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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:26 UTC

Update Date

2022-03-07 02:53:20 UTC

HMDB ID

HMDB0032370

Secondary Accession Numbers

HMDB32370

Metabolite Identification

Common Name

L-Menthyl (R,S)-3-hydroxybutyrate

Description

L-Menthyl (R,S)-3-hydroxybutyrate 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 L-Menthyl (R,S)-3-hydroxybutyrate.

Structure

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

HMDB0032370
     RDKit          3D
L-Menthyl (R,S)-3-hydroxybutyrate
 43 43  0  0  0  0  0  0  0  0999 V2000
    4.3547   -1.5673   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4721   -0.1087   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6925    0.0112    0.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663    0.3597    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    0.2209    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8570   -0.1766   -1.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8616    0.5427    0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3996    0.4105    0.0868 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9654    1.8319    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844    1.8345   -0.6801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7259    3.2747   -0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754    0.9889    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    0.2178    1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3459   -0.4148    0.8925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5295   -1.8301    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -1.8780   -1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -2.6293    0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937   -1.8399   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5988   -2.1142    0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547   -1.8028   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6392    0.5198   -1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9303    0.9526    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626    1.4520    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966   -0.1334    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    0.0329   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    2.1304    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    2.4873   -0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    1.4453   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650    3.9816   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7450    3.3954   -0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221    3.6145   -1.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.6864    0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367    0.3669   -0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748   -0.5963    1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081    0.8731    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419   -0.5862    1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861   -2.3286    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -1.1057   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1892   -1.9750   -1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287   -2.8607   -1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   -3.7098    0.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3730   -2.5601   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3016   -2.4135    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
M  END

  Mrv0541 02241221462D          

 17 17  0  0  1  0            999 V2000
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  1  0  0  0
  5 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032370

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O3/c1-9(2)12-6-5-10(3)7-13(12)17-14(16)8-11(4)15/h9-13,15H,5-8H2,1-4H3/t10-,11?,12+,13-/m1/s1

> <INCHI_KEY>
XSJPRWBZLUYOOI-IBSWDFHHSA-N

> <FORMULA>
C14H26O3

> <MOLECULAR_WEIGHT>
242.3544

> <EXACT_MASS>
242.188194698

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.639436437763543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-hydroxybutanoate

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.9417382723333327

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.407216476262743

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6206835132826756

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.4172

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032370
     RDKit          3D
L-Menthyl (R,S)-3-hydroxybutyrate
 43 43  0  0  0  0  0  0  0  0999 V2000
    4.3547   -1.5673   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4721   -0.1087   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6925    0.0112    0.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663    0.3597    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    0.2209    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8570   -0.1766   -1.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8616    0.5427    0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3996    0.4105    0.0868 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9654    1.8319    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844    1.8345   -0.6801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7259    3.2747   -0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754    0.9889    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    0.2178    1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3459   -0.4148    0.8925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5295   -1.8301    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -1.8780   -1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -2.6293    0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937   -1.8399   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5988   -2.1142    0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547   -1.8028   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6392    0.5198   -1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9303    0.9526    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626    1.4520    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966   -0.1334    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    0.0329   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    2.1304    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    2.4873   -0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    1.4453   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650    3.9816   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7450    3.3954   -0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221    3.6145   -1.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.6864    0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367    0.3669   -0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748   -0.5963    1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081    0.8731    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419   -0.5862    1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861   -2.3286    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -1.1057   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1892   -1.9750   -1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287   -2.8607   -1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   -3.7098    0.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3730   -2.5601   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3016   -2.4135    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  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  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8                                                            
CONECT   11    5   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0032370
HETATM    1  C1  UNL     1       4.355  -1.567  -0.537  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.472  -0.109  -0.193  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.693   0.011   0.524  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.366   0.360   0.665  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.050   0.221   0.013  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.857  -0.177  -1.164  1.00  0.00           O  
HETATM    7  O3  UNL     1       0.862   0.543   0.706  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.400   0.410   0.087  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.965   1.832   0.054  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.284   1.834  -0.680  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.726   3.275  -0.825  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.275   0.989   0.077  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.663   0.218   1.203  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.346  -0.415   0.893  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.529  -1.830   0.343  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.064  -1.878  -1.041  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.266  -2.629   0.458  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.094  -1.840  -1.326  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.599  -2.114   0.425  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.355  -1.803  -0.870  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.639   0.520  -1.099  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.930   0.953   0.676  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.563   1.452   0.893  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.397  -0.133   1.662  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.240   0.033  -0.938  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.118   2.130   1.107  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.237   2.487  -0.480  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.079   1.445  -1.700  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.065   3.982  -0.268  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.745   3.395  -0.395  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.722   3.615  -1.883  1.00  0.00           H  
HETATM   32  H15 UNL     1      -4.020   1.686   0.521  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.837   0.367  -0.647  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.375  -0.596   1.468  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.608   0.873   2.101  1.00  0.00           H  
HETATM   36  H19 UNL     1      -0.842  -0.586   1.892  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.286  -2.329   1.015  1.00  0.00           H  
HETATM   38  H21 UNL     1      -1.725  -1.106  -1.729  1.00  0.00           H  
HETATM   39  H22 UNL     1      -3.189  -1.975  -1.026  1.00  0.00           H  
HETATM   40  H23 UNL     1      -1.729  -2.861  -1.489  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.568  -3.710   0.539  1.00  0.00           H  
HETATM   42  H25 UNL     1       0.373  -2.560  -0.436  1.00  0.00           H  
HETATM   43  H26 UNL     1       0.302  -2.414   1.388  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22
CONECT    4    5   23   24
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   14   25
CONECT    9   10   26   27
CONECT   10   11   12   28
CONECT   11   29   30   31
CONECT   12   13   32   33
CONECT   13   14   34   35
CONECT   14   15   36
CONECT   15   16   17   37
CONECT   16   38   39   40
CONECT   17   41   42   43
END

HMDB0032370
     RDKit          3D
L-Menthyl (R,S)-3-hydroxybutyrate
 43 43  0  0  0  0  0  0  0  0999 V2000
    4.3547   -1.5673   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4721   -0.1087   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6925    0.0112    0.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663    0.3597    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    0.2209    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8570   -0.1766   -1.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8616    0.5427    0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3996    0.4105    0.0868 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9654    1.8319    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844    1.8345   -0.6801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7259    3.2747   -0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754    0.9889    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    0.2178    1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3459   -0.4148    0.8925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5295   -1.8301    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -1.8780   -1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -2.6293    0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937   -1.8399   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5988   -2.1142    0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547   -1.8028   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6392    0.5198   -1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9303    0.9526    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626    1.4520    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966   -0.1334    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    0.0329   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    2.1304    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    2.4873   -0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    1.4453   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650    3.9816   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7450    3.3954   -0.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221    3.6145   -1.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.6864    0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367    0.3669   -0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748   -0.5963    1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081    0.8731    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419   -0.5862    1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861   -2.3286    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -1.1057   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1892   -1.9750   -1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287   -2.8607   -1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   -3.7098    0.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3730   -2.5601   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3016   -2.4135    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 10 28  1  6
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
L-Menthyl (R,S)-3-hydroxybutyric acid	Generator
3-(2-Carboxyethyl)-2-methylbenzothiazolium bromide	HMDB
3-(2-Carboxyethyl)-2-methylbenzothiozolium bromide	HMDB
Benzothiazolium, 3-(2-carboxyethyl)-2-methyl-, bromide	HMDB
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-hydroxybutanoic acid	Generator

Chemical Formula

C₁₄H₂₆O₃

Average Molecular Weight

242.3544

Monoisotopic Molecular Weight

242.188194698

IUPAC Name

(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-hydroxybutanoate

Traditional Name

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3-hydroxybutanoate

CAS Registry Number

108766-16-1

SMILES

CC(O)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C

InChI Identifier

InChI=1S/C14H26O3/c1-9(2)12-6-5-10(3)7-13(12)17-14(16)8-11(4)15/h9-13,15H,5-8H2,1-4H3/t10-,11?,12+,13-/m1/s1

InChI Key

XSJPRWBZLUYOOI-IBSWDFHHSA-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
Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Hydroxy acid
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032370)

Source

Endogenous

Endogenous (HMDB: HMDB0032370)

Animal

Animal (HMDB: HMDB0032370)

Exogenous

Food

Food (HMDB: HMDB0032370)

Exogenous (HMDB: HMDB0032370)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032370)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032370)

Lipid metabolism pathway (HMDB: HMDB0032370)

Cellular process

Cell signaling (HMDB: HMDB0032370)

Biochemical process

Lipid transport (HMDB: HMDB0032370)

Role

Biological role

Energy source (HMDB: HMDB0032370)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032370)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.94	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.42 m³·mol⁻¹	ChemAxon
Polarizability	28.64 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]+	156.848	31661259
DarkChem	[M-H]-	156.495	31661259
DeepCCS	[M+H]+	163.952	30932474
DeepCCS	[M-H]-	161.594	30932474
DeepCCS	[M-2H]-	195.091	30932474
DeepCCS	[M+Na]+	170.318	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	157.1	32859911
AllCCS	[M+NH4]+	163.7	32859911
AllCCS	[M+Na]+	164.6	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	164.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Menthyl (R,S)-3-hydroxybutyrate	CC(O)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C	2168.2	Standard polar	33892256
L-Menthyl (R,S)-3-hydroxybutyrate	CC(O)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C	1554.6	Standard non polar	33892256
L-Menthyl (R,S)-3-hydroxybutyrate	CC(O)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C	1642.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Menthyl (R,S)-3-hydroxybutyrate,1TMS,isomer #1	CC(CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C)O[Si](C)(C)C	1709.2	Semi standard non polar	33892256
L-Menthyl (R,S)-3-hydroxybutyrate,1TBDMS,isomer #1	CC(CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C)O[Si](C)(C)C(C)(C)C	1924.0	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 - L-Menthyl (R,S)-3-hydroxybutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-054x-9210000000-c565198613d639d1f9d7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9410000000-ad4b0e8ac0909350819a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 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 - L-Menthyl (R,S)-3-hydroxybutyrate 10V, Negative-QTOF	splash10-0006-2690000000-ceae3deb60a592b5d7d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 20V, Negative-QTOF	splash10-0a4i-4920000000-5dcfe876523ff927babd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 40V, Negative-QTOF	splash10-0a4r-4900000000-8d1c2c2faf0f8f47d27e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 10V, Negative-QTOF	splash10-0a4l-0950000000-55d04d133fec770b2d0f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 20V, Negative-QTOF	splash10-0a4r-9600000000-d6d78d008d2d7611aa01	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 40V, Negative-QTOF	splash10-0a4i-9800000000-782a881e4e8e68c24369	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 10V, Positive-QTOF	splash10-004i-2390000000-e8a0221c61a25ee63a95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 20V, Positive-QTOF	splash10-05n0-9830000000-00bf223b26463cb568d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 40V, Positive-QTOF	splash10-066r-9300000000-d8f4466e43e928b5c56d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 10V, Positive-QTOF	splash10-0002-9100000000-e5069dfeb3c456c01452	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 20V, Positive-QTOF	splash10-0002-9200000000-7268b69df44b3a6a8e68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl (R,S)-3-hydroxybutyrate 40V, Positive-QTOF	splash10-00xv-9000000000-ae9a1157fd520cb647a7	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

FDB009784

KNApSAcK ID

Not Available

Chemspider ID

8395936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10220444

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 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for L-Menthyl (R,S)-3-hydroxybutyrate (HMDB0032370)

MOL for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

3D MOL for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

3D SDF for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

3D-SDF for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

PDB for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

3D PDB for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

SMILES for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

INCHI for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

Structure for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

3D Structure for HMDB0032370 (L-Menthyl (R,S)-3-hydroxybutyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra