Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:37:51 UTC
Update Date2022-03-07 03:18:05 UTC
HMDB IDHMDB0112192
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-Hydroxyhexadecanoic acid
Description6-hydroxyhexadecanoic acid 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. 6-hydroxyhexadecanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563873227
Synonyms
ValueSource
6-HydroxyhexadecanoateGenerator
16:0(6-OH)SMPDB, HMDB
6-hydroxypalmitic acidSMPDB, HMDB
6-hydroxyhexadecanoic acidSMPDB
Chemical FormulaC16H32O3
Average Molecular Weight272.429
Monoisotopic Molecular Weight272.23514489
IUPAC Name6-hydroxyhexadecanoic acid
Traditional Name6-hydroxyhexadecanoic acid
CAS Registry Number58763-57-8
SMILES
CCCCCCCCCCC(O)CCCCC(O)=O
InChI Identifier
InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-12-15(17)13-10-11-14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)
InChI KeyDLMIUMCETWCTHV-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
  • Hydroxy fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP5.6ALOGPS
logP4.87ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.71ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity78.75 m³·mol⁻¹ChemAxon
Polarizability35.11 ųChemAxon
Number of Rings0ChemAxon
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]+171.41931661259
DarkChem[M-H]-170.46931661259
DeepCCS[M+H]+171.24630932474
DeepCCS[M-H]-167.22730932474
DeepCCS[M-2H]-204.82930932474
DeepCCS[M+Na]+180.51930932474
AllCCS[M+H]+175.832859911
AllCCS[M+H-H2O]+172.732859911
AllCCS[M+NH4]+178.732859911
AllCCS[M+Na]+179.532859911
AllCCS[M-H]-173.332859911
AllCCS[M+Na-2H]-174.432859911
AllCCS[M+HCOO]-175.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-Hydroxyhexadecanoic acidCCCCCCCCCCC(O)CCCCC(O)=O3331.2Standard polar33892256
6-Hydroxyhexadecanoic acidCCCCCCCCCCC(O)CCCCC(O)=O2061.1Standard non polar33892256
6-Hydroxyhexadecanoic acidCCCCCCCCCCC(O)CCCCC(O)=O2163.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Hydroxyhexadecanoic acid,1TMS,isomer #1CCCCCCCCCCC(CCCCC(=O)O)O[Si](C)(C)C2211.6Semi standard non polar33892256
6-Hydroxyhexadecanoic acid,1TMS,isomer #2CCCCCCCCCCC(O)CCCCC(=O)O[Si](C)(C)C2208.4Semi standard non polar33892256
6-Hydroxyhexadecanoic acid,2TMS,isomer #1CCCCCCCCCCC(CCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2244.3Semi standard non polar33892256
6-Hydroxyhexadecanoic acid,1TBDMS,isomer #1CCCCCCCCCCC(CCCCC(=O)O)O[Si](C)(C)C(C)(C)C2455.5Semi standard non polar33892256
6-Hydroxyhexadecanoic acid,1TBDMS,isomer #2CCCCCCCCCCC(O)CCCCC(=O)O[Si](C)(C)C(C)(C)C2457.1Semi standard non polar33892256
6-Hydroxyhexadecanoic acid,2TBDMS,isomer #1CCCCCCCCCCC(CCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2705.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxyhexadecanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00bi-9212100000-d2ece668513d01d71e0e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxyhexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ug3-6930000000-f957258f454624ca07482017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxyhexadecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxyhexadecanoic 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 - 6-Hydroxyhexadecanoic acid 10V, Positive-QTOFsplash10-0a4i-0090000000-2ea155966664bf463d622019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 20V, Positive-QTOFsplash10-0a4i-4490000000-f7467b3a973096464a372019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 40V, Positive-QTOFsplash10-052f-9400000000-92a1b992c74990b7cab02019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 10V, Negative-QTOFsplash10-00di-0090000000-914d0471e20a1d2262f22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 20V, Negative-QTOFsplash10-0uk9-0190000000-e3725647c44c4bd03a152019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 40V, Negative-QTOFsplash10-052f-9620000000-a4afae922a0e53ce10a02019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 10V, Negative-QTOFsplash10-0uk9-0090000000-0ee8338012e0b67282852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 20V, Negative-QTOFsplash10-0uk9-1190000000-60fb7d7f3187c278f3f72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 40V, Negative-QTOFsplash10-0a6u-9840000000-a1d56c82da29e1590c722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 10V, Positive-QTOFsplash10-0ab9-2390000000-a6dfffbfc010b0acbb362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 20V, Positive-QTOFsplash10-0a4r-9640000000-cc775a0b3a12ddab21c22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyhexadecanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-9d4d102097bbfc7a435b2021-09-22Wishart 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 Compound12398972
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. Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. [PubMed:25303528 ]
  2. Lopez-Bascon MA, Calderon-Santiago M, Priego-Capote F: Confirmatory and quantitative analysis of fatty acid esters of hydroxy fatty acids in serum by solid phase extraction coupled to liquid chromatography tandem mass spectrometry. Anal Chim Acta. 2016 Nov 2;943:82-88. doi: 10.1016/j.aca.2016.09.014. Epub 2016 Sep 20. [PubMed:27769381 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.