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Showing metabocard for (R)-3-Hydroxy-hexadecanoic acid (HMDB0010734)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2017-12-20 20:21:19 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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(R)-beta-Hydroxypalmitic acidChEBI
(R)-b-HydroxypalmitateGenerator
(R)-b-Hydroxypalmitic acidGenerator
(R)-beta-HydroxypalmitateGenerator
(R)-β-hydroxypalmitateGenerator
(R)-β-hydroxypalmitic acidGenerator
(R)-3-Hydroxy-hexadecanoateGenerator
3-Hydroxypalmitic acidMeSH
beta-Hydroxypalmitic acidMeSH
3-Hydroxypalmitic acid, (+-)-isomerMeSH
beta-HydroxypalmitateMeSH
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
DescriptionThis compound 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP5.75ALOGPS
logP5.03ChemAxon
logS-4.7ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9340000000-7f3268f819048bc0fb4cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-009i-9231100000-2ee529fc9d520d001aeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0090000000-170f4b78f38f50653281View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3590000000-72735537a44743fc49f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-18c6bb5829efbdfd8324View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-69dd00738d6e82b5a71aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-2090000000-a29b15501f484eac1a95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-34c29dc88bb32e93e509View in MoNA
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
FoodDB IDFDB027881
KNApSAcK IDNot Available
Chemspider ID21865352
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15569776
PDB IDNot Available
ChEBI ID38247
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

Enzyme Details
1. Fatty acid synthase
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
Enzyme Details
2. 3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial
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