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Showing metabocard for Butanone (HMDB0000474)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:52 UTC
HMDB IDHMDB0000474
Secondary Accession Numbers
  • HMDB00474
Metabolite Identification
Common NameButanone
DescriptionButanone, also known as aethylmethylketon or methyl acetone, 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, butanone is considered to be an oxygenated hydrocarbon. Butanone is an acetone, camphor, and ethereal tasting compound. Butanone is found, on average, in the highest concentration within milk (cow) and peppermints (Mentha X piperita). Butanone has also been detected, but not quantified in, several different foods, such as japanese chestnuts (Castanea crenata), saskatoon berries (Amelanchier alnifolia), red onion, almonds (Prunus dulcis), and burbots (Lota lota). This could make butanone a potential biomarker for the consumption of these foods. Butanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Butanone, with regard to humans, has been found to be associated with several diseases such as crohn's disease, pervasive developmental disorder not otherwise specified, asthma, and ulcerative colitis; butanone has also been linked to the inborn metabolic disorder celiac disease. Based on a literature review a significant number of articles have been published on Butanone.
Structure
Data?1676999692
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000474 (Butanone)


  Mrv1652309042000012D          

  5  4  0  0  0  0            999 V2000
   -1.0717   -0.6187    0.0000 C   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
    0.3572   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  2  0  0  0  0
M  END
Download

3D MOL for HMDB0000474 (Butanone)

HMDB0000474
     RDKit          3D
Butanone
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.8621   -0.1213    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -0.6405   -0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    0.4970    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9607    0.3062   -0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0900    1.5974    0.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460   -0.9453   -0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9822    0.7294   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711    0.2539    1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2246   -1.5158    0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004   -0.9415   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3502    0.1311    0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    1.1980   -0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598   -0.5488   -0.7016 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
  3  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  4 11  1  0
  4 12  1  0
  4 13  1  0
M  END
Download

3D SDF for HMDB0000474 (Butanone)


  Mrv1652309042000012D          

  5  4  0  0  0  0            999 V2000
   -1.0717   -0.6187    0.0000 C   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
    0.3572   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000474

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3

> <INCHI_KEY>
ZWEHNKRNPOVVGH-UHFFFAOYSA-N

> <FORMULA>
C4H8O

> <MOLECULAR_WEIGHT>
72.1057

> <EXACT_MASS>
72.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.283031498013756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butan-2-one

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
0.8068156553333333

> <ALOGPS_LOGS>
0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.68029359996891

> <JCHEM_PKA_STRONGEST_BASIC>
-7.264650301548389

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
20.8217

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl(ethyl) ketone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000474 (Butanone)

HMDB0000474
     RDKit          3D
Butanone
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.8621   -0.1213    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -0.6405   -0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    0.4970    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9607    0.3062   -0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0900    1.5974    0.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460   -0.9453   -0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9822    0.7294   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711    0.2539    1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2246   -1.5158    0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004   -0.9415   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3502    0.1311    0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    1.1980   -0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598   -0.5488   -0.7016 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
  3  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  4 11  1  0
  4 12  1  0
  4 13  1  0
M  END
Download

PDB for HMDB0000474 (Butanone)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -2.001  -1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.667   1.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0000474 (Butanone)

COMPND    HMDB0000474
HETATM    1  C1  UNL     1      -1.862  -0.121   0.111  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.444  -0.640  -0.148  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.473   0.497   0.135  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.961   0.306  -0.028  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.090   1.597   0.499  1.00  0.00           O  
HETATM    6  H1  UNL     1      -2.546  -0.945  -0.146  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.982   0.729  -0.624  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.971   0.254   1.143  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.225  -1.516   0.509  1.00  0.00           H  
HETATM   10  H5  UNL     1      -0.400  -0.941  -1.216  1.00  0.00           H  
HETATM   11  H6  UNL     1       2.350   0.131   0.989  1.00  0.00           H  
HETATM   12  H7  UNL     1       2.397   1.198  -0.523  1.00  0.00           H  
HETATM   13  H8  UNL     1       2.160  -0.549  -0.702  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9   10
CONECT    3    4    5    5
CONECT    4   11   12   13
END
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SMILES for HMDB0000474 (Butanone)

CCC(C)=O
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INCHI for HMDB0000474 (Butanone)

InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-ButanonChEBI
2-ButanoneChEBI
3-ButanoneChEBI
AethylmethylketonChEBI
Butanone 2ChEBI
C2H5COCH3ChEBI
Ethyl methyl cetoneChEBI
Ethyl methyl ketoneChEBI
Ethyl(methyl) ketoneChEBI
Ethylmethyl ketoneChEBI
EthylmethylketonChEBI
MeetcoChEBI
MEKChEBI
Methyl acetoneChEBI
Methyl ethyl cetoneChEBI
Methyl ethyl ketoneChEBI
Methyl(ethyl) ketoneChEBI
MethylacetoneChEBI
Methylethyl ketoneChEBI
MethylethylketonChEBI
OxobutaneChEBI
Butan-2-oneKegg
ButanoneChEBI
Chemical FormulaC4H8O
Average Molecular Weight72.1057
Monoisotopic Molecular Weight72.057514878
IUPAC Namebutan-2-one
Traditional Namemethyl(ethyl) ketone
CAS Registry Number78-93-3
SMILES
CCC(C)=O
InChI Identifier
InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
InChI KeyZWEHNKRNPOVVGH-UHFFFAOYSA-N
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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-86.6 °CNot Available
Boiling Point78.60 to 80.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility223 mg/mLNot Available
LogP0.29HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility93 g/LALOGPS
logP0.41ALOGPS
logP0.81ChemAxon
logS0.11ALOGPS
pKa (Strongest Acidic)19.68ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.82 m³·mol⁻¹ChemAxon
Polarizability8.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+113.41231661259
DarkChem[M-H]-106.64831661259
AllCCS[M+H]+120.28532859911
AllCCS[M-H]-133.34932859911
DeepCCS[M+H]+123.90630932474
DeepCCS[M-H]-122.01130932474
DeepCCS[M-2H]-157.38730932474
DeepCCS[M+Na]+131.72530932474
AllCCS[M+H]+120.332859911
AllCCS[M+H-H2O]+115.732859911
AllCCS[M+NH4]+124.532859911
AllCCS[M+Na]+125.832859911
AllCCS[M-H]-133.332859911
AllCCS[M+Na-2H]-138.932859911
AllCCS[M+HCOO]-145.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ButanoneCCC(C)=O843.5Standard polar33892256
ButanoneCCC(C)=O553.5Standard non polar33892256
ButanoneCCC(C)=O586.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Butanone,1TMS,isomer #1CC=C(C)O[Si](C)(C)C846.3Semi standard non polar33892256
Butanone,1TMS,isomer #1CC=C(C)O[Si](C)(C)C793.3Standard non polar33892256
Butanone,1TMS,isomer #1CC=C(C)O[Si](C)(C)C897.6Standard polar33892256
Butanone,1TMS,isomer #2C=C(CC)O[Si](C)(C)C776.6Semi standard non polar33892256
Butanone,1TMS,isomer #2C=C(CC)O[Si](C)(C)C809.5Standard non polar33892256
Butanone,1TMS,isomer #2C=C(CC)O[Si](C)(C)C901.3Standard polar33892256
Butanone,1TBDMS,isomer #1CC=C(C)O[Si](C)(C)C(C)(C)C1040.5Semi standard non polar33892256
Butanone,1TBDMS,isomer #1CC=C(C)O[Si](C)(C)C(C)(C)C1007.9Standard non polar33892256
Butanone,1TBDMS,isomer #1CC=C(C)O[Si](C)(C)C(C)(C)C1095.7Standard polar33892256
Butanone,1TBDMS,isomer #2C=C(CC)O[Si](C)(C)C(C)(C)C1003.6Semi standard non polar33892256
Butanone,1TBDMS,isomer #2C=C(CC)O[Si](C)(C)C(C)(C)C1022.7Standard non polar33892256
Butanone,1TBDMS,isomer #2C=C(CC)O[Si](C)(C)C(C)(C)C1102.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Butanone EI-B (Non-derivatized)splash10-0006-9000000000-6d2b5f585a1d1bc5a8fb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butanone EI-B (Non-derivatized)splash10-0006-9000000000-9d38ccb9b91100a7ec9a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butanone EI-B (Non-derivatized)splash10-0006-9000000000-c956d364a703ad576f742017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butanone EI-B (Non-derivatized)splash10-0006-9000000000-6d2b5f585a1d1bc5a8fb2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butanone EI-B (Non-derivatized)splash10-0006-9000000000-9d38ccb9b91100a7ec9a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butanone EI-B (Non-derivatized)splash10-0006-9000000000-c956d364a703ad576f742018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-4e6c1888a6b9f92a7e0c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-389580382a5be690811f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Butanone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-05fr-9000000000-ce6384a82cdbc3c321312012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butanone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-05fr-9000000000-d2220466d540748715a62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butanone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00di-9000000000-5c396f6150d62df63bf82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butanone EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-0006-9000000000-342b15824555f25c17ae2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butanone EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0006-9000000000-9d38ccb9b91100a7ec9a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Butanone EI-B (HITACHI M-80) , Positive-QTOFsplash10-0006-9000000000-c956d364a703ad576f742012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 10V, Positive-QTOFsplash10-05fr-9000000000-df1c4f4393ad8e083cee2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 20V, Positive-QTOFsplash10-0ab9-9000000000-5db9dc68e554d23fe4ca2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 40V, Positive-QTOFsplash10-0a4i-9000000000-e76aaa16e1218b6b92e02015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 10V, Positive-QTOFsplash10-05fr-9000000000-df1c4f4393ad8e083cee2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 20V, Positive-QTOFsplash10-0ab9-9000000000-5db9dc68e554d23fe4ca2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 40V, Positive-QTOFsplash10-0a4i-9000000000-e76aaa16e1218b6b92e02015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 10V, Negative-QTOFsplash10-00di-9000000000-75ee4bf0cca979df2fee2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 20V, Negative-QTOFsplash10-00di-9000000000-a0882d603db69a60cd2b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 40V, Negative-QTOFsplash10-0pb9-9000000000-2b71687b4480da0a40a82015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 10V, Negative-QTOFsplash10-00di-9000000000-75ee4bf0cca979df2fee2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 20V, Negative-QTOFsplash10-00di-9000000000-a0882d603db69a60cd2b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 40V, Negative-QTOFsplash10-0pb9-9000000000-2b71687b4480da0a40a82015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 10V, Positive-QTOFsplash10-0a4i-9000000000-1924391f943e092b44862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 20V, Positive-QTOFsplash10-0a4i-9000000000-b1f7b08e06d7bb20906d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 40V, Positive-QTOFsplash10-052o-9000000000-d0609c2afd15f75e6cbb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 10V, Negative-QTOFsplash10-00di-9000000000-77e5dcf17bd83eca2c672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 20V, Negative-QTOFsplash10-00dl-9000000000-91a2cd469019aa3b0b9c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butanone 40V, Negative-QTOFsplash10-0006-9000000000-fa8f185babb9571dbb912021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Breath
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Epidermis
  • Pancreas
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified10308.940-194575.464 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
UrineDetected and Quantified5.5 (0.0-11.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified0.07 (0.0-0.26) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified682.0 (69.0-1998.0) uMAdult (>18 years old)BothAlcohol intoxication details
BreathDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected and Quantified0-629584.994 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothCeliac disease details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. [PubMed:2779169 ]
Asthma
  1. Ibrahim B, Basanta M, Cadden P, Singh D, Douce D, Woodcock A, Fowler SJ: Non-invasive phenotyping using exhaled volatile organic compounds in asthma. Thorax. 2011 Sep;66(9):804-9. doi: 10.1136/thx.2010.156695. Epub 2011 Jul 11. [PubMed:21749985 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
  2. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003383
KNApSAcK IDC00054019
Chemspider ID6321
KEGG Compound IDC02845
BioCyc IDMEK
BiGG IDNot Available
Wikipedia LinkButanone
METLIN ID5461
PubChem Compound6569
PDB IDNot Available
ChEBI ID28398
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029983
Good Scents IDrw1007581
References
Synthesis ReferenceVergnaud, Paul. The manufacture of butanediol and butanone. (1950),
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Weddle DL, Tithoff P, Williams M, Schuller HM: Beta-adrenergic growth regulation of human cancer cell lines derived from pancreatic ductal carcinomas. Carcinogenesis. 2001 Mar;22(3):473-9. [PubMed:11238189 ]
  2. Goldsmith LB, Friberg SE, Wahlberg JE: The effect of solvent extraction on the lipids of the stratum corneum in relation to observed immediate whitening of the skin. Contact Dermatitis. 1988 Nov;19(5):348-50. [PubMed:3233954 ]
  3. Carmella SG, Akerkar S, Hecht SS: Metabolites of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers' urine. Cancer Res. 1993 Feb 15;53(4):721-4. [PubMed:8428352 ]
  4. Stich HF, Parida BB, Brunnemann KD: Localized formation of micronuclei in the oral mucosa and tobacco-specific nitrosamines in the saliva of "reverse" smokers, Khaini-tobacco chewers and gudakhu users. Int J Cancer. 1992 Jan 21;50(2):172-6. [PubMed:1730509 ]
  5. Nair J, Ohshima H, Friesen M, Croisy A, Bhide SV, Bartsch H: Tobacco-specific and betel nut-specific N-nitroso compounds: occurrence in saliva and urine of betel quid chewers and formation in vitro by nitrosation of betel quid. Carcinogenesis. 1985 Feb;6(2):295-303. [PubMed:3971493 ]
  6. Prokopczyk B, Cox JE, Hoffmann D, Waggoner SE: Identification of tobacco-specific carcinogen in the cervical mucus of smokers and nonsmokers. J Natl Cancer Inst. 1997 Jun 18;89(12):868-73. [PubMed:9196253 ]
  7. Hecht SS, Carmella SG, Ye M, Le KA, Jensen JA, Zimmerman CL, Hatsukami DK: Quantitation of metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone after cessation of smokeless tobacco use. Cancer Res. 2002 Jan 1;62(1):129-34. [PubMed:11782369 ]