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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:40:46 UTC
Update Date2022-03-07 02:52:48 UTC
HMDB IDHMDB0031067
Secondary Accession Numbers
  • HMDB31067
Metabolite Identification
Common Name(S)-14-Methylhexadecanoic acid
Description(S)-14-Methylhexadecanoic acid, also known as 14-methylpalmitic acid or anteisoheptadecanoate, 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. Based on a literature review a significant number of articles have been published on (S)-14-Methylhexadecanoic acid.
Structure
Data?1563862077
Synonyms
ValueSource
14-Methylpalmitic acidChEBI
14-MethylpalmitateGenerator
(S)-14-MethylhexadecanoateGenerator
14-Methylhexadecanoic acid, (+-)-isomerHMDB
AnteisoheptadecanoateHMDB
14-Methylhexadecanoic acidHMDB
Chemical FormulaC17H34O2
Average Molecular Weight270.4507
Monoisotopic Molecular Weight270.255880332
IUPAC Name14-methylhexadecanoic acid
Traditional Name(+)-14-methyl palmitic acid
CAS Registry Number5746-59-8
SMILES
CCC(C)CCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C17H34O2/c1-3-16(2)14-12-10-8-6-4-5-7-9-11-13-15-17(18)19/h16H,3-15H2,1-2H3,(H,18,19)
InChI KeyFXUKWLSZZHVEJD-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
  • 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
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point39.5 - 40 °CNot Available
Boiling Point386.10 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.022 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP7.500 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.63ALOGPS
logP6.54ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity81.63 m³·mol⁻¹ChemAxon
Polarizability36.07 ųChemAxon
Number of Rings0ChemAxon
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]+171.47731661259
DarkChem[M-H]-171.8331661259
DeepCCS[M+H]+170.77430932474
DeepCCS[M-H]-166.75430932474
DeepCCS[M-2H]-204.4630932474
DeepCCS[M+Na]+180.12330932474
AllCCS[M+H]+178.232859911
AllCCS[M+H-H2O]+175.132859911
AllCCS[M+NH4]+181.032859911
AllCCS[M+Na]+181.832859911
AllCCS[M-H]-176.332859911
AllCCS[M+Na-2H]-177.732859911
AllCCS[M+HCOO]-179.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-14-Methylhexadecanoic acidCCC(C)CCCCCCCCCCCCC(O)=O2961.5Standard polar33892256
(S)-14-Methylhexadecanoic acidCCC(C)CCCCCCCCCCCCC(O)=O1962.6Standard non polar33892256
(S)-14-Methylhexadecanoic acidCCC(C)CCCCCCCCCCCCC(O)=O2049.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-14-Methylhexadecanoic acid,1TMS,isomer #1CCC(C)CCCCCCCCCCCCC(=O)O[Si](C)(C)C2121.6Semi standard non polar33892256
(S)-14-Methylhexadecanoic acid,1TBDMS,isomer #1CCC(C)CCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2381.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-14-Methylhexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9420000000-227dc22195b4a320e5aa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-14-Methylhexadecanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-056r-9331000000-66336baf886a12667cd82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-14-Methylhexadecanoic 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 - (S)-14-Methylhexadecanoic acid 10V, Positive-QTOFsplash10-0fk9-0090000000-8fd320690cbfe873915e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 20V, Positive-QTOFsplash10-0fmi-6690000000-2c3ef3b9e1e7f3b752bc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 40V, Positive-QTOFsplash10-0a4i-9400000000-05304dfda2a1976653c22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 10V, Negative-QTOFsplash10-014i-0090000000-d59e1c0613e3b4b6fe352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 20V, Negative-QTOFsplash10-016r-1090000000-64825023c5e41833a6ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 40V, Negative-QTOFsplash10-0a4i-9230000000-1e1c0f9de3e1884a06c82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 10V, Positive-QTOFsplash10-0fk9-3190000000-a06b4b0912b4097e36a72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 20V, Positive-QTOFsplash10-0aba-9210000000-815ec68f705dcd84cf902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-27c125614e357e7cc3382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 10V, Negative-QTOFsplash10-014i-0090000000-ae5b777e86dbd2f5172a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 20V, Negative-QTOFsplash10-0gb9-0090000000-fbd4711f4fb6af5092de2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-14-Methylhexadecanoic acid 40V, Negative-QTOFsplash10-0006-9210000000-83bfe38f5f6e24e3afb12021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003069
KNApSAcK IDC00052559
Chemspider ID20849
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22207
PDB IDNot Available
ChEBI ID84874
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1438711
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.