Showing metabocard for cyclohexanone (MMDBc0054414)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:11:22 UTC
Update Date2024-09-27 17:10:58 UTC
Metabolite IDMMDBc0054414
Metabolite Identification
Common Namecyclohexanone
DescriptionCyclohexanone is a colorless oily liquid with an odor resembling acetone and peppermint. Cyclohexanone is occasionally found as a volatile component of human urine. Biological fluids such as blood and urine have been shown to contain a large number of components, some of them volatiles (low boiling point) apparently present in all individuals, while others such are much more variable. In some cases differences up to an order of magnitude are observed. Although some of these changes may have dietary origins, others seem to be characteristic of the individual. Cyclohexanone is obtained through oxidation of cyclohexane or dehydrogenation of phenol. Approx. 95% of its manufacturing is used for the production of nylon. Information on toxicity to human beings is fragmentary. Acute exposure is characterized by irritation of the eyes, nose, and throat. In two persons, drowsiness and renal impairment were found; however, these workers were also exposed to other compounds. Hepatic disorders were found in a group of workers exposed for over five years. In animals, cyclohexanone is characterized by relatively low acute toxicity (DL50 by intragastric administration is approximately 2 g/kg body wt.). Effects on the central nervous system (CNS) were found (narcosis), as well as irritation of the eyes and skin. Following multiple administration, effects were found in the CNS, liver, and kidneys as well as irritation of the conjunctiva. Mutagenic and genotoxic effects were found, but no teratogenic effects were detected; however, there were embryotoxic effects and influence on reproduction Cyclohexanone is well absorbed through the skin, respiratory tract, and alimentary tract. The main metabolic pathway leads to cyclohexanol, which is excreted in urine coupled with glucuronic acid. A high correlation was found between the concentration of cyclohexanone in the working environment and its concentration in urine. Cyclohexanone is formed from the hydrocarbons cyclohexane and 1-, 2-, and 3-hexanol. A patient's case report documents the development of anosmia (an olfactory disorder) and rhinitis caused by occupational exposure to organic solvents, including cyclohexanone (PMID:10476412 , 16925936 , 16477465 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb4c114a70>


  Mrv1652305271900062D          

  7  7  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   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
    1.4289    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb4c114a70>

HMDB0003315
     RDKit          3D
Cyclohexanone
 17 17  0  0  0  0  0  0  0  0999 V2000
   -0.9717    2.1198    1.3710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5738    1.2920    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8307    1.2675    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4160   -0.0901   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5072   -1.1583   -0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927   -1.0859   -0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.2750    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8954    1.8437   -0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492    1.8374    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274   -0.4021    0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663   -0.0198   -0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354   -2.1435   -0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5571   -1.2446   -1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392   -1.6095    0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -1.6989   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815    0.6068   -0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4147    0.2105    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  3  8  1  0
  3  9  1  0
  4 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb4c114a70>


  Mrv1652305271900062D          

  7  7  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   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
    1.4289    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054414

> <DATABASE_NAME>
MIME

> <SMILES>
O=C1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2

> <INCHI_KEY>
JHIVVAPYMSGYDF-UHFFFAOYSA-N

> <FORMULA>
C6H10O

> <MOLECULAR_WEIGHT>
98.143

> <EXACT_MASS>
98.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.155039696155914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
cyclohexanone

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.4881942646666666

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.3469833344911795

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
28.247399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclohexanone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007fdb4c114a70>

HMDB0003315
     RDKit          3D
Cyclohexanone
 17 17  0  0  0  0  0  0  0  0999 V2000
   -0.9717    2.1198    1.3710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5738    1.2920    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8307    1.2675    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4160   -0.0901   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5072   -1.1583   -0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927   -1.0859   -0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.2750    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8954    1.8437   -0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492    1.8374    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274   -0.4021    0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663   -0.0198   -0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354   -2.1435   -0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5571   -1.2446   -1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392   -1.6095    0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -1.6989   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815    0.6068   -0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4147    0.2105    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  3  8  1  0
  3  9  1  0
  4 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  7 17  1  0
M  END
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PDB for #<Metabolite:0x00007fdb4c114a70>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   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
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for #<Metabolite:0x00007fdb4c114a70>

COMPND    HMDB0003315
HETATM    1  O1  UNL     1      -0.972   2.120   1.371  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.574   1.292   0.568  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.831   1.267   0.110  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.416  -0.090  -0.017  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.507  -1.158  -0.471  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.893  -1.086  -0.018  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.500   0.275   0.021  1.00  0.00           C  
HETATM    8  H1  UNL     1       0.895   1.844  -0.837  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.449   1.837   0.858  1.00  0.00           H  
HETATM   10  H3  UNL     1       1.927  -0.402   0.939  1.00  0.00           H  
HETATM   11  H4  UNL     1       2.266  -0.020  -0.759  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.935  -2.143  -0.115  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.557  -1.245  -1.594  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.039  -1.609   0.967  1.00  0.00           H  
HETATM   15  H8  UNL     1      -1.511  -1.699  -0.739  1.00  0.00           H  
HETATM   16  H9  UNL     1      -1.881   0.607  -0.964  1.00  0.00           H  
HETATM   17  H10 UNL     1      -2.415   0.210   0.679  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4    8    9
CONECT    4    5   10   11
CONECT    5    6   12   13
CONECT    6    7   14   15
CONECT    7   16   17
END
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SMILES for #<Metabolite:0x00007fdb4c114a70>

O=C1CCCCC1
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INCHI for #<Metabolite:0x00007fdb4c114a70>

InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
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Synonyms
ValueSource
Cyclohexyl ketoneChEBI
KetocyclohexaneChEBI
KetohexamethyleneChEBI
OxocyclohexaneChEBI
ANONHMDB
AnoneHMDB
CicloesanoneHMDB
Cyclic ketoneHMDB
CyclohexanonHMDB
Cyclohexanone homopolymerHMDB
CykloheksanonHMDB
HexanonHMDB
Hytrol OHMDB
HytroloHMDB
NadoneHMDB
Pimelic ketoneHMDB
Pimelin ketoneHMDB
Rcra waste number u057HMDB
SextoneHMDB
Molecular FormulaC6H10O
Average Mass98.143
Monoisotopic Mass98.073164942
IUPAC Namecyclohexanone
Traditional Namecyclohexanone
CAS Registry NumberNot Available
SMILES
O=C1CCCCC1
InChI Identifier
InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
InChI KeyJHIVVAPYMSGYDF-UHFFFAOYSA-N