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Showing NP-Card for Menthol (NP0000342)

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Record Information
Version2.0
Created at2006-08-12 19:15:31 UTC
Updated at2024-09-17 15:41:42 UTC
NP-MRD IDNP0000342
Natural Product DOIhttps://doi.org/10.57994/0861
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000342 (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
Download

3D MOL for NP0000342 (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
Download

3D SDF for NP0000342 (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>
NP0000342

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000342 (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
Download

PDB for NP0000342 (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
Download

3D PDB for NP0000342 (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 NP0000342 (Menthol)

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
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INCHI for NP0000342 (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 NMR Assignments
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 Mass156.2690 Da
Monoisotopic Mass156.15142 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-17View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-17View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-17View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-05View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 201.216488466, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Artemisia spp.Plant
Calamintha nepetaPlant
Cunila angustifoliaPlant
Glechoma hederaceaPlant
Mentha arvensisLOTUS Database
Mentha spp.Plant
Mentha x piperitaPlant
Ocimum basilicumPlant
Xylopia sericeaPlant
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point43 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.49 mg/mL at 25 °CNot Available
LogP3.40Griffin, S., Wyllie, S. G., & Markham, J. (1999). Determination of octanol-water partition coefficient for terpenoids using reversed-phase high-performance liquid chromatography. Journal of Chromatography A, 864(2), 221-228.
Predicted 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
HMDB IDHMDB0003352
DrugBank IDDB00825
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015462
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
Good Scents IDrw1030471
References
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 ]