Showing metabocard for (R)-3-Hydroxydodecanoic acid (BMDB0010728)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:12:38 UTC
Update Date2020-05-21 16:27:15 UTC
BMDB IDBMDB0010728
Secondary Accession Numbers
  • BMDB10728
Metabolite Identification
Common Name(R)-3-Hydroxydodecanoic acid
Description(R)-3-Hydroxydodecanoic acid, also known as (3R)-3-hydroxylauric acid or (R)-beta-OH lauric acid, 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 (R)-3-Hydroxydodecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-3-Hydroxydodecanoic acid exists in all eukaryotes, ranging from yeast to humans (R)-3-Hydroxydodecanoic acid participates in a number of enzymatic reactions, within cattle. In particular, (R)-3-Hydroxydodecanoic acid can be biosynthesized from 3-oxododecanoic acid through its interaction with the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In addition, (R)-3-Hydroxydodecanoic acid can be converted into trans-dodec-2-enoic acid; which is catalyzed by the enzyme fatty acid synthase. dyhydrase domain. In cattle, (R)-3-hydroxydodecanoic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
(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
(R)-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
Description 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
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • 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
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
BioavailabilityYesChemAxon
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-9500000000-ce0e4abc46c623ad5053View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bc-9042000000-0d213d881baf293e004cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1190000000-5af11549237f298c2ea2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9210000000-0ad9609790293200ce6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-abdab144438d186cdcc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-8950000000-eef6079ee3aba96447b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-2cc48879a8d7f0de8899View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-b899673a8a3334e8f36aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0010728
DrugBank IDDB07930
Phenol Explorer Compound IDNot Available
FooDB 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

Enzyme Details
1. Fatty acid synthase
General function:
Secondary metabolites biosynthesis, transport and catabolism
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 as an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
Q71SP7
Molecular weight:
274554.0
Reactions
3-Oxododecanoic acid → (R)-3-Hydroxydodecanoic aciddetails
(R)-3-Hydroxydodecanoic acid → trans-Dodec-2-enoic aciddetails