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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 00:32:41 UTC

Update Date

2021-09-24 00:32:41 UTC

HMDB ID

HMDB0303255

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Menthyl valerate

Description

Menthyl valerate, also known as menthyl valeric acid, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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. Menthyl valerate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Menthyl valerate is a mild, sweet, and fruity tasting compound found in orange mint and peppermint, which makes menthyl valerate a potential biomarker for the consumption of these food products.

Structure

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

HMDB0303255
     RDKit          3D
Menthyl valerate
 45 45  0  0  0  0  0  0  0  0999 V2000
    6.4632   -0.0884   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763    0.6807    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9909   -0.2383    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7261    0.5487    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -0.3120    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5743   -1.5299   -0.1674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621    0.2058    0.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   -0.5072    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7077   -0.5970    1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423   -1.5818    1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -3.0130    1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6154   -1.3260    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2111   -0.1614   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420    0.0841   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4138    1.5577   -1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    2.1030   -2.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    2.3962    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1836    0.6327   -0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -0.3854    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2900   -0.9685   -0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0457    1.4917   -0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1848    1.1391    1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0097   -0.6387   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -1.0658    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7478    0.9023    1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.4189   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780   -1.5498   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767    0.3389    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0437   -1.0447    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5325   -1.4291    2.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534   -3.0461    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964   -3.6303    1.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0796   -3.4477    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7037   -1.2861    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5122   -2.2513   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6715   -0.2875   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807    0.7477   -0.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820   -0.4019   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    1.6370   -1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722    3.2237   -2.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2806    1.7455   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394    1.9347   -3.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6846    2.2882    0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    2.2535    0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    3.4575   -0.1965 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  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
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 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  0
 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 02241220542D          

 17 17  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -0.7145   -0.4125    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303255

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC(=O)OC1CC(C)CCC1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H28O2/c1-5-6-7-15(16)17-14-10-12(4)8-9-13(14)11(2)3/h11-14H,5-10H2,1-4H3

> <INCHI_KEY>
LCJPVSLESAPYMK-UHFFFAOYSA-N

> <FORMULA>
C15H28O2

> <MOLECULAR_WEIGHT>
240.3816

> <EXACT_MASS>
240.20893014

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
29.513076489093024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-2-(propan-2-yl)cyclohexyl pentanoate

> <ALOGPS_LOGP>
5.10

> <JCHEM_LOGP>
4.695071734333332

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.042148038090602

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
70.42569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
menthyl valerate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0303255
     RDKit          3D
Menthyl valerate
 45 45  0  0  0  0  0  0  0  0999 V2000
    6.4632   -0.0884   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763    0.6807    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9909   -0.2383    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7261    0.5487    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -0.3120    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5743   -1.5299   -0.1674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621    0.2058    0.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   -0.5072    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7077   -0.5970    1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423   -1.5818    1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -3.0130    1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6154   -1.3260    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2111   -0.1614   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420    0.0841   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4138    1.5577   -1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    2.1030   -2.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    2.3962    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1836    0.6327   -0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -0.3854    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2900   -0.9685   -0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0457    1.4917   -0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1848    1.1391    1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0097   -0.6387   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -1.0658    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7478    0.9023    1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.4189   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780   -1.5498   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767    0.3389    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0437   -1.0447    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5325   -1.4291    2.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534   -3.0461    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964   -3.6303    1.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0796   -3.4477    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7037   -1.2861    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5122   -2.2513   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6715   -0.2875   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807    0.7477   -0.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820   -0.4019   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    1.6370   -1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722    3.2237   -2.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2806    1.7455   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394    1.9347   -3.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6846    2.2882    0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    2.2535    0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    3.4575   -0.1965 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  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
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 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  0
 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  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    6                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0303255
HETATM    1  C1  UNL     1       6.463  -0.088  -0.096  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.176   0.681   0.173  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.991  -0.238   0.013  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.726   0.549   0.285  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.514  -0.312   0.141  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.574  -1.530  -0.167  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.262   0.206   0.345  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.945  -0.507   0.238  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.708  -0.597   1.528  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.842  -1.582   1.286  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.364  -3.013   1.418  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.615  -1.326   0.052  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.211  -0.161  -0.786  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.742   0.084  -0.881  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.414   1.558  -1.099  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.246   2.103  -2.239  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.683   2.396   0.116  1.00  0.00           C  
HETATM   18  H1  UNL     1       7.184   0.633  -0.516  1.00  0.00           H  
HETATM   19  H2  UNL     1       6.863  -0.385   0.910  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.290  -0.969  -0.740  1.00  0.00           H  
HETATM   21  H4  UNL     1       5.046   1.492  -0.597  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.185   1.139   1.173  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.010  -0.639  -1.021  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.035  -1.066   0.758  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.748   0.902   1.328  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.691   1.419  -0.371  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.678  -1.550  -0.039  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.177   0.339   1.840  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.044  -1.045   2.286  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.532  -1.429   2.170  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.553  -3.046   2.165  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.196  -3.630   1.818  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.080  -3.448   0.439  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.704  -1.286   0.275  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.512  -2.251  -0.594  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.671  -0.287  -1.790  1.00  0.00           H  
HETATM   37  H20 UNL     1      -3.681   0.748  -0.354  1.00  0.00           H  
HETATM   38  H21 UNL     1      -1.382  -0.402  -1.815  1.00  0.00           H  
HETATM   39  H22 UNL     1      -0.340   1.637  -1.340  1.00  0.00           H  
HETATM   40  H23 UNL     1      -2.272   3.224  -2.117  1.00  0.00           H  
HETATM   41  H24 UNL     1      -3.281   1.745  -2.220  1.00  0.00           H  
HETATM   42  H25 UNL     1      -1.739   1.935  -3.211  1.00  0.00           H  
HETATM   43  H26 UNL     1      -2.685   2.288   0.536  1.00  0.00           H  
HETATM   44  H27 UNL     1      -0.882   2.253   0.901  1.00  0.00           H  
HETATM   45  H28 UNL     1      -1.578   3.458  -0.197  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   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

