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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:17:57 UTC
Update Date2022-03-07 03:18:04 UTC
HMDB IDHMDB0112088
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Hexyl-2-furanhexanoic acid
Description5-Hexyl-2-furanhexanoic 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-Hexyl-2-furanhexanoic acid, in particular, can be described by the shorthand notation 6F6. This refers to its 6-carbon carboxyalkyl moiety, the non-methylated furan moiety, and its 6-carbon alkyl moiety. It has been identified in carp.
Structure
Data?1563873216
Synonyms
ValueSource
6-(5-Hexylfuran-2-yl)hexanoateGenerator
6F6SMPDB, HMDB
6-(5-hexyl-2-furyl)hexanoic acidSMPDB, HMDB
5-hexyl-2-furanhexanoic acidSMPDB
7,10-epoxy-7,9-hexadecadienoic acidSMPDB, HMDB
7,10-epoxyhexadeca-7,9-dienoic acidSMPDB, HMDB
6-(5-hexylfuran-2-yl)hexanoic acidSMPDB, HMDB
5-Hexyl-2-furanhexanoateGenerator
Chemical FormulaC16H26O3
Average Molecular Weight266.381
Monoisotopic Molecular Weight266.188194697
IUPAC Name6-(5-hexylfuran-2-yl)hexanoic acid
Traditional Name6-(5-hexylfuran-2-yl)hexanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCC1=CC=C(CCCCCC(O)=O)O1
InChI Identifier
InChI=1S/C16H26O3/c1-2-3-4-6-9-14-12-13-15(19-14)10-7-5-8-11-16(17)18/h12-13H,2-11H2,1H3,(H,17,18)
InChI KeyHPFDAHYFHAOXSC-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
logP5.25ALOGPS
logP4.79ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity76.39 m³·mol⁻¹ChemAxon
Polarizability32.97 ųChemAxon
Number of Rings1ChemAxon
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]+165.91331661259
DarkChem[M-H]-165.88431661259
DeepCCS[M+H]+175.00330932474
DeepCCS[M-H]-171.19930932474
DeepCCS[M-2H]-207.52830932474
DeepCCS[M+Na]+183.81830932474
AllCCS[M+H]+169.932859911
AllCCS[M+H-H2O]+166.532859911
AllCCS[M+NH4]+173.032859911
AllCCS[M+Na]+174.032859911
AllCCS[M-H]-173.332859911
AllCCS[M+Na-2H]-174.332859911
AllCCS[M+HCOO]-175.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Hexyl-2-furanhexanoic acidCCCCCCC1=CC=C(CCCCCC(O)=O)O13191.5Standard polar33892256
5-Hexyl-2-furanhexanoic acidCCCCCCC1=CC=C(CCCCCC(O)=O)O12035.3Standard non polar33892256
5-Hexyl-2-furanhexanoic acidCCCCCCC1=CC=C(CCCCCC(O)=O)O12022.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hexyl-2-furanhexanoic acid,1TMS,isomer #1CCCCCCC1=CC=C(CCCCCC(=O)O[Si](C)(C)C)O12136.5Semi standard non polar33892256
5-Hexyl-2-furanhexanoic acid,1TBDMS,isomer #1CCCCCCC1=CC=C(CCCCCC(=O)O[Si](C)(C)C(C)(C)C)O12371.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hexyl-2-furanhexanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9431000000-868e3eaa46f06e9448ed2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hexyl-2-furanhexanoic 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-Hexyl-2-furanhexanoic acid 10V, Negative-QTOFsplash10-014i-0090000000-1c460253ee8a98114c4b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 20V, Negative-QTOFsplash10-014j-1490000000-e46d47d559514f94e6d72019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 40V, Negative-QTOFsplash10-0a4m-9810000000-d72b15e890868319a6cf2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 10V, Negative-QTOFsplash10-00kb-0090000000-a43d33b757cb42eeac402021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 20V, Negative-QTOFsplash10-014j-1190000000-e2dc7262e69bdccaf8c92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 40V, Negative-QTOFsplash10-0abd-7910000000-db77be00ddb0fc7060402021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 10V, Positive-QTOFsplash10-0002-0090000000-6620d950382c676f6a582019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 20V, Positive-QTOFsplash10-00xs-9580000000-31bc19b35bfcc8c070442019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 40V, Positive-QTOFsplash10-052o-9400000000-e858dc229ae70b60d1272019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 10V, Positive-QTOFsplash10-014j-2190000000-39676845753168f9e73a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 20V, Positive-QTOFsplash10-00kb-9460000000-67cdd01614f7320c3fb62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyl-2-furanhexanoic acid 40V, Positive-QTOFsplash10-0a4l-9300000000-c450b94ce2f3576f059e2021-09-24Wishart 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131819624
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. Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.
  2. Vetter W, Ulms K, Wendlinger C, van Rijn J (2016). Novel non-methylated furan fatty acids in fish from a zero discharge aquaculture system. NFS Journal.