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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:05:32 UTC

Update Date

2022-03-07 02:55:31 UTC

HMDB ID

HMDB0037834

Secondary Accession Numbers

HMDB37834

Metabolite Identification

Common Name

Ethyl menthane carboxamide

Description

Ethyl menthane carboxamide 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 Ethyl menthane carboxamide.

Structure

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

HMDB0037834
     RDKit          3D
Ethyl menthane carboxamide
 40 40  0  0  0  0  0  0  0  0999 V2000
    4.2350   -0.9744    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109    0.2056    1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2437   -0.1810    0.6110 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137    0.7563    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5286    1.9814    0.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001    0.3938   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6799    1.6100   -1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029    2.0429   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5357    3.5079    0.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6507    1.2648    1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7756   -0.1852    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442   -0.6668    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2299   -1.6965   -0.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372   -2.3408   -1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -2.7209   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158   -1.9452    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4526   -0.8981    2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1882   -1.0293    1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783    0.8897    0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    0.7791    2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886   -1.2051    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712   -0.0557   -1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0455    2.4494   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    1.5141   -1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7372    1.9371   -0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086    3.6560    1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683    3.9430   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    4.1186    0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591    1.5454    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758    1.5092    1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -0.3227    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -0.7512    1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -1.2498    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643   -1.1199   -1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -1.7878   -2.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5372   -3.3316   -2.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385   -2.5379   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9352   -3.6918   -0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6883   -2.9233    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1404   -2.4893   -0.2117 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 12  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
M  END


  Mrv0541 02241217382D          

 15 15  0  0  0  0            999 V2000
   -0.7131   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007    0.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    1.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284    0.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4283   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4283    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 13  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
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037834

> <DATABASE_NAME>
hmdb

> <SMILES>
CCNC(=O)C1CC(C)CCC1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H25NO/c1-5-14-13(15)12-8-10(4)6-7-11(12)9(2)3/h9-12H,5-8H2,1-4H3,(H,14,15)

> <INCHI_KEY>
VUNOFAIHSALQQH-UHFFFAOYSA-N

> <FORMULA>
C13H25NO

> <MOLECULAR_WEIGHT>
211.3437

> <EXACT_MASS>
211.193614427

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.115429721210816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-ethyl-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxamide

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
2.9693238639999997

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.453944065604716

> <JCHEM_PKA_STRONGEST_BASIC>
1.234485132756193

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
63.5602

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl menthane carboxamide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037834
     RDKit          3D
Ethyl menthane carboxamide
 40 40  0  0  0  0  0  0  0  0999 V2000
    4.2350   -0.9744    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109    0.2056    1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2437   -0.1810    0.6110 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137    0.7563    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5286    1.9814    0.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001    0.3938   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6799    1.6100   -1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029    2.0429   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5357    3.5079    0.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6507    1.2648    1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7756   -0.1852    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442   -0.6668    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2299   -1.6965   -0.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372   -2.3408   -1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -2.7209   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158   -1.9452    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4526   -0.8981    2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1882   -1.0293    1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783    0.8897    0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    0.7791    2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886   -1.2051    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712   -0.0557   -1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0455    2.4494   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    1.5141   -1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7372    1.9371   -0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086    3.6560    1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683    3.9430   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    4.1186    0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591    1.5454    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758    1.5092    1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -0.3227    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -0.7512    1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -1.2498    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643   -1.1199   -1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -1.7878   -2.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5372   -3.3316   -2.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385   -2.5379   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9352   -3.6918   -0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6883   -2.9233    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1404   -2.4893   -0.2117 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 12  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  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  C   UNK     0      -1.331  -0.384   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.331  -1.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.001  -2.694   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.331  -1.924   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.331  -0.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.001   0.384   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.001   1.924   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.331   2.694   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       1.331   2.694   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.666   0.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.666   1.924   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.666  -2.694   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.666   1.924   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   2.694   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   14                                                       
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2                                                            
CONECT   14    8   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0037834
HETATM    1  C1  UNL     1       4.235  -0.974   1.759  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.411   0.206   1.367  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.244  -0.181   0.611  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.314   0.756   0.130  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.529   1.981   0.382  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.100   0.394  -0.652  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.680   1.610  -1.009  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.703   2.043  -0.011  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.536   3.508   0.356  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.651   1.265   1.280  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.776  -0.185   0.925  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.644  -0.667   0.089  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.230  -1.697  -0.891  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.137  -2.341  -1.674  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.050  -2.721  -0.182  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.716  -1.945   1.586  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.453  -0.898   2.855  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.188  -1.029   1.196  1.00  0.00           H  
HETATM   19  H4  UNL     1       4.078   0.890   0.769  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.070   0.779   2.258  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.089  -1.205   0.415  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.471  -0.056  -1.599  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.046   2.449  -1.140  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.194   1.514  -1.990  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.737   1.937  -0.401  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.309   3.656   1.424  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.668   3.943  -0.204  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.407   4.119   0.098  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.559   1.545   1.862  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.776   1.509   1.888  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.767  -0.323   0.449  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.834  -0.751   1.888  1.00  0.00           H  
HETATM   33  H18 UNL     1       0.034  -1.250   0.746  1.00  0.00           H  
HETATM   34  H19 UNL     1      -1.864  -1.120  -1.600  1.00  0.00           H  
HETATM   35  H20 UNL     1       0.108  -1.788  -2.610  1.00  0.00           H  
HETATM   36  H21 UNL     1      -0.537  -3.332  -2.035  1.00  0.00           H  
HETATM   37  H22 UNL     1       0.739  -2.538  -1.050  1.00  0.00           H  
HETATM   38  H23 UNL     1      -1.935  -3.692  -0.740  1.00  0.00           H  
HETATM   39  H24 UNL     1      -1.688  -2.923   0.843  1.00  0.00           H  
HETATM   40  H25 UNL     1      -3.140  -2.489  -0.212  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   21
CONECT    4    5    5    6
CONECT    6    7   12   22
CONECT    7    8   23   24
CONECT    8    9   10   25
CONECT    9   26   27   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33
CONECT   13   14   15   34
CONECT   14   35   36   37
CONECT   15   38   39   40
END

HMDB0037834
     RDKit          3D
Ethyl menthane carboxamide
 40 40  0  0  0  0  0  0  0  0999 V2000
    4.2350   -0.9744    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109    0.2056    1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2437   -0.1810    0.6110 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137    0.7563    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5286    1.9814    0.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001    0.3938   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6799    1.6100   -1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029    2.0429   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5357    3.5079    0.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6507    1.2648    1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7756   -0.1852    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442   -0.6668    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2299   -1.6965   -0.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372   -2.3408   -1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -2.7209   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158   -1.9452    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4526   -0.8981    2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1882   -1.0293    1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783    0.8897    0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    0.7791    2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886   -1.2051    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712   -0.0557   -1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0455    2.4494   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    1.5141   -1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7372    1.9371   -0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086    3.6560    1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683    3.9430   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    4.1186    0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591    1.5454    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758    1.5092    1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -0.3227    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -0.7512    1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -1.2498    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643   -1.1199   -1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -1.7878   -2.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5372   -3.3316   -2.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385   -2.5379   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9352   -3.6918   -0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6883   -2.9233    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1404   -2.4893   -0.2117 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 12  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Framidice 3	HMDB
Menthol carboxamide WS-3	HMDB
N-Ethyl-2-(isopropyl)-5-methylcyclohexanecarboxamide	HMDB
N-Ethyl-2-isopropyl-5-methylcyclohexane carboxamide	HMDB
N-Ethyl-2-isopropyl-5-methylcyclohexanecarboxamide	HMDB
N-Ethyl-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide	HMDB
N-Ethyl-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide	HMDB
N-Ethyl-P-menthane-3-carboxamide	HMDB
N-Ethyl-P-methane-3-carboxamide	HMDB
N-Ethyl-5-methyl-2-(propan-2-yl)cyclohexane-1-carboximidate	Generator

Chemical Formula

C₁₃H₂₅NO

Average Molecular Weight

211.3437

Monoisotopic Molecular Weight

211.193614427

IUPAC Name

N-ethyl-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxamide

Traditional Name

ethyl menthane carboxamide

CAS Registry Number

39711-79-0

SMILES

CCNC(=O)C1CC(C)CCC1C(C)C

InChI Identifier

InChI=1S/C13H25NO/c1-5-14-13(15)12-8-10(4)6-7-11(12)9(2)3/h9-12H,5-8H2,1-4H3,(H,14,15)

InChI Key

VUNOFAIHSALQQH-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
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037834)

Source

Endogenous

Endogenous (HMDB: HMDB0037834)

Animal

Animal (HMDB: HMDB0037834)

Exogenous

Food

Food (HMDB: HMDB0037834)

Exogenous (HMDB: HMDB0037834)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037834)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037834)

Lipid metabolism pathway (HMDB: HMDB0037834)

Cellular process

Cell signaling (HMDB: HMDB0037834)

Biochemical process

Lipid transport (HMDB: HMDB0037834)

Role

Biological role

Energy source (HMDB: HMDB0037834)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037834)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	91 - 93 °C	Not Available
Boiling Point	340.55 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	21.38 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.717 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.53	ALOGPS
logP	2.97	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	16.45	ChemAxon
pKa (Strongest Basic)	1.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.56 m³·mol⁻¹	ChemAxon
Polarizability	26.12 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
DarkChem	[M+H]+	150.725	31661259
DarkChem	[M-H]-	147.311	31661259
DeepCCS	[M+H]+	157.061	30932474
DeepCCS	[M-H]-	154.703	30932474
DeepCCS	[M-2H]-	189.412	30932474
DeepCCS	[M+Na]+	164.072	30932474
AllCCS	[M+H]+	150.0	32859911
AllCCS	[M+H-H2O]+	146.2	32859911
AllCCS	[M+NH4]+	153.5	32859911
AllCCS	[M+Na]+	154.5	32859911
AllCCS	[M-H]-	156.6	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	158.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.97 minutes	32390414
Predicted by Siyang on May 30, 2022	16.6166 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.89 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2326.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	506.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	252.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	685.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	783.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1265.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	502.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1513.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	323.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	395.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl menthane carboxamide	CCNC(=O)C1CC(C)CCC1C(C)C	2091.8	Standard polar	33892256
Ethyl menthane carboxamide	CCNC(=O)C1CC(C)CCC1C(C)C	1635.2	Standard non polar	33892256
Ethyl menthane carboxamide	CCNC(=O)C1CC(C)CCC1C(C)C	1626.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl menthane carboxamide,1TMS,isomer #1	CCN(C(=O)C1CC(C)CCC1C(C)C)[Si](C)(C)C	1631.8	Semi standard non polar	33892256
Ethyl menthane carboxamide,1TMS,isomer #1	CCN(C(=O)C1CC(C)CCC1C(C)C)[Si](C)(C)C	1659.9	Standard non polar	33892256
Ethyl menthane carboxamide,1TBDMS,isomer #1	CCN(C(=O)C1CC(C)CCC1C(C)C)[Si](C)(C)C(C)(C)C	1887.3	Semi standard non polar	33892256
Ethyl menthane carboxamide,1TBDMS,isomer #1	CCN(C(=O)C1CC(C)CCC1C(C)C)[Si](C)(C)C(C)(C)C	1887.0	Standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

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

FDB016984

KNApSAcK ID

Not Available

Chemspider ID

56632

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62907

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036281

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 Ethyl menthane carboxamide (HMDB0037834)

MOL for HMDB0037834 (Ethyl menthane carboxamide)

3D MOL for HMDB0037834 (Ethyl menthane carboxamide)

3D SDF for HMDB0037834 (Ethyl menthane carboxamide)

3D-SDF for HMDB0037834 (Ethyl menthane carboxamide)

PDB for HMDB0037834 (Ethyl menthane carboxamide)

3D PDB for HMDB0037834 (Ethyl menthane carboxamide)

SMILES for HMDB0037834 (Ethyl menthane carboxamide)

INCHI for HMDB0037834 (Ethyl menthane carboxamide)

Structure for HMDB0037834 (Ethyl menthane carboxamide)

3D Structure for HMDB0037834 (Ethyl menthane carboxamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized