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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:27:04 UTC

Update Date

2022-03-07 02:55:14 UTC

HMDB ID

HMDB0037211

Secondary Accession Numbers

HMDB37211

Metabolite Identification

Common Name

Menthyl isovalerate

Description

Menthyl isovalerate 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 Menthyl isovalerate.

Structure

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

HMDB0037211
     RDKit          3D
Menthyl isovalerate
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.1334    0.2046   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937    0.1365   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9086    1.4802    0.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7522   -0.2111   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5583   -0.3011    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556   -0.0986    1.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -0.6123   -0.4011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547   -0.7102    0.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3998   -2.1137    0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6775   -2.2816   -0.3235 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4382   -2.2632   -1.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7506   -1.3080    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1624   -0.1307    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9138    0.2678    0.0672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5925    1.6913    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499    1.8918    1.8920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    2.2373   -0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184    1.2248   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9481   -0.4923   -1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1047   -0.0909   -0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -0.6134    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9731    1.7720    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5291    2.2653   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834    1.4571    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -1.2206   -1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.5060   -1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -0.4876    1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -2.7649   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058   -2.5086    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0650   -3.2994   -0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2386   -1.6623   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5042   -3.2846   -2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4385   -1.8516   -2.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884   -1.7679    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816   -0.8528   -0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845    0.6870    0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.5453    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1359    0.2265   -1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    2.2941    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7744    2.8700    2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542    1.1180    2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2570    1.9345    2.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    2.4907    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241    1.5317   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802    3.1854   -0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  1
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  6
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
M  END


  Mrv0541 02241215372D          

 17 17  0  0  0  0            999 V2000
   -1.7876   -0.6173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5012   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7876    1.0327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7876    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -0.2048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3575   -0.6173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7876   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711   -0.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    0.6202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012   -0.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037211

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H28O2/c1-10(2)8-15(16)17-14-9-12(5)6-7-13(14)11(3)4/h10-14H,6-9H2,1-5H3/t12-,13+,14-/m1/s1

> <INCHI_KEY>
VYQSSWZYPCCBRN-HZSPNIEDSA-N

> <FORMULA>
C15H28O2

> <MOLECULAR_WEIGHT>
240.3816

> <EXACT_MASS>
240.20893014

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
29.553375634303087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-methylbutanoate

> <ALOGPS_LOGP>
4.64

> <JCHEM_LOGP>
4.537522165666666

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.044998796422264

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
70.37330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037211
     RDKit          3D
Menthyl isovalerate
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.1334    0.2046   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937    0.1365   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9086    1.4802    0.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7522   -0.2111   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5583   -0.3011    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556   -0.0986    1.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -0.6123   -0.4011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547   -0.7102    0.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3998   -2.1137    0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6775   -2.2816   -0.3235 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4382   -2.2632   -1.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7506   -1.3080    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1624   -0.1307    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9138    0.2678    0.0672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5925    1.6913    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499    1.8918    1.8920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    2.2373   -0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184    1.2248   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9481   -0.4923   -1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1047   -0.0909   -0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -0.6134    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9731    1.7720    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5291    2.2653   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834    1.4571    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -1.2206   -1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.5060   -1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -0.4876    1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -2.7649   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058   -2.5086    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0650   -3.2994   -0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2386   -1.6623   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5042   -3.2846   -2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4385   -1.8516   -2.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884   -1.7679    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816   -0.8528   -0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845    0.6870    0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.5453    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1359    0.2265   -1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    2.2941    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7744    2.8700    2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542    1.1180    2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2570    1.9345    2.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    2.4907    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241    1.5317   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802    3.1854   -0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  1
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  6
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  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      -3.337  -1.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.669  -0.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.669   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.337   1.928   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.337   3.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.002   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.002  -0.382   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.667  -1.152   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.669  -3.465   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.337  -2.692   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.002  -3.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.667  -0.382   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.999  -1.152   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.667   1.158   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.334  -0.382   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.669  -1.152   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.334   1.158   0.000  0.00  0.00           C+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7   12                                                       
CONECT    9   10                                                            
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0037211
HETATM    1  C1  UNL     1       5.133   0.205  -1.062  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.994   0.136  -0.068  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.909   1.480   0.610  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.752  -0.211  -0.824  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.558  -0.301   0.091  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.656  -0.099   1.329  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.301  -0.612  -0.401  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.855  -0.710   0.412  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.400  -2.114   0.450  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.677  -2.282  -0.323  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.438  -2.263  -1.813  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.751  -1.308   0.076  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.162  -0.131   0.855  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.914   0.268   0.067  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.593   1.691   0.420  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.350   1.892   1.892  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.478   2.237  -0.439  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.218   1.225  -1.514  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.948  -0.492  -1.928  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.105  -0.091  -0.617  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.235  -0.613   0.699  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.973   1.772   0.848  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.529   2.265  -0.088  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.383   1.457   1.572  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.905  -1.221  -1.270  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.535   0.506  -1.615  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.505  -0.488   1.463  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.638  -2.765  -0.042  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.506  -2.509   1.487  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.065  -3.299  -0.079  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.239  -1.662  -2.314  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.504  -3.285  -2.263  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.439  -1.852  -2.065  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.588  -1.768   0.624  1.00  0.00           H  
HETATM   35  H18 UNL     1      -4.182  -0.853  -0.853  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.885   0.687   0.924  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.858  -0.545   1.839  1.00  0.00           H  
HETATM   38  H21 UNL     1      -2.136   0.227  -1.010  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.511   2.294   0.169  1.00  0.00           H  
HETATM   40  H23 UNL     1      -1.774   2.870   2.236  1.00  0.00           H  
HETATM   41  H24 UNL     1      -1.854   1.118   2.507  1.00  0.00           H  
HETATM   42  H25 UNL     1      -0.257   1.935   2.115  1.00  0.00           H  
HETATM   43  H26 UNL     1       0.427   2.491   0.149  1.00  0.00           H  
HETATM   44  H27 UNL     1      -0.224   1.532  -1.278  1.00  0.00           H  
HETATM   45  H28 UNL     1      -0.780   3.185  -0.968  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22   23   24
CONECT    4    5   25   26
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   14   27
CONECT    9   10   28   29
CONECT   10   11   12   30
CONECT   11   31   32   33
CONECT   12   13   34   35
CONECT   13   14   36   37
CONECT   14   15   38
CONECT   15   16   17   39
CONECT   16   40   41   42
CONECT   17   43   44   45
END

HMDB0037211
     RDKit          3D
Menthyl isovalerate
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.1334    0.2046   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937    0.1365   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9086    1.4802    0.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7522   -0.2111   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5583   -0.3011    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556   -0.0986    1.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -0.6123   -0.4011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547   -0.7102    0.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3998   -2.1137    0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6775   -2.2816   -0.3235 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4382   -2.2632   -1.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7506   -1.3080    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1624   -0.1307    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9138    0.2678    0.0672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5925    1.6913    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499    1.8918    1.8920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    2.2373   -0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184    1.2248   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9481   -0.4923   -1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1047   -0.0909   -0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -0.6134    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9731    1.7720    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5291    2.2653   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834    1.4571    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -1.2206   -1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.5060   -1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -0.4876    1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -2.7649   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058   -2.5086    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0650   -3.2994   -0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2386   -1.6623   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5042   -3.2846   -2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4385   -1.8516   -2.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884   -1.7679    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816   -0.8528   -0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845    0.6870    0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.5453    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1359    0.2265   -1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    2.2941    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7744    2.8700    2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8542    1.1180    2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2570    1.9345    2.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    2.4907    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241    1.5317   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802    3.1854   -0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  1
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  6
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Menthyl isovaleric acid	Generator
FEMA 2669	HMDB
Validol	HMDB
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-methylbutanoic acid	Generator
Validol, (1R-(1alpha,2beta,5alpha))-isomer	MeSH
Validol, (1alpha,2beta,5alpha)-isomer	MeSH
3-p-Menthyl isovalerate	MeSH

Chemical Formula

C₁₅H₂₈O₂

Average Molecular Weight

240.3816

Monoisotopic Molecular Weight

240.20893014

IUPAC Name

(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-methylbutanoate

Traditional Name

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3-methylbutanoate

CAS Registry Number

16409-46-4

SMILES

CC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C

InChI Identifier

InChI=1S/C15H28O2/c1-10(2)8-15(16)17-14-9-12(5)6-7-13(14)11(3)4/h10-14H,6-9H2,1-5H3/t12-,13+,14-/m1/s1

InChI Key

VYQSSWZYPCCBRN-HZSPNIEDSA-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

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037211)

Source

Endogenous

Endogenous (HMDB: HMDB0037211)

Plant

Plant (HMDB: HMDB0037211)

Animal

Animal (HMDB: HMDB0037211)

Exogenous

Food

Food (HMDB: HMDB0037211)

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)

Exogenous (HMDB: HMDB0037211)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037211)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037211)

Lipid metabolism pathway (HMDB: HMDB0037211)

Cellular process

Cell signaling (HMDB: HMDB0037211)

Biochemical process

Lipid transport (HMDB: HMDB0037211)

Role

Biological role

Energy source (HMDB: HMDB0037211)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037211)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037211)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	260.00 to 262.00 °C. @ 750.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.31 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.555 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	4.64	ALOGPS
logP	4.54	ChemAxon
logS	-4.9	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	70.37 m³·mol⁻¹	ChemAxon
Polarizability	29.55 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]+	157.331	31661259
DarkChem	[M-H]-	156.911	31661259
DeepCCS	[M+H]+	172.425	30932474
DeepCCS	[M-H]-	170.067	30932474
DeepCCS	[M-2H]-	203.163	30932474
DeepCCS	[M+Na]+	178.518	30932474
AllCCS	[M+H]+	159.6	32859911
AllCCS	[M+H-H2O]+	156.2	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.7	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	166.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.97 minutes	32390414
Predicted by Siyang on May 30, 2022	22.4304 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.76 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2981.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	786.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	280.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	449.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	511.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1069.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	993.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1751.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	682.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1951.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	597.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	509.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	535.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	679.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Menthyl isovalerate	CC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C	1702.0	Standard polar	33892256
Menthyl isovalerate	CC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C	1440.9	Standard non polar	33892256
Menthyl isovalerate	CC(C)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C	1510.8	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 - Menthyl isovalerate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-9410000000-20d3309958a96e8159ba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthyl isovalerate 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 - Menthyl isovalerate 10V, Positive-QTOF	splash10-000f-5690000000-58d938249b983d9a1f60	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 20V, Positive-QTOF	splash10-0a4u-9400000000-c366cb5007bb4fb41f82	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 40V, Positive-QTOF	splash10-0a4i-9100000000-4891817e2d7deda642fd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 10V, Negative-QTOF	splash10-052r-2590000000-25bffb0452c80aa6923d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 20V, Negative-QTOF	splash10-0a4i-3920000000-359566a58414ed825da0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 40V, Negative-QTOF	splash10-0a4r-4900000000-73ec9cd3e036215cf704	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 10V, Positive-QTOF	splash10-0002-9100000000-f462aba699529497ed4b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 20V, Positive-QTOF	splash10-052n-9200000000-1b1658a7492e5cc434e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 40V, Positive-QTOF	splash10-0006-9000000000-1d4ccceaa876483fc613	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 10V, Negative-QTOF	splash10-000i-0290000000-ab29b4f3b63e0a126d08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 20V, Negative-QTOF	splash10-001i-9600000000-3aa3801ec84c36aebe9e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl isovalerate 40V, Negative-QTOF	splash10-067l-9500000000-3ee6d39922b667e4cd68	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016218

KNApSAcK ID

Not Available

Chemspider ID

107053

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Menthyl isovalerate

METLIN ID

Not Available

PubChem Compound

119900

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1020381

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 Menthyl isovalerate (HMDB0037211)

MOL for HMDB0037211 (Menthyl isovalerate)

3D MOL for HMDB0037211 (Menthyl isovalerate)

3D SDF for HMDB0037211 (Menthyl isovalerate)

3D-SDF for HMDB0037211 (Menthyl isovalerate)

PDB for HMDB0037211 (Menthyl isovalerate)

3D PDB for HMDB0037211 (Menthyl isovalerate)

SMILES for HMDB0037211 (Menthyl isovalerate)

INCHI for HMDB0037211 (Menthyl isovalerate)

Structure for HMDB0037211 (Menthyl isovalerate)

3D Structure for HMDB0037211 (Menthyl isovalerate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra