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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:17:27 UTC
Update Date2022-03-07 03:18:04 UTC
HMDB IDHMDB0112083
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,4-Dimethyl-5-pentyl-2-furanpropanoic acid
Description3,4-Dimethyl-5-pentyl-2-furanpropanoic 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-furanpropanoic acid, in particular, can be described by the shorthand notation 3D5. This refers to its 3-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?1563873215
Synonyms
ValueSource
3-(3,4-Dimethyl-5-pentylfuran-2-yl)-propanoateGenerator
3D5SMPDB, HMDB
DiMe(3,5)SMPDB, HMDB
3-(3,4-dimethyl-5-pentyl-2-furyl)propanoic acidSMPDB, HMDB
3,4-dimethyl-5-pentyl-2-furanpropanoic acidSMPDB
4,7-epoxy-5,6-dimethyl-4,6-dodecadienoic acidSMPDB, HMDB
4,7-epoxy-5,6-dimethyldodeca-4,6-dienoic acidSMPDB, HMDB
3-(3,4-dimethyl-5-pentylfuran-2-yl)propanoic acidSMPDB, HMDB
3,4-Dimethyl-5-pentyl-2-furanpropanoateGenerator
Chemical FormulaC14H22O3
Average Molecular Weight238.327
Monoisotopic Molecular Weight238.156894568
IUPAC Name3-(3,4-dimethyl-5-pentylfuran-2-yl)propanoic acid
Traditional Name3-(3,4-dimethyl-5-pentylfuran-2-yl)propanoic acid
CAS Registry Number116627-39-5
SMILES
CCCCCC1=C(C)C(C)=C(CCC(O)=O)O1
InChI Identifier
InChI=1S/C14H22O3/c1-4-5-6-7-12-10(2)11(3)13(17-12)8-9-14(15)16/h4-9H2,1-3H3,(H,15,16)
InChI KeyOSCJFAHVJDDMFL-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
  • 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
logP3.96ALOGPS
logP4.04ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.77ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.07 m³·mol⁻¹ChemAxon
Polarizability28.59 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]+159.04631661259
DarkChem[M-H]-156.78231661259
DeepCCS[M+H]+165.03330932474
DeepCCS[M-H]-161.89330932474
DeepCCS[M-2H]-197.02730932474
DeepCCS[M+Na]+173.31730932474
AllCCS[M+H]+159.432859911
AllCCS[M+H-H2O]+155.832859911
AllCCS[M+NH4]+162.932859911
AllCCS[M+Na]+163.932859911
AllCCS[M-H]-163.132859911
AllCCS[M+Na-2H]-163.832859911
AllCCS[M+HCOO]-164.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Dimethyl-5-pentyl-2-furanpropanoic acidCCCCCC1=C(C)C(C)=C(CCC(O)=O)O12788.3Standard polar33892256
3,4-Dimethyl-5-pentyl-2-furanpropanoic acidCCCCCC1=C(C)C(C)=C(CCC(O)=O)O11744.5Standard non polar33892256
3,4-Dimethyl-5-pentyl-2-furanpropanoic acidCCCCCC1=C(C)C(C)=C(CCC(O)=O)O11824.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dimethyl-5-pentyl-2-furanpropanoic acid,1TMS,isomer #1CCCCCC1=C(C)C(C)=C(CCC(=O)O[Si](C)(C)C)O11905.8Semi standard non polar33892256
3,4-Dimethyl-5-pentyl-2-furanpropanoic acid,1TBDMS,isomer #1CCCCCC1=C(C)C(C)=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O12139.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g3-9330000000-08d03f0453adfc4756332017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0036-5920000000-0095d93d10252bfa380b2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic 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-furanpropanoic acid 10V, Positive-QTOFsplash10-00di-0190000000-95ea1172d603c7e9b0be2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 20V, Positive-QTOFsplash10-062c-5930000000-820f898e717a374d8a892019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 40V, Positive-QTOFsplash10-0abd-9300000000-b6c871bea5e02ecded8a2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 10V, Negative-QTOFsplash10-000i-0190000000-49147f8560d8b7a6ad722019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 20V, Negative-QTOFsplash10-00ku-3790000000-fc27f12d39e2e2a95e0c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 40V, Negative-QTOFsplash10-0a4u-6900000000-392c5b88ec516281600b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 10V, Negative-QTOFsplash10-000i-0090000000-cd6561de33b62b5ac25f2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 20V, Negative-QTOFsplash10-0006-5920000000-426098b91781d2c35c8b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 40V, Negative-QTOFsplash10-006w-3900000000-e491924e8c2442bbca842021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 10V, Positive-QTOFsplash10-000i-0290000000-ef833a5cf8ef6ba7be1a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 20V, Positive-QTOFsplash10-004r-0910000000-898d465a788fd5a014b02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpropanoic acid 40V, Positive-QTOFsplash10-00fu-8900000000-b8e7101f1c64189ca60e2021-09-25Wishart 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 Compound23425504
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. 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. Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.