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Record Information
Version4.0
Creation Date2008-10-15 12:12:16 UTC
Update Date2017-09-27 08:26:25 UTC
HMDB IDHMDB0010730
Secondary Accession Numbers
  • HMDB10730
Metabolite Identification
Common Name3-Oxotetradecanoic acid
Description3-Oxo-tetradecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-tetradecanoic 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). In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation.
Structure
Thumb
Synonyms
ValueSource
3-Oxomyristic acidChEBI
3-OxomyristateGenerator
3-OxotetradecanoateGenerator
3-oxo-TetradecanoateHMDB
3-oxo-Tetradecanoic acidHMDB
Chemical FormulaC14H26O3
Average Molecular Weight242.3544
Monoisotopic Molecular Weight242.188194698
IUPAC Name3-oxotetradecanoic acid
Traditional Name3-oxotetradecanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCC(=O)CC(O)=O
InChI Identifier
InChI=1S/C14H26O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h2-12H2,1H3,(H,16,17)
InChI KeyXLKOZYOVXNPWGT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Beta-keto acid
  • Keto fatty acid
  • Beta-hydroxy ketone
  • Keto acid
  • 1,3-dicarbonyl compound
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

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 Solubility0.0047 g/LALOGPS
logP4.58ALOGPS
logP4.7ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity68.57 m³·mol⁻¹ChemAxon
Polarizability29.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0290000000-8e607f12b728cd17d0ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-4920000000-4703c7195a11feeb2b5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-a7e2659c4534794225d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-1890000000-62a40531fb987abfd8b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3910000000-d4867d427aeab7a02553View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-4b25931f846416282ccaView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Fatty Acid BiosynthesisPw000167Pw000167 greyscalePw000167 simpleNot Available
Displaying 1 entry
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Bothnon-inflamed (NI) control anaemic details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
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 IDFDB027877
KNApSAcK IDNot Available
Chemspider ID399829
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound454064
PDB IDNot Available
ChEBI ID37270
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]

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