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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:28 UTC

Update Date

2023-02-21 17:21:34 UTC

HMDB ID

HMDB0032052

Secondary Accession Numbers

HMDB32052

Metabolite Identification

Common Name

alpha-Terpineol propanoate

Description

alpha-Terpineol propanoate, also known as a-terpineol propanoic acid, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a small amount of articles have been published on alpha-Terpineol propanoate.

Structure

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

HMDB0032052
     RDKit          3D
alpha-Terpineol propanoate
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.3833    1.6176   -1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9069    0.2901   -0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    0.3285   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054    1.4285   -0.1678 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -0.7326    0.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -0.9047    0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298   -2.3987    1.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -0.1132    2.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658   -0.8784   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668   -1.1000    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9002   -0.0645    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    0.5883   -0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805    1.6441   -1.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    0.2244   -1.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242    0.3162   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613    1.7192   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3259    1.6422   -2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    2.4847   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0493   -0.4555   -1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5308   -0.0182    0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5459   -2.6940    1.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630   -2.5001    2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773   -3.0422    0.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -0.7761    2.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5049    0.7101    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    0.2673    2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3673   -1.7798   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362   -1.3429    1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -2.0617    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6249    0.1923    1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3477    2.0982   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8483    1.2261   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4596    2.4074   -1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241    0.9422   -2.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0839   -0.8332   -2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    1.2736   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1431    0.2950   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
M  END


  Mrv0541 05061306192D          

 15 15  0  0  0  0            999 V2000
   -0.7145    4.5375    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
   -0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    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
    0.0000    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
    0.0000    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032052

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)OC(C)(C)C1CCC(C)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O2/c1-5-12(14)15-13(3,4)11-8-6-10(2)7-9-11/h6,11H,5,7-9H2,1-4H3

> <INCHI_KEY>
CMKQOKAXUWQAHG-UHFFFAOYSA-N

> <FORMULA>
C13H22O2

> <MOLECULAR_WEIGHT>
210.3126

> <EXACT_MASS>
210.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.089459787090803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methylcyclohex-3-en-1-yl)propan-2-yl propanoate

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
3.315958764999999

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.046649476117831

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
62.2403

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
terpineol, propanoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032052
     RDKit          3D
alpha-Terpineol propanoate
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.3833    1.6176   -1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9069    0.2901   -0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    0.3285   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054    1.4285   -0.1678 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -0.7326    0.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -0.9047    0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298   -2.3987    1.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -0.1132    2.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658   -0.8784   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668   -1.1000    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9002   -0.0645    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    0.5883   -0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805    1.6441   -1.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    0.2244   -1.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242    0.3162   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613    1.7192   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3259    1.6422   -2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    2.4847   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0493   -0.4555   -1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5308   -0.0182    0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5459   -2.6940    1.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630   -2.5001    2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773   -3.0422    0.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -0.7761    2.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5049    0.7101    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    0.2673    2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3673   -1.7798   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362   -1.3429    1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -2.0617    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6249    0.1923    1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3477    2.0982   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8483    1.2261   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4596    2.4074   -1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241    0.9422   -2.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0839   -0.8332   -2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    1.2736   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1431    0.2950   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  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   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   10                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    1   12                                                       
CONECT    6    8   10                                                       
CONECT    7    9   10                                                       
CONECT    8    6   11                                                       
CONECT    9    7   11                                                       
CONECT   10    2    6    7                                                  
CONECT   11    8    9   13                                                  
CONECT   12    5   14   15                                                  
CONECT   13    3    4   11   15                                             
CONECT   14   12                                                            
CONECT   15   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0032052
HETATM    1  C1  UNL     1       4.383   1.618  -1.112  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.907   0.290  -0.641  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.502   0.328  -0.138  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.905   1.428  -0.168  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.825  -0.733   0.346  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.552  -0.905   0.832  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.530  -2.399   1.293  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.212  -0.113   2.046  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.566  -0.878  -0.191  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.867  -1.100   0.495  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.900  -0.065   0.298  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.978   0.588  -0.849  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.980   1.644  -1.149  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.954   0.224  -1.888  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.624   0.316  -1.070  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.461   1.719  -0.868  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.326   1.642  -2.226  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.868   2.485  -0.651  1.00  0.00           H  
HETATM   19  H4  UNL     1       4.049  -0.456  -1.435  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.531  -0.018   0.227  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.546  -2.694   1.625  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.163  -2.500   2.142  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.277  -3.042   0.439  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.225  -0.776   2.812  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.505   0.710   1.864  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.168   0.267   2.498  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.367  -1.780  -0.860  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.736  -1.343   1.589  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.332  -2.062   0.104  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.625   0.192   1.085  1.00  0.00           H  
HETATM   31  H16 UNL     1      -4.348   2.098  -0.193  1.00  0.00           H  
HETATM   32  H17 UNL     1      -4.848   1.226  -1.702  1.00  0.00           H  
HETATM   33  H18 UNL     1      -3.460   2.407  -1.776  1.00  0.00           H  
HETATM   34  H19 UNL     1      -1.924   0.942  -2.703  1.00  0.00           H  
HETATM   35  H20 UNL     1      -2.084  -0.833  -2.173  1.00  0.00           H  
HETATM   36  H21 UNL     1      -0.700   1.274  -0.509  1.00  0.00           H  
HETATM   37  H22 UNL     1       0.143   0.295  -1.861  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7    8    9
CONECT    7   21   22   23
CONECT    8   24   25   26
CONECT    9   10   15   27
CONECT   10   11   28   29
CONECT   11   12   12   30
CONECT   12   13   14
CONECT   13   31   32   33
CONECT   14   15   34   35
CONECT   15   36   37
END

HMDB0032052
     RDKit          3D
alpha-Terpineol propanoate
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.3833    1.6176   -1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9069    0.2901   -0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    0.3285   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054    1.4285   -0.1678 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254   -0.7326    0.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -0.9047    0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298   -2.3987    1.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -0.1132    2.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658   -0.8784   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668   -1.1000    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9002   -0.0645    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    0.5883   -0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805    1.6441   -1.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    0.2244   -1.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242    0.3162   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613    1.7192   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3259    1.6422   -2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    2.4847   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0493   -0.4555   -1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5308   -0.0182    0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5459   -2.6940    1.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630   -2.5001    2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773   -3.0422    0.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -0.7761    2.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5049    0.7101    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    0.2673    2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3673   -1.7798   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362   -1.3429    1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -2.0617    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6249    0.1923    1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3477    2.0982   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8483    1.2261   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4596    2.4074   -1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241    0.9422   -2.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0839   -0.8332   -2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    1.2736   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1431    0.2950   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Terpineol propanoate	Generator
a-Terpineol propanoic acid	Generator
alpha-Terpineol propanoic acid	Generator
Α-terpineol propanoate	Generator
Α-terpineol propanoic acid	Generator
1-Methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl propionate	HMDB
4-Terpinenyl ester OF propanoic acid	HMDB
alpha -Terpinyl ester OF propanoic acid	HMDB
alpha -Terpinyl propionate	HMDB
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methyl propionate	HMDB
FEMA 3053	HMDB
P-Menth-1-en-8-yl propanoate	HMDB
P-Menth-1-en-8-yl propionate	HMDB
P-Menth-1-en-8-yl-propionate	HMDB
P-Menthanyl propionate	HMDB
Propionic acid, terpineol ester	HMDB
Terpenyl propionate	HMDB
Terpineol propionate	HMDB
Terpineol, propanoate	HMDB
Terpinyl N-propionate	HMDB
Terpinyl propionate	HMDB
2-(4-Methylcyclohex-3-en-1-yl)propan-2-yl propanoic acid	Generator
a-Terpinyl propanoate	Generator
a-Terpinyl propanoic acid	Generator
alpha-Terpinyl propanoic acid	Generator
Α-terpinyl propanoate	Generator
Α-terpinyl propanoic acid	Generator

Chemical Formula

C₁₃H₂₂O₂

Average Molecular Weight

210.3126

Monoisotopic Molecular Weight

210.161979948

IUPAC Name

2-(4-methylcyclohex-3-en-1-yl)propan-2-yl propanoate

Traditional Name

terpineol, propanoate

CAS Registry Number

80-27-3

SMILES

CCC(=O)OC(C)(C)C1CCC(C)=CC1

InChI Identifier

InChI=1S/C13H22O2/c1-5-12(14)15-13(3,4)11-8-6-10(2)7-9-11/h6,11H,5,7-9H2,1-4H3

InChI Key

CMKQOKAXUWQAHG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Bitter

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032052)

Source

Endogenous

Endogenous (HMDB: HMDB0032052)

Plant

Plant (HMDB: HMDB0032052)

Animal

Animal (HMDB: HMDB0032052)

Exogenous

Food

Food (HMDB: HMDB0032052)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Fruit

Citrus

Lemon (FooDB: FOOD00054)

Vegetable

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032052)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032052)

Cellular process

Cell signaling (HMDB: HMDB0032052)

Biochemical process

Lipid transport (HMDB: HMDB0032052)

Role

Biological role

Energy storage (HMDB: HMDB0032052)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032052)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032052)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	274.00 to 275.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.77 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.236 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	4.38	ALOGPS
logP	3.32	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.24 m³·mol⁻¹	ChemAxon
Polarizability	25.09 Å³	ChemAxon
Number of Rings	1	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]+	152.814	31661259
DarkChem	[M-H]-	147.93	31661259
DeepCCS	[M+H]+	150.395	30932474
DeepCCS	[M-H]-	148.037	30932474
DeepCCS	[M-2H]-	182.41	30932474
DeepCCS	[M+Na]+	157.361	30932474
AllCCS	[M+H]+	151.0	32859911
AllCCS	[M+H-H2O]+	147.2	32859911
AllCCS	[M+NH4]+	154.5	32859911
AllCCS	[M+Na]+	155.5	32859911
AllCCS	[M-H]-	155.6	32859911
AllCCS	[M+Na-2H]-	156.6	32859911
AllCCS	[M+HCOO]-	157.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Terpineol propanoate	CCC(=O)OC(C)(C)C1CCC(C)=CC1	1739.3	Standard polar	33892256
alpha-Terpineol propanoate	CCC(=O)OC(C)(C)C1CCC(C)=CC1	1400.6	Standard non polar	33892256
alpha-Terpineol propanoate	CCC(=O)OC(C)(C)C1CCC(C)=CC1	1394.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - alpha-Terpineol propanoate EI-B (Non-derivatized)	splash10-059f-9500000000-efa383b242ac218473ab	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - alpha-Terpineol propanoate EI-B (Non-derivatized)	splash10-059f-9500000000-efa383b242ac218473ab	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Terpineol propanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-054t-9300000000-4bc3584e944e0f90a0cb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Terpineol propanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Terpineol propanoate 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 - alpha-Terpineol propanoate 10V, Positive-QTOF	splash10-08fr-7890000000-ccf705697c559a60c7f7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 20V, Positive-QTOF	splash10-0a4i-9500000000-c567c0834ead64f419d9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 40V, Positive-QTOF	splash10-0a4i-9200000000-9b5b6b11e7d2bab7fa6c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 10V, Negative-QTOF	splash10-0a4i-2590000000-1df40840fa103282692a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 20V, Negative-QTOF	splash10-0zfr-4920000000-c73f57ae8fcd51aa021c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 40V, Negative-QTOF	splash10-0k9i-7900000000-0f72a85f502bca5b3842	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 10V, Negative-QTOF	splash10-000i-0900000000-be4915e909c99588aba4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 20V, Negative-QTOF	splash10-0079-4900000000-143644d3e47c4e91deea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 40V, Negative-QTOF	splash10-0ktf-8900000000-030f3c7f8869bade2996	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 10V, Positive-QTOF	splash10-000i-9800000000-b45e89de2223c3f1da7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 20V, Positive-QTOF	splash10-053m-9200000000-08d17b44832697eb87e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol propanoate 40V, Positive-QTOF	splash10-0006-9200000000-76d1ab1b57bf7a22fe9b	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB008757

KNApSAcK ID

Not Available

Chemspider ID

56122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62328

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1051521

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 alpha-Terpineol propanoate (HMDB0032052)

MOL for HMDB0032052 (alpha-Terpineol propanoate)

3D MOL for HMDB0032052 (alpha-Terpineol propanoate)

3D SDF for HMDB0032052 (alpha-Terpineol propanoate)

3D-SDF for HMDB0032052 (alpha-Terpineol propanoate)

PDB for HMDB0032052 (alpha-Terpineol propanoate)

3D PDB for HMDB0032052 (alpha-Terpineol propanoate)

SMILES for HMDB0032052 (alpha-Terpineol propanoate)

INCHI for HMDB0032052 (alpha-Terpineol propanoate)

Structure for HMDB0032052 (alpha-Terpineol propanoate)

3D Structure for HMDB0032052 (alpha-Terpineol propanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra