmatrien-12-Oic acid	Generator
2-(5-Hydroxy-4a-methyl-8-methylidene-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-yl)prop-2-enoate	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

2-(5-hydroxy-4a-methyl-8-methylidene-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-yl)prop-2-enoic acid

Traditional Name

2-(5-hydroxy-4a-methyl-8-methylidene-1,2,3,4,5,8a-hexahydronaphthalen-2-yl)prop-2-enoic acid

CAS Registry Number

135594-81-9

SMILES

CC12CCC(CC1C(=C)C=CC2O)C(=C)C(O)=O

InChI Identifier

InChI=1S/C15H20O3/c1-9-4-5-13(16)15(3)7-6-11(8-12(9)15)10(2)14(17)18/h4-5,11-13,16H,1-2,6-8H2,3H3,(H,17,18)

InChI Key

GQPOONXHFROSAO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037557)

Source

Endogenous

Endogenous (HMDB: HMDB0037557)

Animal

Animal (HMDB: HMDB0037557)

Exogenous

Food

Food (HMDB: HMDB0037557)

Exogenous (HMDB: HMDB0037557)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037557)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037557)

Lipid metabolism pathway (HMDB: HMDB0037557)

Cellular process

Cell signaling (HMDB: HMDB0037557)

Biochemical process

Lipid transport (HMDB: HMDB0037557)

Role

Biological role

Energy source (HMDB: HMDB0037557)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037557)

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	247.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	2.44	ALOGPS
logP	2.33	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.58 m³·mol⁻¹	ChemAxon
Polarizability	27.11 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]+	159.565	31661259
DarkChem	[M-H]-	157.395	31661259
DeepCCS	[M-2H]-	188.031	30932474
DeepCCS	[M+Na]+	163.509	30932474
AllCCS	[M+H]+	159.5	32859911
AllCCS	[M+H-H2O]+	155.8	32859911
AllCCS	[M+NH4]+	162.9	32859911
AllCCS	[M+Na]+	163.9	32859911
AllCCS	[M-H]-	162.1	32859911
AllCCS	[M+Na-2H]-	162.3	32859911
AllCCS	[M+HCOO]-	162.7	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.	5.78 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7745 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2107.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	315.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	136.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	439.0 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	538.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1072.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	410.8 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	1279.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	350.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	320.6 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	16.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid	CC12CCC(CC1C(=C)C=CC2O)C(=C)C(O)=O	3620.7	Standard polar	33892256
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid	CC12CCC(CC1C(=C)C=CC2O)C(=C)C(O)=O	1831.4	Standard non polar	33892256
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid	CC12CCC(CC1C(=C)C=CC2O)C(=C)C(O)=O	2092.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid,1TMS,isomer #1	C=C(C(=O)O)C1CCC2(C)C(O[Si](C)(C)C)C=CC(=C)C2C1	2211.6	Semi standard non polar	33892256
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid,1TMS,isomer #2	C=C(C(=O)O[Si](C)(C)C)C1CCC2(C)C(O)C=CC(=C)C2C1	2090.0	Semi standard non polar	33892256
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid,2TMS,isomer #1	C=C(C(=O)O[Si](C)(C)C)C1CCC2(C)C(O[Si](C)(C)C)C=CC(=C)C2C1	2139.7	Semi standard non polar	33892256
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid,1TBDMS,isomer #1	C=C(C(=O)O)C1CCC2(C)C(O[Si](C)(C)C(C)(C)C)C=CC(=C)C2C1	2446.7	Semi standard non polar	33892256
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid,1TBDMS,isomer #2	C=C(C(=O)O[Si](C)(C)C(C)(C)C)C1CCC2(C)C(O)C=CC(=C)C2C1	2349.4	Semi standard non polar	33892256
1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid,2TBDMS,isomer #1	C=C(C(=O)O[Si](C)(C)C(C)(C)C)C1CCC2(C)C(O[Si](C)(C)C(C)(C)C)C=CC(=C)C2C1	2639.7	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 - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0041-2940000000-49630b4f1f37d55af6b2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid GC-MS (2 TMS) - 70eV, Positive	splash10-004i-4269000000-f9b198c8a0f74b1a8402	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1alpha-1-Hydroxy-2,4(18),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 - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 10V, Positive-QTOF	splash10-001j-0290000000-133d4fcdc5ab047a78ac	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 20V, Positive-QTOF	splash10-01qi-0970000000-316da0e4bd5b11b0a750	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 40V, Positive-QTOF	splash10-0udi-6900000000-8600e25c32e2d15ed099	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 10V, Negative-QTOF	splash10-0002-0190000000-f1c24a00b8a74475c1a5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 20V, Negative-QTOF	splash10-0ug1-1490000000-bfcee355ef45b5e4d11c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 40V, Negative-QTOF	splash10-0ug0-4930000000-b36d33a7f0025288ba63	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 10V, Negative-QTOF	splash10-0udi-0290000000-2db5fd353228080a54a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 20V, Negative-QTOF	splash10-0f79-0950000000-56dc05ef69d2cf2638e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 40V, Negative-QTOF	splash10-000i-1920000000-7839d1b381bacec39cf0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 10V, Positive-QTOF	splash10-003r-0490000000-9d0d4cef5650c5cd39b8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 20V, Positive-QTOF	splash10-05gi-0930000000-dc70b5891d018dba9292	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid 40V, Positive-QTOF	splash10-0gb9-4900000000-b5c751ed3936e24ef001	2021-09-23	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

FDB016639

KNApSAcK ID

Not Available

Chemspider ID

35014430

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14864221

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1862021

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 1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid (HMDB0037557)

MOL for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

3D MOL for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

3D SDF for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

3D-SDF for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

PDB for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

3D PDB for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

SMILES for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

INCHI for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

Structure for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

3D Structure for HMDB0037557 (1alpha-1-Hydroxy-2,4(18),11(13)-eudesmatrien-12-oic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra