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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:17:45 UTC
Update Date2022-03-07 03:18:04 UTC
HMDB IDHMDB0112086
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Methyl-5-pentyl-2-furanpentanoic acid
Description3-Methyl-5-pentyl-2-furanpentanoic 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-Methyl-5-pentyl-2-furanpentanoic acid, in particular, can be described by the shorthand notation 5M5. This refers to its 5-carbon carboxyalkyl moiety, the methyl substitution in the 3-position of its furan moiety, and its 5-carbon alkyl moiety. It has been identified in fish oil.
Structure
Data?1563873216
Synonyms
ValueSource
5-(3-Methyl-5-pentylfuran-2-yl)-pentanoateGenerator
5M5SMPDB, HMDB
MonoMe(5,5)SMPDB, HMDB
5-(3-methyl-5-pentyl-2-furyl)pentanoic acidSMPDB, HMDB
3-methyl-5-pentyl-2-furanpentanoic acidSMPDB
6,9-epoxy-7-methyl-6,8-tetradecadienoic acidSMPDB, HMDB
6,9-epoxy-7-methyltetradeca-6,8-dienoic acidSMPDB, HMDB
5-(3-methyl-5-pentylfuran-2-yl)pentanoic acidSMPDB, HMDB
3-Methyl-5-pentylfuran-2-pentanoateGenerator, HMDB
3-Methyl-5-pentyl-2-furanpentanoateGenerator
Chemical FormulaC15H24O3
Average Molecular Weight252.354
Monoisotopic Molecular Weight252.172544633
IUPAC Name5-(3-methyl-5-pentylfuran-2-yl)pentanoic acid
Traditional Name5-(3-methyl-5-pentylfuran-2-yl)pentanoic acid
CAS Registry Number157686-84-5
SMILES
CCCCCC1=CC(C)=C(CCCCC(O)=O)O1
InChI Identifier
InChI=1S/C15H24O3/c1-3-4-5-8-13-11-12(2)14(18-13)9-6-7-10-15(16)17/h11H,3-10H2,1-2H3,(H,16,17)
InChI KeyOVQQXXHYNCJQNP-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
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
logP4.48ALOGPS
logP4.42ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.71ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity72.23 m³·mol⁻¹ChemAxon
Polarizability30.66 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]+162.36931661259
DarkChem[M-H]-161.52231661259
DeepCCS[M+H]+169.34630932474
DeepCCS[M-H]-165.89430932474
DeepCCS[M-2H]-201.84230932474
DeepCCS[M+Na]+178.13230932474
AllCCS[M+H]+165.432859911
AllCCS[M+H-H2O]+161.832859911
AllCCS[M+NH4]+168.732859911
AllCCS[M+Na]+169.632859911
AllCCS[M-H]-168.432859911
AllCCS[M+Na-2H]-169.332859911
AllCCS[M+HCOO]-170.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methyl-5-pentyl-2-furanpentanoic acidCCCCCC1=CC(C)=C(CCCCC(O)=O)O12990.6Standard polar33892256
3-Methyl-5-pentyl-2-furanpentanoic acidCCCCCC1=CC(C)=C(CCCCC(O)=O)O11888.3Standard non polar33892256
3-Methyl-5-pentyl-2-furanpentanoic acidCCCCCC1=CC(C)=C(CCCCC(O)=O)O11921.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methyl-5-pentyl-2-furanpentanoic acid,1TMS,isomer #1CCCCCC1=CC(C)=C(CCCCC(=O)O[Si](C)(C)C)O12001.6Semi standard non polar33892256
3-Methyl-5-pentyl-2-furanpentanoic acid,1TBDMS,isomer #1CCCCCC1=CC(C)=C(CCCCC(=O)O[Si](C)(C)C(C)(C)C)O12221.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-062i-9520000000-3ebbfb4b72671a3d15322017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic 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-Methyl-5-pentyl-2-furanpentanoic acid 10V, Positive-QTOFsplash10-000i-0090000000-8927f5968b546862b3cb2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 20V, Positive-QTOFsplash10-0pb9-9880000000-cc40240697e41611f9c92019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 40V, Positive-QTOFsplash10-0k96-9500000000-817f09003190e3604b2f2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 10V, Negative-QTOFsplash10-0udi-0090000000-6c3ca79f4a77863876c42019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 20V, Negative-QTOFsplash10-0zgi-1490000000-08bbbeb1441065c4b7162019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 40V, Negative-QTOFsplash10-0a4i-6900000000-b1886890907b321b8c362019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 10V, Negative-QTOFsplash10-0udi-0090000000-cce227597bc03fb5e7022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 20V, Negative-QTOFsplash10-0udi-2490000000-803cc38dddbb289a02142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 40V, Negative-QTOFsplash10-05fs-3900000000-e1b45ebbd4ac01956f452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 10V, Positive-QTOFsplash10-0udi-1290000000-05d87f28373e4e2c43e12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 20V, Positive-QTOFsplash10-0udr-5980000000-2ffd546e858b7732e56d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 40V, Positive-QTOFsplash10-0a4l-9300000000-6cca901aaf8fc15aa3c12021-09-22Wishart 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 Compound54171982
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. Wendlinger C, Hammann S, Vetter W (2016). Detailed Study of Furan Fatty Acids in Total Lipids and the Cholesteryl Ester Fraction of Fish Liver. Food Analytical Methods.