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Showing metabocard for Menthol (HMDB0003352)

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enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-12 19:15:31 UTC
Update Date2023-02-21 17:16:37 UTC
HMDB IDHMDB0003352
Secondary Accession Numbers
  • HMDB03352
Metabolite Identification
Common NameMenthol
DescriptionMenthol is an alcohol produced from mint oils or prepared synthetically. Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation.
Structure
Data?1676999797
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003352 (Menthol)

menthol
  Mrv1652305271900202D          

 11 11  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  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  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
M  END
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3D MOL for HMDB0003352 (Menthol)

HMDB0003352
     RDKit          3D
Menthol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.4893   -0.2512    1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    0.3752   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -0.3313   -1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    0.2796   -0.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1323   -1.1308   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531   -1.1647   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0986   -0.2923    0.4170 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5508   -0.2350   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499    1.1312    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777    1.0109    0.7827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4860    2.2780    0.9422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704   -1.3264    1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6071   -0.1681    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    0.2289    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920    1.4485   -0.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6500    0.1708   -2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464   -0.1682   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -1.3942   -1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    0.7824   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -1.6998    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881   -1.6311   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6886   -2.2178   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -0.9447   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -0.6910    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822   -1.1275    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -0.2675   -1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0058    0.7136    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    1.6748    1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719    1.5713   -0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    0.4332    1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185    2.9429    0.4015 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END
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3D SDF for HMDB0003352 (Menthol)

menthol
  Mrv1652305271900202D          

 11 11  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  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  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0003352

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1

> <INCHI_KEY>
NOOLISFMXDJSKH-KXUCPTDWSA-N

> <FORMULA>
C10H20O

> <MOLECULAR_WEIGHT>
156.269

> <EXACT_MASS>
156.151415264

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
19.69012569770345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.6642731470000007

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.54964736878105

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8087842408951696

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.445299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
menthol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0003352 (Menthol)

HMDB0003352
     RDKit          3D
Menthol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.4893   -0.2512    1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    0.3752   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -0.3313   -1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    0.2796   -0.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1323   -1.1308   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531   -1.1647   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0986   -0.2923    0.4170 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5508   -0.2350   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499    1.1312    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777    1.0109    0.7827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4860    2.2780    0.9422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704   -1.3264    1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6071   -0.1681    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    0.2289    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920    1.4485   -0.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6500    0.1708   -2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464   -0.1682   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -1.3942   -1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    0.7824   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -1.6998    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881   -1.6311   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6886   -2.2178   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -0.9447   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -0.6910    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822   -1.1275    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -0.2675   -1.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0058    0.7136    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    1.6748    1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719    1.5713   -0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    0.4332    1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185    2.9429    0.4015 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END
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PDB for HMDB0003352 (Menthol)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: menthol                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0003352 (Menthol)

COMPND    HMDB0003352
HETATM    1  C1  UNL     1      -2.489  -0.251   1.220  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.104   0.375  -0.101  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.857  -0.331  -1.198  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.627   0.280  -0.340  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.132  -1.131  -0.374  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.353  -1.165  -0.553  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.099  -0.292   0.417  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.551  -0.235  -0.002  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.550   1.131   0.416  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.078   1.011   0.783  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.486   2.278   0.942  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.270  -1.326   1.207  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.607  -0.168   1.313  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.008   0.229   2.079  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.392   1.448  -0.112  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.650   0.171  -2.184  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.946  -0.168  -0.989  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.614  -1.394  -1.265  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.360   0.782  -1.276  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.379  -1.700   0.539  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.588  -1.631  -1.255  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.689  -2.218  -0.355  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.683  -0.945  -1.590  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.048  -0.691   1.452  1.00  0.00           H  
HETATM   25  H14 UNL     1       4.082  -1.128   0.411  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.599  -0.268  -1.105  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.006   0.714   0.338  1.00  0.00           H  
HETATM   28  H17 UNL     1       2.092   1.675   1.217  1.00  0.00           H  
HETATM   29  H18 UNL     1       1.672   1.571  -0.574  1.00  0.00           H  
HETATM   30  H19 UNL     1      -0.009   0.433   1.723  1.00  0.00           H  
HETATM   31  H20 UNL     1       0.019   2.943   0.402  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   10   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8    9   24
CONECT    8   25   26   27
CONECT    9   10   28   29
CONECT   10   11   30
CONECT   11   31
END
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SMILES for HMDB0003352 (Menthol)

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
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INCHI for HMDB0003352 (Menthol)

InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(-)-(1R,3R,4S)-MentholChEBI
(1alpha,2beta,5alpha)-5-Methyl-2(1-methylethyl)cyclohexanolChEBI
(1R,3R,4S)-(-)-MentholChEBI
(1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanolChEBI
L-MentholChEBI
LevomentholChEBI
LevomentholumChEBI
LevomentolChEBI
(1a,2b,5a)-5-Methyl-2(1-methylethyl)cyclohexanolGenerator
(1Α,2β,5α)-5-methyl-2(1-methylethyl)cyclohexanolGenerator
(1R-(1-a,2-b,5-a))-5-Methyl-2-(1-methylethyl)cyclohexanolGenerator
(1R-(1-Α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanolGenerator
(-)-Menthyl alcoholHMDB
(-)-trans-p-Menthan-cis-olHMDB
(1R)-(-)-MentholHMDB
(1R,2S,5R)-(-)-MentholHMDB
(R)-(-)-MentholHMDB
1-MentholHMDB
2-Isopropyl-5-methylcyclohexanolHMDB
5-Methyl-2-(1-methylethyl)cyclohexanolHMDB
5-Methyl-2-propan-2-ylcyclohexan-1-olHMDB
D-(-)-MentholHMDB
HexahydrothymolHMDB
L-(-)-MentholHMDB
MenthacamphorHMDB
MenthomentholHMDB
p-Menthan-3-olHMDB
Peppermint camphorHMDB
U.S.p. mentholHMDB
KerasalHMDB
Menthol, (1alpha,2beta,5alpha)-isomerHMDB
MentholMeSH
Chemical FormulaC10H20O
Average Molecular Weight156.269
Monoisotopic Molecular Weight156.151415264
IUPAC Name(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
Traditional Namementhol
CAS Registry Number2216-51-5
SMILES
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
InChI Identifier
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
InChI KeyNOOLISFMXDJSKH-KXUCPTDWSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point43 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.49 mg/mL at 25 °CNot Available
LogP3.40GRIFFIN,S ET AL. (1999)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP2.68ALOGPS
logP2.66ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.45 m³·mol⁻¹ChemAxon
Polarizability19.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.80831661259
DarkChem[M-H]-135.5631661259
DeepCCS[M+H]+143.20530932474
DeepCCS[M-H]-140.84730932474
DeepCCS[M-2H]-175.17730932474
DeepCCS[M+Na]+150.21330932474
AllCCS[M+H]+135.832859911
AllCCS[M+H-H2O]+131.432859911
AllCCS[M+NH4]+139.832859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-141.332859911
AllCCS[M+Na-2H]-143.032859911
AllCCS[M+HCOO]-145.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.4.36 minutes32390414
Predicted by Siyang on May 30, 202214.836 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.29 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid26.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2101.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid481.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid172.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid261.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid337.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid681.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid677.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)102.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1131.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid441.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1362.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid365.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid371.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate396.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA475.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water13.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MentholCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O1626.6Standard polar33892256
MentholCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O1167.3Standard non polar33892256
MentholCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O1195.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Menthol,1TMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[Si](C)(C)C1244.5Semi standard non polar33892256
Menthol,1TBDMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[Si](C)(C)C(C)(C)C1470.1Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Bladder
  • Epidermis
  • Neuron
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.064 (0.033 - 0.159) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothCeliac disease details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDDB00825
Phenol Explorer Compound IDNot Available
FooDB IDFDB014499
KNApSAcK IDC00000810
Chemspider ID15803
KEGG Compound IDC00400
BioCyc ID--MENTHOL
BiGG IDNot Available
Wikipedia LinkMenthol
METLIN IDNot Available
PubChem Compound16666
PDB IDNot Available
ChEBI ID15409
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBergner, Eike Johannes; Ebel, Klaus; Johann, Thorsten; Loeber, Oliver. Method for the production of menthol. PCT Int. Appl. (2006), 32 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. [PubMed:12654248 ]
  2. Stein RJ, Santos S, Nagatomi J, Hayashi Y, Minnery BS, Xavier M, Patel AS, Nelson JB, Futrell WJ, Yoshimura N, Chancellor MB, De Miguel F: Cool (TRPM8) and hot (TRPV1) receptors in the bladder and male genital tract. J Urol. 2004 Sep;172(3):1175-8. [PubMed:15311065 ]
  3. Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. [PubMed:7529306 ]
  4. Haeseler G, Maue D, Grosskreutz J, Bufler J, Nentwig B, Piepenbrock S, Dengler R, Leuwer M: Voltage-dependent block of neuronal and skeletal muscle sodium channels by thymol and menthol. Eur J Anaesthesiol. 2002 Aug;19(8):571-9. [PubMed:12200946 ]
  5. Stich HF, Stich W: Chromosome-damaging activity of saliva of betel nut and tobacco chewers. Cancer Lett. 1982 Mar-Apr;15(3):193-202. [PubMed:7116324 ]
  6. Haahr AM, Bardow A, Thomsen CE, Jensen SB, Nauntofte B, Bakke M, Adler-Nissen J, Bredie WL: Release of peppermint flavour compounds from chewing gum: effect of oral functions. Physiol Behav. 2004 Sep 15;82(2-3):531-40. [PubMed:15276819 ]
  7. Mukerji G, Yiangou Y, Corcoran SL, Selmer IS, Smith GD, Benham CD, Bountra C, Agarwal SK, Anand P: Cool and menthol receptor TRPM8 in human urinary bladder disorders and clinical correlations. BMC Urol. 2006 Mar 6;6:6. [PubMed:16519806 ]
  8. Rohacs T, Lopes CM, Michailidis I, Logothetis DE: PI(4,5)P2 regulates the activation and desensitization of TRPM8 channels through the TRP domain. Nat Neurosci. 2005 May;8(5):626-34. Epub 2005 Apr 24. [PubMed:15852009 ]
  9. Valdez JS, Martin DK, Mayersohn M: Sensitive and selective gas chromatographic methods for the quantitation of camphor, menthol and methyl salicylate from human plasma. J Chromatogr B Biomed Sci Appl. 1999 Jun 11;729(1-2):163-71. [PubMed:10410939 ]
  10. Gelal A, Jacob P 3rd, Yu L, Benowitz NL: Disposition kinetics and effects of menthol. Clin Pharmacol Ther. 1999 Aug;66(2):128-35. [PubMed:10460066 ]
  11. Grigoleit HG, Grigoleit P: Pharmacology and preclinical pharmacokinetics of peppermint oil. Phytomedicine. 2005 Aug;12(8):612-6. [PubMed:16121523 ]
  12. Xu H, Blair NT, Clapham DE: Camphor activates and strongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid-independent mechanism. J Neurosci. 2005 Sep 28;25(39):8924-37. [PubMed:16192383 ]
  13. Narishetty ST, Panchagnula R: Effect of L-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine. J Control Release. 2005 Jan 20;102(1):59-70. [PubMed:15653134 ]
  14. Prescott J: The generalizability of capsaicin sensitization and desensitization. Physiol Behav. 1999 Jul;66(5):741-9. [PubMed:10405101 ]
  15. Liu Y, Ye X, Feng X, Zhou G, Rong Z, Fang C, Chen H: Menthol facilitates the skin analgesic effect of tetracaine gel. Int J Pharm. 2005 Nov 23;305(1-2):31-6. Epub 2005 Oct 10. [PubMed:16219435 ]

Enzymes

Enzyme Details
1. Transient receptor potential cation channel subfamily M member 8
General function:
Involved in ion channel activity
Specific function:
Receptor-activated non-selective cation channel involved in detection of sensations such as coolness, by being activated by cold temperature below 25 degrees Celsius. Activated by icilin, eucalyptol, menthol, cold and modulation of intracellular pH. Involved in menthol sensation. Permeable for monovalent cations sodium, potassium, and cesium and divalent cation calcium. Temperature sensing is tightly linked to voltage-dependent gating. Activated upon depolarization, changes in temperature resulting in graded shifts of its voltage-dependent activation curves. The chemical agonists menthol functions as a gating modifier, shifting activation curves towards physiological membrane potentials. Temperature sensitivity arises from a tenfold difference in the activation energies associated with voltage-dependent opening and closing
Gene Name:
TRPM8
Uniprot ID:
Q7Z2W7
Molecular weight:
127684.0
References
  1. Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. [PubMed:12654248 ]
  2. Behrendt HJ, Germann T, Gillen C, Hatt H, Jostock R: Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. Br J Pharmacol. 2004 Feb;141(4):737-45. Epub 2004 Feb 2. [PubMed:14757700 ]
  3. Bandell M, Story GM, Hwang SW, Viswanath V, Eid SR, Petrus MJ, Earley TJ, Patapoutian A: Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron. 2004 Mar 25;41(6):849-57. [PubMed:15046718 ]
  4. Andersson DA, Chase HW, Bevan S: TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH. J Neurosci. 2004 Jun 9;24(23):5364-9. [PubMed:15190109 ]
  5. Stein RJ, Santos S, Nagatomi J, Hayashi Y, Minnery BS, Xavier M, Patel AS, Nelson JB, Futrell WJ, Yoshimura N, Chancellor MB, De Miguel F: Cool (TRPM8) and hot (TRPV1) receptors in the bladder and male genital tract. J Urol. 2004 Sep;172(3):1175-8. [PubMed:15311065 ]
  6. Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. [PubMed:7529306 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Enzyme Details
2. Kappa-type opioid receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular weight:
42644.7
References
  1. Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A, Ghelardini C: Menthol: a natural analgesic compound. Neurosci Lett. 2002 Apr 12;322(3):145-8. [PubMed:11897159 ]
  2. Taniguchi Y, Deguchi Y, Saita M, Noda K: [Antinociceptive effects of counterirritants]. Nihon Yakurigaku Zasshi. 1994 Dec;104(6):433-46. [PubMed:7851817 ]
Enzyme Details
3. Transient receptor potential cation channel subfamily V member 3
General function:
Involved in calcium channel activity
Specific function:
Putative receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 degrees Celsius. Activation exhibits an outward rectification. May associate with TRPV1 and may modulate its activity
Gene Name:
TRPV3
Uniprot ID:
Q8NET8
Molecular weight:
90635.1
References
  1. Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Patapoutian A, Story GM: More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43. Epub 2006 Jul 7. [PubMed:16829128 ]
Enzyme Details
4. Transient receptor potential cation channel subfamily A member 1
General function:
Not Available
Specific function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function. Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes. Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)- tetrahydrocannabinol (THC), the psychoactive component of marijuana. Not involved in menthol sensation. May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular weight:
127485.8
References
  1. Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. [PubMed:12654248 ]
  2. Namer B, Seifert F, Handwerker HO, Maihofner C: TRPA1 and TRPM8 activation in humans: effects of cinnamaldehyde and menthol. Neuroreport. 2005 Jun 21;16(9):955-9. [PubMed:15931068 ]
  3. Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Patapoutian A, Story GM: More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43. Epub 2006 Jul 7. [PubMed:16829128 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]