HMDB0303255
     RDKit          3D
Menthyl valerate
 45 45  0  0  0  0  0  0  0  0999 V2000
    6.4632   -0.0884   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763    0.6807    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9909   -0.2383    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7261    0.5487    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -0.3120    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5743   -1.5299   -0.1674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621    0.2058    0.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   -0.5072    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7077   -0.5970    1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423   -1.5818    1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -3.0130    1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6154   -1.3260    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2111   -0.1614   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420    0.0841   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4138    1.5577   -1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    2.1030   -2.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    2.3962    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1836    0.6327   -0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -0.3854    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2900   -0.9685   -0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0457    1.4917   -0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1848    1.1391    1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0097   -0.6387   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -1.0658    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7478    0.9023    1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.4189   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780   -1.5498   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767    0.3389    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0437   -1.0447    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5325   -1.4291    2.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534   -3.0461    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964   -3.6303    1.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0796   -3.4477    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7037   -1.2861    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5122   -2.2513   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6715   -0.2875   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807    0.7477   -0.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820   -0.4019   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    1.6370   -1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722    3.2237   -2.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2806    1.7455   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394    1.9347   -3.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6846    2.2882    0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    2.2535    0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    3.4575   -0.1965 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  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
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 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  0
 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
5-Methyl-2-(propan-2-yl)cyclohexyl pentanoic acid	Generator
Menthyl valeric acid	Generator

Chemical Formula

C₁₅H₂₈O₂

Average Molecular Weight

240.3816

Monoisotopic Molecular Weight

240.20893014

IUPAC Name

5-methyl-2-(propan-2-yl)cyclohexyl pentanoate

Traditional Name

menthyl valerate

CAS Registry Number

Not Available

SMILES

CCCCC(=O)OC1CC(C)CCC1C(C)C

InChI Identifier

InChI=1S/C15H28O2/c1-5-6-7-15(16)17-14-10-12(4)8-9-13(14)11(2)3/h11-14H,5-10H2,1-4H3

InChI Key

LCJPVSLESAPYMK-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

Peppermint (FooDB: FOOD00113)
Orange mint (FooDB: FOOD00110)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

sedative (HMDB: HMDB0303255)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.1	ALOGPS
logP	4.7	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	6	ChemAxon
Refractivity	70.43 m³·mol⁻¹	ChemAxon
Polarizability	29.51 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
AllCCS	[M+H]+	162.154	32859911
AllCCS	[M+H-H2O]+	158.751	32859911
AllCCS	[M+Na]+	166.219	32859911
AllCCS	[M+NH4]+	165.311	32859911
AllCCS	[M-H]-	164.246	32859911
AllCCS	[M+Na-2H]-	165.234	32859911
AllCCS	[M+HCOO]-	166.429	32859911
DeepCCS	[M+H]+	166.526	30932474
DeepCCS	[M-H]-	164.168	30932474
DeepCCS	[M-2H]-	197.937	30932474
DeepCCS	[M+Na]+	173.103	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 10V, Positive-QTOF	splash10-000f-6790000000-e2b07d1e05cf8350492a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 20V, Positive-QTOF	splash10-052r-9610000000-2ce82c352b5ad2240e3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 40V, Positive-QTOF	splash10-0aou-9200000000-1004c0f56a8499715ad7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 10V, Negative-QTOF	splash10-000i-1590000000-8138c1ba0be992be8479	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 20V, Negative-QTOF	splash10-0a4i-2920000000-1b28754dcc6273701c34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 40V, Negative-QTOF	splash10-0a4r-4900000000-b0d3af6be33551068d88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 10V, Positive-QTOF	splash10-0002-9100000000-1634a5f138628d58dc1b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 20V, Positive-QTOF	splash10-000b-9200000000-a557f65a5dadf24a410d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 40V, Positive-QTOF	splash10-0aou-9000000000-cb32be7b39ab5f33e559	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 10V, Negative-QTOF	splash10-000i-0090000000-f892fcbd162695893533	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 20V, Negative-QTOF	splash10-001r-9410000000-4eaed428541d33080abf	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl valerate 40V, Negative-QTOF	splash10-066r-9100000000-c755bb5bb42c75b3336c	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB009787

KNApSAcK ID

Not Available

Chemspider ID

71274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Menthyl valerate (HMDB0303255)

MOL for HMDB0303255 (Menthyl valerate)

3D MOL for HMDB0303255 (Menthyl valerate)

3D SDF for HMDB0303255 (Menthyl valerate)

3D-SDF for HMDB0303255 (Menthyl valerate)

PDB for HMDB0303255 (Menthyl valerate)

3D PDB for HMDB0303255 (Menthyl valerate)

SMILES for HMDB0303255 (Menthyl valerate)

INCHI for HMDB0303255 (Menthyl valerate)

Structure for HMDB0303255 (Menthyl valerate)

3D Structure for HMDB0303255 (Menthyl valerate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra