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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:12:20 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036141

Secondary Accession Numbers

HMDB36141

Metabolite Identification

Common Name

Menthyl ethylene glycol carbonate

Description

Menthyl ethylene glycol carbonate 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 Menthyl ethylene glycol carbonate.

Structure

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

HMDB0036141
     RDKit          3D
Menthyl ethylene glycol carbonate
 41 41  0  0  0  0  0  0  0  0999 V2000
   -2.4926    3.4035    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1009    1.9954    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153    1.0556   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -0.1886   -0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3550   -0.5358    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -1.9840    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384   -2.7952    0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -2.3963   -0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    0.4003    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842    0.0114   -0.5417 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -0.1612   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810    0.0491    1.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092   -0.5358   -1.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373   -0.7234   -0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481    0.4255   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7663    0.9412    0.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027    1.7549   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    3.8300    0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0819    3.3617   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925    4.0517   -0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425    1.9558    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7861    0.6955    0.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7417    1.5251   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1085   -1.0277   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381   -0.0069   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477   -0.3655    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972   -2.1999    1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6756   -3.0517   -0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710   -2.2545    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9386   -3.7660    1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632   -2.6696   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295   -3.2935   -1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856   -1.5984   -1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728    0.5379    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179   -1.6179   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9177   -1.0692   -1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3889    1.2101   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3093    0.1039   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986    0.5825    1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514    1.8172   -1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570    2.5331    0.4305 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  1  0
 17  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv0541 05061308542D          

 17 17  0  0  0  0            999 V2000
    8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    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
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  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  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 14  6  1  0  0  0  0
 15 13  2  0  0  0  0
 16  7  1  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036141

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CCC(C)CC1OC(=O)OCCO

> <INCHI_IDENTIFIER>
InChI=1S/C13H24O4/c1-9(2)11-5-4-10(3)8-12(11)17-13(15)16-7-6-14/h9-12,14H,4-8H2,1-3H3

> <INCHI_KEY>
JFKCVAZSEWPOIX-UHFFFAOYSA-N

> <FORMULA>
C13H24O4

> <MOLECULAR_WEIGHT>
244.3273

> <EXACT_MASS>
244.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.02676463090184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[({[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}carbonyl)oxy]ethan-1-ol

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
3.034587681333334

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.092018402799408

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7585511506155393

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
64.5127

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({[(2-isopropyl-5-methylcyclohexyl)oxy]carbonyl}oxy)ethanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036141
     RDKit          3D
Menthyl ethylene glycol carbonate
 41 41  0  0  0  0  0  0  0  0999 V2000
   -2.4926    3.4035    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1009    1.9954    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153    1.0556   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -0.1886   -0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3550   -0.5358    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -1.9840    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384   -2.7952    0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -2.3963   -0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    0.4003    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842    0.0114   -0.5417 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -0.1612   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810    0.0491    1.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092   -0.5358   -1.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373   -0.7234   -0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481    0.4255   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7663    0.9412    0.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027    1.7549   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    3.8300    0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0819    3.3617   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925    4.0517   -0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425    1.9558    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7861    0.6955    0.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7417    1.5251   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1085   -1.0277   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381   -0.0069   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477   -0.3655    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972   -2.1999    1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6756   -3.0517   -0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710   -2.2545    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9386   -3.7660    1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632   -2.6696   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295   -3.2935   -1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856   -1.5984   -1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728    0.5379    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179   -1.6179   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9177   -1.0692   -1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3889    1.2101   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3093    0.1039   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986    0.5825    1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514    1.8172   -1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570    2.5331    0.4305 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  1  0
 17  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  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      16.004   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337   9.240   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      16.004   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    7   14                                                       
CONECT    7    6   16                                                       
CONECT    8   10   12                                                       
CONECT    9    1    2   11                                                  
CONECT   10    3    4    8                                                  
CONECT   11    5    9   12                                                  
CONECT   12    8   11   17                                                  
CONECT   13   15   16   17                                                  
CONECT   14    6                                                            
CONECT   15   13                                                            
CONECT   16    7   13                                                       
CONECT   17   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0036141
HETATM    1  C1  UNL     1      -2.493   3.403   0.080  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.101   1.995   0.519  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.115   1.056  -0.056  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.407  -0.189  -0.570  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.355  -0.536   0.480  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.968  -1.984   0.411  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.238  -2.795   0.662  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.419  -2.396  -0.914  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.178   0.400   0.405  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.784   0.011  -0.542  1.00  0.00           O  
HETATM   11  C10 UNL     1       2.121  -0.161  -0.170  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.381   0.049   1.020  1.00  0.00           O  
HETATM   13  O3  UNL     1       3.109  -0.536  -1.028  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.437  -0.723  -0.758  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.248   0.425  -0.287  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.766   0.941   0.892  1.00  0.00           O  
HETATM   17  C13 UNL     1      -0.703   1.755  -0.015  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.094   3.830   0.907  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.082   3.362  -0.857  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.593   4.052  -0.034  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.043   1.956   1.625  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.786   0.695   0.777  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.742   1.525  -0.859  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.108  -1.028  -0.636  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.938  -0.007  -1.558  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.848  -0.365   1.464  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.297  -2.200   1.254  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.676  -3.052  -0.332  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.971  -2.255   1.266  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.939  -3.766   1.133  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.663  -2.670  -0.754  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.929  -3.293  -1.333  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.486  -1.598  -1.692  1.00  0.00           H  
HETATM   34  H17 UNL     1       0.273   0.538   1.427  1.00  0.00           H  
HETATM   35  H18 UNL     1       4.618  -1.618  -0.087  1.00  0.00           H  
HETATM   36  H19 UNL     1       4.918  -1.069  -1.729  1.00  0.00           H  
HETATM   37  H20 UNL     1       5.389   1.210  -1.075  1.00  0.00           H  
HETATM   38  H21 UNL     1       6.309   0.104  -0.062  1.00  0.00           H  
HETATM   39  H22 UNL     1       5.199   0.583   1.698  1.00  0.00           H  
HETATM   40  H23 UNL     1      -0.651   1.817  -1.104  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.057   2.533   0.431  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   17   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6    9   26
CONECT    6    7    8   27
CONECT    7   28   29   30
CONECT    8   31   32   33
CONECT    9   10   17   34
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   35   36
CONECT   15   16   37   38
CONECT   16   39
CONECT   17   40   41
END

HMDB0036141
     RDKit          3D
Menthyl ethylene glycol carbonate
 41 41  0  0  0  0  0  0  0  0999 V2000
   -2.4926    3.4035    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1009    1.9954    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153    1.0556   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -0.1886   -0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3550   -0.5358    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -1.9840    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384   -2.7952    0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -2.3963   -0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    0.4003    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842    0.0114   -0.5417 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -0.1612   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810    0.0491    1.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092   -0.5358   -1.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373   -0.7234   -0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481    0.4255   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7663    0.9412    0.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027    1.7549   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940    3.8300    0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0819    3.3617   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925    4.0517   -0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425    1.9558    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7861    0.6955    0.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7417    1.5251   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1085   -1.0277   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381   -0.0069   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477   -0.3655    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972   -2.1999    1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6756   -3.0517   -0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710   -2.2545    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9386   -3.7660    1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632   -2.6696   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295   -3.2935   -1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856   -1.5984   -1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728    0.5379    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179   -1.6179   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9177   -1.0692   -1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3889    1.2101   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3093    0.1039   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986    0.5825    1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514    1.8172   -1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570    2.5331    0.4305 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  1  0
 17  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Menthyl ethylene glycol carbonic acid	Generator
2-Hydroxyethyl 5-methyl-2-(1-methylethyl)cyclohexyl carbonate, 9ci	HMDB
Anc 1	HMDB
FEMA 3805	HMDB
L-Menthyl ethylene glycol carbonate	HMDB
Menthol glycol carbonate	HMDB
Menthyl glycol carbonate	HMDB
7,8-Dicarbaundecaborate(1-), 7-(3-aminopropyl)undecahydro-, hydrogen	MeSH
ANC-1	MeSH
7-(3-Aminopropyl)-7,8-dicarba-nido-undecarborate(-1)	MeSH

Chemical Formula

C₁₃H₂₄O₄

Average Molecular Weight

244.3273

Monoisotopic Molecular Weight

244.167459256

IUPAC Name

2-[({[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}carbonyl)oxy]ethan-1-ol

Traditional Name

2-({[(2-isopropyl-5-methylcyclohexyl)oxy]carbonyl}oxy)ethanol

CAS Registry Number

156324-78-6

SMILES

CC(C)C1CCC(C)CC1OC(=O)OCCO

InChI Identifier

InChI=1S/C13H24O4/c1-9(2)11-5-4-10(3)8-12(11)17-13(15)16-7-6-14/h9-12,14H,4-8H2,1-3H3

InChI Key

JFKCVAZSEWPOIX-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
Carbonic acid diester
Carbonic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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: HMDB0036141)

Source

Endogenous

Endogenous (HMDB: HMDB0036141)

Animal

Animal (HMDB: HMDB0036141)

Exogenous

Food

Food (HMDB: HMDB0036141)

Exogenous (HMDB: HMDB0036141)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036141)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036141)

Lipid metabolism pathway (HMDB: HMDB0036141)

Cellular process

Cell signaling (HMDB: HMDB0036141)

Biochemical process

Lipid transport (HMDB: HMDB0036141)

Role

Biological role

Energy source (HMDB: HMDB0036141)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036141)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036141)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	51.5 °C	Not Available
Boiling Point	357.62 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	131.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.256 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	2.81	ALOGPS
logP	3.03	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	15.09	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	64.51 m³·mol⁻¹	ChemAxon
Polarizability	28.03 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]+	156.039	31661259
DarkChem	[M-H]-	154.758	31661259
DeepCCS	[M+H]+	154.089	30932474
DeepCCS	[M-H]-	151.731	30932474
DeepCCS	[M-2H]-	186.743	30932474
DeepCCS	[M+Na]+	161.87	30932474
AllCCS	[M+H]+	158.2	32859911
AllCCS	[M+H-H2O]+	154.7	32859911
AllCCS	[M+NH4]+	161.5	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	161.5	32859911
AllCCS	[M+Na-2H]-	162.3	32859911
AllCCS	[M+HCOO]-	163.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.37 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5386 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.5 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2576.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	424.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	179.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	207.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	735.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	820.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1238.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	492.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1584.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	417.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	441.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	393.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	417.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Menthyl ethylene glycol carbonate	CC(C)C1CCC(C)CC1OC(=O)OCCO	2236.2	Standard polar	33892256
Menthyl ethylene glycol carbonate	CC(C)C1CCC(C)CC1OC(=O)OCCO	1587.8	Standard non polar	33892256
Menthyl ethylene glycol carbonate	CC(C)C1CCC(C)CC1OC(=O)OCCO	1681.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Menthyl ethylene glycol carbonate,1TMS,isomer #1	CC1CCC(C(C)C)C(OC(=O)OCCO[Si](C)(C)C)C1	1725.2	Semi standard non polar	33892256
Menthyl ethylene glycol carbonate,1TBDMS,isomer #1	CC1CCC(C(C)C)C(OC(=O)OCCO[Si](C)(C)C(C)(C)C)C1	1951.3	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 - Menthyl ethylene glycol carbonate GC-MS (Non-derivatized) - 70eV, Positive	splash10-055p-9430000000-45ace2bab196ac18eef1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthyl ethylene glycol carbonate GC-MS (1 TMS) - 70eV, Positive	splash10-0uk9-9811000000-997e39be92eb6522f704	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthyl ethylene glycol carbonate 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 - Menthyl ethylene glycol carbonate 10V, Positive-QTOF	splash10-0002-9880000000-0f98d8a495ebdbc8b76b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 20V, Positive-QTOF	splash10-052b-9620000000-1c427af87fa157cdad8e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 40V, Positive-QTOF	splash10-0ap0-9200000000-320b324cc04fe0cf841c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 10V, Negative-QTOF	splash10-0007-4970000000-543b5b4de3ca4e0cd124	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 20V, Negative-QTOF	splash10-0540-5910000000-7231eb9e2dbfcbb4187d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 40V, Negative-QTOF	splash10-052f-8900000000-b47de61b5287880dd7b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 10V, Positive-QTOF	splash10-0002-9300000000-cfa0a7218f2b573e31fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 20V, Positive-QTOF	splash10-0002-9200000000-4932f23748448a8d0084	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 40V, Positive-QTOF	splash10-05ne-9000000000-571b1605dc06ed3e6a9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 10V, Negative-QTOF	splash10-0006-9780000000-4ecc537a101cb26794ef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 20V, Negative-QTOF	splash10-06rf-9400000000-2af5e73dc848ea893952	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthyl ethylene glycol carbonate 40V, Negative-QTOF	splash10-052f-9000000000-42d116b76bed8a6826c2	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB014992

KNApSAcK ID

Not Available

Chemspider ID

8013448

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9837728

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1586261

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.. .
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Showing metabocard for Menthyl ethylene glycol carbonate (HMDB0036141)

MOL for HMDB0036141 (Menthyl ethylene glycol carbonate)

3D MOL for HMDB0036141 (Menthyl ethylene glycol carbonate)

3D SDF for HMDB0036141 (Menthyl ethylene glycol carbonate)

3D-SDF for HMDB0036141 (Menthyl ethylene glycol carbonate)

PDB for HMDB0036141 (Menthyl ethylene glycol carbonate)

3D PDB for HMDB0036141 (Menthyl ethylene glycol carbonate)

SMILES for HMDB0036141 (Menthyl ethylene glycol carbonate)

INCHI for HMDB0036141 (Menthyl ethylene glycol carbonate)

Structure for HMDB0036141 (Menthyl ethylene glycol carbonate)

3D Structure for HMDB0036141 (Menthyl ethylene glycol carbonate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra