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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:21:27 UTC

Update Date

2021-09-23 20:21:27 UTC

HMDB ID

HMDB0302748

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-8-Acetoxycarvone

Description

(+)-8-acetoxycarvone is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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 (+)-8-acetoxycarvone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (+)-8-acetoxycarvone can be found in cornmint, which makes (+)-8-acetoxycarvone a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302748
     RDKit          3D
(+)-8-Acetoxycarvone
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.3955    1.3313    0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    1.4759   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3028    2.6330   -1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802    0.5674    0.0051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5664   -0.5264    0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6041   -1.3260    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -2.5105    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690   -1.1680   -0.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3290   -0.0247   -1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3580   -1.0210   -0.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2852   -0.6252   -0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397   -1.5952    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2354    0.7313    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.3022    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245    1.3747    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2405    2.0506    0.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5884    0.5888    1.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3404    2.7389   -1.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9636    3.5517   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762    2.3768   -1.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725   -2.7823    1.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108   -2.2253    1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089   -3.3743    0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7560    0.7557   -1.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4710   -0.5365   -1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657   -2.0407   -1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964   -2.6115    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717   -1.3577    1.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1524   -1.6172   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    2.4000    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7319    1.4642    1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  1
  5  6  1  0
  6  7  1  0
  6  8  2  0
  4  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  4  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
M  END


  Mrv0541 02241212492D          

 15 15  0  0  0  0            999 V2000
    0.1768    0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1768   -0.9723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8913   -0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8913    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2522    0.6777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1768    1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1768   -1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8913   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -1.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2522   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9666   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2522   -0.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  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
  2  7  2  0  0  0  0
  1  8  1  0  0  0  0
  4  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302748

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)O[C@@]1(CC=C(C)C(=O)C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O3/c1-8(2)12(15-10(4)13)6-5-9(3)11(14)7-12/h5H,1,6-7H2,2-4H3/t12-/m1/s1

> <INCHI_KEY>
GEACSAQGZQDKCB-GFCCVEGCSA-N

> <FORMULA>
C12H16O3

> <MOLECULAR_WEIGHT>
208.2536

> <EXACT_MASS>
208.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.16208234408383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-4-methyl-5-oxo-1-(prop-1-en-2-yl)cyclohex-3-en-1-yl acetate

