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Showing metabocard for 2-Ketohexanoic acid (HMDB0001864)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-02-23 10:34:24 UTC
Update Date2023-02-21 17:15:52 UTC
HMDB IDHMDB0001864
Secondary Accession Numbers
  • HMDB01864
Metabolite Identification
Common Name2-Ketohexanoic acid
Description2-Ketohexanoic acid, also known as alpha-ketocaproic acid or 2-oxohexanoate, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 2-Ketohexanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-ketohexanoic acid a potential biomarker for the consumption of these foods. 2-Ketohexanoic acid 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. Based on a literature review a small amount of articles have been published on 2-Ketohexanoic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001864 (2-Ketohexanoic acid)

  Mrv1652305261923542D          

  9  8  0  0  0  0            999 V2000
   19.6857   -4.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9711   -2.9285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2568   -4.9910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8280   -4.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1134   -3.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5423   -3.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3990   -4.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9711   -3.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2568   -4.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  8  2  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for HMDB0001864 (2-Ketohexanoic acid)

HMDB0001864
     RDKit          3D
2-Ketohexanoic acid
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.7860    0.7440    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162    0.1173   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.0479    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442   -0.6435   -0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366   -0.8596   -0.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.0565   -0.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.2387   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4296    1.4174   -0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -0.0032    0.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6321    0.3321    1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003    1.8614    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8163    0.4373    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295   -0.9078   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8297    0.6967   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    0.9199    0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4891   -0.7365    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121   -1.6112   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034    0.0203   -1.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    0.0812    1.1368 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  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
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3D SDF for HMDB0001864 (2-Ketohexanoic acid)

  Mrv1652305261923542D          

  9  8  0  0  0  0            999 V2000
   19.6857   -4.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9711   -2.9285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2568   -4.9910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8280   -4.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1134   -3.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5423   -3.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3990   -4.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9711   -3.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2568   -4.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  8  2  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001864

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O3/c1-2-3-4-5(7)6(8)9/h2-4H2,1H3,(H,8,9)

> <INCHI_KEY>
XNIHZNNZJHYHLC-UHFFFAOYSA-N

> <FORMULA>
C6H10O3

> <MOLECULAR_WEIGHT>
130.1418

> <EXACT_MASS>
130.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.188514079718631

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxohexanoic acid

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
1.6555471303333333

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.528763234882678

> <JCHEM_PKA_STRONGEST_BASIC>
-9.656705905216171

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
31.818599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-oxohexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001864 (2-Ketohexanoic acid)

HMDB0001864
     RDKit          3D
2-Ketohexanoic acid
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.7860    0.7440    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162    0.1173   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.0479    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442   -0.6435   -0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366   -0.8596   -0.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.0565   -0.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.2387   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4296    1.4174   -0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -0.0032    0.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6321    0.3321    1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003    1.8614    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8163    0.4373    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295   -0.9078   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8297    0.6967   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    0.9199    0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4891   -0.7365    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121   -1.6112   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034    0.0203   -1.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    0.0812    1.1368 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  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
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PDB for HMDB0001864 (2-Ketohexanoic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      36.747  -7.777   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.413  -5.467   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.079  -9.317   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      31.412  -7.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.078  -7.006   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.746  -7.006   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.745  -7.777   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.413  -7.006   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.079  -7.777   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5                                                            
CONECT    8    1    2    9                                                  
CONECT    9    3    6    8                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0001864 (2-Ketohexanoic acid)

COMPND    HMDB0001864
HETATM    1  C1  UNL     1      -2.786   0.744   0.648  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.816   0.117  -0.326  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.437  -0.048   0.266  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.444  -0.643  -0.772  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.837  -0.860  -0.342  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.185  -2.056  -0.129  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.784   0.239  -0.162  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.430   1.417  -0.339  1.00  0.00           O  
HETATM    9  O3  UNL     1       4.097  -0.003   0.207  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.632   0.332   1.657  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.700   1.861   0.664  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.816   0.437   0.333  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.229  -0.908  -0.531  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.830   0.697  -1.261  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.003   0.920   0.590  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.489  -0.737   1.126  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.012  -1.611  -1.095  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.503   0.020  -1.671  1.00  0.00           H  
HETATM   19  H10 UNL     1       4.447   0.081   1.137  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6    6    7
CONECT    7    8    8    9
CONECT    9   19
END
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SMILES for HMDB0001864 (2-Ketohexanoic acid)

CCCCC(=O)C(O)=O
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INCHI for HMDB0001864 (2-Ketohexanoic acid)

InChI=1S/C6H10O3/c1-2-3-4-5(7)6(8)9/h2-4H2,1H3,(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H10O3
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
IUPAC Name2-oxohexanoic acid
Traditional Name2-oxohexanoic acid
CAS Registry Number2492-75-3
SMILES
CCCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-2-3-4-5(7)6(8)9/h2-4H2,1H3,(H,8,9)
InChI KeyXNIHZNNZJHYHLC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point198.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility145000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.350 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022718
KNApSAcK IDNot Available
Chemspider ID140384
KEGG Compound IDC00902
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4144
PubChem Compound159664
PDB IDNot Available
ChEBI ID17308
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1620931
References
Synthesis ReferenceIgarashi, Minoru; Midorikawa, Hiroshi. Synthesis of a-oxo acids from diethyl alkylidenemalonates. Journal of Organic Chemistry (1964), 29(7), 2080-2.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakahara T, Ishida J, Yamaguchi M, Nakamura M: Determination of alpha-keto acids including phenylpyruvic acid in human plasma by high-performance liquid chromatography with chemiluminescence detection. Anal Biochem. 1990 Nov 1;190(2):309-13. [PubMed:2291475 ]
  2. Shroads AL, Henderson GN, Cheung J, James MO, Stacpoole PW: Unified gas chromatographic-mass spectrometric method for quantitating tyrosine metabolites in urine and plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Sep 5;808(2):153-61. [PubMed:15261808 ]
  3. Lenzen S, Formanek H, Panten U: Signal function of metabolism of neutral amino acids and 2-keto acids for initiation of insulin secretion. J Biol Chem. 1982 Jun 25;257(12):6631-3. [PubMed:7045091 ]
  4. Heissig H, Urban KA, Hastedt K, Zunkler BJ, Panten U: Mechanism of the insulin-releasing action of alpha-ketoisocaproate and related alpha-keto acid anions. Mol Pharmacol. 2005 Oct;68(4):1097-105. Epub 2005 Jul 13. [PubMed:16014804 ]