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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 17:44:27 UTC

Update Date

2021-09-26 22:47:35 UTC

HMDB ID

HMDB0242216

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(-)-Menthyl chloroformate

Description

(-)-Menthyl chloroformate belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a significant number of articles have been published on (-)-Menthyl chloroformate. This compound has been identified in human blood as reported by (PMID: 31557052 ). (-)-menthyl chloroformate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (-)-Menthyl chloroformate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0242216
     RDKit          3D
(-)-Menthyl chloroformate
 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.8520   -1.0242   -0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225   -0.4513    0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985   -1.4095    1.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870   -0.7145    1.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6463    0.2946    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093   -0.3481    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -1.5705   -0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7689    0.6209   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968    0.9003   -0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1832    2.2593   -0.3379 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5306    2.7995   -1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017    2.0346   -2.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    4.4956   -1.7333 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592    0.9251    0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5185   -0.4030   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9615   -0.9462   -0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169   -2.0623   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0506   -0.3247    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153   -2.0616    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8258   -2.0933    0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373   -0.2597    2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6002   -1.5105    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537    1.1209    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5219   -0.6031    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893   -1.7493   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9744   -1.3798   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.4961    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018    1.6229    0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320    0.5661   -1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8532    0.4020   -0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.4149   -1.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8304    1.5834    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    1.3677   -0.6365 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
  9 14  1  0
 14  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 14 32  1  0
 14 33  1  0
M  END

  Mrv1652308282119542D          

 14 14  0  0  0  0            999 V2000
    0.7145    2.0625    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    0.8250    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  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 O   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
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 Cl  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
   -0.0000   -1.6500    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242216

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H19ClO2/c1-7(2)9-5-4-8(3)6-10(9)14-11(12)13/h7-10H,4-6H2,1-3H3

> <INCHI_KEY>
KIUPCUCGVCGPPA-UHFFFAOYSA-N

> <FORMULA>
C11H19ClO2

> <MOLECULAR_WEIGHT>
218.72

> <EXACT_MASS>
218.1073576

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.803661661317562

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-2-(propan-2-yl)cyclohexyl chloroformate

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
4.112125282333333

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.9805191752725015

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
57.309799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isopropyl-5-methylcyclohexyl chloroformate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0242216
     RDKit          3D
(-)-Menthyl chloroformate
 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.8520   -1.0242   -0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225   -0.4513    0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985   -1.4095    1.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870   -0.7145    1.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6463    0.2946    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093   -0.3481    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -1.5705   -0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7689    0.6209   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968    0.9003   -0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1832    2.2593   -0.3379 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5306    2.7995   -1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017    2.0346   -2.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    4.4956   -1.7333 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592    0.9251    0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5185   -0.4030   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9615   -0.9462   -0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169   -2.0623   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0506   -0.3247    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153   -2.0616    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8258   -2.0933    0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373   -0.2597    2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6002   -1.5105    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537    1.1209    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5219   -0.6031    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893   -1.7493   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9744   -1.3798   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.4961    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018    1.6229    0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320    0.5661   -1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8532    0.4020   -0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.4149   -1.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8304    1.5834    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    1.3677   -0.6365 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
  9 14  1  0
 14  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 14 32  1  0
 14 33  1  0
M  END

HEADER    PROTEIN                                 28-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-AUG-21         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11 Cl   UNK     0      -2.667   1.540   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0242216
HETATM    1  C1  UNL     1      -2.852  -1.024  -0.792  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.222  -0.451   0.461  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.198  -1.409   1.007  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.087  -0.714   1.749  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.646   0.295   0.897  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.909  -0.348   0.417  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.725  -1.570  -0.399  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.769   0.621  -0.368  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.197   0.900  -0.164  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.183   2.259  -0.338  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.531   2.800  -1.569  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.502   2.035  -2.567  1.00  0.00           O  
HETATM   13 CL1  UNL     1       0.996   4.496  -1.733  1.00  0.00          CL  
HETATM   14  C11 UNL     1      -1.659   0.925   0.229  1.00  0.00           C  
HETATM   15  H1  UNL     1      -2.519  -0.403  -1.669  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.961  -0.946  -0.782  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.517  -2.062  -0.997  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.051  -0.325   1.216  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.715  -2.062   1.742  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.826  -2.093   0.211  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.537  -0.260   2.660  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.600  -1.511   2.116  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.954   1.121   1.598  1.00  0.00           H  
HETATM   24  H10 UNL     1       2.522  -0.603   1.333  1.00  0.00           H  
HETATM   25  H11 UNL     1       2.689  -1.749  -0.961  1.00  0.00           H  
HETATM   26  H12 UNL     1       0.974  -1.380  -1.206  1.00  0.00           H  
HETATM   27  H13 UNL     1       1.539  -2.496   0.160  1.00  0.00           H  
HETATM   28  H14 UNL     1       2.602   1.623   0.081  1.00  0.00           H  
HETATM   29  H15 UNL     1       2.532   0.566  -1.441  1.00  0.00           H  
HETATM   30  H16 UNL     1       3.853   0.402  -0.192  1.00  0.00           H  
HETATM   31  H17 UNL     1      -0.151   0.415  -1.151  1.00  0.00           H  
HETATM   32  H18 UNL     1      -1.830   1.583   1.089  1.00  0.00           H  
HETATM   33  H19 UNL     1      -2.205   1.368  -0.636  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   14   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6    9   23
CONECT    6    7    8   24
CONECT    7   25   26   27
CONECT    8   28   29   30
CONECT    9   10   14   31
CONECT   10   11
CONECT   11   12   12   13
CONECT   14   32   33
END

HMDB0242216
     RDKit          3D
(-)-Menthyl chloroformate
 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.8520   -1.0242   -0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225   -0.4513    0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985   -1.4095    1.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870   -0.7145    1.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6463    0.2946    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093   -0.3481    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -1.5705   -0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7689    0.6209   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968    0.9003   -0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1832    2.2593   -0.3379 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5306    2.7995   -1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017    2.0346   -2.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    4.4956   -1.7333 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592    0.9251    0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5185   -0.4030   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9615   -0.9462   -0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169   -2.0623   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0506   -0.3247    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153   -2.0616    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8258   -2.0933    0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373   -0.2597    2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6002   -1.5105    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537    1.1209    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5219   -0.6031    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893   -1.7493   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9744   -1.3798   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.4961    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018    1.6229    0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320    0.5661   -1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8532    0.4020   -0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.4149   -1.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8304    1.5834    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    1.3677   -0.6365 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
  9 14  1  0
 14  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 14 32  1  0
 14 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Menthyl chloroformic acid	Generator
S(-)-Menthyl chloroformate	HMDB

Chemical Formula

C₁₁H₁₉ClO₂

Average Molecular Weight

218.72

Monoisotopic Molecular Weight

218.1073576

IUPAC Name

5-methyl-2-(propan-2-yl)cyclohexyl chloroformate

Traditional Name

2-isopropyl-5-methylcyclohexyl chloroformate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H19ClO2/c1-7(2)9-5-4-8(3)6-10(9)14-11(12)13/h7-10H,4-6H2,1-3H3

InChI Key

KIUPCUCGVCGPPA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Carbonic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

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
logP	3.8	ALOGPS
logP	4.11	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	57.31 m³·mol⁻¹	ChemAxon
Polarizability	23.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	147.473	30932474
DeepCCS	[M-H]-	143.471	30932474
DeepCCS	[M-2H]-	180.693	30932474
DeepCCS	[M+Na]+	156.39	30932474
AllCCS	[M+H]+	148.1	32859911
AllCCS	[M+H-H2O]+	144.2	32859911
AllCCS	[M+NH4]+	151.7	32859911
AllCCS	[M+Na]+	152.7	32859911
AllCCS	[M-H]-	151.4	32859911
AllCCS	[M+Na-2H]-	152.4	32859911
AllCCS	[M+HCOO]-	153.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Menthyl chloroformate	CC(C)C1CCC(C)CC1OC(Cl)=O	1356.9	Standard non polar	33892256
(-)-Menthyl chloroformate	CC(C)C1CCC(C)CC1OC(Cl)=O	1357.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Menthyl chloroformate GC-MS (Non-derivatized) - 70eV, Positive	splash10-053l-9500000000-2a313072a09206890f80	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Menthyl chloroformate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Menthyl chloroformate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Menthyl chloroformate 10V, Positive-QTOF	splash10-0002-9300000000-f5456e7d322fdd614e44	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Menthyl chloroformate 20V, Positive-QTOF	splash10-00kk-9410000000-ef403aa288bff4c2659f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Menthyl chloroformate 40V, Positive-QTOF	splash10-00l7-9000000000-fa2681423565b8f4dfa2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Menthyl chloroformate 10V, Negative-QTOF	splash10-014i-0090000000-ee0e0a01f46d8115cfde	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Menthyl chloroformate 20V, Negative-QTOF	splash10-001i-9010000000-453deb1d3e76153fe8f5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Menthyl chloroformate 40V, Negative-QTOF	splash10-001i-9100000000-eb461defac11cda50bbc	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

133909

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151928

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (-)-Menthyl chloroformate (HMDB0242216)

MOL for HMDB0242216 ((-)-Menthyl chloroformate)

3D MOL for HMDB0242216 ((-)-Menthyl chloroformate)

3D SDF for HMDB0242216 ((-)-Menthyl chloroformate)

3D-SDF for HMDB0242216 ((-)-Menthyl chloroformate)

PDB for HMDB0242216 ((-)-Menthyl chloroformate)

3D PDB for HMDB0242216 ((-)-Menthyl chloroformate)

SMILES for HMDB0242216 ((-)-Menthyl chloroformate)

INCHI for HMDB0242216 ((-)-Menthyl chloroformate)

Structure for HMDB0242216 ((-)-Menthyl chloroformate)

3D Structure for HMDB0242216 ((-)-Menthyl chloroformate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra