Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:09 UTC
Update Date2022-03-07 02:52:50 UTC
HMDB IDHMDB0031126
Secondary Accession Numbers
  • HMDB31126
Metabolite Identification
Common Name3,4-Dimethyl-5-pentyl-2-furanundecanoic acid
Description3,​4-​dimethyl-​5-​pentyl-2-​furanundecanoic 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-​furanundecanoic acid, in particular, can be described by the shorthand notation 11D5. This refers to its 11-carbon carboxyalkyl moiety, the dimethyl substitutions in the 3- and 4-positions of its furan moiety, and its 5-carbon alkyl moiety. It is found in animal foods, fish lipids, and is a component of F acid fraction present in beef blood serum.
Structure
Data?1563862085
Synonyms
ValueSource
3,4-Dimethyl-5-pentyl-2-furanundecanoateGenerator
12,15-Epoxy-13,14-dimethyleicosa-12,14-dienoic acidHMDB
DiMe(11,5)HMDB
F6 acidHMDB
Furanoid F-acid F6MeSH
Chemical FormulaC22H38O3
Average Molecular Weight350.5353
Monoisotopic Molecular Weight350.282095082
IUPAC Name11-(3,4-dimethyl-5-pentylfuran-2-yl)undecanoic acid
Traditional Name11-(3,4-dimethyl-5-pentylfuran-2-yl)undecanoic acid
CAS Registry Number57818-36-7
SMILES
CCCCCC1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O1
InChI Identifier
InChI=1S/C22H38O3/c1-4-5-12-15-20-18(2)19(3)21(25-20)16-13-10-8-6-7-9-11-14-17-22(23)24/h4-17H2,1-3H3,(H,23,24)
InChI KeyMCTXSZNBSIMKTO-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00022 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP7ALOGPS
logP7.6ChemAxon
logS-5.2ALOGPS
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 Count15ChemAxon
Refractivity104.88 m³·mol⁻¹ChemAxon
Polarizability45.73 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]+190.10131661259
DarkChem[M-H]-189.0331661259
DeepCCS[M+H]+198.530932474
DeepCCS[M-H]-196.14230932474
DeepCCS[M-2H]-229.04930932474
DeepCCS[M+Na]+204.73930932474
AllCCS[M+H]+197.532859911
AllCCS[M+H-H2O]+194.932859911
AllCCS[M+NH4]+200.032859911
AllCCS[M+Na]+200.732859911
AllCCS[M-H]-196.632859911
AllCCS[M+Na-2H]-198.632859911
AllCCS[M+HCOO]-201.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Dimethyl-5-pentyl-2-furanundecanoic acidCCCCCC1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O13759.0Standard polar33892256
3,4-Dimethyl-5-pentyl-2-furanundecanoic acidCCCCCC1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O12525.7Standard non polar33892256
3,4-Dimethyl-5-pentyl-2-furanundecanoic acidCCCCCC1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O12620.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dimethyl-5-pentyl-2-furanundecanoic acid,1TMS,isomer #1CCCCCC1=C(C)C(C)=C(CCCCCCCCCCC(=O)O[Si](C)(C)C)O12717.7Semi standard non polar33892256
3,4-Dimethyl-5-pentyl-2-furanundecanoic acid,1TBDMS,isomer #1CCCCCC1=C(C)C(C)=C(CCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O12970.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-4291000000-506436a626ecbea165322017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05di-8393100000-6dbb13ee662c52466ab82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic 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-furanundecanoic acid 10V, Positive-QTOFsplash10-0ue9-0019000000-11144e269538532e83362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 20V, Positive-QTOFsplash10-0aor-5897000000-5b2f923335c4dcbe01d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 40V, Positive-QTOFsplash10-066u-9840000000-91d3449fab1ba02a393f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 10V, Negative-QTOFsplash10-0002-0009000000-70d08ea419435b7f396b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 20V, Negative-QTOFsplash10-052b-1329000000-5e144399635b4d427bd72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 40V, Negative-QTOFsplash10-0ab9-8950000000-36add8f7dadbf0aa9b612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 10V, Positive-QTOFsplash10-0fsi-0129000000-078583666869a14d64fe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 20V, Positive-QTOFsplash10-0pyi-6569000000-3af1ec89b43aa3567da92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 40V, Positive-QTOFsplash10-0a4i-9300000000-3406ce2e3ea994f0ddbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 10V, Negative-QTOFsplash10-0002-0009000000-728bbc6fc65dc4787c442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 20V, Negative-QTOFsplash10-000t-0019000000-568e4035f9042f3013d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid 40V, Negative-QTOFsplash10-0006-6972000000-7566e01aca32a422f40c2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB003137
KNApSAcK IDNot Available
Chemspider ID23255373
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13963867
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1636731
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.