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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:20:43 UTC
Update Date2022-03-07 03:18:05 UTC
HMDB IDHMDB0112102
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-pentyl-2-furannonanoic acid
Description5-pentyl-2-furannonanoic acid is a furan fatty acid (F-acid). F-acids are heterocyclic fatty acids containing a central furan moiety with a carboxylalkyl chain (mostly 7, 9, 11, or 13 carbons) in the 2-position and an alkyl chain (mostly 3 or 5 carbons) in the 5-position. Despite being found in low concentrations in food lipids, they are excellent antixoxidants and radical scavengers. This allows them to play an important role in preventing lipid peroxidation and protecting polyunsaturated fatty acids. They are often incorporated into phospholipids and cholesterol esters of fish and other marine organisms. 5-pentyl-2-furannonanoic acid, in particular, can be described by the shorthand notation 9F5. This refers to its 9-carbon carboxyalkyl moiety, the non-methylated furan moiety, and its 5-carbon alkyl moiety. It has been identified in carp.
Structure
Data?1563873218
Synonyms
ValueSource
9-(5-Pentylfuran-2-yl)-nonanoateGenerator
9F5SMPDB, HMDB
9-(5-pentyl-2-furyl)nonanoic acidSMPDB, HMDB
5-pentyl-2-furannonanoic acidSMPDB
10,13-epoxy-10,12-octadecadienoic acidSMPDB, HMDB
10,13-epoxyoctadeca-10,12-dienoic acidSMPDB, HMDB
9-(5-pentylfuran-2-yl)nonanoic acidSMPDB, HMDB
9-(5-Pentylfuran-2-yl)nonanoateGenerator, HMDB
5-Pentyl-2-furannonanoateGenerator
Chemical FormulaC18H30O3
Average Molecular Weight294.435
Monoisotopic Molecular Weight294.219494826
IUPAC Name9-(5-pentylfuran-2-yl)nonanoic acid
Traditional Name9-(5-pentylfuran-2-yl)nonanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC=C(CCCCCCCCC(O)=O)O1
InChI Identifier
InChI=1S/C18H30O3/c1-2-3-8-11-16-14-15-17(21-16)12-9-6-4-5-7-10-13-18(19)20/h14-15H,2-13H2,1H3,(H,19,20)
InChI KeyBJTONYHCPUUWFX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentFuranoid fatty acids
Alternative Parents
Substituents
  • Furanoid fatty acid
  • Medium-chain fatty acid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
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
logP6.09ALOGPS
logP5.68ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity85.59 m³·mol⁻¹ChemAxon
Polarizability37.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.70931661259
DarkChem[M-H]-173.55131661259
DeepCCS[M+H]+179.93830932474
DeepCCS[M-H]-176.48630932474
DeepCCS[M-2H]-212.31230932474
DeepCCS[M+Na]+188.60130932474
AllCCS[M+H]+179.532859911
AllCCS[M+H-H2O]+176.432859911
AllCCS[M+NH4]+182.432859911
AllCCS[M+Na]+183.332859911
AllCCS[M-H]-181.832859911
AllCCS[M+Na-2H]-183.132859911
AllCCS[M+HCOO]-184.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-pentyl-2-furannonanoic acidCCCCCC1=CC=C(CCCCCCCCC(O)=O)O13413.8Standard polar33892256
5-pentyl-2-furannonanoic acidCCCCCC1=CC=C(CCCCCCCCC(O)=O)O12221.0Standard non polar33892256
5-pentyl-2-furannonanoic acidCCCCCC1=CC=C(CCCCCCCCC(O)=O)O12221.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-pentyl-2-furannonanoic acid,1TMS,isomer #1CCCCCC1=CC=C(CCCCCCCCC(=O)O[Si](C)(C)C)O12338.4Semi standard non polar33892256
5-pentyl-2-furannonanoic acid,1TBDMS,isomer #1CCCCCC1=CC=C(CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O12575.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-pentyl-2-furannonanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fic-9642000000-b13e8b765eb5b82945982017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-pentyl-2-furannonanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8980000000-318307d21f98d5602dba2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-pentyl-2-furannonanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-pentyl-2-furannonanoic 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 - 5-pentyl-2-furannonanoic acid 10V, Negative-QTOFsplash10-0006-0090000000-0ca2e152c8c0f191ed162019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 20V, Negative-QTOFsplash10-002g-1290000000-3c4cb9a1a3e3f9bd5eb42019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 40V, Negative-QTOFsplash10-0a4m-9620000000-104e833259fd977e918b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 10V, Negative-QTOFsplash10-0006-0090000000-622b0481e999bad50a592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 20V, Negative-QTOFsplash10-002f-1190000000-1a7338100b3d159a09f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 40V, Negative-QTOFsplash10-0596-7930000000-7a3d82b42088a7be10d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 10V, Positive-QTOFsplash10-004j-0090000000-4f919ef4dbd6f36b51a02019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 20V, Positive-QTOFsplash10-054k-7590000000-5c688f7e60ea1240be8e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 40V, Positive-QTOFsplash10-0a4u-9310000000-93ec3ab3490de172417c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 10V, Positive-QTOFsplash10-054t-2490000000-a9acb230cb918b9dd2802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 20V, Positive-QTOFsplash10-0a70-8940000000-30d7d47f78f83d3327692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 40V, Positive-QTOFsplash10-0apl-9300000000-0902754a43825ecb81952021-09-22Wishart 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53685760
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. Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.
  6. Wahl HG, Liebich HM, Hoffmann A (1994). Identification of fatty acid methyl esters as minor components of fish oil by multidimensional GC-MSD: New furan fatty acids. Journal of High Resolution Chromatography.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.