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Showing metabocard for Ethyl pentyl ketone (HMDB0031295)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:10 UTC
Update Date2023-02-21 17:20:17 UTC
HMDB IDHMDB0031295
Secondary Accession Numbers
  • HMDB31295
Metabolite Identification
Common NameEthyl pentyl ketone
DescriptionEthyl pentyl ketone, also known as 3-oxooctane or EAK, 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, ethyl pentyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group. Ethyl pentyl ketone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Ethyl pentyl ketone has been detected, but not quantified, in cardamoms and lemons. This could make ethyl pentyl ketone a potential biomarker for the consumption of these foods. Ethyl pentyl ketone, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1677000017
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031295 (Ethyl pentyl ketone)

  Mrv1652303202019012D          

  9  8  0  0  0  0            999 V2000
    0.6336   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
M  END
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3D MOL for HMDB0031295 (Ethyl pentyl ketone)

HMDB0031295
     RDKit          3D
Ethyl pentyl ketone
 25 24  0  0  0  0  0  0  0  0999 V2000
    3.9298    0.2350    0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    0.5905   -0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7320   -0.5219   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -0.1322   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622    0.1990    0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8425    0.5598   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827    1.6965   -0.3818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911   -0.4918   -0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253   -0.3515    0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    0.2484   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0493   -0.7464    0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    1.0716    0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5124    1.4517   -0.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079    0.8762    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803   -1.4077   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.8276   -1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2528   -0.9108   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    0.7700   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382    1.0746    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -0.6823    0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637   -1.5256   -0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4880   -0.3362   -1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480    0.7280    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4465   -0.9714    1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760   -0.5961    0.6417 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
  6  7  2  0
  6  8  1  0
  8  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
  5 19  1  0
  5 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
M  END
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3D SDF for HMDB0031295 (Ethyl pentyl ketone)

  Mrv1652303202019012D          

  9  8  0  0  0  0            999 V2000
    0.6336   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031295

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(=O)CC

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3

> <INCHI_KEY>
RHLVCLIPMVJYKS-UHFFFAOYSA-N

> <FORMULA>
C8H16O

> <MOLECULAR_WEIGHT>
128.212

> <EXACT_MASS>
128.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.283690500006315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octan-3-one

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.841057497333334

> <ALOGPS_LOGS>
-1.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.340913554139979

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
39.2516

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-octanone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031295 (Ethyl pentyl ketone)

HMDB0031295
     RDKit          3D
Ethyl pentyl ketone
 25 24  0  0  0  0  0  0  0  0999 V2000
    3.9298    0.2350    0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    0.5905   -0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7320   -0.5219   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -0.1322   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622    0.1990    0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8425    0.5598   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827    1.6965   -0.3818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911   -0.4918   -0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253   -0.3515    0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    0.2484   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0493   -0.7464    0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    1.0716    0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5124    1.4517   -0.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079    0.8762    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803   -1.4077   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.8276   -1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2528   -0.9108   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    0.7700   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382    1.0746    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -0.6823    0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637   -1.5256   -0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4880   -0.3362   -1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480    0.7280    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4465   -0.9714    1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760   -0.5961    0.6417 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
  6  7  2  0
  6  8  1  0
  8  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
  5 19  1  0
  5 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
M  END
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PDB for HMDB0031295 (Ethyl pentyl ketone)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       1.183  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.518  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.185  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.517  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.851  -0.564   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.851   0.976   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    4    7    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0031295 (Ethyl pentyl ketone)

COMPND    HMDB0031295
HETATM    1  C1  UNL     1       3.930   0.235   0.238  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.487   0.590  -0.036  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.732  -0.522  -0.705  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.303  -0.132  -0.957  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.462   0.199   0.314  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.842   0.560  -0.124  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.183   1.697  -0.382  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.891  -0.492  -0.267  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.825  -0.352   0.916  1.00  0.00           C  
HETATM   10  H1  UNL     1       4.561   0.248  -0.668  1.00  0.00           H  
HETATM   11  H2  UNL     1       4.049  -0.746   0.734  1.00  0.00           H  
HETATM   12  H3  UNL     1       4.337   1.072   0.874  1.00  0.00           H  
HETATM   13  H4  UNL     1       2.512   1.452  -0.766  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.008   0.876   0.896  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.780  -1.408  -0.032  1.00  0.00           H  
HETATM   16  H7  UNL     1       2.160  -0.828  -1.675  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.253  -0.911  -1.482  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.316   0.770  -1.599  1.00  0.00           H  
HETATM   19  H10 UNL     1      -0.038   1.075   0.851  1.00  0.00           H  
HETATM   20  H11 UNL     1      -0.560  -0.682   0.977  1.00  0.00           H  
HETATM   21  H12 UNL     1      -2.464  -1.526  -0.248  1.00  0.00           H  
HETATM   22  H13 UNL     1      -3.488  -0.336  -1.194  1.00  0.00           H  
HETATM   23  H14 UNL     1      -3.848   0.728   1.182  1.00  0.00           H  
HETATM   24  H15 UNL     1      -3.447  -0.971   1.737  1.00  0.00           H  
HETATM   25  H16 UNL     1      -4.876  -0.596   0.642  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   19   20
CONECT    6    7    7    8
CONECT    8    9   21   22
CONECT    9   23   24   25
END
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SMILES for HMDB0031295 (Ethyl pentyl ketone)

CCCCCC(=O)CC
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INCHI for HMDB0031295 (Ethyl pentyl ketone)

InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-OxooctaneChEBI
Amyl ethyl ketoneChEBI
EAKChEBI
Ethyl amyl ketoneChEBI
Ethyl N-amyl ketoneChEBI
Ethyl N-pentyl ketoneChEBI
N-Amyl ethyl ketoneChEBI
Octan-3-oneChEBI
3-OctanonHMDB
3-OctanoneHMDB
Ethyl N-amylketoneHMDB
FEMA 2803HMDB
N-Octanone-3HMDB
Ethyl pentyl ketoneChEBI
Chemical FormulaC8H16O
Average Molecular Weight128.212
Monoisotopic Molecular Weight128.120115134
IUPAC Nameoctan-3-one
Traditional Name3-octanone
CAS Registry Number106-68-3
SMILES
CCCCCC(=O)CC
InChI Identifier
InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3
InChI KeyRHLVCLIPMVJYKS-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
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-23.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point167.00 to 170.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.6 mg/mL at 20 °CNot Available
LogP2.506 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Treated celiac disease		 details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005050
KNApSAcK IDC00034765
Chemspider ID215929
KEGG Compound IDC17145
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Octanone
METLIN IDNot Available
PubChem Compound246728
PDB IDNot Available
ChEBI ID80946
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004231
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.. .