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.990262395666667

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.743550792354664

> <JCHEM_PKA_STRONGEST_BASIC>
-4.929672430392446

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
57.69910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-4-methyl-5-oxo-1-(prop-1-en-2-yl)cyclohex-3-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302748
     RDKit          3D
(+)-8-Acetoxycarvone
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.3955    1.3313    0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    1.4759   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3028    2.6330   -1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802    0.5674    0.0051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5664   -0.5264    0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6041   -1.3260    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -2.5105    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690   -1.1680   -0.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3290   -0.0247   -1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3580   -1.0210   -0.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2852   -0.6252   -0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397   -1.5952    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2354    0.7313    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.3022    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245    1.3747    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2405    2.0506    0.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5884    0.5888    1.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3404    2.7389   -1.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9636    3.5517   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762    2.3768   -1.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725   -2.7823    1.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108   -2.2253    1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089   -3.3743    0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7560    0.7557   -1.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4710   -0.5365   -1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657   -2.0407   -1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964   -2.6115    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717   -1.3577    1.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1524   -1.6172   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    2.4000    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7319    1.4642    1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  1
  5  6  1  0
  6  7  1  0
  6  8  2  0
  4  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  4  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  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       0.330   1.265   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.004   0.495   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.004  -1.045   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.330  -1.815   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.664  -1.045   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.664   0.495   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.337   1.265   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.330   2.805   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.330  -3.355   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.664  -4.125   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.004  -4.125   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.004  -2.585   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.337  -1.815   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.671  -2.585   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.337  -0.275   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9   12                                             
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    2                                                            
CONECT    8    1                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0302748
HETATM    1  C1  UNL     1      -2.396   1.331   0.606  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.323   1.476  -0.134  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.303   2.633  -1.106  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.180   0.567   0.005  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.566  -0.526   0.795  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.604  -1.326   0.370  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.043  -2.510   1.183  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.269  -1.168  -0.689  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.329  -0.025  -1.290  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.358  -1.021  -0.910  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.285  -0.625  -0.049  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.340  -1.595   0.361  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.235   0.731   0.457  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.334   1.302   0.679  1.00  0.00           O  
HETATM   15  C12 UNL     1       0.925   1.375   0.686  1.00  0.00           C  
HETATM   16  H1  UNL     1      -3.241   2.051   0.496  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.588   0.589   1.359  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.340   2.739  -1.493  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.964   3.552  -0.598  1.00  0.00           H  
HETATM   20  H5  UNL     1      -0.676   2.377  -1.987  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.272  -2.782   1.924  1.00  0.00           H  
HETATM   22  H7  UNL     1      -3.011  -2.225   1.635  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.209  -3.374   0.503  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.756   0.756  -1.957  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.471  -0.536  -1.825  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.366  -2.041  -1.314  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.896  -2.611   0.449  1.00  0.00           H  
HETATM   28  H13 UNL     1       3.772  -1.358   1.353  1.00  0.00           H  
HETATM   29  H14 UNL     1       4.152  -1.617  -0.406  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.976   2.400   0.267  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.732   1.464   1.757  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3    4
CONECT    3   18   19   20
CONECT    4    5    9   15
CONECT    5    6
CONECT    6    7    8    8
CONECT    7   21   22   23
CONECT    9   10   24   25
CONECT   10   11   11   26
CONECT   11   12   13
CONECT   12   27   28   29
CONECT   13   14   14   15
CONECT   15   30   31
END

HMDB0302748
     RDKit          3D
(+)-8-Acetoxycarvone
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.3955    1.3313    0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    1.4759   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3028    2.6330   -1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802    0.5674    0.0051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5664   -0.5264    0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6041   -1.3260    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -2.5105    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690   -1.1680   -0.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3290   -0.0247   -1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3580   -1.0210   -0.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2852   -0.6252   -0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397   -1.5952    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2354    0.7313    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.3022    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245    1.3747    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2405    2.0506    0.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5884    0.5888    1.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3404    2.7389   -1.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9636    3.5517   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762    2.3768   -1.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725   -2.7823    1.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108   -2.2253    1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089   -3.3743    0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7560    0.7557   -1.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4710   -0.5365   -1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657   -2.0407   -1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964   -2.6115    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717   -1.3577    1.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1524   -1.6172   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    2.4000    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7319    1.4642    1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  1
  5  6  1  0
  6  7  1  0
  6  8  2  0
  4  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  4  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R)-4-Methyl-5-oxo-1-(prop-1-en-2-yl)cyclohex-3-en-1-yl acetic acid	Generator

Chemical Formula

C₁₂H₁₆O₃

Average Molecular Weight

208.2536

Monoisotopic Molecular Weight

208.109944378

IUPAC Name

(1R)-4-methyl-5-oxo-1-(prop-1-en-2-yl)cyclohex-3-en-1-yl acetate

Traditional Name

(1R)-4-methyl-5-oxo-1-(prop-1-en-2-yl)cyclohex-3-en-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@]1(CC=C(C)C(=O)C1)C(C)=C

InChI Identifier

InChI=1S/C12H16O3/c1-8(2)12(15-10(4)13)6-5-9(3)11(14)7-12/h5H,1,6-7H2,2-4H3/t12-/m1/s1

InChI Key

GEACSAQGZQDKCB-GFCCVEGCSA-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

Not Available

Exogenous (HMDB: HMDB0302748)

Food

Herb and spice

Herb

Cornmint (FooDB: FOOD00111)

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	1.79	ALOGPS
logP	1.99	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	18.74	ChemAxon
pKa (Strongest Basic)	-4.9	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	57.7 m³·mol⁻¹	ChemAxon
Polarizability	22.16 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
AllCCS	[M+H]+	146.407	32859911
AllCCS	[M+H-H2O]+	142.434	32859911
AllCCS	[M+Na]+	151.168	32859911
AllCCS	[M+NH4]+	150.103	32859911
AllCCS	[M-H]-	149.463	32859911
AllCCS	[M+Na-2H]-	150.166	32859911
AllCCS	[M+HCOO]-	151.03	32859911
DeepCCS	[M+H]+	148.681	30932474
DeepCCS	[M-H]-	146.285	30932474
DeepCCS	[M-2H]-	179.475	30932474
DeepCCS	[M+Na]+	154.65	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-8-Acetoxycarvone,1TMS,isomer #1	C=C(C)[C@]1(OC(C)=O)C=C(O[Si](C)(C)C)C(C)=CC1	1589.1	Semi standard non polar	33892256
(+)-8-Acetoxycarvone,1TMS,isomer #1	C=C(C)[C@]1(OC(C)=O)C=C(O[Si](C)(C)C)C(C)=CC1	1565.8	Standard non polar	33892256
(+)-8-Acetoxycarvone,1TMS,isomer #1	C=C(C)[C@]1(OC(C)=O)C=C(O[Si](C)(C)C)C(C)=CC1	2045.9	Standard polar	33892256
(+)-8-Acetoxycarvone,1TBDMS,isomer #1	C=C(C)[C@]1(OC(C)=O)C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC1	1802.0	Semi standard non polar	33892256
(+)-8-Acetoxycarvone,1TBDMS,isomer #1	C=C(C)[C@]1(OC(C)=O)C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC1	1763.5	Standard non polar	33892256
(+)-8-Acetoxycarvone,1TBDMS,isomer #1	C=C(C)[C@]1(OC(C)=O)C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC1	2178.8	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 10V, Positive-QTOF	splash10-0a4i-0960000000-a2188afdb2ef1b1573ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 20V, Positive-QTOF	splash10-05mk-3910000000-85646a1c36b733cd95ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 40V, Positive-QTOF	splash10-0zfs-9300000000-bdd2f63a5f5aafbf1642	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 10V, Negative-QTOF	splash10-0aor-1790000000-5ce90f7e685e659ad739	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 20V, Negative-QTOF	splash10-0aor-3920000000-07a14c86e3d2cbcacf13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 40V, Negative-QTOF	splash10-0l2g-9800000000-74052fe4e1d74ae97609	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 10V, Positive-QTOF	splash10-0002-0900000000-5651220bc564f6499b53	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 20V, Positive-QTOF	splash10-0a4j-3900000000-c97a11b7f2104a3d7a56	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 40V, Positive-QTOF	splash10-052f-9600000000-f0e1e2315944ce5a0937	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 10V, Negative-QTOF	splash10-0a4j-0890000000-c084bb569d7e0bf7aa17	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 20V, Negative-QTOF	splash10-00kb-0900000000-1c3e3ffad856c0a0ecde	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-8-Acetoxycarvone 40V, Negative-QTOF	splash10-0a4i-9200000000-0878c45f7c99122c93dd	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB006040

KNApSAcK ID

Not Available

Chemspider ID

59696385

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for (+)-8-Acetoxycarvone (HMDB0302748)

MOL for HMDB0302748 ((+)-8-Acetoxycarvone)

3D MOL for HMDB0302748 ((+)-8-Acetoxycarvone)

3D SDF for HMDB0302748 ((+)-8-Acetoxycarvone)

3D-SDF for HMDB0302748 ((+)-8-Acetoxycarvone)

PDB for HMDB0302748 ((+)-8-Acetoxycarvone)

3D PDB for HMDB0302748 ((+)-8-Acetoxycarvone)

SMILES for HMDB0302748 ((+)-8-Acetoxycarvone)

INCHI for HMDB0302748 ((+)-8-Acetoxycarvone)

Structure for HMDB0302748 ((+)-8-Acetoxycarvone)

3D Structure for HMDB0302748 ((+)-8-Acetoxycarvone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra