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Showing NP-Card for 2-Oxohexane (NP0001021)

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Record Information
Version1.0
Created at2007-04-12 15:37:12 UTC
Updated at2021-10-07 20:41:10 UTC
NP-MRD IDNP0001021
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Oxohexane
Description2-Oxohexane, also known as hexan-2-one or MNBK, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2-oxohexane is considered to be an oxygenated hydrocarbon lipid molecule. 2-Oxohexane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Oxohexane is an gasoline tasting compound. 2-Oxohexane is found, on average, in the highest concentration within a few different foods, such as hyssops, milk (cow), and corns. 2-Oxohexane has also been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, red bell peppers, nuts, and peppers. This could make 2-oxohexane a potential biomarker for the consumption of these foods. 2-Oxohexane is a potentially toxic compound. 2-Oxohexane, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, crohn's disease, and nonalcoholic fatty liver disease; 2-oxohexane has also been linked to the inborn metabolic disorder celiac disease. 2-Oxohexane is absorbed via ingestion, inhalation, and dermal routes, then distributed widely throughout the body, with the highest levels in the liver and blood. The main neurological disorders associated with chronic volatile substance are peripheral neuropathy, cerebellar disease, chronic encephalopathy and dementia. This may include pathologies such as peripheral neuropathy and developmental defects. Apart from peripheral neuropathy, the clinical features are non-specific, evidence for solvent-related toxicity is in most cases circumstantial and there is no clear dose/response relationship. 2-Oxohexane is occasionally found as a volatile component of normal human biofluids. In addition, 2,5-hexanedione can covalently cross-link neurofilaments, causing large axonal swellings. 2-Oxohexane and 2,5-hexanedione may also inhibit sulfhydryl-dependent enzymes such as fructose-6-phosphate kinase and glyceraldehyde-3-phosphate dehydrogenase, as well as certain creatine kinases and adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001021 (2-Oxohexane)


  Mrv1652304082022482D          

  7  6  0  0  0  0            999 V2000
   -1.0721    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7865   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
Download

3D MOL for NP0001021 (2-Oxohexane)

HMDB0005842
     RDKit          3D
2-Oxohexane
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.0534    0.0625   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052   -0.2399    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5693    0.2051   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7260   -0.1504    0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9151    0.2385   -0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2520   -0.0475    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121    0.7726   -1.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909    0.4992   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -0.8566   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6288    0.8017    0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849   -1.3181    0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6530    0.2884    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6124   -0.3860   -1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5815    1.2777   -0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -1.2294    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752    0.4099    1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    0.8887    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2675   -0.8972    0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9412   -0.3191   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  6 19  1  0
M  END
Download

3D SDF for NP0001021 (2-Oxohexane)


  Mrv1652304082022482D          

  7  6  0  0  0  0            999 V2000
   -1.0721    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7865   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3

> <INCHI_KEY>
QQZOPKMRPOGIEB-UHFFFAOYSA-N

> <FORMULA>
C6H12O

> <MOLECULAR_WEIGHT>
100.1589

> <EXACT_MASS>
100.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
12.260542829270914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexan-2-one

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.6959529853333333

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.643570107729342

> <JCHEM_PKA_STRONGEST_BASIC>
-7.270862577082193

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
30.023699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexanone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001021 (2-Oxohexane)

HMDB0005842
     RDKit          3D
2-Oxohexane
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.0534    0.0625   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052   -0.2399    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5693    0.2051   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7260   -0.1504    0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9151    0.2385   -0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2520   -0.0475    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121    0.7726   -1.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909    0.4992   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -0.8566   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6288    0.8017    0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849   -1.3181    0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6530    0.2884    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6124   -0.3860   -1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5815    1.2777   -0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -1.2294    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752    0.4099    1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    0.8887    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2675   -0.8972    0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9412   -0.3191   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  6 19  1  0
M  END
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PDB for NP0001021 (2-Oxohexane)

HEADER    PROTEIN                                 08-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-APR-20         0                                  
HETATM    1  O   UNK     0      -2.001   1.155   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.335  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.335  -1.155   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3                                                            
CONECT    6    1    4    7                                                  
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0001021 (2-Oxohexane)

COMPND    HMDB0005842
HETATM    1  C1  UNL     1       3.053   0.062  -0.147  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.705  -0.240   0.450  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.569   0.205  -0.459  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.726  -0.150   0.245  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.915   0.238  -0.551  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.252  -0.048   0.012  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.812   0.773  -1.627  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.991   0.499  -1.162  1.00  0.00           H  
HETATM    9  H2  UNL     1       3.675  -0.857  -0.164  1.00  0.00           H  
HETATM   10  H3  UNL     1       3.629   0.802   0.465  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.585  -1.318   0.681  1.00  0.00           H  
HETATM   12  H5  UNL     1       1.653   0.288   1.424  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.612  -0.386  -1.397  1.00  0.00           H  
HETATM   14  H7  UNL     1       0.582   1.278  -0.652  1.00  0.00           H  
HETATM   15  H8  UNL     1      -0.733  -1.229   0.527  1.00  0.00           H  
HETATM   16  H9  UNL     1      -0.775   0.410   1.208  1.00  0.00           H  
HETATM   17  H10 UNL     1      -3.633   0.889   0.483  1.00  0.00           H  
HETATM   18  H11 UNL     1      -3.268  -0.897   0.712  1.00  0.00           H  
HETATM   19  H12 UNL     1      -3.941  -0.319  -0.828  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4   13   14
CONECT    4    5   15   16
CONECT    5    6    7    7
CONECT    6   17   18   19
END
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SMILES for NP0001021 (2-Oxohexane)

CCCCC(C)=O
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INCHI for NP0001021 (2-Oxohexane)

InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3
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View in JSmol
Synonyms
ValueSource
Hexan-2-oneHMDB
2-HexanoneHMDB
2-Hexanone methyl N-butyl ketoneHMDB
Butyl methyl ketoneHMDB
Methyl butyl ketoneHMDB
Methyl N-butyl ketoneHMDB
MNBKHMDB
N-Butyl methyl ketoneHMDB
N-C4H9COCH3HMDB
PropylacetoneHMDB
Butylmethyl ketoneHMDB
Ketone, butylmethylHMDB
2 HexanoneHMDB
Hexan 2 oneHMDB
Ketone, methyl N-butylHMDB
Methyl N butyl ketoneHMDB
N-Butyl ketone, methylHMDB
MBKHMDB
2-OxohexaneHMDB
Chemical FormulaC6H12O
Average Mass100.1589 Da
Monoisotopic Mass100.08882 Da
IUPAC Namehexan-2-one
Traditional Namehexanone
CAS Registry Number591-78-6
SMILES
CCCCC(C)=O
InChI Identifier
InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3
InChI KeyQQZOPKMRPOGIEB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)V.dorna832021-08-23View 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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-12View Spectrum
Species
Species of Origin
Species NameSourceReference
Acca sellowianaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arachis hypogaeaKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica junceaLOTUS Database
Bubalus bubalisFooDB
Canella winteranaLOTUS Database
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Glycyrrhiza glabraLOTUS Database
Humulus lupulusKNApSAcK Database
Hyssopus officinalis L.FooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Musa paradisiacaLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
Origanum minutiflorumLOTUS Database
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Solanum stuckertiiLOTUS Database
Solanum tuberosumKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Trifolium pratenseLOTUS Database
Zea maysLOTUS Database
Zea mays L.FooDB
    • Carlos Macku, and Takayuki Shibamoto. Headspace volatile compounds formed from heated corn oil an...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-55.5 °CNot Available
Boiling Point127.60 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility17.5 mg/mL at 20 °CNot Available
LogP1.38Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility8.14 g/LALOGPS
logP1.45ALOGPS
logP1.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.02 m³·mol⁻¹ChemAxon
Polarizability12.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0005842
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008079
KNApSAcK IDC00053953
Chemspider ID11095
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11583
PDB IDNot Available
ChEBI ID89206
Good Scents IDrw1046671
References
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Griffin JW: Hexacarbon neurotoxicity. Neurobehav Toxicol Teratol. 1981 Winter;3(4):437-44. [PubMed:6278344 ]
  3. Lolin Y: Chronic neurological toxicity associated with exposure to volatile substances. Hum Toxicol. 1989 Jul;8(4):293-300. [PubMed:2550357 ]
  4. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. doi: 10.1017/s0022029902005782. [PubMed:12463694 ]
  5. Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Patient Version. 2002. [PubMed:34403226 ]
  6. Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:28876831 ]
  7. Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
  8. Authors unspecified: Adult Soft Tissue Sarcoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389481 ]