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Showing NP-Card for Cyclohexanone (NP0000360)

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Record Information
Version1.0
Created at2006-05-22 15:12:49 UTC
Updated at2021-10-07 20:40:58 UTC
NP-MRD IDNP0000360
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000360 (Cyclohexanone)


  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
Download

3D MOL for NP0000360 (Cyclohexanone)

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
Download

3D SDF for NP0000360 (Cyclohexanone)


  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>
NP0000360

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000360 (Cyclohexanone)

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 NP0000360 (Cyclohexanone)

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 NP0000360 (Cyclohexanone)

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 NP0000360 (Cyclohexanone)

O=C1CCCCC1
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INCHI for NP0000360 (Cyclohexanone)

InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
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View in JSmol
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
Chemical FormulaC6H10O
Average Mass98.1430 Da
Monoisotopic Mass98.07316 Da
IUPAC Namecyclohexanone
Traditional Namecyclohexanone
CAS Registry Number108-94-1
SMILES
O=C1CCCCC1
InChI Identifier
InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
InChI KeyJHIVVAPYMSGYDF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
CervidaeFooDB
Cervus canadensisFooDB
Cichorium endiviaLOTUS Database
Cistus ladaniferusKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Gossypium hirsutumLOTUS Database
Gymnodinium nagasakienseLOTUS Database
Ilex purpureaLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melaleuca alternifoliaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Paraburkholderia phymatum-
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tamarix aphyllaLOTUS Database
Vitis viniferaLOTUS Database
Zingiber miogaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclic ketones
Alternative Parents
Substituents
  • Cyclic ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-31 °CNot Available
Boiling Point154.00 to 156.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility25 mg/mL at 25 °CNot Available
LogP0.81Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility19.6 g/LALOGPS
logP1.03ALOGPS
logP1.49ChemAxon
logS-0.7ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.25 m³·mol⁻¹ChemAxon
Polarizability11.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003315
DrugBank IDDB02060
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003418
KNApSAcK IDC00052902
Chemspider ID7679
KEGG Compound IDC00414
BioCyc IDCYCLOHEXANONE
BiGG IDNot Available
Wikipedia LinkCyclohexanone
METLIN IDNot Available
PubChem Compound7967
PDB IDNot Available
ChEBI ID17854
Good Scents IDrw1098591
References
General References
  1. Zheng M, McErlane KM, Ong MC: Hydromorphone metabolites: isolation and identification from pooled urine samples of a cancer patient. Xenobiotica. 2002 May;32(5):427-39. [PubMed:12065064 ]
  2. Authors unspecified: Cyclohexanone. IARC Monogr Eval Carcinog Risks Hum. 1999;71 Pt 3:1359-64. [PubMed:10476412 ]
  3. Muttray A, Haxel B, Mann W, Letzel S: [Toxic anosmia and rhinitis due to occupational solvent exposure]. HNO. 2006 Nov;54(11):883-7. [PubMed:16477465 ]
  4. Walker R, Flanagan RJ, Lennard MS, Mills GA, Walker V: Solid-phase microextraction: investigation of the metabolism of substances that may be abused by inhalation. J Chromatogr Sci. 2006 Aug;44(7):387-93. [PubMed:16925936 ]
  5. Sun H, Zhang D: Theoretical elucidation on the functional role of pyrrolidine-type ionic liquids in inducing stereoselectivity of the Michael addition of cyclohexanone with trans-beta-nitrostyrene. Chirality. 2011 Mar;23(3):260-4. doi: 10.1002/chir.20908. Epub 2010 Oct 6. [PubMed:20928898 ]