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Showing metabocard for 5-Methyl-2-hexanone (HMDB0031549)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:00 UTC
Update Date2023-02-21 17:20:48 UTC
HMDB IDHMDB0031549
Secondary Accession Numbers
  • HMDB31549
Metabolite Identification
Common Name5-Methyl-2-hexanone
Description5-Methyl-2-hexanone, also known as methyl isoamyl ketone or MIAK, 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. 5-Methyl-2-hexanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, 5-methyl-2-hexanone is considered to be an oxygenated hydrocarbon lipid molecule. 5-Methyl-2-hexanone has been detected, but not quantified, in a few different foods, such as eggs, fruits, and tea. This could make 5-methyl-2-hexanone a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031549 (5-Methyl-2-hexanone)

  Mrv1652305271900002D          

  8  7  0  0  0  0            999 V2000
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  2  0  0  0  0
M  END
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3D MOL for HMDB0031549 (5-Methyl-2-hexanone)

HMDB0031549
     RDKit          3D
5-Methyl-2-hexanone
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.3228   -0.2241    0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -0.0818   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3421    0.0087   -1.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7645   -0.0451    0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419    0.1071   -1.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409    0.1429   -0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648   -1.1216    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9494    1.3113    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294    0.2628    0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5027   -1.3222    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1170    0.1803    1.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    0.7836    0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455   -0.9749    0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446   -0.8166   -1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007    0.9482   -1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212    0.2045   -1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -1.1059    1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637   -1.1253    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -1.9898   -0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086    1.1436    1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4546    2.2316   -0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0505    1.4826    0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
M  END
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3D SDF for HMDB0031549 (5-Methyl-2-hexanone)

  Mrv1652305271900002D          

  8  7  0  0  0  0            999 V2000
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031549

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O/c1-6(2)4-5-7(3)8/h6H,4-5H2,1-3H3

> <INCHI_KEY>
FFWSICBKRCICMR-UHFFFAOYSA-N

> <FORMULA>
C7H14O

> <MOLECULAR_WEIGHT>
114.1855

> <EXACT_MASS>
114.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.11659884624607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methylhexan-2-one

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.982972081666667

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.640413173614338

> <JCHEM_PKA_STRONGEST_BASIC>
-7.271085028734452

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
34.572300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-2-hexanone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031549 (5-Methyl-2-hexanone)

HMDB0031549
     RDKit          3D
5-Methyl-2-hexanone
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.3228   -0.2241    0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -0.0818   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3421    0.0087   -1.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7645   -0.0451    0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419    0.1071   -1.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409    0.1429   -0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648   -1.1216    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9494    1.3113    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294    0.2628    0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5027   -1.3222    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1170    0.1803    1.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    0.7836    0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455   -0.9749    0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446   -0.8166   -1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007    0.9482   -1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212    0.2045   -1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -1.1059    1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637   -1.1253    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -1.9898   -0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086    1.1436    1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4546    2.2316   -0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0505    1.4826    0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
M  END
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PDB for HMDB0031549 (5-Methyl-2-hexanone)

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  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    1    2    4                                                  
CONECT    7    3    5    8                                                  
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0031549 (5-Methyl-2-hexanone)

COMPND    HMDB0031549
HETATM    1  C1  UNL     1       3.323  -0.224   0.512  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.155  -0.082  -0.385  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.342   0.009  -1.578  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.764  -0.045   0.113  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.242   0.107  -1.007  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.641   0.143  -0.492  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.965  -1.122   0.243  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.949   1.311   0.382  1.00  0.00           C  
HETATM    9  H1  UNL     1       4.229   0.263   0.100  1.00  0.00           H  
HETATM   10  H2  UNL     1       3.503  -1.322   0.666  1.00  0.00           H  
HETATM   11  H3  UNL     1       3.117   0.180   1.532  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.675   0.784   0.843  1.00  0.00           H  
HETATM   13  H5  UNL     1       0.546  -0.975   0.669  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.145  -0.817  -1.634  1.00  0.00           H  
HETATM   15  H7  UNL     1      -0.001   0.948  -1.678  1.00  0.00           H  
HETATM   16  H8  UNL     1      -2.321   0.205  -1.381  1.00  0.00           H  
HETATM   17  H9  UNL     1      -1.418  -1.106   1.208  1.00  0.00           H  
HETATM   18  H10 UNL     1      -3.064  -1.125   0.505  1.00  0.00           H  
HETATM   19  H11 UNL     1      -1.696  -1.990  -0.395  1.00  0.00           H  
HETATM   20  H12 UNL     1      -1.709   1.144   1.454  1.00  0.00           H  
HETATM   21  H13 UNL     1      -1.455   2.232  -0.017  1.00  0.00           H  
HETATM   22  H14 UNL     1      -3.051   1.483   0.340  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5   12   13
CONECT    5    6   14   15
CONECT    6    7    8   16
CONECT    7   17   18   19
CONECT    8   20   21   22
END
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SMILES for HMDB0031549 (5-Methyl-2-hexanone)

CC(C)CCC(C)=O
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INCHI for HMDB0031549 (5-Methyl-2-hexanone)

InChI=1S/C7H14O/c1-6(2)4-5-7(3)8/h6H,4-5H2,1-3H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(CH3)2chch2ch2coch3HMDB
2-Hexanone-5-methylHMDB
2-Methyl-5-hexanoneHMDB
5-Methylhexan-2-oneHMDB
Isoamyl methyl ketoneHMDB
IsobutylacetoneHMDB
Isopentyl methyl ketoneHMDB
Ketone, methyl isoamylHMDB
Methyl isoamyl ketoneHMDB
Methyl isopentyl ketoneHMDB
MIAKHMDB
Chemical FormulaC7H14O
Average Molecular Weight114.1855
Monoisotopic Molecular Weight114.10446507
IUPAC Name5-methylhexan-2-one
Traditional Name5-methyl-2-hexanone
CAS Registry Number110-12-3
SMILES
CC(C)CCC(C)=O
InChI Identifier
InChI=1S/C7H14O/c1-6(2)4-5-7(3)8/h6H,4-5H2,1-3H3
InChI KeyFFWSICBKRCICMR-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
Health effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-74 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.4 mg/mL at 25 °CNot Available
LogP1.88Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
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 ]
Crohn's disease
  1. 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 ]
Ulcerative colitis
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008160
KNApSAcK IDC00052167
Chemspider ID7743
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8034
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .