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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:42:24 UTC

Update Date

2022-03-07 02:54:14 UTC

HMDB ID

HMDB0034783

Secondary Accession Numbers

HMDB34783

Metabolite Identification

Common Name

cis-p-Menthane-1,7,8-triol

Description

cis-p-Menthane-1,7,8-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 cis-p-Menthane-1,7,8-triol.

Structure

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

HMDB0034783
     RDKit          3D
cis-p-Menthane-1,7,8-triol
 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.7562    0.8388    1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2486   -0.1484    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6932    0.3316   -1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8933   -1.3576    0.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -0.3047    0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176    0.9909   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149    0.8051    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621   -0.4788    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473   -1.4112    1.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837   -0.1275   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422    0.4159    0.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -1.1292   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1853   -1.2957   -0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781    0.7509    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252    1.8806    0.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4413    0.5779    2.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -0.3811   -2.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2222    1.3371   -1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    0.5312   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7304   -1.2405    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -0.6864    1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531    1.0998   -1.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467    1.8703    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    0.6823    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    1.6844    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746   -1.2117    1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9341   -0.9765   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2853    0.6939   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1007    1.4018    0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -2.1430   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5857   -0.5665   -1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6251   -1.0802   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557   -2.3140   -0.4395 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
M  END


  Mrv0541 02241219272D          

 13 13  0  0  0  0            999 V2000
    0.3736    0.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4575    0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2759   -0.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    0.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515    0.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2168    1.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758    1.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0794    1.8886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5414   -1.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049   -1.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -1.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7959    1.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -1.9876    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 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034783

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(O)C1CCC(O)(CO)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O3/c1-9(2,12)8-3-5-10(13,7-11)6-4-8/h8,11-13H,3-7H2,1-2H3

> <INCHI_KEY>
TVWCVYDBLMOUAI-UHFFFAOYSA-N

> <FORMULA>
C10H20O3

> <MOLECULAR_WEIGHT>
188.264

> <EXACT_MASS>
188.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.146579253658373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(hydroxymethyl)-4-(2-hydroxypropan-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.1398060673333325

> <ALOGPS_LOGS>
-0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.378134308741846

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.866843919945946

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9202794989106565

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
50.914699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(hydroxymethyl)-4-(2-hydroxypropan-2-yl)cyclohexan-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034783
     RDKit          3D
cis-p-Menthane-1,7,8-triol
 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.7562    0.8388    1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2486   -0.1484    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6932    0.3316   -1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8933   -1.3576    0.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -0.3047    0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176    0.9909   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149    0.8051    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621   -0.4788    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473   -1.4112    1.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837   -0.1275   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422    0.4159    0.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -1.1292   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1853   -1.2957   -0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781    0.7509    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252    1.8806    0.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4413    0.5779    2.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -0.3811   -2.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2222    1.3371   -1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    0.5312   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7304   -1.2405    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -0.6864    1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531    1.0998   -1.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467    1.8703    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    0.6823    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    1.6844    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746   -1.2117    1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9341   -0.9765   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2853    0.6939   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1007    1.4018    0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -2.1430   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5857   -0.5665   -1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6251   -1.0802   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557   -2.3140   -0.4395 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 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       0.697   1.630   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.854   0.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.515  -0.684   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.827   0.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.776   1.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.405   2.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.515   3.710   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.015   3.525   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.011  -2.318   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.569  -2.261   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.015  -2.287   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.486   3.656   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.543  -3.710   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7   12                                             
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    3    9   11   13                                             
CONECT   11   10                                                            
CONECT   12    6                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0034783
HETATM    1  C1  UNL     1      -2.756   0.839   1.067  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.249  -0.148   0.036  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.693   0.332  -1.316  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.893  -1.358   0.290  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.765  -0.305   0.156  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.018   0.991  -0.057  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.315   0.805   0.674  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.962  -0.479   0.238  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.047  -1.411   1.270  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.384  -0.128  -0.166  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.042   0.416   0.963  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.303  -1.129  -0.934  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.185  -1.296  -0.804  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.878   0.751   1.069  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.525   1.881   0.796  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.441   0.578   2.099  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.521  -0.381  -2.128  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.222   1.337  -1.510  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.784   0.531  -1.269  1.00  0.00           H  
HETATM   20  H7  UNL     1      -3.730  -1.241   0.806  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.560  -0.686   1.186  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.253   1.100  -1.142  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.547   1.870   0.299  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.061   0.682   1.760  1.00  0.00           H  
HETATM   25  H12 UNL     1       1.958   1.684   0.603  1.00  0.00           H  
HETATM   26  H13 UNL     1       2.875  -1.212   1.781  1.00  0.00           H  
HETATM   27  H14 UNL     1       3.934  -0.977  -0.582  1.00  0.00           H  
HETATM   28  H15 UNL     1       3.285   0.694  -0.926  1.00  0.00           H  
HETATM   29  H16 UNL     1       4.101   1.402   0.882  1.00  0.00           H  
HETATM   30  H17 UNL     1       1.743  -2.143  -1.045  1.00  0.00           H  
HETATM   31  H18 UNL     1       1.586  -0.566  -1.855  1.00  0.00           H  
HETATM   32  H19 UNL     1      -0.625  -1.080  -1.803  1.00  0.00           H  
HETATM   33  H20 UNL     1      -0.456  -2.314  -0.440  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4    5
CONECT    3   17   18   19
CONECT    4   20
CONECT    5    6   13   21
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9   10   12
CONECT    9   26
CONECT   10   11   27   28
CONECT   11   29
CONECT   12   13   30   31
CONECT   13   32   33
END

HMDB0034783
     RDKit          3D
cis-p-Menthane-1,7,8-triol
 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.7562    0.8388    1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2486   -0.1484    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6932    0.3316   -1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8933   -1.3576    0.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -0.3047    0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176    0.9909   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149    0.8051    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621   -0.4788    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473   -1.4112    1.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837   -0.1275   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422    0.4159    0.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -1.1292   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1853   -1.2957   -0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781    0.7509    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252    1.8806    0.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4413    0.5779    2.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -0.3811   -2.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2222    1.3371   -1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    0.5312   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7304   -1.2405    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -0.6864    1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531    1.0998   -1.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467    1.8703    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    0.6823    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    1.6844    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746   -1.2117    1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9341   -0.9765   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2853    0.6939   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1007    1.4018    0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -2.1430   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5857   -0.5665   -1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6251   -1.0802   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557   -2.3140   -0.4395 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Menthane-1,7,8-triol	MeSH

Chemical Formula

C₁₀H₂₀O₃

Average Molecular Weight

188.264

Monoisotopic Molecular Weight

188.141244506

IUPAC Name

1-(hydroxymethyl)-4-(2-hydroxypropan-2-yl)cyclohexan-1-ol

Traditional Name

1-(hydroxymethyl)-4-(2-hydroxypropan-2-yl)cyclohexan-1-ol

CAS Registry Number

154843-72-8

SMILES

CC(C)(O)C1CCC(O)(CO)CC1

InChI Identifier

InChI=1S/C10H20O3/c1-9(2,12)8-3-5-10(13,7-11)6-4-8/h8,11-13H,3-7H2,1-2H3

InChI Key

TVWCVYDBLMOUAI-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
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

Cell membrane (HMDB: HMDB0034783)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034783)

Source

Endogenous

Endogenous (HMDB: HMDB0034783)

Plant

Plant (HMDB: HMDB0034783)

Animal

Animal (HMDB: HMDB0034783)

Exogenous

Food

Food (HMDB: HMDB0034783)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034783)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034783)

Cellular process

Cell signaling (HMDB: HMDB0034783)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034783)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034783)

Nutrient

Nutrient (HMDB: HMDB0034783)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034783)

Emulsifier (HMDB: HMDB0034783)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	137 - 139 °C	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	30.6 g/L	ALOGPS
logP	0.67	ALOGPS
logP	0.14	ChemAxon
logS	-0.79	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	-0.92	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	50.91 m³·mol⁻¹	ChemAxon
Polarizability	21.15 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]+	142.453	31661259
DarkChem	[M-H]-	139.973	31661259
DeepCCS	[M+H]+	141.623	30932474
DeepCCS	[M-H]-	138.269	30932474
DeepCCS	[M-2H]-	175.332	30932474
DeepCCS	[M+Na]+	150.87	30932474
AllCCS	[M+H]+	143.2	32859911
AllCCS	[M+H-H2O]+	139.2	32859911
AllCCS	[M+NH4]+	146.9	32859911
AllCCS	[M+Na]+	148.0	32859911
AllCCS	[M-H]-	146.1	32859911
AllCCS	[M+Na-2H]-	147.4	32859911
AllCCS	[M+HCOO]-	148.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-p-Menthane-1,7,8-triol	CC(C)(O)C1CCC(O)(CO)CC1	2707.8	Standard polar	33892256
cis-p-Menthane-1,7,8-triol	CC(C)(O)C1CCC(O)(CO)CC1	1538.4	Standard non polar	33892256
cis-p-Menthane-1,7,8-triol	CC(C)(O)C1CCC(O)(CO)CC1	1583.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-p-Menthane-1,7,8-triol,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CCC(O)(CO)CC1	1729.2	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,1TMS,isomer #2	CC(C)(O)C1CCC(CO)(O[Si](C)(C)C)CC1	1702.9	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,1TMS,isomer #3	CC(C)(O)C1CCC(O)(CO[Si](C)(C)C)CC1	1679.8	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,2TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CCC(CO)(O[Si](C)(C)C)CC1	1754.0	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,2TMS,isomer #2	CC(C)(O[Si](C)(C)C)C1CCC(O)(CO[Si](C)(C)C)CC1	1743.3	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,2TMS,isomer #3	CC(C)(O)C1CCC(CO[Si](C)(C)C)(O[Si](C)(C)C)CC1	1738.4	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,3TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CCC(CO[Si](C)(C)C)(O[Si](C)(C)C)CC1	1782.5	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CCC(O)(CO)CC1	1964.2	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,1TBDMS,isomer #2	CC(C)(O)C1CCC(CO)(O[Si](C)(C)C(C)(C)C)CC1	1937.6	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,1TBDMS,isomer #3	CC(C)(O)C1CCC(O)(CO[Si](C)(C)C(C)(C)C)CC1	1907.5	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,2TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CCC(CO)(O[Si](C)(C)C(C)(C)C)CC1	2195.4	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,2TBDMS,isomer #2	CC(C)(O[Si](C)(C)C(C)(C)C)C1CCC(O)(CO[Si](C)(C)C(C)(C)C)CC1	2173.3	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,2TBDMS,isomer #3	CC(C)(O)C1CCC(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)CC1	2189.0	Semi standard non polar	33892256
cis-p-Menthane-1,7,8-triol,3TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CCC(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)CC1	2451.1	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 - cis-p-Menthane-1,7,8-triol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abj-9600000000-92d528dd9153dfe3c33f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-p-Menthane-1,7,8-triol GC-MS (3 TMS) - 70eV, Positive	splash10-0fg9-6309000000-fafb408023d2e6bcbd44	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-p-Menthane-1,7,8-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 - cis-p-Menthane-1,7,8-triol 10V, Positive-QTOF	splash10-00dr-0900000000-3c7f29ff953f76a93f2d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 20V, Positive-QTOF	splash10-0h90-1900000000-ea8f7300c06314b9cd37	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 40V, Positive-QTOF	splash10-0wmj-9700000000-3f2cc145fdbd913d096c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 10V, Negative-QTOF	splash10-000i-0900000000-58cef6c13a08005f9633	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 20V, Negative-QTOF	splash10-000i-1900000000-086ee8fc43d3ece12d42	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 40V, Negative-QTOF	splash10-052k-4900000000-477d23267a42c49a68c2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 10V, Positive-QTOF	splash10-0uk9-0900000000-d7cbfb640a5ac4d2efe1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 20V, Positive-QTOF	splash10-0w29-4900000000-d618bb38b29ff60d934d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 40V, Positive-QTOF	splash10-001i-9100000000-0418d4e574814356c4f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 10V, Negative-QTOF	splash10-000i-0900000000-ffab34726f462d716387	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 20V, Negative-QTOF	splash10-000i-0900000000-54db45d18b0547e2c668	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-p-Menthane-1,7,8-triol 40V, Negative-QTOF	splash10-052u-3900000000-0cb3bdb2c0aa8e8f7e9c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

FDB013336

KNApSAcK ID

Not Available

Chemspider ID

112663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126863

PDB ID

Not Available

ChEBI ID

Not Available

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 cis-p-Menthane-1,7,8-triol (HMDB0034783)

MOL for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

3D MOL for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

3D SDF for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

3D-SDF for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

PDB for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

3D PDB for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

SMILES for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

INCHI for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

Structure for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

3D Structure for HMDB0034783 (cis-p-Menthane-1,7,8-triol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra