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Showing NP-Card for 2-Ketohexanoic acid (NP0000155)

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Record Information
Version1.0
Created at2006-02-23 10:34:24 UTC
Updated at2021-08-19 20:22:35 UTC
NP-MRD IDNP0000155
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Ketohexanoic acid
Description2-Ketohexanoic acid is a potent insulin secretagogue (PMID 7045091 ). 2-Ketohexanoic acid directly inhibits the ATP-sensitive K+ channel (KATP channel) in pancreatic beta-cells (stimulated in isolated mouse islets), but it is unknown whether direct KATP channel inhibition contributes to insulin release by 2-ketohexanoic acid and related alpha-keto acid anions, which are generally believed to act via beta-cell metabolism (PMID 16014804 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000155 (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
Download

3D MOL for NP0000155 (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
Download

3D SDF for NP0000155 (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>
NP0000155

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000155 (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
Download

PDB for NP0000155 (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
Download

3D PDB for NP0000155 (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 NP0000155 (2-Ketohexanoic acid)

CCCCC(=O)C(O)=O
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INCHI for NP0000155 (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 JSmol
Synonyms
ValueSource
2-Keto-N-caproic acidChEBI
2-oxo 6:0ChEBI
2-oxo C6:0ChEBI
2-OxohexanoateChEBI
alpha-Ketocaproic acidChEBI
alpha-Ketohexanoic acidChEBI
2-Keto-N-caproateGenerator
2-Oxohexanoic acidGenerator
a-KetocaproateGenerator
a-Ketocaproic acidGenerator
alpha-KetocaproateGenerator
Α-ketocaproateGenerator
Α-ketocaproic acidGenerator
a-KetohexanoateGenerator
a-Ketohexanoic acidGenerator
alpha-KetohexanoateGenerator
Α-ketohexanoateGenerator
Α-ketohexanoic acidGenerator
2-KetohexanoateGenerator
2-KetocaproateHMDB
alpha-Ketocaproic acid, sodium saltHMDB
2-Ketocaproic acidHMDB
2-oxo-HexanoateHMDB
2-oxo-Hexanoic acidHMDB
2-Ketohexanoic acidChEBI
Chemical FormulaC6H10O3
Average Mass130.1418 Da
Monoisotopic Mass130.06299 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 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
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental 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
Predicted Properties
PropertyValueSource
Water Solubility8.02 g/LALOGPS
logP0.94ALOGPS
logP1.66ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.82 m³·mol⁻¹ChemAxon
Polarizability13.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001864
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1620931
References
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 ]
  5. Chen H, Prater MB, Cai R, Dong F, Chen H, Minteer SD: Bioelectrocatalytic Conversion from N2 to Chiral Amino Acids in a H2/alpha-Keto Acid Enzymatic Fuel Cell. J Am Chem Soc. 2020 Feb 26;142(8):4028-4036. doi: 10.1021/jacs.9b13968. Epub 2020 Feb 12. [PubMed:32017556 ]
  6. Rea D, Hovington R, Rakus JF, Gerlt JA, Fulop V, Bugg TD, Roper DI: Crystal structure and functional assignment of YfaU, a metal ion dependent class II aldolase from Escherichia coli K12. Biochemistry. 2008 Sep 23;47(38):9955-65. doi: 10.1021/bi800943g. Epub 2008 Aug 29. [PubMed:18754683 ]