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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:20:56 UTC

Update Date

2023-02-21 17:25:34 UTC

HMDB ID

HMDB0037104

Secondary Accession Numbers

HMDB37104

Metabolite Identification

Common Name

(R)-8-Acetoxycarvotanacetone

Description

(R)-8-Acetoxycarvotanacetone 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 (R)-8-Acetoxycarvotanacetone.

Structure

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

HMDB0037104
     RDKit          3D
(R)-8-Acetoxycarvotanacetone
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.5524    0.3562    0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2876   -0.1670   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3974   -0.8134   -1.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    0.0362    0.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -0.5303   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    0.0891   -1.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1673   -2.0212   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530   -0.2916    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    1.1944    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    1.5459    0.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9448    0.8552    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2961    1.1579    1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -0.2548   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7399   -0.6637   -1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4861   -0.9644   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5377    0.3390    1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4164   -0.2870   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7555    1.3789   -0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    1.0116   -1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    0.4268   -2.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -0.5819   -2.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6386   -2.3528   -1.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327   -2.6048   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8388   -2.3331    0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899   -0.7435    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    1.6702   -0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2480    1.6127    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    2.3771    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666    1.8709    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9435    1.5512    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096    0.2413    1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734   -2.0074   -0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -1.0979   -1.5579 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  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 15 32  1  0
 15 33  1  0
M  END

  Mrv0541 05061309342D          

 15 15  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    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
    1.4289    0.8250    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 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
    0.7145    1.2375    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   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
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  9  2  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 14 11  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037104

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC(C)(C)C1CC=C(C)C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O3/c1-8-5-6-10(7-11(8)14)12(3,4)15-9(2)13/h5,10H,6-7H2,1-4H3

> <INCHI_KEY>
FTCAQUBXEGKQTD-UHFFFAOYSA-N

> <FORMULA>
C12H18O3

> <MOLECULAR_WEIGHT>
210.2695

> <EXACT_MASS>
210.125594442

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.179638762697998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methyl-5-oxocyclohex-3-en-1-yl)propan-2-yl acetate

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
1.948139556666666

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.051243282518566

> <JCHEM_PKA_STRONGEST_BASIC>
-4.640080954451363

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
58.3066

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-methyl-5-oxocyclohex-3-en-1-yl)propan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037104
     RDKit          3D
(R)-8-Acetoxycarvotanacetone
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.5524    0.3562    0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2876   -0.1670   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3974   -0.8134   -1.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    0.0362    0.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -0.5303   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    0.0891   -1.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1673   -2.0212   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530   -0.2916    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    1.1944    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    1.5459    0.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9448    0.8552    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2961    1.1579    1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -0.2548   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7399   -0.6637   -1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4861   -0.9644   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5377    0.3390    1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4164   -0.2870   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7555    1.3789   -0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    1.0116   -1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    0.4268   -2.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -0.5819   -2.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6386   -2.3528   -1.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327   -2.6048   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8388   -2.3331    0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899   -0.7435    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    1.6702   -0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2480    1.6127    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    2.3771    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666    1.8709    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9435    1.5512    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096    0.2413    1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734   -2.0074   -0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -1.0979   -1.5579 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  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 15 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7   10   11                                                       
CONECT    8    1    5   11                                                  
CONECT    9    2   13   15                                                  
CONECT   10    6    7   12                                                  
CONECT   11    7    8   14                                                  
CONECT   12    3    4   10   15                                             
CONECT   13    9                                                            
CONECT   14   11                                                            
CONECT   15    9   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0037104
HETATM    1  C1  UNL     1       4.552   0.356   0.156  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.288  -0.167  -0.436  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.397  -0.813  -1.508  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.046   0.036   0.148  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.920  -0.530  -0.541  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.877   0.089  -1.908  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.167  -2.021  -0.577  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.353  -0.292   0.238  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.549   1.194   0.385  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.868   1.546   0.952  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.945   0.855   0.625  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.296   1.158   1.159  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.785  -0.255  -0.306  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.740  -0.664  -1.025  1.00  0.00           O  
HETATM   15  C12 UNL     1      -1.486  -0.964  -0.456  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.538   0.339   1.251  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.416  -0.287  -0.157  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.755   1.379  -0.259  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.525   1.012  -1.952  1.00  0.00           H  
HETATM   20  H5  UNL     1      -0.129   0.427  -2.214  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.283  -0.582  -2.697  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.639  -2.353  -1.523  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.233  -2.605  -0.475  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.839  -2.333   0.263  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.190  -0.743   1.251  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.430   1.670  -0.625  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.248   1.613   1.017  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.941   2.377   1.639  1.00  0.00           H  
HETATM   29  H14 UNL     1      -4.267   1.871   1.995  1.00  0.00           H  
HETATM   30  H15 UNL     1      -4.944   1.551   0.336  1.00  0.00           H  
HETATM   31  H16 UNL     1      -4.810   0.241   1.528  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.673  -2.007  -0.065  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.318  -1.098  -1.558  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    7    8
CONECT    6   19   20   21
CONECT    7   22   23   24
CONECT    8    9   15   25
CONECT    9   10   26   27
CONECT   10   11   11   28
CONECT   11   12   13
CONECT   12   29   30   31
CONECT   13   14   14   15
CONECT   15   32   33
END

HMDB0037104
     RDKit          3D
(R)-8-Acetoxycarvotanacetone
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.5524    0.3562    0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2876   -0.1670   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3974   -0.8134   -1.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    0.0362    0.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -0.5303   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    0.0891   -1.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1673   -2.0212   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530   -0.2916    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    1.1944    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    1.5459    0.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9448    0.8552    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2961    1.1579    1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -0.2548   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7399   -0.6637   -1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4861   -0.9644   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5377    0.3390    1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4164   -0.2870   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7555    1.3789   -0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    1.0116   -1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    0.4268   -2.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -0.5819   -2.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6386   -2.3528   -1.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327   -2.6048   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8388   -2.3331    0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1899   -0.7435    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    1.6702   -0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2480    1.6127    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    2.3771    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666    1.8709    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9435    1.5512    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096    0.2413    1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734   -2.0074   -0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -1.0979   -1.5579 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  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 15 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-Methyl-5-oxocyclohex-3-en-1-yl)propan-2-yl acetic acid	Generator

Chemical Formula

C₁₂H₁₈O₃

Average Molecular Weight

210.2695

Monoisotopic Molecular Weight

210.125594442

IUPAC Name

2-(4-methyl-5-oxocyclohex-3-en-1-yl)propan-2-yl acetate

Traditional Name

2-(4-methyl-5-oxocyclohex-3-en-1-yl)propan-2-yl acetate

CAS Registry Number

56691-69-1

SMILES

CC(=O)OC(C)(C)C1CC=C(C)C(=O)C1

InChI Identifier

InChI=1S/C12H18O3/c1-8-5-6-10(7-11(8)14)12(3,4)15-9(2)13/h5,10H,6-7H2,1-4H3

InChI Key

FTCAQUBXEGKQTD-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
Cyclohexenone
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037104)

Source

Endogenous

Endogenous (HMDB: HMDB0037104)

Plant

Plant (HMDB: HMDB0037104)

Animal

Animal (HMDB: HMDB0037104)

Exogenous

Food

Food (HMDB: HMDB0037104)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0037104)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037104)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037104)

Lipid metabolism pathway (HMDB: HMDB0037104)

Cellular process

Cell signaling (HMDB: HMDB0037104)

Biochemical process

Lipid transport (HMDB: HMDB0037104)

Role

Biological role

Energy source (HMDB: HMDB0037104)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037104)

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	0.75 g/L	ALOGPS
logP	2.13	ALOGPS
logP	1.95	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	19.05	ChemAxon
pKa (Strongest Basic)	-4.6	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	3	ChemAxon
Refractivity	58.31 m³·mol⁻¹	ChemAxon
Polarizability	23.18 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]+	151.075	31661259
DarkChem	[M-H]-	147.174	31661259
DeepCCS	[M+H]+	148.956	30932474
DeepCCS	[M-H]-	146.598	30932474
DeepCCS	[M-2H]-	180.443	30932474
DeepCCS	[M+Na]+	155.237	30932474
AllCCS	[M+H]+	147.4	32859911
AllCCS	[M+H-H2O]+	143.6	32859911
AllCCS	[M+NH4]+	151.1	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	152.3	32859911
AllCCS	[M+Na-2H]-	153.2	32859911
AllCCS	[M+HCOO]-	154.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-8-Acetoxycarvotanacetone	CC(=O)OC(C)(C)C1CC=C(C)C(=O)C1	2016.6	Standard polar	33892256
(R)-8-Acetoxycarvotanacetone	CC(=O)OC(C)(C)C1CC=C(C)C(=O)C1	1492.0	Standard non polar	33892256
(R)-8-Acetoxycarvotanacetone	CC(=O)OC(C)(C)C1CC=C(C)C(=O)C1	1541.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-8-Acetoxycarvotanacetone,1TMS,isomer #1	CC(=O)OC(C)(C)C1C=C(O[Si](C)(C)C)C(C)=CC1	1647.8	Semi standard non polar	33892256
(R)-8-Acetoxycarvotanacetone,1TMS,isomer #1	CC(=O)OC(C)(C)C1C=C(O[Si](C)(C)C)C(C)=CC1	1589.4	Standard non polar	33892256
(R)-8-Acetoxycarvotanacetone,1TBDMS,isomer #1	CC(=O)OC(C)(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC1	1862.6	Semi standard non polar	33892256
(R)-8-Acetoxycarvotanacetone,1TBDMS,isomer #1	CC(=O)OC(C)(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC1	1774.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-8-Acetoxycarvotanacetone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9500000000-d8b0bc737b24e30c4eb1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-8-Acetoxycarvotanacetone 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 - (R)-8-Acetoxycarvotanacetone 10V, Positive-QTOF	splash10-03di-0960000000-19dd2d20080c10038077	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 20V, Positive-QTOF	splash10-0wmi-3910000000-26fc95bcaa36f7c8f92f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 40V, Positive-QTOF	splash10-0udi-9500000000-84e75bc541791e0ff7b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 10V, Negative-QTOF	splash10-0a4i-1790000000-2a494da57777a48a86bc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 20V, Negative-QTOF	splash10-0aor-3930000000-41d3710bae215c2e7ff8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 40V, Negative-QTOF	splash10-0pb9-5900000000-980b86d7de9209ca497f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 10V, Negative-QTOF	splash10-0002-0900000000-69cc9f06af6687026cc9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 20V, Negative-QTOF	splash10-0002-1900000000-c360b1ef3c49f855c5c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 40V, Negative-QTOF	splash10-0a4i-9300000000-bda7616f1668286d5aca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 10V, Positive-QTOF	splash10-0pb9-1900000000-711392476ab2db57b866	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 20V, Positive-QTOF	splash10-0bt9-7900000000-f6d0979ad11ecbcd9e05	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-8-Acetoxycarvotanacetone 40V, Positive-QTOF	splash10-0006-9300000000-b428a5fc3c9c24297c82	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB016094

KNApSAcK ID

Not Available

Chemspider ID

469307

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

538920

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

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 (R)-8-Acetoxycarvotanacetone (HMDB0037104)

MOL for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

3D MOL for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

3D SDF for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

3D-SDF for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

PDB for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

3D PDB for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

SMILES for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

INCHI for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

Structure for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

3D Structure for HMDB0037104 ((R)-8-Acetoxycarvotanacetone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra