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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:16 UTC

Update Date

2022-03-07 02:53:22 UTC

HMDB ID

HMDB0032524

Secondary Accession Numbers

HMDB32524

Metabolite Identification

Common Name

Terpinyl isobutyrate

Description

Terpinyl isobutyrate 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 Terpinyl isobutyrate.

Structure

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

HMDB0032524
     RDKit          3D
Terpinyl isobutyrate
 40 40  0  0  0  0  0  0  0  0999 V2000
   -5.0488    1.0061    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6103    0.6581   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232    1.4137   -0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2871    1.0668   -0.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955   -0.3926   -0.7999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295   -0.7349    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182   -2.2387    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1803   -0.2088    1.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3371   -0.1741   -0.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065   -0.3215   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.9360    0.9505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7537    0.2880   -0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025    1.7747   -0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0548    0.0472   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1718   -1.2390   -0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -0.6435    0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2256    1.2935    1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2650    1.8409   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250    0.1726   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    2.3673   -1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607    1.5424   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7330    1.6657   -0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6760   -0.6844   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -2.6934   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966   -2.5224   -0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0601   -2.6585    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869    0.4662    1.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0768    0.4151    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -1.0157    2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377   -0.1501   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    2.2199   -1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135    1.9007   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572    2.2142    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3463    0.8923    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9533   -0.8475    0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8998   -0.1667   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8992   -2.2372   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -1.4584   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397   -1.3642    0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8484   -0.5577    1.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  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  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  5 15  1  0
 15 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 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 02241215112D          

 16 16  0  0  0  0            999 V2000
    1.4292    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156    1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156    2.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -2.6811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142   -1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032524

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O2/c1-10(2)13(15)16-14(4,5)12-8-6-11(3)7-9-12/h6,10,12H,7-9H2,1-5H3

> <INCHI_KEY>
SMQUXKIIXFOJKI-UHFFFAOYSA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.3392

> <EXACT_MASS>
224.177630012

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.89105842014803

> <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 2-methylpropanoate

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
3.8589450433333314

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.08249565668742

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.8148

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.16e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032524
     RDKit          3D
Terpinyl isobutyrate
 40 40  0  0  0  0  0  0  0  0999 V2000
   -5.0488    1.0061    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6103    0.6581   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232    1.4137   -0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2871    1.0668   -0.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955   -0.3926   -0.7999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295   -0.7349    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182   -2.2387    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1803   -0.2088    1.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3371   -0.1741   -0.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065   -0.3215   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.9360    0.9505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7537    0.2880   -0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025    1.7747   -0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0548    0.0472   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1718   -1.2390   -0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -0.6435    0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2256    1.2935    1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2650    1.8409   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250    0.1726   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    2.3673   -1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607    1.5424   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7330    1.6657   -0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6760   -0.6844   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -2.6934   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966   -2.5224   -0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0601   -2.6585    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869    0.4662    1.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0768    0.4151    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -1.0157    2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377   -0.1501   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    2.2199   -1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135    1.9007   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572    2.2142    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3463    0.8923    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9533   -0.8475    0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8998   -0.1667   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8992   -2.2372   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -1.4584   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397   -1.3642    0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8484   -0.5577    1.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  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  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  5 15  1  0
 15 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.668   2.695   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.668   1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.336   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.001   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.001   2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.336   3.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.336   5.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.336  -1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.668  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.001  -1.925   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.336  -2.695   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.001  -3.465   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.001  -5.005   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.333  -2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.668  -3.465   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.333  -1.155   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    3    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0032524
HETATM    1  C1  UNL     1      -5.049   1.006   0.043  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.610   0.658  -0.103  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.723   1.414  -0.697  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.287   1.067  -0.844  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.996  -0.393  -0.800  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.229  -0.735   0.039  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.418  -2.239   0.004  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.180  -0.209   1.429  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.337  -0.174  -0.640  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.606  -0.321  -0.117  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.859  -0.936   0.951  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.754   0.288  -0.866  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.502   1.775  -0.950  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.055   0.047  -0.143  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.172  -1.239  -0.472  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.168  -0.643   0.471  1.00  0.00           C  
HETATM   17  H1  UNL     1      -5.226   1.293   1.120  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.265   1.841  -0.633  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.725   0.173  -0.168  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.097   2.367  -1.108  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.961   1.542  -1.817  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.733   1.666  -0.075  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.676  -0.684  -1.849  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.081  -2.693  -0.883  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.497  -2.522  -0.094  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.060  -2.658   0.897  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.687   0.466   1.565  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.077   0.415   1.618  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.213  -1.016   2.192  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.838  -0.150  -1.877  1.00  0.00           H  
HETATM   31  H15 UNL     1       4.305   2.220  -1.567  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.513   1.901  -1.467  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.457   2.214   0.049  1.00  0.00           H  
HETATM   34  H18 UNL     1       5.346   0.892   0.516  1.00  0.00           H  
HETATM   35  H19 UNL     1       4.953  -0.847   0.534  1.00  0.00           H  
HETATM   36  H20 UNL     1       5.900  -0.167  -0.814  1.00  0.00           H  
HETATM   37  H21 UNL     1      -1.899  -2.237  -0.077  1.00  0.00           H  
HETATM   38  H22 UNL     1      -2.740  -1.458  -1.425  1.00  0.00           H  
HETATM   39  H23 UNL     1      -4.040  -1.364   0.487  1.00  0.00           H  
HETATM   40  H24 UNL     1      -2.848  -0.558   1.507  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   16
CONECT    3    4   20
CONECT    4    5   21   22
CONECT    5    6   15   23
CONECT    6    7    8    9
CONECT    7   24   25   26
CONECT    8   27   28   29
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   14   30
CONECT   13   31   32   33
CONECT   14   34   35   36
CONECT   15   16   37   38
CONECT   16   39   40
END

HMDB0032524
     RDKit          3D
Terpinyl isobutyrate
 40 40  0  0  0  0  0  0  0  0999 V2000
   -5.0488    1.0061    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6103    0.6581   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232    1.4137   -0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2871    1.0668   -0.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955   -0.3926   -0.7999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295   -0.7349    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182   -2.2387    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1803   -0.2088    1.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3371   -0.1741   -0.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065   -0.3215   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.9360    0.9505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7537    0.2880   -0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025    1.7747   -0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0548    0.0472   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1718   -1.2390   -0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -0.6435    0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2256    1.2935    1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2650    1.8409   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250    0.1726   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    2.3673   -1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607    1.5424   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7330    1.6657   -0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6760   -0.6844   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -2.6934   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966   -2.5224   -0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0601   -2.6585    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869    0.4662    1.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0768    0.4151    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -1.0157    2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377   -0.1501   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    2.2199   -1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135    1.9007   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572    2.2142    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3463    0.8923    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9533   -0.8475    0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8998   -0.1667   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8992   -2.2372   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -1.4584   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397   -1.3642    0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8484   -0.5577    1.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  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  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  5 15  1  0
 15 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 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
Terpinyl isobutyric acid	Generator
alpha-Terpinyl ester OF isobutanoic acid	HMDB
alpha-Terpinyl isobutyrate	HMDB
Terpinyl iso-butyrate	HMDB
2-(4-Methylcyclohex-3-en-1-yl)propan-2-yl 2-methylpropanoic 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 2-methylpropanoate

Traditional Name

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

CAS Registry Number

7774-65-4

SMILES

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

InChI Identifier

InChI=1S/C14H24O2/c1-10(2)13(15)16-14(4,5)12-8-6-11(3)7-9-12/h6,10,12H,7-9H2,1-5H3

InChI Key

SMQUXKIIXFOJKI-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

Cellular substructure

Membrane (HMDB: HMDB0032524)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032524)

Source

Endogenous

Endogenous (HMDB: HMDB0032524)

Animal

Animal (HMDB: HMDB0032524)

Exogenous

Food

Food (HMDB: HMDB0032524)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0032524)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0032524)

Cellular process

Cell signaling (HMDB: HMDB0032524)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0032524)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0032524)

Nutrient

Nutrient (HMDB: HMDB0032524)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0032524)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	242.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	4.598 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.062 g/L	ALOGPS
logP	4.78	ALOGPS
logP	3.86	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-7.1	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	66.81 m³·mol⁻¹	ChemAxon
Polarizability	26.89 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]+	153.89	31661259
DarkChem	[M-H]-	149.715	31661259
DeepCCS	[M+H]+	158.46	30932474
DeepCCS	[M-H]-	156.102	30932474
DeepCCS	[M-2H]-	189.332	30932474
DeepCCS	[M+Na]+	164.553	30932474
AllCCS	[M+H]+	153.5	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	156.9	32859911
AllCCS	[M+Na]+	157.8	32859911
AllCCS	[M-H]-	160.1	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Terpinyl isobutyrate	CC(C)C(=O)OC(C)(C)C1CCC(C)=CC1	1720.2	Standard polar	33892256
Terpinyl isobutyrate	CC(C)C(=O)OC(C)(C)C1CCC(C)=CC1	1434.3	Standard non polar	33892256
Terpinyl isobutyrate	CC(C)C(=O)OC(C)(C)C1CCC(C)=CC1	1419.0	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 - Terpinyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-9200000000-477863814bce74cdda8e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Terpinyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Terpinyl isobutyrate 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 - Terpinyl isobutyrate 10V, Positive-QTOF	splash10-004i-5490000000-c5f0961ba8a22aaa5fa0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 20V, Positive-QTOF	splash10-00du-9310000000-3286f4b62fd4eea6d993	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 40V, Positive-QTOF	splash10-05fu-9000000000-6fcbe45529d98e8b9bf1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 10V, Negative-QTOF	splash10-00di-1290000000-ff03c7e6446cda87574f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 20V, Negative-QTOF	splash10-00dr-7690000000-57134d920be2aa7f7351	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 40V, Negative-QTOF	splash10-000i-9700000000-95cef31b4f964000357a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 10V, Positive-QTOF	splash10-000i-8900000000-7ca978d0f0f57da6dd41	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 20V, Positive-QTOF	splash10-0006-9200000000-3a4a25fd0d773225bfdf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 40V, Positive-QTOF	splash10-0006-9000000000-58d568d9ef432b97f738	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 10V, Negative-QTOF	splash10-000i-5900000000-f313c9e8c51b20ceca04	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 20V, Negative-QTOF	splash10-000i-9500000000-ecf40e8a0c0b8fc19507	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terpinyl isobutyrate 40V, Negative-QTOF	splash10-0079-7900000000-b0090b8929fc2c1991c8	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010375

KNApSAcK ID

Not Available

Chemspider ID

455931

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

522673

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1034861

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 Terpinyl isobutyrate (HMDB0032524)

MOL for HMDB0032524 (Terpinyl isobutyrate)

3D MOL for HMDB0032524 (Terpinyl isobutyrate)

3D SDF for HMDB0032524 (Terpinyl isobutyrate)

3D-SDF for HMDB0032524 (Terpinyl isobutyrate)

PDB for HMDB0032524 (Terpinyl isobutyrate)

3D PDB for HMDB0032524 (Terpinyl isobutyrate)

SMILES for HMDB0032524 (Terpinyl isobutyrate)

INCHI for HMDB0032524 (Terpinyl isobutyrate)

Structure for HMDB0032524 (Terpinyl isobutyrate)

3D Structure for HMDB0032524 (Terpinyl isobutyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra