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Record Information
Version3.6
Creation Date2008-10-15 12:12:16 UTC
Update Date2016-02-11 01:20:07 UTC
HMDB IDHMDB10734
Secondary Accession NumbersNone
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
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
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 KeyInChIKey=CBWALJHXHCJYTE-OAHLLOKOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity78.6 m3·mol-1ChemAxon
Polarizability35.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027881
KNApSAcK IDNot Available
Chemspider ID21865352
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10734
Metagene LinkHMDB10734
METLIN IDNot Available
PubChem Compound15569776
PDB IDNot Available
ChEBI ID38247
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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