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Record Information
Version3.6
Creation Date2008-10-15 12:12:16 UTC
Update Date2016-02-11 01:20:07 UTC
HMDB IDHMDB10733
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Oxohexadecanoic acid
DescriptionIn humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. 3-Oxo-hexadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-hexadecanoic acid is converted from Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179).
Structure
Thumb
Synonyms
ValueSource
3-keto Palmitic acidChEBI
3-keto PalmitateGenerator
3-OxohexadecanoateGenerator
3-oxo-HexadecanoateHMDB
3-oxo-Hexadecanoic acidHMDB
Chemical FormulaC16H30O3
Average Molecular Weight270.4076
Monoisotopic Molecular Weight270.219494826
IUPAC Name3-oxohexadecanoic acid
Traditional Name3-oxohexadecanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC(=O)CC(O)=O
InChI Identifier
InChI=1S/C16H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h2-14H2,1H3,(H,18,19)
InChI KeyInChIKey=ASICPMTWQSESKX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as keto fatty acids. These are fatty acids containing a ketone group attached to the acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentKeto fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Keto fatty acid
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Keto acid
  • Beta-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0012 mg/mLALOGPS
logP5.59ALOGPS
logP5.59ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.78 m3·mol-1ChemAxon
Polarizability33.9 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027880
KNApSAcK IDNot Available
Chemspider ID4446124
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10733
Metagene LinkHMDB10733
METLIN IDNot Available
PubChem Compound5282997
PDB IDNot Available
ChEBI ID37251
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06
General function:
Involved in catalytic activity
Specific function:
May play a role in the biosynthesis of lipoic acid as well as longer chain fatty acids required for optimal mitochondrial function.
Gene Name:
OXSM
Uniprot ID:
Q9NWU1
Molecular weight:
40034.535