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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2014-04-11 22:16:46 UTC
Update Date2020-09-25 17:35:24 UTC
HMDB IDHMDB0061649
Secondary Accession Numbers
  • HMDB61649
Metabolite Identification
Common Name3,4-Dimethyl-5-pentyl-2-furantridecanoic acid
Description3,​4-​dimethyl-​5-​pentyl-2-​furantridecanoic 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-​furantridecanoic acid, in particular, can be described by the shorthand notation 13D5. This refers to its 13-carbon carboxyalkyl moiety, the dimethyl substitutions in the 3- and 4-positions of its furan moiety, and its 5-carbon alkyl moiety.
Structure
Data?1563866215
Synonyms
ValueSource
3,​4-​dimethyl-​5-​pentyl-2-​furantridecanoateGenerator
13D5HMDB
DiMe(13,5)HMDB
F8 acidHMDB
13-(3,4-Dimethyl-5-pentyl-2-furyl)tridecanoic acidHMDB
14,17-Epoxy-15,16-dimethyl-14,16-docosadienoic acidHMDB
14,17-Epoxy-15,16-dimethyldocosa-14,16-dienoic acidHMDB
13-(3,4-Dimethyl-5-pentylfuran-2-yl)tridecanoic acidHMDB
3,​4-​dimethyl-​5-​pentyl-2-​furantridecanoic acidSMPDB
14,17-epoxy-15,16-dimethyldocosa-14,16-dienoic acid SMPDB, HMDB
13-(3,4-Dimethyl-5-pentylfuran-2-yl)tridecanoateGenerator
13-(3,4-Dimethyl-5-pentylfuran-2-yl)-tridecanoateGenerator
Chemical FormulaC24H42O3
Average Molecular Weight378.5885
Monoisotopic Molecular Weight378.31339521
IUPAC Name13-(3,4-dimethyl-5-pentylfuran-2-yl)tridecanoic acid
Traditional Name13-(3,4-dimethyl-5-pentylfuran-2-yl)tridecanoic acid
CAS Registry Number57818-43-6
SMILES
CCCCCC1=C(C)C(C)=C(CCCCCCCCCCCCC(O)=O)O1
InChI Identifier
InChI=1S/C24H42O3/c1-4-5-14-17-22-20(2)21(3)23(27-22)18-15-12-10-8-6-7-9-11-13-16-19-24(25)26/h4-19H2,1-3H3,(H,25,26)
InChI KeyRCISJPUCXSEESK-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
  • Furanoid fatty acid
  • Heterocyclic fatty acid
  • Furan
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP7.65ALOGPS
logP8.49ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity114.08 m³·mol⁻¹ChemAxon
Polarizability49.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5494000000-28b5e17647e2b8f81965Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bl-7394100000-7d58ce07aea90c26992aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-86fb776738fba082ce6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07yi-4849000000-8e468648ee30c0632d8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07be-9750000000-c022cb33a06d6c5fb0cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-a1021272f7e080735d21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1209000000-c98add1f314b6c60cd7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adi-7923000000-44fee4afffb402cbcaddSpectrum
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 Compound71443942
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Spiteller G: Furan fatty acids: occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet? Lipids. 2005 Aug;40(8):755-71. [PubMed:16296395 ]
  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.
  7. The AOCS Lipid Library [Link]