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Record Information
Version3.6
Creation Date2008-10-15 12:12:16 UTC
Update Date2016-02-11 01:20:06 UTC
HMDB IDHMDB10728
Secondary Accession NumbersNone
Metabolite Identification
Common Name(R)-3-Hydroxydodecanoic acid
DescriptionIn humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation.(R)-3-Hydroxydodecanoic acid is an intermediate in fatty acid biosynthesis. Specifically,(R)-3-Hydroxydodecanoic acid is converted from 3-Oxo-Dodecanoic acid via two enzymes; fatty-acid Synthase and 3-oxoacyl-[acyl-carrier-protein] reductase (EC: 2.3.1.85 and EC: 1.1.1.100).
Structure
Thumb
Synonyms
ValueSource
(3R)-3-HYDROXYDODECANOIC ACIDChEBI
(R)-3-OH Dodecanoic acidChEBI
(R)-3-OH Lauric acidChEBI
(R)-beta-Hydroxydodecanoic acidChEBI
(R)-beta-Hydroxylauric acidChEBI
(R)-beta-OH Dodecanoic acidChEBI
(R)-beta-OH Lauric aciChEBI
(3R)-3-HYDROXYDODECANOateGenerator
(R)-3-HydroxydodecanoateGenerator
(R)-3-OH DodecanoateGenerator
(R)-3-OH LaateGenerator
(R)-3-OH Laic acidGenerator
(R)-b-HydroxydodecanoateGenerator
(R)-b-Hydroxydodecanoic acidGenerator
(R)-beta-HydroxydodecanoateGenerator
(R)-β-hydroxydodecanoateGenerator
(R)-β-hydroxydodecanoic acidGenerator
(R)-b-HydroxylaateGenerator
(R)-b-Hydroxylaic acidGenerator
(R)-beta-HydroxylaateGenerator
(R)-beta-Hydroxylaic acidGenerator
(R)-β-hydroxylaateGenerator
(R)-β-hydroxylaic acidGenerator
(R)-b-OH DodecanoateGenerator
(R)-b-OH Dodecanoic acidGenerator
(R)-beta-OH DodecanoateGenerator
(R)-β-OH dodecanoateGenerator
(R)-β-OH dodecanoic acidGenerator
(R)-b-OH Lauric aciGenerator
(R)-β-OH lauric aciGenerator
Chemical FormulaC12H24O3
Average Molecular Weight216.3172
Monoisotopic Molecular Weight216.172544634
IUPAC Name(3R)-3-hydroxydodecanoic acid
Traditional Name(R)-3-hydroxydodecanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CCCCCCCCC)CC(O)=O
InChI Identifier
InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)/t11-/m1/s1
InChI KeyInChIKey=MUCMKTPAZLSKTL-LLVKDONJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty 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 Solubility0.34 mg/mLALOGPS
logP3.63ALOGPS
logP3.25ChemAxon
logS-2.8ALOGPS
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 Count10ChemAxon
Refractivity60.2 m3·mol-1ChemAxon
Polarizability26.59 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
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 IDFDB027875
KNApSAcK IDNot Available
Chemspider ID4472229
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10728
Metagene LinkHMDB10728
METLIN IDNot Available
PubChem Compound5312804
PDB IDHXD
ChEBI ID43197
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