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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:40:08 UTC
Update Date2022-03-07 02:52:46 UTC
HMDB IDHMDB0030972
Secondary Accession Numbers
  • HMDB30972
Metabolite Identification
Common Name8-Oxohexadecanoic acid
Description8-Oxohexadecanoic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Based on a literature review a small amount of articles have been published on 8-Oxohexadecanoic acid.
Structure
Data?1563862065
Synonyms
ValueSource
8-OxohexadecanoateGenerator
8-keto Palmitic acidHMDB
8-Ketopalmitic acidHMDB
8-Oxopalmitic acidHMDB
8-Keto palmitateGenerator
Chemical FormulaC16H30O3
Average Molecular Weight270.4076
Monoisotopic Molecular Weight270.219494826
IUPAC Name8-oxohexadecanoic acid
Traditional Name8-keto palmitic acid
CAS Registry Number2777-52-8
SMILES
CCCCCCCCC(=O)CCCCCCC(O)=O
InChI Identifier
InChI=1S/C16H30O3/c1-2-3-4-5-6-9-12-15(17)13-10-7-8-11-14-16(18)19/h2-14H2,1H3,(H,18,19)
InChI KeySEWAOKNHYLYQEL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Keto fatty acid
  • 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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point77 - 78 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0048 g/LALOGPS
logP4.91ALOGPS
logP5.08ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.55ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.72 m³·mol⁻¹ChemAxon
Polarizability34.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.07531661259
DarkChem[M-H]-170.87331661259
DeepCCS[M+H]+176.0430932474
DeepCCS[M-H]-172.02130932474
DeepCCS[M-2H]-209.11830932474
DeepCCS[M+Na]+185.06730932474
AllCCS[M+H]+173.832859911
AllCCS[M+H-H2O]+170.732859911
AllCCS[M+NH4]+176.732859911
AllCCS[M+Na]+177.532859911
AllCCS[M-H]-173.232859911
AllCCS[M+Na-2H]-174.332859911
AllCCS[M+HCOO]-175.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Oxohexadecanoic acidCCCCCCCCC(=O)CCCCCCC(O)=O3347.4Standard polar33892256
8-Oxohexadecanoic acidCCCCCCCCC(=O)CCCCCCC(O)=O2038.6Standard non polar33892256
8-Oxohexadecanoic acidCCCCCCCCC(=O)CCCCCCC(O)=O2112.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Oxohexadecanoic acid,1TMS,isomer #1CCCCCCCCC(=O)CCCCCCC(=O)O[Si](C)(C)C2197.2Semi standard non polar33892256
8-Oxohexadecanoic acid,1TMS,isomer #2CCCCCCCCC(=CCCCCCC(=O)O)O[Si](C)(C)C2294.3Semi standard non polar33892256
8-Oxohexadecanoic acid,1TMS,isomer #3CCCCCCCC=C(CCCCCCC(=O)O)O[Si](C)(C)C2295.8Semi standard non polar33892256
8-Oxohexadecanoic acid,2TMS,isomer #1CCCCCCCCC(=CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2324.7Semi standard non polar33892256
8-Oxohexadecanoic acid,2TMS,isomer #1CCCCCCCCC(=CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2316.3Standard non polar33892256
8-Oxohexadecanoic acid,2TMS,isomer #2CCCCCCCC=C(CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2334.7Semi standard non polar33892256
8-Oxohexadecanoic acid,2TMS,isomer #2CCCCCCCC=C(CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2315.0Standard non polar33892256
8-Oxohexadecanoic acid,1TBDMS,isomer #1CCCCCCCCC(=O)CCCCCCC(=O)O[Si](C)(C)C(C)(C)C2449.6Semi standard non polar33892256
8-Oxohexadecanoic acid,1TBDMS,isomer #2CCCCCCCCC(=CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2533.1Semi standard non polar33892256
8-Oxohexadecanoic acid,1TBDMS,isomer #3CCCCCCCC=C(CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2533.1Semi standard non polar33892256
8-Oxohexadecanoic acid,2TBDMS,isomer #1CCCCCCCCC(=CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2819.7Semi standard non polar33892256
8-Oxohexadecanoic acid,2TBDMS,isomer #1CCCCCCCCC(=CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2655.0Standard non polar33892256
8-Oxohexadecanoic acid,2TBDMS,isomer #2CCCCCCCC=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2827.9Semi standard non polar33892256
8-Oxohexadecanoic acid,2TBDMS,isomer #2CCCCCCCC=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2655.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Oxohexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5900000000-e7e31eb0025e73e5efa62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Oxohexadecanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g3-9640000000-b6c9960db3ec19e429642017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Oxohexadecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Oxohexadecanoic 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 - 8-Oxohexadecanoic acid 10V, Positive-QTOFsplash10-0fk9-0190000000-98808ddaff65ba607c982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 20V, Positive-QTOFsplash10-0itd-9660000000-00208552624c3cfa58a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 40V, Positive-QTOFsplash10-05mo-9300000000-5ca91a18a3ef1166f07f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 10V, Negative-QTOFsplash10-014i-0190000000-ddea81b5696d59ac80052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 20V, Negative-QTOFsplash10-014i-2790000000-db2f1f28391c409bc05a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 40V, Negative-QTOFsplash10-0a4i-9600000000-dbbeae69747de259003e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 10V, Positive-QTOFsplash10-0uki-0190000000-a5786731582118a26c432021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 20V, Positive-QTOFsplash10-00dm-9520000000-153d7ca45b52a9d4d73e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 40V, Positive-QTOFsplash10-0a4l-9100000000-b24ce578ead0ab58902c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 10V, Negative-QTOFsplash10-014i-0090000000-585ee0bd5ea12d4dac902021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 20V, Negative-QTOFsplash10-014i-0290000000-fd73438e47d77d44e2d52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Oxohexadecanoic acid 40V, Negative-QTOFsplash10-0bvl-9700000000-d00c114c2acb23a63e8f2021-09-25Wishart 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 IDFDB002960
KNApSAcK IDNot Available
Chemspider ID4446128
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283001
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 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.