Hmdb loader
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 Date2017-09-08 16:20:23 UTC
Update Date2022-03-07 03:18:05 UTC
HMDB IDHMDB0112100
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Butyl-3,4-dimethyl-2-furannonanoic acid
Description5-Butyl-3,4-dimethyl-2-furannonanoic 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-furannonanoic acid, in particular, can be described by the shorthand notation 9D4. This refers to its 9-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 crayfish hepatopancreas.
Structure
Data?1563873217
Synonyms
ValueSource
9-(3,4-Dimethyl-5-butylfuran-2-yl)-nonanoateGenerator
9D4SMPDB, HMDB
DiMe(9,4)SMPDB, HMDB
9-(5-butyl-3,4-dimethyl-2-furyl)nonanoic acidSMPDB, HMDB
5-butyl-3,4-dimethyl-2-furannonanoic acidSMPDB
10,13-epoxy-11,12-dimethyl-10,12-heptadecadienoic acidSMPDB, HMDB
10,13-epoxy-11,12-dimethylheptadeca-10,12-dienoic acidSMPDB, HMDB
9-(5-butyl-3,4-dimethylfuran-2-yl)nonanoic acidSMPDB, HMDB
5-Butyl-3,4-dimethyl-2-furannonanoateGenerator
Chemical FormulaC19H32O3
Average Molecular Weight308.462
Monoisotopic Molecular Weight308.23514489
IUPAC Name9-(5-butyl-3,4-dimethylfuran-2-yl)nonanoic acid
Traditional Name9-(5-butyl-3,4-dimethylfuran-2-yl)nonanoic acid
CAS Registry Number116627-46-4
SMILES
CCCCC1=C(C)C(C)=C(CCCCCCCCC(O)=O)O1
InChI Identifier
InChI=1S/C19H32O3/c1-4-5-12-17-15(2)16(3)18(22-17)13-10-8-6-7-9-11-14-19(20)21/h4-14H2,1-3H3,(H,20,21)
InChI KeyIZEBSZFMLJHHME-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
Disposition

Source

Route of exposure

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
logP6.02ALOGPS
logP6.27ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)4.87ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity91.08 m³·mol⁻¹ChemAxon
Polarizability39.2 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]+174.50931661259
DarkChem[M-H]-177.2531661259
DeepCCS[M+H]+186.10730932474
DeepCCS[M-H]-183.74930932474
DeepCCS[M-2H]-216.85630932474
DeepCCS[M+Na]+192.44830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Butyl-3,4-dimethyl-2-furannonanoic acidCCCCC1=C(C)C(C)=C(CCCCCCCCC(O)=O)O13376.2Standard polar33892256
5-Butyl-3,4-dimethyl-2-furannonanoic acidCCCCC1=C(C)C(C)=C(CCCCCCCCC(O)=O)O12245.4Standard non polar33892256
5-Butyl-3,4-dimethyl-2-furannonanoic acidCCCCC1=C(C)C(C)=C(CCCCCCCCC(O)=O)O12330.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Butyl-3,4-dimethyl-2-furannonanoic acid,1TMS,isomer #1CCCCC1=C(C)C(C)=C(CCCCCCCCC(=O)O[Si](C)(C)C)O12413.4Semi standard non polar33892256
5-Butyl-3,4-dimethyl-2-furannonanoic acid,1TBDMS,isomer #1CCCCC1=C(C)C(C)=C(CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O12665.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00vr-9562000000-42dce4b041203112ca802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5590000000-8ef7882ab9607cc4ec7a2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic 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-furannonanoic acid 10V, Positive-QTOFsplash10-0006-0092000000-6b68dba0111d82eb606d2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 20V, Positive-QTOFsplash10-0f6x-5591000000-1ac84c58252bf2617cf92019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 40V, Positive-QTOFsplash10-0k97-9520000000-0992986496d3c69f17512019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 10V, Negative-QTOFsplash10-0a4i-0039000000-1461885e28e1b9ed980e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 20V, Negative-QTOFsplash10-0bti-1394000000-0b8a6940b5188bd4c54c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 40V, Negative-QTOFsplash10-0ab9-8970000000-89b2c67051ad5c6ec6a92019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 10V, Positive-QTOFsplash10-0596-0293000000-a310572bface13a661312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 20V, Positive-QTOFsplash10-00xu-2950000000-056f2f3303fc73d524362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 40V, Positive-QTOFsplash10-05fr-9700000000-41f484e2c104622366112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 10V, Negative-QTOFsplash10-0a4i-0029000000-704d4e4990c3a5bdd80b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 20V, Negative-QTOFsplash10-0a4r-1196000000-4592fc8f4b114abe3bd42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Butyl-3,4-dimethyl-2-furannonanoic acid 40V, Negative-QTOFsplash10-0596-2950000000-19e0d45a7cbe7c03602b2021-09-23Wishart 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 Compound131819629
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.