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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2023-02-21 17:16:22 UTC
HMDB IDHMDB0002373
Secondary Accession Numbers
  • HMDB02373
Metabolite Identification
Common Name4,6-Dimethylnonanoic acid
Description4,6-Dimethylnonanoic acid is produced in the peroxisomes from pristanic acid (where undergoes three cycles of β-oxidation) and then exported to the mitochondria or hydrolyzed by an acyl-CoA thioesterase and transported to the mitochondrion, followed by reactivation to its CoA-ester inside the mitochondria for full oxidation to CO2 and H2O. (PMID: 11785945 ).
Structure
Data?1676999782
Synonyms
ValueSource
4,8-Dimethyl-nonanoic acidChEBI
4,8-Dimethyl-nonanoateGenerator
4,6-DimethylnonanoateGenerator
4,8-DimethylnonanoateHMDB
4,8-Dimethylnonanoic acidHMDB
Chemical FormulaC11H22O2
Average Molecular Weight186.2912
Monoisotopic Molecular Weight186.161979948
IUPAC Name4,8-dimethylnonanoic acid
Traditional Name4,8-dimethylnonanoic acid
CAS Registry Number7540-70-7
SMILES
CC(C)CCCC(C)CCC(O)=O
InChI Identifier
InChI=1S/C11H22O2/c1-9(2)5-4-6-10(3)7-8-11(12)13/h9-10H,4-8H2,1-3H3,(H,12,13)
InChI KeyVZPIUNDOWLDCTC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
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
Water Solubility0.05 g/LALOGPS
logP3.86ALOGPS
logP3.72ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)5.28ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity53.97 m³·mol⁻¹ChemAxon
Polarizability22.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.6831661259
DarkChem[M-H]-142.84831661259
DeepCCS[M+H]+145.60930932474
DeepCCS[M-H]-141.68130932474
DeepCCS[M-2H]-179.03130932474
DeepCCS[M+Na]+154.69630932474
AllCCS[M+H]+148.332859911
AllCCS[M+H-H2O]+144.532859911
AllCCS[M+NH4]+151.732859911
AllCCS[M+Na]+152.732859911
AllCCS[M-H]-149.732859911
AllCCS[M+Na-2H]-151.332859911
AllCCS[M+HCOO]-153.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,6-Dimethylnonanoic acidCC(C)CCCC(C)CCC(O)=O2252.9Standard polar33892256
4,6-Dimethylnonanoic acidCC(C)CCCC(C)CCC(O)=O1351.3Standard non polar33892256
4,6-Dimethylnonanoic acidCC(C)CCCC(C)CCC(O)=O1412.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4,6-Dimethylnonanoic acid,1TMS,isomer #1CC(C)CCCC(C)CCC(=O)O[Si](C)(C)C1463.9Semi standard non polar33892256
4,6-Dimethylnonanoic acid,1TBDMS,isomer #1CC(C)CCCC(C)CCC(=O)O[Si](C)(C)C(C)(C)C1688.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4,6-Dimethylnonanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kfx-9600000000-1bd8a7bd6e048ac133c82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,6-Dimethylnonanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9310000000-3b74350fd0a3aff4d9272017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,6-Dimethylnonanoic 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 - 4,6-Dimethylnonanoic acid 10V, Positive-QTOFsplash10-014i-0900000000-0edfc9e9815787a6b2682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 20V, Positive-QTOFsplash10-066u-5900000000-af6dd2960ceb85267f3d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-dcda2b36bf23de08ea6b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 10V, Negative-QTOFsplash10-000i-0900000000-ab8c8aa7c0bd3c6d68b42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 20V, Negative-QTOFsplash10-00ku-1900000000-ddc0070ed6d0ea7fc27e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 40V, Negative-QTOFsplash10-0a4l-9400000000-9e2f70863aad687050122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 10V, Positive-QTOFsplash10-00ei-9400000000-5f602d83eec71a6230af2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 20V, Positive-QTOFsplash10-05mx-9000000000-8806c95c05bf425d15592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-630ed9fcdfec85d2ecb82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 10V, Negative-QTOFsplash10-000i-0900000000-1d1d4e785d40d3c134c02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 20V, Negative-QTOFsplash10-000i-0900000000-b0042def4c258a61c41e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dimethylnonanoic acid 40V, Negative-QTOFsplash10-05mp-9400000000-9ca4bcaf2dd7f6925a372021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
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 IDFDB022984
KNApSAcK IDNot Available
Chemspider ID12283491
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13628864
PDB IDNot Available
ChEBI ID63864
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSvishchuk, A. A.; Nikitenko, V. G. Synthesis of 4,8-dimethylnonanoic acid and some of its derivatives. Ukrainskii Khimicheskii Zhurnal (Russian Edition) (1976), 42(12), 1297-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ofman R, el Mrabet L, Dacremont G, Spijer D, Wanders RJ: Demonstration of dimethylnonanoyl-CoA thioesterase activity in rat liver peroxisomes followed by purification and molecular cloning of the thioesterase involved. Biochem Biophys Res Commun. 2002 Jan 18;290(2):629-34. [PubMed:11785945 ]