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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-07 19:57:16 UTC
Update Date2022-03-07 03:18:04 UTC
HMDB IDHMDB0112067
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,4-Dimethyl-5-pentyl-2-furandecanoic acid
Description3,4-Dimethyl-5-pentyl-2-furandecanoic 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. 3,4-Dimethyl-5-pentyl-2-furandecanoic acid, in particular, can be described by the shorthand notation 10D5. This refers to its 10-carbon carboxyalkyl moiety, the dimethyl substitutions in the 3- and 4-positions of its furan moiety, and its 5-carbon alkyl moiety. It has been identified in the fish liver.
Structure
Data?1563873214
Synonyms
ValueSource
10-(3,4-Dimethyl-5-pentylfuran-2-yl)-decanoateGenerator
10D5SMPDB, HMDB
DiMe(10,5)SMPDB, HMDB
10-(3,4-dimethyl-5-pentyl-2-furyl)decanoic acidSMPDB, HMDB
3,4-dimethyl-5-pentyl-2-furandecanoic acidSMPDB
11,14-epoxy-12,13-dimethyl-11,13-nonadecadienoic acidSMPDB, HMDB
11,14-epoxy-12,13-dimethylnonadeca-11,13-dienoic acidSMPDB, HMDB
10-(3,4-dimethyl-5-pentylfuran-2-yl)decanoic acidSMPDB, HMDB
10-(3,4-Dimethyl-5-pentylfuran-2-yl)decanoateGenerator, HMDB
3,4-Dimethyl-5-pentyl-2-furandecanoateGenerator
Chemical FormulaC21H36O3
Average Molecular Weight336.516
Monoisotopic Molecular Weight336.266445019
IUPAC Name10-(3,4-dimethyl-5-pentylfuran-2-yl)decanoic acid
Traditional Name10-(3,4-dimethyl-5-pentylfuran-2-yl)decanoic acid
CAS Registry Number116627-45-3
SMILES
CCCCCC1=C(C)C(C)=C(CCCCCCCCCC(O)=O)O1
InChI Identifier
InChI=1S/C21H36O3/c1-4-5-11-14-19-17(2)18(3)20(24-19)15-12-9-7-6-8-10-13-16-21(22)23/h4-16H2,1-3H3,(H,22,23)
InChI KeySWOLPSUMESXJAB-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
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
logP6.7ALOGPS
logP7.15ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity100.28 m³·mol⁻¹ChemAxon
Polarizability43.52 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]+186.62231661259
DarkChem[M-H]-183.98431661259
DeepCCS[M+H]+195.40830932474
DeepCCS[M-H]-193.01530932474
DeepCCS[M-2H]-226.06130932474
DeepCCS[M+Na]+201.75130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Dimethyl-5-pentyl-2-furandecanoic acidCCCCCC1=C(C)C(C)=C(CCCCCCCCCC(O)=O)O13628.7Standard polar33892256
3,4-Dimethyl-5-pentyl-2-furandecanoic acidCCCCCC1=C(C)C(C)=C(CCCCCCCCCC(O)=O)O12431.0Standard non polar33892256
3,4-Dimethyl-5-pentyl-2-furandecanoic acidCCCCCC1=C(C)C(C)=C(CCCCCCCCCC(O)=O)O12521.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dimethyl-5-pentyl-2-furandecanoic acid,1TMS,isomer #1CCCCCC1=C(C)C(C)=C(CCCCCCCCCC(=O)O[Si](C)(C)C)O12611.7Semi standard non polar33892256
3,4-Dimethyl-5-pentyl-2-furandecanoic acid,1TBDMS,isomer #1CCCCCC1=C(C)C(C)=C(CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O12863.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-009f-9483000000-8b3d2357245db2675f542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic 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 - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 10V, Positive-QTOFsplash10-014i-0029000000-cc17bbce2fed727a62372019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 20V, Positive-QTOFsplash10-014i-5694000000-d95a4b0336a21e4a56862019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 40V, Positive-QTOFsplash10-066v-9440000000-dbca3fc6a9ab1935808a2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 10V, Negative-QTOFsplash10-000i-0019000000-65ba948e291fb2fe46b12019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 20V, Negative-QTOFsplash10-00n3-1369000000-7e64130578fb5f75e1702019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 40V, Negative-QTOFsplash10-0adi-7950000000-da54b113ad170c662f022019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 10V, Positive-QTOFsplash10-0gbi-0229000000-b16bcfed0abfb76019d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 20V, Positive-QTOFsplash10-0fy9-3955000000-ddc59684f7c857d703f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 40V, Positive-QTOFsplash10-0a5c-9300000000-1139acdbc0ed6cac262e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 10V, Negative-QTOFsplash10-000i-0009000000-8097d552710e34d9e2722021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 20V, Negative-QTOFsplash10-00kr-0039000000-da4019588066b133c0c92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furandecanoic acid 40V, Negative-QTOFsplash10-000f-4591000000-2033fe960daa5ac0f0ac2021-09-23Wishart 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 Compound85564630
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. 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.