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Record Information
Version4.0
Creation Date2008-10-15 12:12:16 UTC
Update Date2017-09-27 08:26:25 UTC
HMDB IDHMDB0010728
Secondary Accession Numbers
  • HMDB10728
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
(3R)-3-Hydroxylauric 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 acidChEBI
D-(-)-3-Hydroxydodecanoic acidChEBI
D-3-Hydroxydodecanoic acidChEBI
(3R)-3-HydroxydodecanoateGenerator
(R)-3-HydroxydodecanoateGenerator
(3R)-3-HydroxylaateGenerator
(3R)-3-Hydroxylaic acidGenerator
(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 LaateGenerator
(R)-b-OH Laic acidGenerator
(R)-beta-OH LaateGenerator
(R)-beta-OH Laic acidGenerator
(R)-β-OH laateGenerator
(R)-β-OH laic acidGenerator
D-(-)-3-HydroxydodecanoateGenerator
D-3-HydroxydodecanoateGenerator
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 KeyMUCMKTPAZLSKTL-LLVKDONJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassHydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

  Pharmaceutical industry:

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 Solubility0.34 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity60.2 m³·mol⁻¹ChemAxon
Polarizability26.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0930000000-57fa523571a510c84940View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-3900000000-db0ac4f7e5c200e8ffe9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-af4ea991e8885d84f4d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1790000000-438c129b69517f0cd6f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0q29-3920000000-f4f68c93f91c4519ee51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9600000000-05e66928d4652560bee3View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Fatty Acid BiosynthesisPw000167Pw000167 greyscalePw000167 simpleNot Available
Displaying 1 entry
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
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