Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:18:47 UTC

Update Date

2022-03-07 02:53:46 UTC

HMDB ID

HMDB0033574

Secondary Accession Numbers

HMDB33574

Metabolite Identification

Common Name

(1R,2R,4R,8R)-p-Menthane-2,8,9-triol

Description

(1R,2R,4R,8R)-p-Menthane-2,8,9-triol 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 small amount of articles have been published on (1R,2R,4R,8R)-p-Menthane-2,8,9-triol.

Structure

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

HMDB0033574
     RDKit          3D
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.3284    0.5391    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174    0.2518   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.3492   -0.9655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    1.2952   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006   -0.0448   -0.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8063   -0.1028    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4971   -1.4548   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -0.0174    1.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7058    1.0070   -0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9548    0.9307    0.3936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -1.0790    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -1.0973   -0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6067   -1.8604    0.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769    1.4953    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    0.5318    1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0977   -0.2792    0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316    0.1578   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2782    1.4071   -2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430    2.3361   -0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2410    1.4143    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476    2.1399   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513   -0.2387   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -1.8282   -1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890   -1.2753    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0991   -2.2135    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -0.7394    2.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    1.9937    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8420    0.9375   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4755    1.7065    0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405   -2.0830   -0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -0.8926    1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7425   -1.6503   -1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0747   -2.6365    0.6698 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
  6  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 12  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
M  END

  Mrv0541 02241208052D          

 13 13  0  0  0  0            999 V2000
   -1.0714    0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    2.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0714    1.2379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714   -1.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -1.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0714   -1.2379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 13  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033574

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC(CC1O)C(C)(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O3/c1-7-3-4-8(5-9(7)12)10(2,13)6-11/h7-9,11-13H,3-6H2,1-2H3

> <INCHI_KEY>
QOYJDVFOAJUXAR-UHFFFAOYSA-N

> <FORMULA>
C10H20O3

> <MOLECULAR_WEIGHT>
188.264

> <EXACT_MASS>
188.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.502013693150083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-hydroxy-4-methylcyclohexyl)propane-1,2-diol

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
0.22420222533333278

> <ALOGPS_LOGS>
-0.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.847642084513687

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.834836489324335

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8225775743555097

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
50.748099999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.80e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-hydroxy-4-methylcyclohexyl)propane-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033574
     RDKit          3D
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.3284    0.5391    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174    0.2518   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.3492   -0.9655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    1.2952   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006   -0.0448   -0.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8063   -0.1028    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4971   -1.4548   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -0.0174    1.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7058    1.0070   -0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9548    0.9307    0.3936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -1.0790    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -1.0973   -0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6067   -1.8604    0.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769    1.4953    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    0.5318    1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0977   -0.2792    0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316    0.1578   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2782    1.4071   -2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430    2.3361   -0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2410    1.4143    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476    2.1399   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513   -0.2387   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -1.8282   -1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890   -1.2753    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0991   -2.2135    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -0.7394    2.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    1.9937    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8420    0.9375   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4755    1.7065    0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405   -2.0830   -0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -0.8926    1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7425   -1.6503   -1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0747   -2.6365    0.6698 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
  6  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 12  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  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      -2.000   1.543   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.000   0.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667  -0.769   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.664   0.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.664   1.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667   2.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667   3.852   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.000   2.311   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.667  -2.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.000  -3.081   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.664  -3.081   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.000  -2.311   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.667  -3.852   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    3   10   11   13                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0033574
HETATM    1  C1  UNL     1       3.328   0.539   0.538  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.417   0.252  -0.648  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.485   1.349  -0.966  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.147   1.295  -0.272  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.501  -0.045  -0.528  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.806  -0.103   0.196  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.497  -1.455  -0.039  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.570  -0.017   1.571  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.706   1.007  -0.270  1.00  0.00           C  
HETATM   10  O2  UNL     1      -3.955   0.931   0.394  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.424  -1.079   0.100  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.789  -1.097  -0.482  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.607  -1.860   0.350  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.877   1.495   0.338  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.807   0.532   1.492  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.098  -0.279   0.522  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.132   0.158  -1.520  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.278   1.407  -2.056  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.943   2.336  -0.668  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.241   1.414   0.816  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.448   2.140  -0.733  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.651  -0.239  -1.611  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.333  -1.828  -1.052  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.589  -1.275   0.111  1.00  0.00           H  
HETATM   25  H12 UNL     1      -2.099  -2.213   0.665  1.00  0.00           H  
HETATM   26  H13 UNL     1      -1.999  -0.739   2.073  1.00  0.00           H  
HETATM   27  H14 UNL     1      -2.293   1.994   0.074  1.00  0.00           H  
HETATM   28  H15 UNL     1      -2.842   0.938  -1.349  1.00  0.00           H  
HETATM   29  H16 UNL     1      -4.476   1.706   0.033  1.00  0.00           H  
HETATM   30  H17 UNL     1      -0.041  -2.083  -0.082  1.00  0.00           H  
HETATM   31  H18 UNL     1       0.415  -0.893   1.190  1.00  0.00           H  
HETATM   32  H19 UNL     1       1.743  -1.650  -1.453  1.00  0.00           H  
HETATM   33  H20 UNL     1       2.075  -2.636   0.670  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   12   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6   11   22
CONECT    6    7    8    9
CONECT    7   23   24   25
CONECT    8   26
CONECT    9   10   27   28
CONECT   10   29
CONECT   11   12   30   31
CONECT   12   13   32
CONECT   13   33
END

HMDB0033574
     RDKit          3D
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.3284    0.5391    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174    0.2518   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.3492   -0.9655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    1.2952   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006   -0.0448   -0.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8063   -0.1028    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4971   -1.4548   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -0.0174    1.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7058    1.0070   -0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9548    0.9307    0.3936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -1.0790    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -1.0973   -0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6067   -1.8604    0.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769    1.4953    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    0.5318    1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0977   -0.2792    0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316    0.1578   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2782    1.4071   -2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430    2.3361   -0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2410    1.4143    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476    2.1399   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513   -0.2387   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -1.8282   -1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890   -1.2753    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0991   -2.2135    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -0.7394    2.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    1.9937    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8420    0.9375   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4755    1.7065    0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405   -2.0830   -0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -0.8926    1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7425   -1.6503   -1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0747   -2.6365    0.6698 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
  6  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 12  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₂₀O₃

Average Molecular Weight

188.264

Monoisotopic Molecular Weight

188.141244506

IUPAC Name

2-(3-hydroxy-4-methylcyclohexyl)propane-1,2-diol

Traditional Name

2-(3-hydroxy-4-methylcyclohexyl)propane-1,2-diol

CAS Registry Number

212516-28-4

SMILES

CC1CCC(CC1O)C(C)(O)CO

InChI Identifier

InChI=1S/C10H20O3/c1-7-3-4-8(5-9(7)12)10(2,13)6-11/h7-9,11-13H,3-6H2,1-2H3

InChI Key

QOYJDVFOAJUXAR-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
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033574)

Source

Exogenous

Food

Food (HMDB: HMDB0033574)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0033574)

Endogenous

Plant

Plant (HMDB: HMDB0033574)

Animal

Animal (HMDB: HMDB0033574)

Endogenous (HMDB: HMDB0033574)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033574)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033574)

Lipid metabolism pathway (HMDB: HMDB0033574)

Cellular process

Cell signaling (HMDB: HMDB0033574)

Biochemical process

Lipid transport (HMDB: HMDB0033574)

Role

Biological role

Energy source (HMDB: HMDB0033574)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033574)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	38 g/L	ALOGPS
logP	0.8	ALOGPS
logP	0.22	ChemAxon
logS	-0.69	ALOGPS
pKa (Strongest Acidic)	13.83	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.75 m³·mol⁻¹	ChemAxon
Polarizability	21.5 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]+	143.898	31661259
DarkChem	[M-H]-	138.071	31661259
DeepCCS	[M+H]+	143.362	30932474
DeepCCS	[M-H]-	139.534	30932474
DeepCCS	[M-2H]-	177.019	30932474
DeepCCS	[M+Na]+	152.635	30932474
AllCCS	[M+H]+	143.9	32859911
AllCCS	[M+H-H2O]+	139.9	32859911
AllCCS	[M+NH4]+	147.7	32859911
AllCCS	[M+Na]+	148.8	32859911
AllCCS	[M-H]-	146.1	32859911
AllCCS	[M+Na-2H]-	147.3	32859911
AllCCS	[M+HCOO]-	148.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol	CC1CCC(CC1O)C(C)(O)CO	2899.0	Standard polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol	CC1CCC(CC1O)C(C)(O)CO	1533.7	Standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol	CC1CCC(CC1O)C(C)(O)CO	1620.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,1TMS,isomer #1	CC1CCC(C(C)(O)CO)CC1O[Si](C)(C)C	1706.7	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,1TMS,isomer #2	CC1CCC(C(C)(CO)O[Si](C)(C)C)CC1O	1718.3	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,1TMS,isomer #3	CC1CCC(C(C)(O)CO[Si](C)(C)C)CC1O	1716.4	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,2TMS,isomer #1	CC1CCC(C(C)(CO)O[Si](C)(C)C)CC1O[Si](C)(C)C	1738.7	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,2TMS,isomer #2	CC1CCC(C(C)(O)CO[Si](C)(C)C)CC1O[Si](C)(C)C	1716.7	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,2TMS,isomer #3	CC1CCC(C(C)(CO[Si](C)(C)C)O[Si](C)(C)C)CC1O	1761.9	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,3TMS,isomer #1	CC1CCC(C(C)(CO[Si](C)(C)C)O[Si](C)(C)C)CC1O[Si](C)(C)C	1767.3	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,1TBDMS,isomer #1	CC1CCC(C(C)(O)CO)CC1O[Si](C)(C)C(C)(C)C	1945.3	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,1TBDMS,isomer #2	CC1CCC(C(C)(CO)O[Si](C)(C)C(C)(C)C)CC1O	1958.7	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,1TBDMS,isomer #3	CC1CCC(C(C)(O)CO[Si](C)(C)C(C)(C)C)CC1O	1953.1	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,2TBDMS,isomer #1	CC1CCC(C(C)(CO)O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C	2164.5	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,2TBDMS,isomer #2	CC1CCC(C(C)(O)CO[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C	2159.3	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,2TBDMS,isomer #3	CC1CCC(C(C)(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC1O	2217.7	Semi standard non polar	33892256
(1R,2R,4R,8R)-p-Menthane-2,8,9-triol,3TBDMS,isomer #1	CC1CCC(C(C)(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C	2430.8	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 - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g0-9500000000-9b87b7661f32df7c6d64	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol GC-MS (3 TMS) - 70eV, Positive	splash10-002r-6319000000-c1d045c0b9b10aef79ae	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 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 - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 10V, Positive-QTOF	splash10-00dr-0900000000-225d50e3feefbaa2afc9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 20V, Positive-QTOF	splash10-0fka-5900000000-48513e4ddbdbec44de7a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 40V, Positive-QTOF	splash10-0pba-9300000000-650569e57e30d49a0112	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 10V, Negative-QTOF	splash10-000i-0900000000-f5f6ee6781547596ed5c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 20V, Negative-QTOF	splash10-000i-2900000000-898790d52c69f2308471	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 40V, Negative-QTOF	splash10-08g4-9800000000-307d9d798d896b6b1016	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 10V, Negative-QTOF	splash10-000i-0900000000-95009f686fe0df41b940	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 20V, Negative-QTOF	splash10-000i-0900000000-0a83d78a9fd096a88488	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 40V, Negative-QTOF	splash10-0a4u-9400000000-5d9c74c7e4b211afa395	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 10V, Positive-QTOF	splash10-0uki-2900000000-6a25c14abf202938a647	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 20V, Positive-QTOF	splash10-0f6t-9700000000-a2ba573d9b6c1afed24b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,4R,8R)-p-Menthane-2,8,9-triol 40V, Positive-QTOF	splash10-052b-9000000000-9cd7b87762a0febb946b	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB019654

KNApSAcK ID

Not Available

Chemspider ID

35013631

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73809747

PDB ID

Not Available

ChEBI ID

171764

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 (1R,2R,4R,8R)-p-Menthane-2,8,9-triol (HMDB0033574)

MOL for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

3D MOL for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

3D SDF for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

3D-SDF for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

PDB for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

3D PDB for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

SMILES for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

INCHI for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

Structure for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

3D Structure for HMDB0033574 ((1R,2R,4R,8R)-p-Menthane-2,8,9-triol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra