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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-07 19:58:22 UTC
Update Date2022-03-07 03:18:04 UTC
HMDB IDHMDB0112072
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Butyl-3,4-dimethyl-2-furanundecanoic acid
Description5-Butyl-3,4-dimethyl-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. 5-Butyl-3,4-dimethyl-2-furanundecanoic acid, in particular, can be described by the shorthand notation 11D4. This refers to its 11-carbon carboxyalkyl moiety, the dimethyl substitutions in the 3- and 4-positions of its furan moiety, and its 4-carbon alkyl moiety. It has been identified in the fish liver.
Structure
Data?1563873214
Synonyms
ValueSource
11-(3,4-Dimethyl-5-butylfuran-2-yl)-undecanoateGenerator
11D4SMPDB, HMDB
DiMe(11,4)SMPDB, HMDB
11-(5-butyl-3,4-dimethyl-2-furyl)undecanoic acidSMPDB, HMDB
5-butyl-3,4-dimethyl-2-furanundecanoic acidSMPDB
12,15-epoxy-13,14-dimethyl-12,14-nonadecadienoic acidSMPDB, HMDB
12,15-epoxy-13,14-dimethylnonadeca-12,14-dienoic acidSMPDB, HMDB
11-(5-butyl-3,4-dimethylfuran-2-yl)undecanoic acidSMPDB, HMDB
11-(5-Butyl-3,4-dimethylfuran-2-yl)undecanoateGenerator, HMDB
5-Butyl-3,4-dimethyl-2-furanundecanoateGenerator
Chemical FormulaC21H36O3
Average Molecular Weight336.516
Monoisotopic Molecular Weight336.266445019
IUPAC Name11-(5-butyl-3,4-dimethylfuran-2-yl)undecanoic acid
Traditional Name11-(5-butyl-3,4-dimethylfuran-2-yl)undecanoic acid
CAS Registry Number107473-41-6
SMILES
CCCCC1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O1
InChI Identifier
InChI=1S/C21H36O3/c1-4-5-14-19-17(2)18(3)20(24-19)15-12-10-8-6-7-9-11-13-16-21(22)23/h4-16H2,1-3H3,(H,22,23)
InChI KeyHHLJTVKQHLQNRZ-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
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
logP6.72ALOGPS
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
Polarizability43.53 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]+182.7431661259
DarkChem[M-H]-183.80831661259
DeepCCS[M+H]+192.83830932474
DeepCCS[M-H]-190.4830932474
DeepCCS[M-2H]-223.42130932474
DeepCCS[M+Na]+199.1130932474
AllCCS[M+H]+193.032859911
AllCCS[M+H-H2O]+190.332859911
AllCCS[M+NH4]+195.632859911
AllCCS[M+Na]+196.332859911
AllCCS[M-H]-192.932859911
AllCCS[M+Na-2H]-194.732859911
AllCCS[M+HCOO]-196.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Butyl-3,4-dimethyl-2-furanundecanoic acidCCCCC1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O13626.6Standard polar33892256
5-Butyl-3,4-dimethyl-2-furanundecanoic acidCCCCC1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O12435.5Standard non polar33892256
5-Butyl-3,4-dimethyl-2-furanundecanoic acidCCCCC1=C(C)C(C)=C(CCCCCCCCCCC(O)=O)O12527.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Butyl-3,4-dimethyl-2-furanundecanoic acid,1TMS,isomer #1CCCCC1=C(C)C(C)=C(CCCCCCCCCCC(=O)O[Si](C)(C)C)O12624.7Semi standard non polar33892256
5-Butyl-3,4-dimethyl-2-furanundecanoic acid,1TBDMS,isomer #1CCCCC1=C(C)C(C)=C(CCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O12879.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00vu-8693000000-7fea695477a7c24685ba2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Butyl-3,4-dimethyl-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 - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 10V, Positive-QTOFsplash10-014i-0029000000-7767e8fdbee1641537602019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 20V, Positive-QTOFsplash10-0f96-4984000000-dbebc160d67ec398c0d12019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 40V, Positive-QTOFsplash10-0udm-9650000000-3eae349837b0684e1b182019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 10V, Negative-QTOFsplash10-000i-0019000000-0738b3e7d72e37c2af562019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 20V, Negative-QTOFsplash10-014u-1369000000-236b9f7ad345f1dd62852019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 40V, Negative-QTOFsplash10-0ab9-7950000000-560228825485443e867e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 10V, Negative-QTOFsplash10-000i-0009000000-8097d552710e34d9e2722021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 20V, Negative-QTOFsplash10-00kr-0029000000-4befd8b0f6c8316779022021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 40V, Negative-QTOFsplash10-0006-5962000000-1928f1f9cd52ddc37d792021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 10V, Positive-QTOFsplash10-0gbi-0239000000-460be721318174cd66672021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 20V, Positive-QTOFsplash10-1029-6977000000-0ab460a94aac60a266802021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furanundecanoic acid 40V, Positive-QTOFsplash10-0a4i-9500000000-b63d913739ec75a26b102021-09-25Wishart 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 Compound13963852
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. Ishii K, Okajima H, Koyamatsu T, Okada Y, Watanabe H: The composition of furan fatty acids in the crayfish. Lipids. 1988 Jul;23(7):694-700. doi: 10.1007/BF02535671. [PubMed:27520122 ]
  2. Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.