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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2020-02-26 21:34:26 UTC
HMDB IDHMDB0010727
Secondary Accession Numbers
  • HMDB10727
Metabolite Identification
Common Name3-Oxododecanoic acid
Description3-Oxododecanoic acid, also known as 3-oxododecanoate, 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. In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. 3-Oxododecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Oxododecanoic acid exists in all eukaryotes, ranging from yeast to humans. Within humans, 3-oxododecanoic acid participates in a number of enzymatic reactions. In particular, 3-oxododecanoic acid can be biosynthesized from capric acid and malonic acid through its interaction with the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In addition, 3-oxododecanoic acid can be converted into (R)-3-hydroxydodecanoic acid; which is catalyzed by the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In humans, 3-oxododecanoic acid is involved in fatty acid biosynthesis. 3-Oxo-Dodecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-Dodecanoic acid is converted form Malonic acid via three enzymes; 3-oxoacyl- synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II.
Structure
Data?1582752866
Synonyms
ValueSource
3-OxododecanoateKegg
3-oxo-DodecanoateHMDB
3-oxo-Dodecanoic acidHMDB
Chemical FormulaC12H22O3
Average Molecular Weight214.3013
Monoisotopic Molecular Weight214.15689457
IUPAC Name3-oxododecanoic acid
Traditional Name3-oxododecanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCC(=O)CC(O)=O
InChI Identifier
InChI=1S/C12H22O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h2-10H2,1H3,(H,14,15)
InChI KeyDZHSPYMHDVROSM-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
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Beta-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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP10(3.63) g/LALOGPS
logP10(3.81) g/LChemAxon
logS10(-3.7) g/LALOGPS
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 Count10ChemAxon
Refractivity59.37 m³·mol⁻¹ChemAxon
Polarizability25.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.42331661259
DarkChem[M-H]-152.52431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Oxododecanoic acidCCCCCCCCCC(=O)CC(O)=O2814.4Standard polar33892256
3-Oxododecanoic acidCCCCCCCCCC(=O)CC(O)=O1615.2Standard non polar33892256
3-Oxododecanoic acidCCCCCCCCCC(=O)CC(O)=O1708.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Oxododecanoic acid,1TMS,isomer #1CCCCCCCCCC(=O)CC(=O)O[Si](C)(C)C1754.2Semi standard non polar33892256
3-Oxododecanoic acid,1TMS,isomer #2CCCCCCCCCC(=CC(=O)O)O[Si](C)(C)C1886.7Semi standard non polar33892256
3-Oxododecanoic acid,1TMS,isomer #3CCCCCCCCC=C(CC(=O)O)O[Si](C)(C)C1831.1Semi standard non polar33892256
3-Oxododecanoic acid,2TMS,isomer #1CCCCCCCCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1911.2Semi standard non polar33892256
3-Oxododecanoic acid,2TMS,isomer #1CCCCCCCCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1915.2Standard non polar33892256
3-Oxododecanoic acid,2TMS,isomer #1CCCCCCCCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1898.9Standard polar33892256
3-Oxododecanoic acid,2TMS,isomer #2CCCCCCCCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1900.3Semi standard non polar33892256
3-Oxododecanoic acid,2TMS,isomer #2CCCCCCCCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1915.1Standard non polar33892256
3-Oxododecanoic acid,2TMS,isomer #2CCCCCCCCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1920.7Standard polar33892256
3-Oxododecanoic acid,1TBDMS,isomer #1CCCCCCCCCC(=O)CC(=O)O[Si](C)(C)C(C)(C)C1983.0Semi standard non polar33892256
3-Oxododecanoic acid,1TBDMS,isomer #2CCCCCCCCCC(=CC(=O)O)O[Si](C)(C)C(C)(C)C2118.9Semi standard non polar33892256
3-Oxododecanoic acid,1TBDMS,isomer #3CCCCCCCCC=C(CC(=O)O)O[Si](C)(C)C(C)(C)C2074.4Semi standard non polar33892256
3-Oxododecanoic acid,2TBDMS,isomer #1CCCCCCCCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2374.4Semi standard non polar33892256
3-Oxododecanoic acid,2TBDMS,isomer #1CCCCCCCCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2293.8Standard non polar33892256
3-Oxododecanoic acid,2TBDMS,isomer #1CCCCCCCCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2190.1Standard polar33892256
3-Oxododecanoic acid,2TBDMS,isomer #2CCCCCCCCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2352.3Semi standard non polar33892256
3-Oxododecanoic acid,2TBDMS,isomer #2CCCCCCCCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2297.5Standard non polar33892256
3-Oxododecanoic acid,2TBDMS,isomer #2CCCCCCCCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2200.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxododecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9200000000-c3efd5dc5b03f04d5bdb2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxododecanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g3-9040000000-3668255b2f3308081ded2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxododecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 10V, Positive-QTOFsplash10-014j-1950000000-a93157a72b9ef9268a8f2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 20V, Positive-QTOFsplash10-0gb9-4900000000-dfdb1c18d9ed356c3b1b2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 40V, Positive-QTOFsplash10-052f-9200000000-9004f44b40e94bab861e2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 10V, Negative-QTOFsplash10-03xr-1970000000-5274dbe54bd51692ba2f2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 20V, Negative-QTOFsplash10-014i-3910000000-634e12095801c51a66c12016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 40V, Negative-QTOFsplash10-0a4i-9400000000-1ce58855669db5a9dce82016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 10V, Positive-QTOFsplash10-01c1-9530000000-98a6253f27311a98a4302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 20V, Positive-QTOFsplash10-0aw9-9100000000-271715ab8449e8724e7d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 40V, Positive-QTOFsplash10-0apl-9000000000-029a41100e87196675282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 10V, Negative-QTOFsplash10-08fr-7190000000-208b6584cdde6bf12f212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 20V, Negative-QTOFsplash10-0a4i-9000000000-967cdd104e31119c88bb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxododecanoic acid 40V, Negative-QTOFsplash10-0006-9100000000-ee7cfdcb9eb86044d9f12021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027874
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02367
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439717
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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