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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:27:08 UTC

Update Date

2022-03-07 02:55:14 UTC

HMDB ID

HMDB0037212

Secondary Accession Numbers

HMDB37212

Metabolite Identification

Common Name

Menthyl lactate

Description

Menthyl lactate 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 significant number of articles have been published on Menthyl lactate.

Structure

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

HMDB0037212
     RDKit          3D
Menthyl lactate
 40 40  0  0  0  0  0  0  0  0999 V2000
    4.9223   -0.0353    0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713    0.9097    0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    1.2798   -1.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.3404    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2180   -0.0685    1.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4737    0.2501   -0.3133 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1897   -0.2769   -0.0527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0430   -1.5681   -0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -2.0957   -0.4072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6428   -3.4619   -0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541   -1.1254   -0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8691    0.1818   -1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552    0.7438   -0.3579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5957    1.2229    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6860    1.8584    1.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6257    2.2474    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957   -0.5256    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8324    0.5979    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0903   -0.7407   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9533    1.8302    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637    2.1655   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -0.5751    1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -1.4373   -1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -2.2814   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808   -2.1656    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6396   -3.4730   -1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6118   -4.2605   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8970   -3.6340   -1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619   -1.5520   -1.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1327   -0.8917    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4317    0.0072   -2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    0.8904   -1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    1.6211   -0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1026    0.3666    1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2634    2.6540    2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    1.1208    2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1974    2.3394    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6144    1.7686    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7676    3.0480    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356    2.7246   -0.5281 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  6
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END


  Mrv0541 02241218362D          

 16 16  0  0  0  0            999 V2000
   -1.4306   -0.6173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1443   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    1.0326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4306    1.8562    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
   -0.7156   -0.2048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0007   -0.6173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -0.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -1.4423    0.0000 O   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  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>
HMDB0037212

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H24O3/c1-8(2)11-6-5-9(3)7-12(11)16-13(15)10(4)14/h8-12,14H,5-7H2,1-4H3/t9-,10?,11+,12-/m1/s1

> <INCHI_KEY>
UJNOLBSYLSYIBM-SGUBAKSOSA-N

> <FORMULA>
C13H24O3

> <MOLECULAR_WEIGHT>
228.3279

> <EXACT_MASS>
228.172544634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.34443951205739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.8569147536666657

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.998140822941853

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6744132040452335

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
62.79290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037212
     RDKit          3D
Menthyl lactate
 40 40  0  0  0  0  0  0  0  0999 V2000
    4.9223   -0.0353    0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713    0.9097    0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    1.2798   -1.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.3404    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2180   -0.0685    1.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4737    0.2501   -0.3133 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1897   -0.2769   -0.0527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0430   -1.5681   -0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -2.0957   -0.4072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6428   -3.4619   -0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541   -1.1254   -0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8691    0.1818   -1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552    0.7438   -0.3579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5957    1.2229    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6860    1.8584    1.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6257    2.2474    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957   -0.5256    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8324    0.5979    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0903   -0.7407   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9533    1.8302    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637    2.1655   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -0.5751    1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -1.4373   -1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -2.2814   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808   -2.1656    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6396   -3.4730   -1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6118   -4.2605   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8970   -3.6340   -1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619   -1.5520   -1.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1327   -0.8917    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4317    0.0072   -2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    0.8904   -1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    1.6211   -0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1026    0.3666    1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2634    2.6540    2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    1.1208    2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1974    2.3394    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6144    1.7686    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7676    3.0480    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356    2.7246   -0.5281 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  6
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 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      -2.670  -1.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.003  -0.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.003   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.670   1.928   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.670   3.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.336   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.336  -0.382   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.001  -1.152   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.003  -3.465   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.670  -2.692   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.336  -3.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.333  -0.382   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.333   1.155   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.668  -1.152   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.003  -0.382   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.668  -2.692   0.000  0.00  0.00           O+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                                                            
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    HMDB0037212
HETATM    1  C1  UNL     1       4.922  -0.035   0.568  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.771   0.910   0.247  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.783   1.280  -1.078  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.470   0.340   0.638  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.218  -0.068   1.795  1.00  0.00           O  
HETATM    6  O3  UNL     1       1.474   0.250  -0.313  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.190  -0.277  -0.053  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.043  -1.568  -0.831  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.398  -2.096  -0.407  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.643  -3.462  -0.964  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.454  -1.125  -0.837  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.869   0.182  -1.327  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.855   0.744  -0.358  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.596   1.223   0.868  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.686   1.858   1.880  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.626   2.247   0.442  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.696  -0.526   1.525  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.832   0.598   0.634  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.090  -0.741  -0.271  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.953   1.830   0.849  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.364   2.166  -1.162  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.187  -0.575   1.023  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.043  -1.437  -1.909  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.745  -2.281  -0.477  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.381  -2.166   0.699  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.640  -3.473  -1.441  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.612  -4.261  -0.196  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.897  -3.634  -1.769  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.062  -1.552  -1.639  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.133  -0.892   0.009  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.432   0.007  -2.332  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.727   0.890  -1.443  1.00  0.00           H  
HETATM   33  H17 UNL     1      -0.388   1.621  -0.854  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.103   0.367   1.356  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.263   2.654   2.400  1.00  0.00           H  
HETATM   36  H20 UNL     1      -0.411   1.121   2.690  1.00  0.00           H  
HETATM   37  H21 UNL     1       0.197   2.339   1.440  1.00  0.00           H  
HETATM   38  H22 UNL     1      -3.614   1.769   0.276  1.00  0.00           H  
HETATM   39  H23 UNL     1      -2.768   3.048   1.205  1.00  0.00           H  
HETATM   40  H24 UNL     1      -2.336   2.725  -0.528  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   20
CONECT    3   21
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   13   22
CONECT    8    9   23   24
CONECT    9   10   11   25
CONECT   10   26   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   33
CONECT   14   15   16   34
CONECT   15   35   36   37
CONECT   16   38   39   40
END

HMDB0037212
     RDKit          3D
Menthyl lactate
 40 40  0  0  0  0  0  0  0  0999 V2000
    4.9223   -0.0353    0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713    0.9097    0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    1.2798   -1.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.3404    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2180   -0.0685    1.7949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4737    0.2501   -0.3133 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1897   -0.2769   -0.0527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0430   -1.5681   -0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -2.0957   -0.4072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6428   -3.4619   -0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541   -1.1254   -0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8691    0.1818   -1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552    0.7438   -0.3579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5957    1.2229    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6860    1.8584    1.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6257    2.2474    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957   -0.5256    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8324    0.5979    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0903   -0.7407   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9533    1.8302    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637    2.1655   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -0.5751    1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -1.4373   -1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -2.2814   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808   -2.1656    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6396   -3.4730   -1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6118   -4.2605   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8970   -3.6340   -1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619   -1.5520   -1.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1327   -0.8917    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4317    0.0072   -2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    0.8904   -1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    1.6211   -0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1026    0.3666    1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2634    2.6540    2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    1.1208    2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1974    2.3394    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6144    1.7686    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7676    3.0480    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356    2.7246   -0.5281 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  6
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Menthyl lactic acid	Generator
L-Menthyl lactate	MeSH
(-)-P-Menthan-3-yl lactate	HMDB
FEMA 3748	HMDB
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 2-hydroxypropanoic acid	Generator

Chemical Formula

C₁₃H₂₄O₃

Average Molecular Weight

228.3279

Monoisotopic Molecular Weight

228.172544634

IUPAC Name

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

Traditional Name

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-hydroxypropanoate

CAS Registry Number

59259-38-0

SMILES

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

InChI Identifier

InChI=1S/C13H24O3/c1-8(2)11-6-5-9(3)7-12(11)16-13(15)10(4)14/h8-12,14H,5-7H2,1-4H3/t9-,10?,11+,12-/m1/s1

InChI Key

UJNOLBSYLSYIBM-SGUBAKSOSA-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
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cytoplasm (HMDB: HMDB0037212)
Cell membrane (HMDB: HMDB0037212)

Cellular substructure

Extracellular (HMDB: HMDB0037212)
Membrane (HMDB: HMDB0037212)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037212)

Source

Endogenous

Endogenous (HMDB: HMDB0037212)

Animal

Animal (HMDB: HMDB0037212)

Exogenous

Food

Food (HMDB: HMDB0037212)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037212)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037212)

Cellular process

Cell signaling (HMDB: HMDB0037212)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037212)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037212)

Nutrient

Nutrient (HMDB: HMDB0037212)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037212)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0037212)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	38 - 40 °C	Not Available
Boiling Point	142.00 °C. @ 5.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	3.358 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	2.78	ALOGPS
logP	2.86	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.79 m³·mol⁻¹	ChemAxon
Polarizability	26.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.87	31661259
DarkChem	[M-H]-	151.646	31661259
DeepCCS	[M+H]+	159.73	30932474
DeepCCS	[M-H]-	157.372	30932474
DeepCCS	[M-2H]-	190.739	30932474
DeepCCS	[M+Na]+	165.966	30932474
AllCCS	[M+H]+	155.4	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	158.7	32859911
AllCCS	[M+Na]+	159.7	32859911
AllCCS	[M-H]-	158.5	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	160.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Menthyl lactate	CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(C)O	2002.8	Standard polar	33892256
Menthyl lactate	CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(C)O	1468.3	Standard non polar	33892256
Menthyl lactate	CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(C)O	1493.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Menthyl lactate,1TMS,isomer #1	CC(O[Si](C)(C)C)C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C	1610.7	Semi standard non polar	33892256
Menthyl lactate,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C	1826.6	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 lactate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9200000000-c48e8eb9e325bf5c81fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthyl lactate GC-MS (1 TMS) - 70eV, Positive	splash10-00ku-9810000000-3204a8c0047d47f59c31	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthyl lactate 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 lactate 10V, Positive-QTOF	splash10-056r-3790000000-656c618ebe79ee17c995	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 20V, Positive-QTOF	splash10-0a4r-9710000000-6125d6ceccc2f46b4ac4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 40V, Positive-QTOF	splash10-0a4i-9400000000-63fcdcc1bb57fb80142d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 10V, Negative-QTOF	splash10-0a6r-1980000000-4e50a980d739641e3afc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 20V, Negative-QTOF	splash10-0a4i-1900000000-5d2874c2be1ece163ff8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 40V, Negative-QTOF	splash10-052r-1900000000-f3921cfdce07deda7464	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 10V, Negative-QTOF	splash10-0a6r-2960000000-f585e586acf3e1ddaaf8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 20V, Negative-QTOF	splash10-00di-9400000000-1a89bb184c19723d72e7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 40V, Negative-QTOF	splash10-0007-9100000000-bedbf62a7ccbf2dcb64a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 10V, Positive-QTOF	splash10-0002-9300000000-cf2188d4102f886cdb3e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 20V, Positive-QTOF	splash10-0002-9400000000-23c4d31979e1b9888ad6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl lactate 40V, Positive-QTOF	splash10-0002-9000000000-6cf7fb94dc69ec979c57	2021-09-24	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

FDB016219

KNApSAcK ID

Not Available

Chemspider ID

55982

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62151

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1038041

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 lactate (HMDB0037212)

MOL for HMDB0037212 (Menthyl lactate)

3D MOL for HMDB0037212 (Menthyl lactate)

3D SDF for HMDB0037212 (Menthyl lactate)

3D-SDF for HMDB0037212 (Menthyl lactate)

PDB for HMDB0037212 (Menthyl lactate)

3D PDB for HMDB0037212 (Menthyl lactate)

SMILES for HMDB0037212 (Menthyl lactate)

INCHI for HMDB0037212 (Menthyl lactate)

Structure for HMDB0037212 (Menthyl lactate)

3D Structure for HMDB0037212 (Menthyl lactate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra