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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:17:23 UTC
Update Date2022-03-07 03:18:04 UTC
HMDB IDHMDB0112082
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Methyl-5-pentyl-2-furanpentadecanoic acid
Description3-Methyl-5-pentyl-2-furanpentadecanoic 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-furanpentadecanoic acid, in particular, can be described by the shorthand notation 15M5. This refers to its 15-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 mussels.
Structure
Data?1563873215
Synonyms
ValueSource
15-(3-Methyl-5-pentylfuran-2-yl)-pentadecanoateGenerator
15M5SMPDB, HMDB
MonoMe(15,5)SMPDB, HMDB
15-(3-methyl-5-pentyl-2-furyl)pentadecanoic acidSMPDB, HMDB
3-methyl-5-pentyl-2-furanpentadecanoic acidSMPDB
16,19-epoxy-17-methyl-16,18-tetracosadienoic acidSMPDB, HMDB
16,19-epoxy-17-methyltetracosa-16,18-dienoic acidSMPDB, HMDB
15-(3-methyl-5-pentylfuran-2-yl)pentadecanoic acidSMPDB, HMDB
15-(3-Methyl-5-pentylfuran-2-yl)pentadecanoateGenerator, HMDB
3-Methyl-5-pentyl-2-furanpentadecanoateGenerator
Chemical FormulaC25H44O3
Average Molecular Weight392.624
Monoisotopic Molecular Weight392.329045277
IUPAC Name15-(3-methyl-5-pentylfuran-2-yl)pentadecanoic acid
Traditional Name15-(3-methyl-5-pentylfuran-2-yl)pentadecanoic acid
CAS Registry Number116627-44-2
SMILES
CCCCCC1=CC(C)=C(CCCCCCCCCCCCCCC(O)=O)O1
InChI Identifier
InChI=1S/C25H44O3/c1-3-4-15-18-23-21-22(2)24(28-23)19-16-13-11-9-7-5-6-8-10-12-14-17-20-25(26)27/h21H,3-20H2,1-2H3,(H,26,27)
InChI KeyZXUFZNDRPGKIFV-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
logP8.34ALOGPS
logP8.86ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity118.24 m³·mol⁻¹ChemAxon
Polarizability51.98 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]+201.531661259
DarkChem[M-H]-200.26431661259
DeepCCS[M+H]+206.86430932474
DeepCCS[M-H]-204.31430932474
DeepCCS[M-2H]-237.51730932474
DeepCCS[M+Na]+213.20730932474
AllCCS[M+H]+211.732859911
AllCCS[M+H-H2O]+209.432859911
AllCCS[M+NH4]+213.832859911
AllCCS[M+Na]+214.432859911
AllCCS[M-H]-207.532859911
AllCCS[M+Na-2H]-210.432859911
AllCCS[M+HCOO]-213.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methyl-5-pentyl-2-furanpentadecanoic acidCCCCCC1=CC(C)=C(CCCCCCCCCCCCCCC(O)=O)O14229.4Standard polar33892256
3-Methyl-5-pentyl-2-furanpentadecanoic acidCCCCCC1=CC(C)=C(CCCCCCCCCCCCCCC(O)=O)O12834.7Standard non polar33892256
3-Methyl-5-pentyl-2-furanpentadecanoic acidCCCCCC1=CC(C)=C(CCCCCCCCCCCCCCC(O)=O)O12916.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methyl-5-pentyl-2-furanpentadecanoic acid,1TMS,isomer #1CCCCCC1=CC(C)=C(CCCCCCCCCCCCCCC(=O)O[Si](C)(C)C)O13021.7Semi standard non polar33892256
3-Methyl-5-pentyl-2-furanpentadecanoic acid,1TBDMS,isomer #1CCCCCC1=CC(C)=C(CCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O13245.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05y3-8592200000-f5e7e46fa5f9ab04b5ca2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic 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-furanpentadecanoic acid 10V, Positive-QTOFsplash10-004i-0009000000-82f2bdae027c4c6000da2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 20V, Positive-QTOFsplash10-0pea-4749000000-cffdf6f3d7e7470926a32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 40V, Positive-QTOFsplash10-0udi-7931000000-63d1dd8847e0e50c516e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 10V, Negative-QTOFsplash10-0006-0009000000-76fdecb8815ba9f5201d2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 20V, Negative-QTOFsplash10-006y-1209000000-4a82c81c39c3a6d8f4d42019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 40V, Negative-QTOFsplash10-0a4i-9833000000-4c88404e4986e7f11ff32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 10V, Negative-QTOFsplash10-0006-0009000000-85560eb5d3c6aa1874752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 20V, Negative-QTOFsplash10-006x-1009000000-d6c7517c7bd6558d025f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 40V, Negative-QTOFsplash10-006x-9317000000-c2bd9ee7022c850c90302021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 10V, Positive-QTOFsplash10-056u-2119000000-432368f27cde07eefce42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 20V, Positive-QTOFsplash10-0a4i-4019000000-8afa1d25b36e677d66af2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentadecanoic acid 40V, Positive-QTOFsplash10-0a4l-9300000000-83d32539ab342d198bb92021-09-24Wishart 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 Compound131819623
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.