Showing metabocard for Menthone (MMDBc0033677)

Plant
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:58:33 UTC
Update Date2022-08-31 22:37:40 UTC
Metabolite IDMMDBc0033677
Metabolite Identification
Common NameMenthone
Description(-)-Menthone, also known as (1R,4S)-menthone or L-menthone, 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. (-)-Menthone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (-)-menthone is considered to be an isoprenoid lipid molecule.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f1240ee8c80>


  Mrv1652309042000382D          

 11 11  0  0  0  0            999 V2000
   -1.8973    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118   -0.4126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8973   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1828   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1828    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4683    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8973    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3262   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4683    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2461    0.4125    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  3  9  1  1  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  1  8  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f1240ee8c80>

HMDB0035162
     RDKit          3D
(-)-Menthone
 29 29  0  0  0  0  0  0  0  0999 V2000
    2.7838    1.4693    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172    0.2608   -0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5547   -1.0175    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197    0.4253   -0.5608 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0379    0.5983    0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.8090    0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0497   -0.5325    0.2932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5262   -0.3086   -0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3826   -1.2442   -0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872   -0.6640   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368   -1.1512   -2.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628    1.6827   -0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1410    2.3535   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428    1.3564    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4428    0.2208   -1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5587   -1.2786   -0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451   -1.8101   -0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476   -0.9244    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4166    1.3834   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829    1.4106    1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -0.3642    1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083    1.4544   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441    1.2997    1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759   -1.1370    1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9996    0.3231    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976    0.2250   -1.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0281   -1.2803   -0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477   -2.3176   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -1.2422   -1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
M  END
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3D SDF for #<Metabolite:0x00007f1240ee8c80>


  Mrv1652309042000382D          

 11 11  0  0  0  0            999 V2000
   -1.8973    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118   -0.4126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8973   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1828   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1828    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4683    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8973    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3262   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4683    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2461    0.4125    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  3  9  1  1  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  1  8  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033677

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)[C@@H]1CC[C@@H](C)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1

> <INCHI_KEY>
NFLGAXVYCFJBMK-BDAKNGLRSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.024394221277838

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
3.0497874006666668

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.420780675838815

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
46.5201

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-menthone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f1240ee8c80>

HMDB0035162
     RDKit          3D
(-)-Menthone
 29 29  0  0  0  0  0  0  0  0999 V2000
    2.7838    1.4693    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172    0.2608   -0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5547   -1.0175    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197    0.4253   -0.5608 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0379    0.5983    0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.8090    0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0497   -0.5325    0.2932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5262   -0.3086   -0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3826   -1.2442   -0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872   -0.6640   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368   -1.1512   -2.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628    1.6827   -0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1410    2.3535   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428    1.3564    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4428    0.2208   -1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5587   -1.2786   -0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451   -1.8101   -0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476   -0.9244    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4166    1.3834   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829    1.4106    1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -0.3642    1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083    1.4544   -0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441    1.2997    1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759   -1.1370    1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9996    0.3231    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976    0.2250   -1.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0281   -1.2803   -0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477   -2.3176   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -1.2422   -1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
M  END
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PDB for #<Metabolite:0x00007f1240ee8c80>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -3.542   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.875   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.875  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.542  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.208  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.208   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.874   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.542   3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.209  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.874   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.459   0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6   10   11                                                  
CONECT    8    1                                                            
CONECT    9    3                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007f1240ee8c80>

COMPND    HMDB0035162
HETATM    1  C1  UNL     1       2.784   1.469   0.061  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.117   0.261  -0.551  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.555  -1.017   0.100  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.620   0.425  -0.561  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.038   0.598   0.820  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.464   0.809   0.585  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.050  -0.533   0.293  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.526  -0.309  -0.060  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.383  -1.244  -0.822  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.087  -0.664  -1.233  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.437  -1.151  -2.237  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.763   1.683  -0.417  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.141   2.353  -0.170  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.943   1.356   1.150  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.443   0.221  -1.611  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.559  -1.279  -0.347  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.845  -1.810  -0.210  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.648  -0.924   1.204  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.417   1.383  -1.117  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.483   1.411   1.396  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.159  -0.364   1.396  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.608   1.454  -0.311  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.944   1.300   1.425  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.076  -1.137   1.243  1.00  0.00           H  
HETATM   25  H14 UNL     1      -4.000   0.323   0.704  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.498   0.225  -1.053  1.00  0.00           H  
HETATM   27  H16 UNL     1      -4.028  -1.280  -0.213  1.00  0.00           H  
HETATM   28  H17 UNL     1      -1.248  -2.318  -0.527  1.00  0.00           H  
HETATM   29  H18 UNL     1      -2.038  -1.242  -1.731  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   10   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8    9   24
CONECT    8   25   26   27
CONECT    9   10   28   29
CONECT   10   11   11
END
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SMILES for #<Metabolite:0x00007f1240ee8c80>

CC(C)[C@@H]1CC[C@@H](C)CC1=O
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INCHI for #<Metabolite:0x00007f1240ee8c80>

InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
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Synonyms
ValueSource
(1R,4S)-MenthoneChEBI
(1R,4S)-p-Menthan-3-oneChEBI
(2S,5R)-2-Isopropyl-5-methylcyclohexanoneChEBI
(2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
(2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
L-MenthoneChEBI
p-Menthan-3-oneChEBI
(2S,5R)-MenthoneChEBI, HMDB
(-)-(1R,4S)-MenthoneHMDB
(-)-(2S,5R)-MenthoneHMDB
(-)-5-Methyl-2-(1-methylethyl)cyclohexanoneHMDB
(1R,4S)-(-)-P-Menthan-3-oneHMDB
(2S, 5R)-trans-2-Isopropyl-5-methylcyclohexanoneHMDB
(2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanoneHMDB
5-Methyl-2-(1-methylethyl)-(2S,5R)-cyclohexanoneHMDB
5-Methyl-2-(1-methylethyl)-(2S-trans)-cyclohexanoneHMDB
MenthoneMeSH, HMDB
(-)-MenthoneHMDB
(1R,4S)-p-Menth-3-oneHMDB
(2S,5R)-(-)-MenthoneHMDB
(2S,5R)-2-Isopropyl-5-methylcyclohexan-1-oneHMDB
trans-(-)-p-Menthan-3-oneHMDB
Molecular FormulaC10H18O
Average Mass154.253
Monoisotopic Mass154.1357652
IUPAC Name(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
Traditional Name(-)-menthone
CAS Registry Number89-80-5
SMILES
CC(C)[C@@H]1CC[C@@H](C)CC1=O
InChI Identifier
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
InChI KeyNFLGAXVYCFJBMK-BDAKNGLRSA-N