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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:11:55 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036133

Secondary Accession Numbers

HMDB36133

Metabolite Identification

Common Name

3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol

Description

3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 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 significant number of articles have been published on 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol.

Structure

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

HMDB0036133
     RDKit          3D
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.5947    2.9068    0.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1681    1.5046    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588    0.7502    1.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.6947    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492   -0.8910    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4035   -1.6051   -1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -1.8378   -2.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9483   -2.9567   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403    0.3235   -0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1022    0.5434    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2675    0.4357   -0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4474    0.6870    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261    0.5807   -0.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -0.3618    1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4757   -0.2095    2.5518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260    1.5795   -0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079    3.5202   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276    3.3820    1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5414    2.8071    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9516    1.0499   -0.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938    1.1781    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059    0.8076    2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510   -1.0757    0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4615   -1.2245    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322   -1.6039    0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -0.9519   -1.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -1.0356   -2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -2.0145   -1.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7065   -2.7816   -2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223   -3.2433    0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -3.6864   -1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300   -2.9160   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3271    0.1134   -1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054   -0.5935   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.1284   -1.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.7089    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9072    1.4412   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -1.3466    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524   -0.2385    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0737    0.4821    2.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    1.9109   -1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774    2.4273    0.0468 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  9 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv0541 05061308542D          

 16 16  0  0  0  0            999 V2000
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036133

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CCC(C)CC1OCC(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C13H26O3/c1-9(2)12-5-4-10(3)6-13(12)16-8-11(15)7-14/h9-15H,4-8H2,1-3H3

> <INCHI_KEY>
MDVYIGJINBYKOM-UHFFFAOYSA-N

> <FORMULA>
C13H26O3

> <MOLECULAR_WEIGHT>
230.3437

> <EXACT_MASS>
230.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.597914271327795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}propane-1,2-diol

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.9869626966666671

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.565186548711623

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.640866223477516

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9682018219085835

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
64.4513

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
menthoxypropanediol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036133
     RDKit          3D
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.5947    2.9068    0.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1681    1.5046    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588    0.7502    1.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.6947    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492   -0.8910    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4035   -1.6051   -1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -1.8378   -2.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9483   -2.9567   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403    0.3235   -0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1022    0.5434    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2675    0.4357   -0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4474    0.6870    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261    0.5807   -0.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -0.3618    1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4757   -0.2095    2.5518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260    1.5795   -0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079    3.5202   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276    3.3820    1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5414    2.8071    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9516    1.0499   -0.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938    1.1781    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059    0.8076    2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510   -1.0757    0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4615   -1.2245    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322   -1.6039    0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -0.9519   -1.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -1.0356   -2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -2.0145   -1.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7065   -2.7816   -2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223   -3.2433    0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -3.6864   -1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300   -2.9160   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3271    0.1134   -1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054   -0.5935   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.1284   -1.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.7089    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9072    1.4412   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -1.3466    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524   -0.2385    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0737    0.4821    2.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    1.9109   -1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774    2.4273    0.0468 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  9 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5   10                                                       
CONECT    5    4   12                                                       
CONECT    6   10   13                                                       
CONECT    7   11   14                                                       
CONECT    8   11   16                                                       
CONECT    9    1    2   12                                                  
CONECT   10    3    4    6                                                  
CONECT   11    7    8   15                                                  
CONECT   12    5    9   13                                                  
CONECT   13    6   12   16                                                  
CONECT   14    7                                                            
CONECT   15   11                                                            
CONECT   16    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0036133
HETATM    1  C1  UNL     1      -2.595   2.907   0.630  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.168   1.505   0.259  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.959   0.750   1.563  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.757  -0.695   1.167  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.749  -0.891   0.106  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.403  -1.605  -1.060  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.418  -1.838  -2.187  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.948  -2.957  -0.649  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.040   0.323  -0.372  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.102   0.543   0.397  1.00  0.00           O  
HETATM   11  C10 UNL     1       2.268   0.436  -0.336  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.447   0.687   0.569  1.00  0.00           C  
HETATM   13  O2  UNL     1       4.626   0.581  -0.160  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.404  -0.362   1.668  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.476  -0.210   2.552  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.826   1.579  -0.413  1.00  0.00           C  
HETATM   17  H1  UNL     1      -2.808   3.520  -0.262  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.828   3.382   1.269  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.541   2.807   1.221  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.952   1.050  -0.369  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.094   1.178   2.070  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.906   0.808   2.148  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.751  -1.076   0.860  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.462  -1.225   2.120  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.032  -1.604   0.488  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.202  -0.952  -1.461  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.451  -1.036  -2.950  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.618  -2.014  -1.809  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.707  -2.782  -2.728  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.422  -3.243   0.294  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.790  -3.686  -1.442  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.030  -2.916  -0.414  1.00  0.00           H  
HETATM   33  H17 UNL     1       0.327   0.113  -1.408  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.305  -0.594  -0.767  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.301   1.128  -1.196  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.357   1.709   0.974  1.00  0.00           H  
HETATM   37  H21 UNL     1       4.907   1.441  -0.552  1.00  0.00           H  
HETATM   38  H22 UNL     1       3.415  -1.347   1.183  1.00  0.00           H  
HETATM   39  H23 UNL     1       2.452  -0.239   2.227  1.00  0.00           H  
HETATM   40  H24 UNL     1       5.074   0.482   2.168  1.00  0.00           H  
HETATM   41  H25 UNL     1      -1.027   1.911  -1.473  1.00  0.00           H  
HETATM   42  H26 UNL     1      -0.277   2.427   0.047  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   16   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6    9   25
CONECT    6    7    8   26
CONECT    7   27   28   29
CONECT    8   30   31   32
CONECT    9   10   16   33
CONECT   10   11
CONECT   11   12   34   35
CONECT   12   13   14   36
CONECT   13   37
CONECT   14   15   38   39
CONECT   15   40
CONECT   16   41   42
END

HMDB0036133
     RDKit          3D
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.5947    2.9068    0.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1681    1.5046    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588    0.7502    1.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.6947    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492   -0.8910    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4035   -1.6051   -1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -1.8378   -2.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9483   -2.9567   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403    0.3235   -0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1022    0.5434    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2675    0.4357   -0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4474    0.6870    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261    0.5807   -0.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -0.3618    1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4757   -0.2095    2.5518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260    1.5795   -0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079    3.5202   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276    3.3820    1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5414    2.8071    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9516    1.0499   -0.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938    1.1781    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059    0.8076    2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510   -1.0757    0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4615   -1.2245    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322   -1.6039    0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -0.9519   -1.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -1.0356   -2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -2.0145   -1.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7065   -2.7816   -2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223   -3.2433    0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -3.6864   -1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300   -2.9160   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3271    0.1134   -1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054   -0.5935   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.1284   -1.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.7089    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9072    1.4412   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -1.3466    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524   -0.2385    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0737    0.4821    2.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    1.9109   -1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774    2.4273    0.0468 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  9 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Menthyl)oxypropanediol	HMDB
3-((L-Menthyl)oxy)propane-1,2-diol	HMDB
3-L-(P-Menthane-3-yloxy)-1,2-propanediol	HMDB
3-L-Menthoxypropane-1,2-diol	HMDB, MeSH
3-Menthyloxy-1,2-propanediol	HMDB
L-1,3-Menthoxypropane-1,2-diol	HMDB
Menthoxypropanediol	HMDB
Brachymelic primordial dwarfism	MeSH, HMDB
Microcephalic osteodysplastic primordial dwarfism, type I	MeSH, HMDB
MopdI	MeSH, HMDB
Osteodysplastic primordial dwarfism, type I	MeSH, HMDB
3-Menthoxypropane-1,2-diol	MeSH, HMDB
Mopd 1	MeSH, HMDB
Mopd1	MeSH, HMDB
Taybi linder syndrome	MeSH, HMDB
Taybi-linder syndrome	MeSH, HMDB
Microcephalic osteodysplastic primordial dwarfism, type 1	MeSH, HMDB
Mopd	MeSH, HMDB
Cephaloskeletal dysplasia	MeSH, HMDB
Low-birth-weight dwarfism with skeletal dysplasia	MeSH, HMDB
Mopd I	MeSH, HMDB
Osteodysplastic primordial dwarfism, type 1	MeSH, HMDB

Chemical Formula

C₁₃H₂₆O₃

Average Molecular Weight

230.3437

Monoisotopic Molecular Weight

230.188194698

IUPAC Name

3-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}propane-1,2-diol

Traditional Name

menthoxypropanediol

CAS Registry Number

87061-04-9

SMILES

CC(C)C1CCC(C)CC1OCC(O)CO

InChI Identifier

InChI=1S/C13H26O3/c1-9(2)12-5-4-10(3)6-13(12)16-8-11(15)7-14/h9-15H,4-8H2,1-3H3

InChI Key

MDVYIGJINBYKOM-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
Glycerolipid
Glycerol ether
Secondary alcohol
1,2-diol
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cell membrane (HMDB: HMDB0036133)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036133)

Source

Endogenous

Endogenous (HMDB: HMDB0036133)

Animal

Animal (HMDB: HMDB0036133)

Exogenous

Food

Food (HMDB: HMDB0036133)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036133)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036133)

Cellular process

Cell signaling (HMDB: HMDB0036133)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036133)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036133)

Nutrient

Nutrient (HMDB: HMDB0036133)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036133)

Emulsifier (HMDB: HMDB0036133)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	121.00 to 125.00 °C. @ 0.25 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	2.625 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.97 g/L	ALOGPS
logP	2.24	ALOGPS
logP	1.99	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.45 m³·mol⁻¹	ChemAxon
Polarizability	27.6 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]+	154.629	31661259
DarkChem	[M-H]-	151.125	31661259
DeepCCS	[M+H]+	153.983	30932474
DeepCCS	[M-H]-	151.185	30932474
DeepCCS	[M-2H]-	187.273	30932474
DeepCCS	[M+Na]+	162.811	30932474
AllCCS	[M+H]+	156.7	32859911
AllCCS	[M+H-H2O]+	153.1	32859911
AllCCS	[M+NH4]+	160.0	32859911
AllCCS	[M+Na]+	160.9	32859911
AllCCS	[M-H]-	159.2	32859911
AllCCS	[M+Na-2H]-	160.1	32859911
AllCCS	[M+HCOO]-	161.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol	CC(C)C1CCC(C)CC1OCC(O)CO	2296.4	Standard polar	33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol	CC(C)C1CCC(C)CC1OCC(O)CO	1677.4	Standard non polar	33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol	CC(C)C1CCC(C)CC1OCC(O)CO	1657.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,1TMS,isomer #1	CC1CCC(C(C)C)C(OCC(CO)O[Si](C)(C)C)C1	1765.2	Semi standard non polar	33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,1TMS,isomer #2	CC1CCC(C(C)C)C(OCC(O)CO[Si](C)(C)C)C1	1794.3	Semi standard non polar	33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,2TMS,isomer #1	CC1CCC(C(C)C)C(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)C1	1832.6	Semi standard non polar	33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,1TBDMS,isomer #1	CC1CCC(C(C)C)C(OCC(CO)O[Si](C)(C)C(C)(C)C)C1	2005.6	Semi standard non polar	33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,1TBDMS,isomer #2	CC1CCC(C(C)C)C(OCC(O)CO[Si](C)(C)C(C)(C)C)C1	2021.3	Semi standard non polar	33892256
3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol,2TBDMS,isomer #1	CC1CCC(C(C)C)C(OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1	2278.3	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 - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-9410000000-98dfbfe970c670ae9068	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol GC-MS (2 TMS) - 70eV, Positive	splash10-0pi9-9423000000-721c23d46517c900aa58	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 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 - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 10V, Positive-QTOF	splash10-001i-1590000000-2fadc1706d969b1f1f94	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 20V, Positive-QTOF	splash10-06s9-5950000000-9b54b9eae57a7880d8c4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 40V, Positive-QTOF	splash10-0ap0-9300000000-95c723635e5dab45c5c7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 10V, Negative-QTOF	splash10-004i-1690000000-8743ab1623786ad4be83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 20V, Negative-QTOF	splash10-0a4i-1910000000-e5047c0a6685c22bba58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 40V, Negative-QTOF	splash10-0a4r-2900000000-750bdade2186d0de6440	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 10V, Positive-QTOF	splash10-01q1-9870000000-77e27c31dee07b091b21	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 20V, Positive-QTOF	splash10-000b-9500000000-5cab84e664f995a8a04e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 40V, Positive-QTOF	splash10-056s-9000000000-9af9d01094ba4af570e6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 10V, Negative-QTOF	splash10-004i-0390000000-063529b4cb405a75b479	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 20V, Negative-QTOF	splash10-0a4i-0900000000-e3a3687bd1938e74168d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol 40V, Negative-QTOF	splash10-0k9i-1900000000-d7e3e42a4a0df375082e	2021-09-24	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

FDB014982

KNApSAcK ID

Not Available

Chemspider ID

4515105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5362595

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1038341

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 3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol (HMDB0036133)

MOL for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

3D MOL for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

3D SDF for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

3D-SDF for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

PDB for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

3D PDB for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

SMILES for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

INCHI for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

Structure for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

3D Structure for HMDB0036133 (3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra