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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

HMDB0032369

Secondary Accession Numbers

HMDB32369

Metabolite Identification

Common Name

L-Menthyl acetoacetate

Description

L-Menthyl acetoacetate 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 acetoacetate.

Structure

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

HMDB0032369
     RDKit          3D
L-Menthyl acetoacetate
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.6013    0.3859    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    0.1955    0.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    1.1417    1.0755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -1.1687    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549   -1.0657    1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111   -1.5637    2.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1673   -0.4402    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2036   -0.3162    0.4329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5906    1.0974    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583    1.9401   -0.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4857    3.3162   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.3613   -1.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5447   -0.0706   -1.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -0.9546   -0.5829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1943   -1.7863    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9994   -2.3759   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286   -1.0390    0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8228    1.4664    0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9097   -0.0371   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695   -0.1152    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193   -1.8237    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6506   -1.5389   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -0.8877    1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2602    1.1419    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653    1.5796    1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2421    2.1773   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818    3.9723    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5580    3.1805    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410    3.7621   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166    1.5740   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8381    1.9448   -2.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672   -0.4433   -2.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6694   -0.0881   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369   -1.7501   -1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078   -2.6354    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776   -3.4600   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5218   -2.1882   -2.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0111   -1.9045   -1.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1860   -1.4024    0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1669    0.0485    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -1.2298    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  4 21  1  0
  4 22  1  0
  8 23  1  1
  9 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  6
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv0541 02241221302D          

 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  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  2  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  1  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  6  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  6  0  0  0
  5 11  1  1  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  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032369

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O3/c1-9(2)12-6-5-10(3)7-13(12)17-14(16)8-11(4)15/h9-10,12-13H,5-8H2,1-4H3/t10-,12+,13-/m0/s1

> <INCHI_KEY>
QSVQIPXQOCAWHP-UHTWSYAYSA-N

> <FORMULA>
C14H24O3

> <MOLECULAR_WEIGHT>
240.3386

> <EXACT_MASS>
240.172544634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.472652124880206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.3272525259999997

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.639853098296628

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9665744330466355

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
66.492

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032369
     RDKit          3D
L-Menthyl acetoacetate
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.6013    0.3859    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    0.1955    0.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    1.1417    1.0755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -1.1687    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549   -1.0657    1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111   -1.5637    2.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1673   -0.4402    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2036   -0.3162    0.4329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5906    1.0974    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583    1.9401   -0.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4857    3.3162   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.3613   -1.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5447   -0.0706   -1.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -0.9546   -0.5829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1943   -1.7863    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9994   -2.3759   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286   -1.0390    0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8228    1.4664    0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9097   -0.0371   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695   -0.1152    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193   -1.8237    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6506   -1.5389   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -0.8877    1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2602    1.1419    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653    1.5796    1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2421    2.1773   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818    3.9723    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5580    3.1805    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410    3.7621   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166    1.5740   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8381    1.9448   -2.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672   -0.4433   -2.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6694   -0.0881   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369   -1.7501   -1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078   -2.6354    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776   -3.4600   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5218   -2.1882   -2.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0111   -1.9045   -1.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1860   -1.4024    0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1669    0.0485    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -1.2298    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  4 21  1  0
  4 22  1  0
  8 23  1  1
  9 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  6
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  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    HMDB0032369
HETATM    1  C1  UNL     1       5.601   0.386   0.663  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.139   0.196   0.860  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.418   1.142   1.076  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.513  -1.169   0.799  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.055  -1.066   1.062  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.511  -1.564   2.098  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.167  -0.440   0.241  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.204  -0.316   0.433  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.591   1.097   0.822  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.158   1.940  -0.240  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.486   3.316  -0.302  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.121   1.361  -1.619  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.545  -0.071  -1.690  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.071  -0.955  -0.583  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.194  -1.786   0.020  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.999  -2.376  -1.139  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.129  -1.039   0.881  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.823   1.466   0.724  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.910  -0.037  -0.331  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.170  -0.115   1.487  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.019  -1.824   1.531  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.651  -1.539  -0.235  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.388  -0.888   1.389  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.260   1.142   1.710  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.365   1.580   1.188  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.242   2.177  -0.029  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.982   3.972   0.455  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.558   3.181   0.089  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.541   3.762  -1.296  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.117   1.574  -2.063  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.838   1.945  -2.233  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.267  -0.443  -2.705  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.669  -0.088  -1.665  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.437  -1.750  -1.087  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.708  -2.635   0.538  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.178  -3.460  -0.966  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.522  -2.188  -2.119  1.00  0.00           H  
HETATM   38  H21 UNL     1      -4.011  -1.905  -1.209  1.00  0.00           H  
HETATM   39  H22 UNL     1      -4.186  -1.402   0.745  1.00  0.00           H  
HETATM   40  H23 UNL     1      -3.167   0.049   0.756  1.00  0.00           H  
HETATM   41  H24 UNL     1      -2.891  -1.230   1.947  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    4
CONECT    4    5   21   22
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   14   23
CONECT    9   10   24   25
CONECT   10   11   12   26
CONECT   11   27   28   29
CONECT   12   13   30   31
CONECT   13   14   32   33
CONECT   14   15   34
CONECT   15   16   17   35
CONECT   16   36   37   38
CONECT   17   39   40   41
END

HMDB0032369
     RDKit          3D
L-Menthyl acetoacetate
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.6013    0.3859    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    0.1955    0.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    1.1417    1.0755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -1.1687    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549   -1.0657    1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111   -1.5637    2.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1673   -0.4402    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2036   -0.3162    0.4329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5906    1.0974    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583    1.9401   -0.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4857    3.3162   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.3613   -1.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5447   -0.0706   -1.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -0.9546   -0.5829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1943   -1.7863    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9994   -2.3759   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286   -1.0390    0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8228    1.4664    0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9097   -0.0371   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695   -0.1152    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193   -1.8237    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6506   -1.5389   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -0.8877    1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2602    1.1419    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653    1.5796    1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2421    2.1773   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818    3.9723    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5580    3.1805    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410    3.7621   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166    1.5740   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8381    1.9448   -2.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672   -0.4433   -2.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6694   -0.0881   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369   -1.7501   -1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078   -2.6354    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776   -3.4600   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5218   -2.1882   -2.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0111   -1.9045   -1.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1860   -1.4024    0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1669    0.0485    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -1.2298    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  4 21  1  0
  4 22  1  0
  8 23  1  1
  9 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  6
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
L-Menthyl acetoacetic acid	Generator
Menthol acetoacetate	HMDB
Menthyl acetoacetate	HMDB
(1S,2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-oxobutanoic acid	Generator

Chemical Formula

C₁₄H₂₄O₃

Average Molecular Weight

240.3386

Monoisotopic Molecular Weight

240.172544634

IUPAC Name

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

Traditional Name

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

CAS Registry Number

59557-05-0

SMILES

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

InChI Identifier

InChI=1S/C14H24O3/c1-9(2)12-6-5-10(3)7-13(12)17-14(16)8-11(4)15/h9-10,12-13H,5-8H2,1-4H3/t10-,12+,13-/m0/s1

InChI Key

QSVQIPXQOCAWHP-UHTWSYAYSA-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-keto acid
Fatty acid ester
Keto acid
Fatty acyl
1,3-dicarbonyl compound
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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	0.039 g/L	ALOGPS
logP	3.18	ALOGPS
logP	3.33	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.64	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.49 m³·mol⁻¹	ChemAxon
Polarizability	27.47 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]+	158.244	31661259
DarkChem	[M-H]-	156.094	31661259
DeepCCS	[M+H]+	161.207	30932474
DeepCCS	[M-H]-	158.812	30932474
DeepCCS	[M-2H]-	191.695	30932474
DeepCCS	[M+Na]+	167.161	30932474
AllCCS	[M+H]+	158.3	32859911
AllCCS	[M+H-H2O]+	154.8	32859911
AllCCS	[M+NH4]+	161.6	32859911
AllCCS	[M+Na]+	162.5	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	162.8	32859911
AllCCS	[M+HCOO]-	163.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Menthyl acetoacetate	CC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(=O)CC(C)=O	2030.4	Standard polar	33892256
L-Menthyl acetoacetate	CC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(=O)CC(C)=O	1514.5	Standard non polar	33892256
L-Menthyl acetoacetate	CC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(=O)CC(C)=O	1609.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Menthyl acetoacetate,1TMS,isomer #1	CC(=CC(=O)O[C@H]1C[C@@H](C)CC[C@@H]1C(C)C)O[Si](C)(C)C	1757.4	Semi standard non polar	33892256
L-Menthyl acetoacetate,1TMS,isomer #1	CC(=CC(=O)O[C@H]1C[C@@H](C)CC[C@@H]1C(C)C)O[Si](C)(C)C	1796.6	Standard non polar	33892256
L-Menthyl acetoacetate,1TMS,isomer #2	C=C(CC(=O)O[C@H]1C[C@@H](C)CC[C@@H]1C(C)C)O[Si](C)(C)C	1717.1	Semi standard non polar	33892256
L-Menthyl acetoacetate,1TMS,isomer #2	C=C(CC(=O)O[C@H]1C[C@@H](C)CC[C@@H]1C(C)C)O[Si](C)(C)C	1782.7	Standard non polar	33892256
L-Menthyl acetoacetate,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	1964.6	Semi standard non polar	33892256
L-Menthyl acetoacetate,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	2012.3	Standard non polar	33892256
L-Menthyl acetoacetate,1TBDMS,isomer #2	C=C(CC(=O)O[C@H]1C[C@@H](C)CC[C@@H]1C(C)C)O[Si](C)(C)C(C)(C)C	1915.7	Semi standard non polar	33892256
L-Menthyl acetoacetate,1TBDMS,isomer #2	C=C(CC(=O)O[C@H]1C[C@@H](C)CC[C@@H]1C(C)C)O[Si](C)(C)C(C)(C)C	1979.9	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 acetoacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9310000000-c033ed706e3b31dcb9a8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Menthyl acetoacetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Menthyl acetoacetate 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 acetoacetate 10V, Positive-QTOF	splash10-0076-3590000000-731d60e9f89574e82297	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 20V, Positive-QTOF	splash10-052r-9710000000-c6d1e5ac6852973edb0a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 40V, Positive-QTOF	splash10-066r-9200000000-bc771999857dd0324d94	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 10V, Negative-QTOF	splash10-052r-3690000000-9451a6e145fa7963eba3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 20V, Negative-QTOF	splash10-0a4i-5920000000-8c56f22d4e9a56081eb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 40V, Negative-QTOF	splash10-0a4r-6900000000-4ddad90a98abcf7ceab6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 10V, Positive-QTOF	splash10-0002-9300000000-843cbdbb4307acf9cc70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 20V, Positive-QTOF	splash10-000g-9200000000-a48a077d7b2f75d0c82c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 40V, Positive-QTOF	splash10-0006-9000000000-2ea1affc30a4c164c26c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 10V, Negative-QTOF	splash10-052r-4890000000-c2b7721d83f54a29eed2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 20V, Negative-QTOF	splash10-0pc0-9500000000-e80ade8fc5fb25db2d7f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Menthyl acetoacetate 40V, Negative-QTOF	splash10-0a4i-9400000000-65a4f2f5b20a8b166818	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

FDB009783

KNApSAcK ID

Not Available

Chemspider ID

39229

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

43045

PDB ID

Not Available

ChEBI ID

168575

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 acetoacetate (HMDB0032369)

MOL for HMDB0032369 (L-Menthyl acetoacetate)

3D MOL for HMDB0032369 (L-Menthyl acetoacetate)

3D SDF for HMDB0032369 (L-Menthyl acetoacetate)

3D-SDF for HMDB0032369 (L-Menthyl acetoacetate)

PDB for HMDB0032369 (L-Menthyl acetoacetate)

3D PDB for HMDB0032369 (L-Menthyl acetoacetate)

SMILES for HMDB0032369 (L-Menthyl acetoacetate)

INCHI for HMDB0032369 (L-Menthyl acetoacetate)

Structure for HMDB0032369 (L-Menthyl acetoacetate)

3D Structure for HMDB0032369 (L-Menthyl acetoacetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra