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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-08-01 02:20:52 UTC
Update Date2022-03-07 03:18:01 UTC
HMDB IDHMDB0094711
Secondary Accession Numbers
  • HMDB94711
Metabolite Identification
Common Name9-Oxo-nonanoic acid
Description9-oxo-nonanoic acid, also known as 8-Formyloctanoic acid or 9-Ketononanoate, is classified as a member of the medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 9-oxo-nonanoic acid is considered to be a slightly soluble (in water) and a weak acidic compound. 9-oxo-nonanoic acid can be synthesized from nonanoic acid. 9-oxo-nonanoic acid can be synthesized into 1-hexadecanoyl-2-(9-oxononanoyl)-sn-glycero-3-phosphocholine. 9-oxo-nonanoic acid is a fatty acid lipid molecule. 9-oxo-nonanoic acid can be found in humans.
Structure
Data?1563871219
Synonyms
ValueSource
8-Formyloctanoic acidChEBI
9-Ketononanoic acidChEBI
8-FormyloctanoateGenerator
9-KetononanoateGenerator
9-OxononanoateGenerator
9-oxo-NonanoateGenerator
Chemical FormulaC9H16O3
Average Molecular Weight172.224
Monoisotopic Molecular Weight172.109944375
IUPAC Name9-oxononanoic acid
Traditional Name9-oxononanoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCCCCCCC=O
InChI Identifier
InChI=1S/C9H16O3/c10-8-6-4-2-1-3-5-7-9(11)12/h8H,1-7H2,(H,11,12)
InChI KeyWLGDDELKYAWBBL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Alpha-hydrogen aldehyde
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
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
logP2.23ALOGPS
logP1.67ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.76ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity45.62 m³·mol⁻¹ChemAxon
Polarizability19.53 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]+140.33231661259
DarkChem[M-H]-138.40531661259
DeepCCS[M+H]+144.62130932474
DeepCCS[M-H]-141.87130932474
DeepCCS[M-2H]-178.130932474
DeepCCS[M+Na]+153.62730932474
AllCCS[M+H]+139.532859911
AllCCS[M+H-H2O]+135.732859911
AllCCS[M+NH4]+143.032859911
AllCCS[M+Na]+144.032859911
AllCCS[M-H]-141.632859911
AllCCS[M+Na-2H]-143.232859911
AllCCS[M+HCOO]-145.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9-Oxo-nonanoic acidOC(=O)CCCCCCCC=O2513.4Standard polar33892256
9-Oxo-nonanoic acidOC(=O)CCCCCCCC=O1340.1Standard non polar33892256
9-Oxo-nonanoic acidOC(=O)CCCCCCCC=O1487.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9-Oxo-nonanoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCC=O1581.0Semi standard non polar33892256
9-Oxo-nonanoic acid,1TMS,isomer #2C[Si](C)(C)OC=CCCCCCCC(=O)O1680.3Semi standard non polar33892256
9-Oxo-nonanoic acid,2TMS,isomer #1C[Si](C)(C)OC=CCCCCCCC(=O)O[Si](C)(C)C1758.5Semi standard non polar33892256
9-Oxo-nonanoic acid,2TMS,isomer #1C[Si](C)(C)OC=CCCCCCCC(=O)O[Si](C)(C)C1736.6Standard non polar33892256
9-Oxo-nonanoic acid,2TMS,isomer #1C[Si](C)(C)OC=CCCCCCCC(=O)O[Si](C)(C)C1802.0Standard polar33892256
9-Oxo-nonanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC=O1811.8Semi standard non polar33892256
9-Oxo-nonanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=CCCCCCCC(=O)O1919.3Semi standard non polar33892256
9-Oxo-nonanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2198.8Semi standard non polar33892256
9-Oxo-nonanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2166.0Standard non polar33892256
9-Oxo-nonanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2042.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9-Oxo-nonanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-05r3-9300000000-3ca0fdf9f18c874f3f872017-09-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-Oxo-nonanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9720000000-4de47dafd69907ec18d32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-Oxo-nonanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Oxo-nonanoic acid LC-ESI-QTOF 6V, negative-QTOFsplash10-004i-1900000000-5c63ce21f6ad8c7b8d2f2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Oxo-nonanoic acid 6V, Negative-QTOFsplash10-004i-1900000000-466d99a6ce02b252155e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 10V, Negative-QTOFsplash10-00di-0900000000-e241dbd089ab81576fc62017-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 20V, Negative-QTOFsplash10-0uml-1900000000-9cf5a738610285626e912017-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 40V, Negative-QTOFsplash10-0006-9100000000-2e6d971d83892292a7ed2017-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-94a0fad0aeedd09445c52017-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 20V, Positive-QTOFsplash10-0a4i-4900000000-7f183c2043e913bac62f2017-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 40V, Positive-QTOFsplash10-0a5c-9000000000-073ae5119a4ca24443ab2017-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 10V, Positive-QTOFsplash10-001i-9500000000-0bc01618d60aeea2bd542021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 20V, Positive-QTOFsplash10-067i-9000000000-f4733ae0f68f5b47120a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 40V, Positive-QTOFsplash10-05mo-9000000000-8799ff5aa6e55a5c96132021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 10V, Negative-QTOFsplash10-00di-0900000000-6b6cc65f545584d290a52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 20V, Negative-QTOFsplash10-0umr-2900000000-f3331073c646145624972021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Oxo-nonanoic acid 40V, Negative-QTOFsplash10-0006-9100000000-0d79708302f92991ed1b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16322
BioCyc IDCPD-8686
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID78700
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. Ren R, Hashimoto T, Mizuno M, Takigawa H, Yoshida M, Azuma T, Kanazawa K: A lipid peroxidation product 9-oxononanoic acid induces phospholipase A2 activity and thromboxane A2 production in human blood. J Clin Biochem Nutr. 2013 May;52(3):228-33. doi: 10.3164/jcbn.12-110. Epub 2013 May 1. [PubMed:23704812 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.