MiMeDB: Showing metabocard for Menthol (MMDBc0033676)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:58:31 UTC

Update Date

2024-04-30 20:14:55 UTC

Metabolite ID

MMDBc0033676

Metabolite Identification

Common Name

Menthol

Description

Menthol 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

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

HMDB0035765
     RDKit          3D
p-Menthan-3-ol
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.0969   -0.4800   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    0.6943    0.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    1.0008   -1.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417    0.4721   -1.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903    0.3477    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928   -0.1412    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.8242   -0.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -1.5050   -0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1918   -0.4398    1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297   -1.6359    0.6949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    0.4477    1.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1629   -0.1770   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9381   -0.9203   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9809   -1.2634    0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8231    1.5904    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8887    0.5837   -1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004    2.1119   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175   -0.4939   -1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    1.1702   -1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7389    1.3959    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -0.1410    1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845    0.5955   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944    0.6853   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617    1.8741   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935   -1.4383   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044   -2.2421   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -1.8981   -0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943   -0.6403    2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8173   -1.6693   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171    1.3929    1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -0.1009    2.1376 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  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11  2  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
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
M  END

HMDB0035765
     RDKit          3D
p-Menthan-3-ol
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.0969   -0.4800   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    0.6943    0.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    1.0008   -1.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417    0.4721   -1.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903    0.3477    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928   -0.1412    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.8242   -0.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -1.5050   -0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1918   -0.4398    1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297   -1.6359    0.6949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    0.4477    1.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1629   -0.1770   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9381   -0.9203   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9809   -1.2634    0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8231    1.5904    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8887    0.5837   -1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004    2.1119   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175   -0.4939   -1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    1.1702   -1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7389    1.3959    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -0.1410    1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845    0.5955   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944    0.6853   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617    1.8741   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935   -1.4383   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044   -2.2421   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -1.8981   -0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943   -0.6403    2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8173   -1.6693   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171    1.3929    1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -0.1009    2.1376 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  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11  2  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
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
M  END

COMPND    HMDB0035765
HETATM    1  C1  UNL     1       3.097  -0.480  -0.069  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.157   0.694   0.165  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.333   1.001  -1.029  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.042   0.472  -1.060  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.690   0.348   0.294  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.093  -0.141   0.192  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.902   0.824  -0.633  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.234  -1.505  -0.383  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.192  -0.440   1.196  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.630  -1.636   0.695  1.00  0.00           O  
HETATM   11  C10 UNL     1       1.420   0.448   1.429  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.163  -0.177  -0.048  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.938  -0.920  -1.090  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.981  -1.263   0.702  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.823   1.590   0.349  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.889   0.584  -1.921  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.300   2.112  -1.234  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.117  -0.494  -1.634  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.708   1.170  -1.652  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.739   1.396   0.710  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.530  -0.141   1.223  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.984   0.595  -0.404  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.794   0.685  -1.717  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.762   1.874  -0.298  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.294  -1.438  -1.488  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.504  -2.242  -0.048  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.242  -1.898  -0.064  1.00  0.00           H  
HETATM   28  H17 UNL     1      -0.294  -0.640   2.177  1.00  0.00           H  
HETATM   29  H18 UNL     1       0.817  -1.669  -0.254  1.00  0.00           H  
HETATM   30  H19 UNL     1       1.117   1.393   1.936  1.00  0.00           H  
HETATM   31  H20 UNL     1       2.072  -0.101   2.138  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   11   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6    9   20
CONECT    6    7    8   21
CONECT    7   22   23   24
CONECT    8   25   26   27
CONECT    9   10   11   28
CONECT   10   29
CONECT   11   30   31
END

HMDB0035765
     RDKit          3D
p-Menthan-3-ol
 31 31  0  0  0  0  0  0  0  0999 V2000
    3.0969   -0.4800   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    0.6943    0.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    1.0008   -1.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417    0.4721   -1.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903    0.3477    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928   -0.1412    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.8242   -0.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -1.5050   -0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1918   -0.4398    1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297   -1.6359    0.6949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    0.4477    1.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1629   -0.1770   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9381   -0.9203   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9809   -1.2634    0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8231    1.5904    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8887    0.5837   -1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004    2.1119   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175   -0.4939   -1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    1.1702   -1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7389    1.3959    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -0.1410    1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845    0.5955   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944    0.6853   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617    1.8741   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935   -1.4383   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044   -2.2421   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -1.8981   -0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943   -0.6403    2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8173   -1.6693   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171    1.3929    1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -0.1009    2.1376 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  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11  2  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
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
M  END

Synonyms

Value	Source
Fisherman's friend lozenges	Kegg
1-Methyl-4-isopropyl-3-hydroxycyclohexane	HMDB
2-Isopropyl-5-methylcyclohexanol	HMDB
3-Hydroxy-P-menthane	HMDB
3-P-Menthanol	HMDB
3-P-Menthol	HMDB
4-Isopropyl-1-methylcyclohexan-3-ol	HMDB
5-Methyl-2-(1-methylethyl)-cyclohexanol	HMDB
5-Methyl-2-(1-methylethyl)cyclohexanol	HMDB
Menthol	HMDB
Menthol, (1alpha,2beta,5alpha)-isomer	MeSH, HMDB

Molecular Formula

C₁₀H₂₀O

Average Mass

156.2652

Monoisotopic Mass

156.151415262

IUPAC Name

5-methyl-2-(propan-2-yl)cyclohexan-1-ol

Traditional Name

menthol natural

CAS Registry Number

2216-51-5

SMILES

CC(C)C1CCC(C)CC1O

InChI Identifier

InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3

InChI Key

NOOLISFMXDJSKH-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
Cyclohexanol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:25187 )
p-menthane monoterpenoid (CHEBI:25187 )
a monoterpenol (CPD-4945 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.56 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.66	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.45 m³·mol⁻¹	ChemAxon
Polarizability	19.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00ry-9000000000-1a50289cf86435b01727	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-3900000000-081c83125641df212ef8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05gm-9100000000-8a126fba3de41f12e6be	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00ry-9000000000-1a50289cf86435b01727	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-3900000000-081c83125641df212ef8	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05gm-9100000000-8a126fba3de41f12e6be	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9600000000-fcf4b2a96455b111f889	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-06y9-9520000000-14606b3a7ce33696837b	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0900000000-fc39fb91c62eb627e3af	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-5900000000-839aa9da0c06f6d09968	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0avi-9200000000-e9b33e704445c7e908ec	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3a700dc611fb070e6b45	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-5a80eb79e919e06fa63a	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bti-7900000000-67a39bf95581e52cb931	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0900000000-fc39fb91c62eb627e3af	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-5900000000-839aa9da0c06f6d09968	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0avi-9200000000-e9b33e704445c7e908ec	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3a700dc611fb070e6b45	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-5a80eb79e919e06fa63a	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bti-7900000000-67a39bf95581e52cb931	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-f6034c6a8245c68a37ac	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-7efa42d43b7858e2c2ce	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zfr-0900000000-b6eef0a7f66ac7e97e78	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05mk-9800000000-bb8a9e58bdc61e2654e6	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053e-9100000000-6405f7fe35f6f6bdc8c5	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-fee5c7d55bf523973cbf	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Bladder
Blood
Epidermis
Feces
Neuron
Saliva
Skeletal Muscle
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.064	0.033	0.159	uM	Adult (>18 years old)	Both	Normal	HMDB	15342616
Human Bladder	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	22284503
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Saliva	Detected but not Quantified					Children (1-13 years old)	Both	Normal	HMDB	24657864
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	19167006
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected but not Quantified					Adult (>18 years old)	Female	Normal	HMDB	23454028
Human Feces	Detected but not Quantified					Children (1-13 years old)	Both	Normal	HMDB	24130822
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24922509
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	26806034

External Links

HMDB ID

HMDB0035765

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014502

KNApSAcK ID

Not Available

Chemspider ID

1216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1254

PDB ID

Not Available

ChEBI ID

25187

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Stich HF, Stich W: Chromosome-damaging activity of saliva of betel nut and tobacco chewers. Cancer Lett. 1982 Mar-Apr;15(3):193-202. doi: 10.1016/0304-3835(82)90118-5. [PubMed:7116324 ]
Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. doi: 10.1111/j.2042-7158.1994.tb03871.x. [PubMed:7529306 ]
Prescott J: The generalizability of capsaicin sensitization and desensitization. Physiol Behav. 1999 Jul;66(5):741-9. doi: 10.1016/s0031-9384(99)00012-8. [PubMed:10405101 ]
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. doi: 10.1016/s0378-4347(99)00161-9. [PubMed:10410939 ]
Gelal A, Jacob P 3rd, Yu L, Benowitz NL: Disposition kinetics and effects of menthol. Clin Pharmacol Ther. 1999 Aug;66(2):128-35. doi: 10.1053/cp.1999.v66.100455001. [PubMed:10460066 ]
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. doi: 10.1017/s0265021502000923. [PubMed:12200946 ]
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. doi: 10.1016/s0092-8674(03)00158-2. [PubMed:12654248 ]
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. doi: 10.1016/j.physbeh.2004.04.061. [PubMed:15276819 ]
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. doi: 10.1097/01.ju.0000134880.55119.cf. [PubMed:15311065 ]
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. doi: 10.1016/j.jconrel.2004.09.016. [PubMed:15653134 ]
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. doi: 10.1038/nn1451. Epub 2005 Apr 24. [PubMed:15852009 ]
Grigoleit HG, Grigoleit P: Pharmacology and preclinical pharmacokinetics of peppermint oil. Phytomedicine. 2005 Aug;12(8):612-6. doi: 10.1016/j.phymed.2004.10.007. [PubMed:16121523 ]
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. doi: 10.1523/JNEUROSCI.2574-05.2005. [PubMed:16192383 ]
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. doi: 10.1016/j.ijpharm.2005.08.005. Epub 2005 Oct 10. [PubMed:16219435 ]
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. doi: 10.1186/1471-2490-6-6. [PubMed:16519806 ]

Showing metabocard for Menthol (MMDBc0033676)

MOL for #<Metabolite:0x00007fece9759d50>

3D MOL for #<Metabolite:0x00007fece9759d50>

3D SDF for #<Metabolite:0x00007fece9759d50>

3D-SDF for #<Metabolite:0x00007fece9759d50>

PDB for #<Metabolite:0x00007fece9759d50>

3D PDB for #<Metabolite:0x00007fece9759d50>

SMILES for #<Metabolite:0x00007fece9759d50>

INCHI for #<Metabolite:0x00007fece9759d50>

Structure for #<Metabolite:0x00007fece9759d50>

3D Structure for #<Metabolite:0x00007fece9759d50>