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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:29 UTC

Update Date

2022-03-07 02:53:13 UTC

HMDB ID

HMDB0032053

Secondary Accession Numbers

HMDB32053

Metabolite Identification

Common Name

alpha-Terpineol butanoate

Description

alpha-Terpineol butanoate, also known as a-terpineol butanoic 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 butanoate.

Structure

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

HMDB0032053
     RDKit          3D
alpha-Terpineol butanoate
 40 40  0  0  0  0  0  0  0  0999 V2000
    5.3539   -1.4482    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0921   -1.4297    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -0.1754    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0896   -0.0341   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.9542   -1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2247    1.0082   -0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0345    1.2768   -0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1320    1.3154   -2.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2845    2.7579   -0.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1805    0.5272   -0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700   -0.9586   -0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675   -1.4473   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148   -0.8010    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8297   -1.3400    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0986    0.4358    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6172    0.7370    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0397   -0.6278    0.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9008   -2.4058    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1048   -1.3390    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884   -1.5290   -0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976   -2.3314    0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180   -0.1088    1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9976    0.6908    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1945    0.3058   -2.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    1.7340   -2.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991    2.0059   -2.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434    2.9503    0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    2.9625   -0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467    3.3593   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238    0.9587   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -1.2236   -1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757   -1.4071    0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728   -2.3375   -1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4970   -0.5651    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1977   -1.6274   -0.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7944   -2.2507    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4865    0.3324    2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6245    1.2679    0.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902    1.7309    1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -0.0152    1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
M  END


  Mrv0541 05061306192D          

 16 16  0  0  0  0            999 V2000
   -0.7145    5.3625    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
   -0.7145    4.5375    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
  6  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032053

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O2/c1-5-6-13(15)16-14(3,4)12-9-7-11(2)8-10-12/h7,12H,5-6,8-10H2,1-4H3

> <INCHI_KEY>
LWKWNIYBQLKBMQ-UHFFFAOYSA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.3392

> <EXACT_MASS>
224.177630012

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.163384880415382

> <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 butanoate

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
3.760527429999999

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.049594076030835

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.84129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-methylcyclohex-3-en-1-yl)propan-2-yl butanoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032053
     RDKit          3D
alpha-Terpineol butanoate
 40 40  0  0  0  0  0  0  0  0999 V2000
    5.3539   -1.4482    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0921   -1.4297    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -0.1754    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0896   -0.0341   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.9542   -1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2247    1.0082   -0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0345    1.2768   -0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1320    1.3154   -2.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2845    2.7579   -0.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1805    0.5272   -0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700   -0.9586   -0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675   -1.4473   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148   -0.8010    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8297   -1.3400    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0986    0.4358    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6172    0.7370    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0397   -0.6278    0.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9008   -2.4058    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1048   -1.3390    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884   -1.5290   -0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976   -2.3314    0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180   -0.1088    1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9976    0.6908    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1945    0.3058   -2.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    1.7340   -2.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991    2.0059   -2.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434    2.9503    0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    2.9625   -0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467    3.3593   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238    0.9587   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -1.2236   -1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757   -1.4071    0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728   -2.3375   -1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4970   -0.5651    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1977   -1.6274   -0.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7944   -2.2507    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4865    0.3324    2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6245    1.2679    0.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902    1.7309    1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -0.0152    1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  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  10.010   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      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5    1    6                                                       
CONECT    6    5   13                                                       
CONECT    7    9   11                                                       
CONECT    8   10   11                                                       
CONECT    9    7   12                                                       
CONECT   10    8   12                                                       
CONECT   11    2    7    8                                                  
CONECT   12    9   10   14                                                  
CONECT   13    6   15   16                                                  
CONECT   14    3    4   12   16                                             
CONECT   15   13                                                            
CONECT   16   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0032053
HETATM    1  C1  UNL     1       5.354  -1.448   0.997  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.092  -1.430   0.155  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.353  -0.175   0.472  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.090  -0.034  -0.290  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.799  -0.954  -1.085  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.225   1.008  -0.196  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.034   1.277  -0.814  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.132   1.315  -2.343  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.285   2.758  -0.426  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.181   0.527  -0.454  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.170  -0.959  -0.671  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.568  -1.447  -0.525  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.415  -0.801   0.244  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.830  -1.340   0.361  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.099   0.436   1.025  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.617   0.737   0.985  1.00  0.00           C  
HETATM   17  H1  UNL     1       6.040  -0.628   0.733  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.901  -2.406   0.900  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.105  -1.339   2.070  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.388  -1.529  -0.901  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.498  -2.331   0.451  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.218  -0.109   1.561  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.998   0.691   0.182  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.194   0.306  -2.774  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.855   1.734  -2.677  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.899   2.006  -2.693  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.043   2.950   0.601  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.333   2.962  -0.642  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.347   3.359  -1.089  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.024   0.959  -1.073  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.772  -1.224  -1.683  1.00  0.00           H  
HETATM   32  H16 UNL     1      -0.576  -1.407   0.158  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.873  -2.338  -1.059  1.00  0.00           H  
HETATM   34  H18 UNL     1      -5.497  -0.565   0.733  1.00  0.00           H  
HETATM   35  H19 UNL     1      -5.198  -1.627  -0.654  1.00  0.00           H  
HETATM   36  H20 UNL     1      -4.794  -2.251   0.965  1.00  0.00           H  
HETATM   37  H21 UNL     1      -3.487   0.332   2.044  1.00  0.00           H  
HETATM   38  H22 UNL     1      -3.625   1.268   0.484  1.00  0.00           H  
HETATM   39  H23 UNL     1      -1.390   1.731   1.373  1.00  0.00           H  
HETATM   40  H24 UNL     1      -1.124  -0.015   1.639  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8    9   10
CONECT    8   24   25   26
CONECT    9   27   28   29
CONECT   10   11   16   30
CONECT   11   12   31   32
CONECT   12   13   13   33
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   16   37   38
CONECT   16   39   40
END

HMDB0032053
     RDKit          3D
alpha-Terpineol butanoate
 40 40  0  0  0  0  0  0  0  0999 V2000
    5.3539   -1.4482    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0921   -1.4297    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -0.1754    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0896   -0.0341   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.9542   -1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2247    1.0082   -0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0345    1.2768   -0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1320    1.3154   -2.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2845    2.7579   -0.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1805    0.5272   -0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700   -0.9586   -0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675   -1.4473   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148   -0.8010    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8297   -1.3400    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0986    0.4358    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6172    0.7370    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0397   -0.6278    0.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9008   -2.4058    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1048   -1.3390    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884   -1.5290   -0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976   -2.3314    0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180   -0.1088    1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9976    0.6908    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1945    0.3058   -2.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    1.7340   -2.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991    2.0059   -2.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434    2.9503    0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    2.9625   -0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467    3.3593   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238    0.9587   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -1.2236   -1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757   -1.4071    0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728   -2.3375   -1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4970   -0.5651    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1977   -1.6274   -0.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7944   -2.2507    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4865    0.3324    2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6245    1.2679    0.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902    1.7309    1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237   -0.0152    1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Terpineol butanoate	Generator
a-Terpineol butanoic acid	Generator
alpha-Terpineol butanoic acid	Generator
Α-terpineol butanoate	Generator
Α-terpineol butanoic acid	Generator
1-Methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl butanoate	HMDB
1-Methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl butyrate	HMDB
4-Terpinenyl ester OF N-butanoic acid	HMDB
alpha -Terpinyl butyrate	HMDB
alpha -Terpinyl ester OF N-butanoic acid	HMDB
alpha-Terpinyl butyrate	HMDB
Butyric acid, P-menth-1-en-8-yl ester	HMDB
FEMA 3049	HMDB
P-Menth-1-en-8-yl butyrate	HMDB
Terpinyl butyrate	HMDB
Terpinyl N-butyrate	HMDB
2-(4-Methylcyclohex-3-en-1-yl)propan-2-yl butanoic acid	Generator
a-Terpinyl butanoate	Generator
a-Terpinyl butanoic acid	Generator
alpha-Terpinyl butanoic acid	Generator
Α-terpinyl butanoate	Generator
Α-terpinyl butanoic acid	Generator

Chemical Formula

C₁₄H₂₄O₂

Average Molecular Weight

224.3392

Monoisotopic Molecular Weight

224.177630012

IUPAC Name

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

Traditional Name

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

CAS Registry Number

2153-28-8

SMILES

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

InChI Identifier

InChI=1S/C14H24O2/c1-5-6-13(15)16-14(3,4)12-9-7-11(2)8-10-12/h7,12H,5-6,8-10H2,1-4H3

InChI Key

LWKWNIYBQLKBMQ-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
Fatty acid ester
Fatty acyl
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

Cytoplasm (HMDB: HMDB0032053)
Cell membrane (HMDB: HMDB0032053)

Cellular substructure

Extracellular (HMDB: HMDB0032053)
Membrane (HMDB: HMDB0032053)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032053)

Source

Endogenous

Endogenous (HMDB: HMDB0032053)

Animal

Animal (HMDB: HMDB0032053)

Exogenous

Food

Food (HMDB: HMDB0032053)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0032053)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0032053)

Cellular process

Cell signaling (HMDB: HMDB0032053)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0032053)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0032053)

Nutrient

Nutrient (HMDB: HMDB0032053)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032053)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0032053)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	244.00 to 246.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.94 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.754 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.041 g/L	ALOGPS
logP	4.58	ALOGPS
logP	3.76	ChemAxon
logS	-3.7	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	5	ChemAxon
Refractivity	66.84 m³·mol⁻¹	ChemAxon
Polarizability	27.16 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]+	153.42	31661259
DarkChem	[M-H]-	151.328	31661259
DeepCCS	[M+H]+	157.06	30932474
DeepCCS	[M-H]-	154.702	30932474
DeepCCS	[M-2H]-	188.26	30932474
DeepCCS	[M+Na]+	163.359	30932474
AllCCS	[M+H]+	156.5	32859911
AllCCS	[M+H-H2O]+	152.9	32859911
AllCCS	[M+NH4]+	159.8	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	160.1	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	162.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Terpineol butanoate	CCCC(=O)OC(C)(C)C1CCC(C)=CC1	1811.8	Standard polar	33892256
alpha-Terpineol butanoate	CCCC(=O)OC(C)(C)C1CCC(C)=CC1	1470.5	Standard non polar	33892256
alpha-Terpineol butanoate	CCCC(=O)OC(C)(C)C1CCC(C)=CC1	1477.1	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 - alpha-Terpineol butanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0077-9200000000-eecaa99639f37fe503c6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Terpineol butanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Terpineol butanoate 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 butanoate 10V, Positive-QTOF	splash10-004i-6690000000-18e23954f646056bc38c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 20V, Positive-QTOF	splash10-05ia-9400000000-1e77ea2b2a80ba65c88b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 40V, Positive-QTOF	splash10-0zfu-9200000000-33074324188a95cea216	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 10V, Negative-QTOF	splash10-00di-2590000000-7f5a2adfdf0ea3438861	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 20V, Negative-QTOF	splash10-0udi-5930000000-7fe8a6ba8e4a4ed2874f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 40V, Negative-QTOF	splash10-0f79-7900000000-e886894ff9529f13e593	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 10V, Negative-QTOF	splash10-000i-2950000000-6c17088bf7b6db3031dd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 20V, Negative-QTOF	splash10-000i-9610000000-8c9f4fe33e9f7224541a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 40V, Negative-QTOF	splash10-0a4i-7900000000-e3c71259e4a0a8cf724b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 10V, Positive-QTOF	splash10-000i-9800000000-369dd6be054b743f246a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 20V, Positive-QTOF	splash10-001d-9400000000-d3af28b9540669ac1d14	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Terpineol butanoate 40V, Positive-QTOF	splash10-0006-9200000000-9dd84134104a4f67834b	2021-09-25	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

FDB008758

KNApSAcK ID

Not Available

Chemspider ID

502793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

578423

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1034831

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 butanoate (HMDB0032053)

MOL for HMDB0032053 (alpha-Terpineol butanoate)

3D MOL for HMDB0032053 (alpha-Terpineol butanoate)

3D SDF for HMDB0032053 (alpha-Terpineol butanoate)

3D-SDF for HMDB0032053 (alpha-Terpineol butanoate)

PDB for HMDB0032053 (alpha-Terpineol butanoate)

3D PDB for HMDB0032053 (alpha-Terpineol butanoate)

SMILES for HMDB0032053 (alpha-Terpineol butanoate)

INCHI for HMDB0032053 (alpha-Terpineol butanoate)

Structure for HMDB0032053 (alpha-Terpineol butanoate)

3D Structure for HMDB0032053 (alpha-Terpineol butanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra