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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2021-09-14 15:00:41 UTC
HMDB IDHMDB0010734
Secondary Accession Numbers
  • HMDB10734
Metabolite Identification
Common Name(R)-3-Hydroxy-hexadecanoic acid
DescriptionIn humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. (R)-3-Hydroxy-hexadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-hexadecanoic acid is converted from 3-Oxo-tetradecanoic acid via fatty-acid Synthase and 3-oxoacyl- [acyl-carrier-protein] reductase. (EC: 2.3.1.85 and EC: 2.3.1.41).
Structure
Data?1582752867
Synonyms
ValueSource
(R)-3-Hydroxy-hexadecanoateGenerator
(R)-beta-Hydroxypalmitic acidChEBI
(R)-b-HydroxypalmitateGenerator
(R)-b-Hydroxypalmitic acidGenerator
(R)-beta-HydroxypalmitateGenerator
(R)-β-hydroxypalmitateGenerator
(R)-β-hydroxypalmitic acidGenerator
3-Hydroxypalmitic acidMeSH, HMDB
beta-Hydroxypalmitic acidMeSH, HMDB
3-Hydroxypalmitic acid, (+-)-isomerMeSH, HMDB
beta-HydroxypalmitateMeSH, HMDB
Chemical FormulaC16H32O3
Average Molecular Weight272.4235
Monoisotopic Molecular Weight272.23514489
IUPAC Name(3R)-3-hydroxyhexadecanoic acid
Traditional Name(R)-3-hydroxypalmitic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CCCCCCCCCCCCC)CC(O)=O
InChI Identifier
InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)/t15-/m1/s1
InChI KeyCBWALJHXHCJYTE-OAHLLOKOSA-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
  • Beta-hydroxy acid
  • Hydroxy 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 Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

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 Solubility0.0056 g/LALOGPS
logP10(5.75) g/LALOGPS
logP10(5.03) g/LChemAxon
logS10(-4.7) g/LALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity78.6 m³·mol⁻¹ChemAxon
Polarizability35.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.87631661259
DarkChem[M-H]-170.5631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxy-hexadecanoic acid[H][C@@](O)(CCCCCCCCCCCCC)CC(O)=O3237.7Standard polar33892256
(R)-3-Hydroxy-hexadecanoic acid[H][C@@](O)(CCCCCCCCCCCCC)CC(O)=O2044.4Standard non polar33892256
(R)-3-Hydroxy-hexadecanoic acid[H][C@@](O)(CCCCCCCCCCCCC)CC(O)=O2178.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxy-hexadecanoic acid,1TMS,isomer #1CCCCCCCCCCCCC[C@H](CC(=O)O)O[Si](C)(C)C2181.6Semi standard non polar33892256
(R)-3-Hydroxy-hexadecanoic acid,1TMS,isomer #2CCCCCCCCCCCCC[C@@H](O)CC(=O)O[Si](C)(C)C2161.4Semi standard non polar33892256
(R)-3-Hydroxy-hexadecanoic acid,2TMS,isomer #1CCCCCCCCCCCCC[C@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2249.9Semi standard non polar33892256
(R)-3-Hydroxy-hexadecanoic acid,1TBDMS,isomer #1CCCCCCCCCCCCC[C@H](CC(=O)O)O[Si](C)(C)C(C)(C)C2426.9Semi standard non polar33892256
(R)-3-Hydroxy-hexadecanoic acid,1TBDMS,isomer #2CCCCCCCCCCCCC[C@@H](O)CC(=O)O[Si](C)(C)C(C)(C)C2413.1Semi standard non polar33892256
(R)-3-Hydroxy-hexadecanoic acid,2TBDMS,isomer #1CCCCCCCCCCCCC[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2717.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9340000000-7f3268f819048bc0fb4c2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-009i-9231100000-2ee529fc9d520d001aee2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxy-hexadecanoic 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 - (R)-3-Hydroxy-hexadecanoic acid 10V, Positive-QTOFsplash10-0ab9-0090000000-170f4b78f38f506532812016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 20V, Positive-QTOFsplash10-0a4i-3590000000-72735537a44743fc49f32016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 40V, Positive-QTOFsplash10-052f-9600000000-18c6bb5829efbdfd83242016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 10V, Negative-QTOFsplash10-00di-0090000000-69dd00738d6e82b5a71a2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 20V, Negative-QTOFsplash10-0adi-2090000000-a29b15501f484eac1a952016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 40V, Negative-QTOFsplash10-0a4l-9240000000-34c29dc88bb32e93e5092016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 10V, Negative-QTOFsplash10-00di-1090000000-b8b5369541b20493e1ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 20V, Negative-QTOFsplash10-0a4i-9020000000-0763938b2406df6b3db32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 40V, Negative-QTOFsplash10-052f-9020000000-405e88be7cf7e93b32692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 10V, Positive-QTOFsplash10-05fr-2190000000-13586bde632215e515492021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 20V, Positive-QTOFsplash10-0ab9-9430000000-96b8600a3183721e00242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-hexadecanoic acid 40V, Positive-QTOFsplash10-0a4i-9100000000-ac851687758f1e0f9afd2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB027881
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15569776
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. 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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06
General function:
Involved in catalytic activity
Specific function:
May play a role in the biosynthesis of lipoic acid as well as longer chain fatty acids required for optimal mitochondrial function.
Gene Name:
OXSM
Uniprot ID:
Q9NWU1
Molecular weight:
40034.535