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Record Information
Version3.6
Creation Date2006-05-22 14:17:34 UTC
Update Date2016-02-11 01:05:15 UTC
HMDB IDHMDB02059
Secondary Accession NumbersNone
Metabolite Identification
Common Name12-Hydroxydodecanoic acid
Description12-hydroxydodecanoic acid is the substrate of the human glutathione-dependent formaldehyde dehydrogenase (EC1.1.1.1). The enzyme that catalyzes the conversion of alcohols to aldehydes is a zinc-containing dimeric enzyme responsible for the oxidation of long-chain alcohols and omega-hydroxy fatty acids. (OMIM). The human glutathione-dependent formaldehyde dehydrogenase is unique among the structurally studied members of the alcohol dehydrogenase family in that it follows a random bi kinetic mechanism forming a binary complex, and a ternary complex with NAD+. (PMID 12196016 ).
Structure
Thumb
Synonyms
ValueSource
12-Hydroxy lauric acidChEBI
12-Hydroxydodecanoic acidChEBI
2-Hydroxy-dodecanoic acidChEBI
Omega-hydroxy lauric acidChEBI
Omega-hydroxydodecanoic acidChEBI
Omega-OH dodecanoic acidChEBI
Omega-OH lauric acidChEBI
12-Hydroxy laateGenerator
12-Hydroxy laic acidGenerator
12-HydroxylaateGenerator
12-Hydroxylaic acidGenerator
12-HydroxydodecanoateGenerator
2-Hydroxy-dodecanoateGenerator
Omega-hydroxy laateGenerator
Omega-hydroxy laic acidGenerator
Omega-hydroxydodecanoateGenerator
Omega-OH dodecanoateGenerator
Omega-OH laateGenerator
Omega-OH laic acidGenerator
12-HydroxylaurateHMDB
Omega hydroxy dodecanoateHMDB
Omega hydroxy dodecanoic acidHMDB
Chemical FormulaC12H24O3
Average Molecular Weight216.3172
Monoisotopic Molecular Weight216.172544634
IUPAC Name12-hydroxydodecanoic acid
Traditional Name12-hydroxydodecanoic acid
CAS Registry Number505-95-3
SMILES
OCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C12H24O3/c13-11-9-7-5-3-1-2-4-6-8-10-12(14)15/h13H,1-11H2,(H,14,15)
InChI KeyInChIKey=ZDHCZVWCTKTBRY-UHFFFAOYSA-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
  • Fatty acyl
  • Fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • 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 (predicted from logP)
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 Solubility0.21 mg/mLALOGPS
logP3.5ALOGPS
logP3.04ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity60.61 m3·mol-1ChemAxon
Polarizability26.85 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-1790000000-86939bdc2617444c9391View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0910000000-844a5190b2e310ec626fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-1900000000-499d158a0890694b2f7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07gv-9600000000-cc905025c302321c2c33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0790000000-ba75e81dad07b4533bfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-1920000000-64041ca2f1e9970c6e5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9600000000-2c68993598743f556da6View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot 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 IDFDB022822
KNApSAcK IDNot Available
Chemspider ID71366
KEGG Compound IDC08317
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02059
Metagene LinkHMDB02059
METLIN ID6465
PubChem Compound79034
PDB ID12H
ChEBI ID39567
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sanghani PC, Robinson H, Bosron WF, Hurley TD: Human glutathione-dependent formaldehyde dehydrogenase. Structures of apo, binary, and inhibitory ternary complexes. Biochemistry. 2002 Sep 3;41(35):10778-86. [12196016 ]