Showing metabocard for 4-oxoisophorone (MMDBc0047660)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 15:36:28 UTC
Update Date2022-09-01 01:47:34 UTC
Metabolite IDMMDBc0047660
Metabolite Identification
Common Name4-oxoisophorone
Description2,6,6-Trimethyl-2-cyclohexene-1,4-dione, also known as 4-ketoisophorone or 2-cyclohexen-1,4-dione, 2,6,6-trimethyl, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 2,6,6-Trimethyl-2-cyclohexene-1,4-dione has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make 2,6,6-trimethyl-2-cyclohexene-1,4-dione a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,6,6-Trimethyl-2-cyclohexene-1,4-dione.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f1240f9cb68>


  Mrv0541 05061311422D          

 11 11  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f1240f9cb68>

HMDB0040216
     RDKit          3D
2,6,6-Trimethyl-2-cyclohexene-1,4-dione
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.9301   -0.4705    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5844    0.1519    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    1.4412   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0978    1.9873   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1128    3.1550    0.3985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    1.1171   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313   -0.2946    0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2882   -1.2246   -1.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9613   -0.4867    1.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214   -0.6612    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -1.7315    1.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9150   -1.4299   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2517   -0.6514    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6329    0.2036   -0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2922    2.1063   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0131    1.1229   -1.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9733    1.6050   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3981   -0.6824   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5196   -2.0044   -1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683   -1.7356   -0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505   -0.9765    0.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    0.5167    1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -1.0575    1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f1240f9cb68>


  Mrv0541 05061311422D          

 11 11  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047660

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=CC(=O)CC(C)(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3

> <INCHI_KEY>
AYJXHIDNNLJQDT-UHFFFAOYSA-N

> <FORMULA>
C9H12O2

> <MOLECULAR_WEIGHT>
152.1904

> <EXACT_MASS>
152.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.325381977702385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6,6-trimethylcyclohex-2-ene-1,4-dione

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
2.1610962450000004

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.85103893019325

> <JCHEM_PKA_STRONGEST_BASIC>
-6.350677474425435

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
43.391400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6,6-trimethylcyclohex-2-ene-1,4-dione

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f1240f9cb68>

HMDB0040216
     RDKit          3D
2,6,6-Trimethyl-2-cyclohexene-1,4-dione
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.9301   -0.4705    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5844    0.1519    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    1.4412   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0978    1.9873   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1128    3.1550    0.3985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    1.1171   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313   -0.2946    0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2882   -1.2246   -1.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9613   -0.4867    1.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4214   -0.6612    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -1.7315    1.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9150   -1.4299   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2517   -0.6514    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6329    0.2036   -0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2922    2.1063   -0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0131    1.1229   -1.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9733    1.6050   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3981   -0.6824   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5196   -2.0044   -1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683   -1.7356   -0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505   -0.9765    0.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    0.5167    1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -1.0575    1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
M  END
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PDB for #<Metabolite:0x00007f1240f9cb68>

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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    6    7                                                       
CONECT    5    7    9                                                       
CONECT    6    1    4    8                                                  
CONECT    7    4    5   10                                                  
CONECT    8    6    9   11                                                  
CONECT    9    2    3    5    8                                             
CONECT   10    7                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007f1240f9cb68>

COMPND    HMDB0040216
HETATM    1  C1  UNL     1       2.930  -0.470   0.151  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.584   0.152   0.179  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.450   1.441  -0.069  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.098   1.987  -0.025  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.113   3.155   0.399  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.007   1.117  -0.497  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.931  -0.295   0.016  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.288  -1.225  -1.124  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.961  -0.487   1.129  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.421  -0.661   0.484  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.514  -1.731   1.172  1.00  0.00           O  
HETATM   12  H1  UNL     1       2.915  -1.430  -0.402  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.252  -0.651   1.204  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.633   0.204  -0.364  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.292   2.106  -0.300  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.013   1.123  -1.626  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.973   1.605  -0.206  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.398  -0.682  -2.090  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.520  -2.004  -1.286  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.268  -1.736  -0.922  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.851  -0.977   0.706  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.282   0.517   1.520  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.484  -1.057   1.953  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   10
CONECT    3    4   15
CONECT    4    5    5    6
CONECT    6    7   16   17
CONECT    7    8    9   10
CONECT    8   18   19   20
CONECT    9   21   22   23
CONECT   10   11   11
END
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SMILES for #<Metabolite:0x00007f1240f9cb68>

CC1=CC(=O)CC(C)(C)C1=O
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INCHI for #<Metabolite:0x00007f1240f9cb68>

InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3
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Synonyms
ValueSource
2,2,6-Trimethyl-2-cyclohexene-1,4-dione (cetoisophorone)HMDB
2,2,6-Trimethylcyclohex-2-en-1,4-dione (4-oxo-isophorone)HMDB
2,6,6-Trimethy-2-cyclohexene-1,4-dione (4-oxoisophorone)HMDB
2,6,6-Trimethyl-2-cyclohexen-1,4-dioneHMDB
2,6,6-Trimethylcyclohex-2-ene-1,4-dioneHMDB
2-Cyclohexen-1,4-dione, 2,6,6-trimethylHMDB
3,5,5-Trimethyl-2-cyclohexene-1,4-dioneHMDB
3,5,5-Trimethylcyclohex-2-en-1,4-dioneHMDB
3,5,5-Trimethylcyclohex-2-ene-1,4-dioneHMDB
4-KetoisophoroneHMDB
4-oxo-alpha-IsophoroneHMDB
4-OxoisophoroneHMDB
6-OxoisophoroneHMDB
FEMA 3421HMDB
Keto-isophoroneHMDB
KetoisophoroneHMDB
OxoisophoroneHMDB
OxopholoneHMDB
OxophoroneHMDB
Molecular FormulaC9H12O2
Average Mass152.1904
Monoisotopic Mass152.083729628
IUPAC Name2,6,6-trimethylcyclohex-2-ene-1,4-dione
Traditional Name2,6,6-trimethylcyclohex-2-ene-1,4-dione
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)CC(C)(C)C1=O
InChI Identifier
InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3
InChI KeyAYJXHIDNNLJQDT-UHFFFAOYSA-N