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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:12:27 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036143

Secondary Accession Numbers

HMDB36143

Metabolite Identification

Common Name

Monomenthyl succinate

Description

Monomenthyl succinate 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 Monomenthyl succinate.

Structure

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

HMDB0036143
     RDKit          3D
Monomenthyl succinate
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.4346    3.5410   -0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971    2.1734    0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1155    1.1592    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6490   -0.0688    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3692   -0.6337    0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6631   -1.4881   -0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985   -2.5923   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4654   -2.1243   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3274    0.4192    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781   -0.0366   -0.3116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615    0.0179    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865    0.5049    1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2354   -0.4866   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728   -0.2799    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -0.7610   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5710   -1.2509   -1.6167 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8963   -0.6634    0.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    1.6147   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519    3.8642    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507    3.5581   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5891    4.2326    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6560    2.2525    1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0042    1.5461    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3359    0.9594   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4633   -0.8193    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5977    0.2085    2.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9644   -1.3114    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860   -0.9039   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6574   -2.3225   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274   -2.8532    0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3705   -3.5217   -0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7989   -3.0717   -1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099   -1.5183   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014   -2.4400   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437    0.8247    1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3824    0.1230   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1236   -1.5670   -0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3801   -0.8599    1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389    0.8027    0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2918    0.1801    0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329    2.3229   -0.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    1.2696   -1.3774 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  2  0
 15 17  1  0
  9 18  1  0
 18  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
M  END


  Mrv0541 05061308542D          

 18 18  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    0.7145    1.2375    0.0000 C   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
    5.0013    1.2375    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
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 12  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036143

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O4/c1-9(2)11-5-4-10(3)8-12(11)18-14(17)7-6-13(15)16/h9-12H,4-8H2,1-3H3,(H,15,16)

> <INCHI_KEY>
BLILOGGUTRWFNI-UHFFFAOYSA-N

> <FORMULA>
C14H24O4

> <MOLECULAR_WEIGHT>
256.338

> <EXACT_MASS>
256.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.742546530716446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-4-oxobutanoic acid

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
2.9302613043333334

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.69402610927732

> <JCHEM_PKA_STRONGEST_BASIC>
-7.047917467713002

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
67.49010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2-isopropyl-5-methylcyclohexyl)oxy]-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036143
     RDKit          3D
Monomenthyl succinate
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.4346    3.5410   -0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971    2.1734    0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1155    1.1592    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6490   -0.0688    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3692   -0.6337    0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6631   -1.4881   -0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985   -2.5923   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4654   -2.1243   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3274    0.4192    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781   -0.0366   -0.3116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615    0.0179    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865    0.5049    1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2354   -0.4866   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728   -0.2799    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -0.7610   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5710   -1.2509   -1.6167 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8963   -0.6634    0.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    1.6147   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519    3.8642    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507    3.5581   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5891    4.2326    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6560    2.2525    1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0042    1.5461    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3359    0.9594   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4633   -0.8193    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5977    0.2085    2.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9644   -1.3114    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860   -0.9039   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6574   -2.3225   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274   -2.8532    0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3705   -3.5217   -0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7989   -3.0717   -1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099   -1.5183   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014   -2.4400   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437    0.8247    1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3824    0.1230   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1236   -1.5670   -0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3801   -0.8599    1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389    0.8027    0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2918    0.1801    0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329    2.3229   -0.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    1.2696   -1.3774 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  2  0
 15 17  1  0
  9 18  1  0
 18  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 18 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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   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   11                                                       
CONECT    6    7   13                                                       
CONECT    7    6   14                                                       
CONECT    8   10   12                                                       
CONECT    9    1    2   11                                                  
CONECT   10    3    4    8                                                  
CONECT   11    5    9   12                                                  
CONECT   12    8   11   18                                                  
CONECT   13    6   15   16                                                  
CONECT   14    7   17   18                                                  
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0036143
HETATM    1  C1  UNL     1      -2.435   3.541  -0.002  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.997   2.173   0.463  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.116   1.159   0.411  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.649  -0.069   1.144  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.369  -0.634   0.634  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.663  -1.488  -0.563  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.598  -2.592  -0.111  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.465  -2.124  -1.182  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.327   0.419   0.390  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.778  -0.037  -0.312  1.00  0.00           O  
HETATM   11  C10 UNL     1       2.061   0.018   0.204  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.187   0.505   1.353  1.00  0.00           O  
HETATM   13  C11 UNL     1       3.235  -0.487  -0.587  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.473  -0.280   0.262  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.659  -0.761  -0.473  1.00  0.00           C  
HETATM   16  O3  UNL     1       5.571  -1.251  -1.617  1.00  0.00           O  
HETATM   17  O4  UNL     1       6.896  -0.663   0.128  1.00  0.00           O  
HETATM   18  C14 UNL     1      -0.878   1.615  -0.375  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.252   3.864   0.686  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.751   3.558  -1.055  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.589   4.233   0.197  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.656   2.253   1.505  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.004   1.546   0.909  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.336   0.959  -0.655  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.463  -0.819   1.073  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.598   0.209   2.228  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.964  -1.311   1.426  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.186  -0.904  -1.368  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.657  -2.322  -0.291  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.427  -2.853   0.972  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.371  -3.522  -0.673  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.799  -3.072  -1.661  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.010  -1.518  -1.993  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.301  -2.440  -0.424  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.044   0.825   1.401  1.00  0.00           H  
HETATM   36  H18 UNL     1       3.382   0.123  -1.511  1.00  0.00           H  
HETATM   37  H19 UNL     1       3.124  -1.567  -0.821  1.00  0.00           H  
HETATM   38  H20 UNL     1       4.380  -0.860   1.213  1.00  0.00           H  
HETATM   39  H21 UNL     1       4.539   0.803   0.473  1.00  0.00           H  
HETATM   40  H22 UNL     1       7.292   0.180   0.479  1.00  0.00           H  
HETATM   41  H23 UNL     1      -0.033   2.323  -0.503  1.00  0.00           H  
HETATM   42  H24 UNL     1      -1.241   1.270  -1.377  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   18   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6    9   27
CONECT    6    7    8   28
CONECT    7   29   30   31
CONECT    8   32   33   34
CONECT    9   10   18   35
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   16   17
CONECT   17   40
CONECT   18   41   42
END

HMDB0036143
     RDKit          3D
Monomenthyl succinate
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.4346    3.5410   -0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971    2.1734    0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1155    1.1592    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6490   -0.0688    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3692   -0.6337    0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6631   -1.4881   -0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985   -2.5923   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4654   -2.1243   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3274    0.4192    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781   -0.0366   -0.3116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615    0.0179    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865    0.5049    1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2354   -0.4866   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728   -0.2799    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -0.7610   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5710   -1.2509   -1.6167 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8963   -0.6634    0.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    1.6147   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519    3.8642    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507    3.5581   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5891    4.2326    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6560    2.2525    1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0042    1.5461    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3359    0.9594   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4633   -0.8193    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5977    0.2085    2.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9644   -1.3114    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860   -0.9039   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6574   -2.3225   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274   -2.8532    0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3705   -3.5217   -0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7989   -3.0717   -1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099   -1.5183   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014   -2.4400   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437    0.8247    1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3824    0.1230   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1236   -1.5670   -0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3801   -0.8599    1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389    0.8027    0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2918    0.1801    0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329    2.3229   -0.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    1.2696   -1.3774 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  2  0
 15 17  1  0
  9 18  1  0
 18  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Monomenthyl succinic acid	Generator
FEMA 3810	HMDB
mono[5-Methyl-2-(1-methylethyl)cyclohexyl] butanedioate, 9ci	HMDB
4-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-4-oxobutanoate	Generator
Monomenthyl succinate	MeSH

Chemical Formula

C₁₄H₂₄O₄

Average Molecular Weight

256.338

Monoisotopic Molecular Weight

256.167459256

IUPAC Name

4-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-4-oxobutanoic acid

Traditional Name

4-[(2-isopropyl-5-methylcyclohexyl)oxy]-4-oxobutanoic acid

CAS Registry Number

188709-97-9

SMILES

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

InChI Identifier

InChI=1S/C14H24O4/c1-9(2)11-5-4-10(3)8-12(11)18-14(17)7-6-13(15)16/h9-12H,4-8H2,1-3H3,(H,15,16)

InChI Key

BLILOGGUTRWFNI-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
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036143)
Cell membrane (HMDB: HMDB0036143)

Cellular substructure

Extracellular (HMDB: HMDB0036143)
Membrane (HMDB: HMDB0036143)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036143)

Source

Endogenous

Endogenous (HMDB: HMDB0036143)

Animal

Animal (HMDB: HMDB0036143)

Exogenous

Food

Food (HMDB: HMDB0036143)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036143)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036143)

Cellular process

Cell signaling (HMDB: HMDB0036143)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036143)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036143)

Nutrient

Nutrient (HMDB: HMDB0036143)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036143)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0036143)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	61.5 - 62.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.096 g/L	ALOGPS
logP	2.97	ALOGPS
logP	2.93	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.69	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	67.49 m³·mol⁻¹	ChemAxon
Polarizability	28.74 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]+	161.856	31661259
DarkChem	[M-H]-	160.023	31661259
DeepCCS	[M+H]+	157.426	30932474
DeepCCS	[M-H]-	155.068	30932474
DeepCCS	[M-2H]-	189.868	30932474
DeepCCS	[M+Na]+	165.158	30932474
AllCCS	[M+H]+	162.7	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	165.8	32859911
AllCCS	[M+Na]+	166.7	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	165.0	32859911
AllCCS	[M+HCOO]-	165.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Monomenthyl succinate	CC(C)C1CCC(C)CC1OC(=O)CCC(O)=O	2972.8	Standard polar	33892256
Monomenthyl succinate	CC(C)C1CCC(C)CC1OC(=O)CCC(O)=O	1728.5	Standard non polar	33892256
Monomenthyl succinate	CC(C)C1CCC(C)CC1OC(=O)CCC(O)=O	1848.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Monomenthyl succinate,1TMS,isomer #1	CC1CCC(C(C)C)C(OC(=O)CCC(=O)O[Si](C)(C)C)C1	1874.8	Semi standard non polar	33892256
Monomenthyl succinate,1TBDMS,isomer #1	CC1CCC(C(C)C)C(OC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)C1	2112.5	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 - Monomenthyl succinate GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9210000000-46c47fcb57e2288b029c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monomenthyl succinate GC-MS (1 TMS) - 70eV, Positive	splash10-059m-9611000000-763ecfaa8ee0bcaff053	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monomenthyl succinate 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 - Monomenthyl succinate 10V, Positive-QTOF	splash10-0a4r-1690000000-3e25d500426c245aea39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 20V, Positive-QTOF	splash10-0a4r-6920000000-6bc3f00bbdc53e580440	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 40V, Positive-QTOF	splash10-0aor-9300000000-871d873ec478d17a20ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 10V, Negative-QTOF	splash10-0a4i-1590000000-f2336c7fbb0bdbf910aa	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 20V, Negative-QTOF	splash10-0a4i-3940000000-c57bae8ce454542ea05e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 40V, Negative-QTOF	splash10-0a4r-5900000000-98ca44dfc90cb4c6e805	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 10V, Negative-QTOF	splash10-0a4i-4790000000-1e9136d02f28ddf96123	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 20V, Negative-QTOF	splash10-0a4i-7900000000-abe5adadd4b760b8192f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 40V, Negative-QTOF	splash10-0a4i-9100000000-49f13b699bcf37d022d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 10V, Positive-QTOF	splash10-000b-9800000000-d0704ed01116f704a1a2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 20V, Positive-QTOF	splash10-008j-9400000000-b53c886a6186338e10c4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monomenthyl succinate 40V, Positive-QTOF	splash10-0ac3-9000000000-3823b28c90e93e61a984	2021-09-23	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

FDB014994

KNApSAcK ID

C00057181

Chemspider ID

8374504

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10199004

PDB ID

Not Available

ChEBI ID

169181

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Monomenthyl succinate (HMDB0036143)

MOL for HMDB0036143 (Monomenthyl succinate)

3D MOL for HMDB0036143 (Monomenthyl succinate)

3D SDF for HMDB0036143 (Monomenthyl succinate)

3D-SDF for HMDB0036143 (Monomenthyl succinate)

PDB for HMDB0036143 (Monomenthyl succinate)

3D PDB for HMDB0036143 (Monomenthyl succinate)

SMILES for HMDB0036143 (Monomenthyl succinate)

INCHI for HMDB0036143 (Monomenthyl succinate)

Structure for HMDB0036143 (Monomenthyl succinate)

3D Structure for HMDB0036143 (Monomenthyl succinate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra