Showing metabocard for (R)-3-Hydroxy-tetradecanoic acid (BMDB0010731)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:12:41 UTC
Update Date2020-05-21 16:27:15 UTC
BMDB IDBMDB0010731
Secondary Accession Numbers
  • BMDB10731
Metabolite Identification
Common Name(R)-3-Hydroxy-tetradecanoic acid
Description(R)-3-Hydroxy-tetradecanoic acid, also known as (3R)-hydroxymyristic acid or (r)-3-hydroxy-tetradecanoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms (R)-3-Hydroxy-tetradecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-3-Hydroxy-tetradecanoic acid exists in all eukaryotes, ranging from yeast to humans (R)-3-Hydroxy-tetradecanoic acid participates in a number of enzymatic reactions, within cattle. In particular, (R)-3-Hydroxy-tetradecanoic acid can be biosynthesized from 3-oxotetradecanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In addition, (R)-3-Hydroxy-tetradecanoic acid can be converted into trans-tetra-dec-2-enoic acid; which is mediated by the enzyme fatty acid synthase. dyhydrase domain. In cattle, (R)-3-hydroxy-tetradecanoic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(R)-3-Hydroxy-tetradecanoateGenerator
(-)-3-Hydroxymyristic acidHMDB
(3R)-Hydroxymyristic acidHMDB
(R)-(-)-3-Hydroxytetradecanoic acidHMDB
(R)-3-Hydroxymyristic acidHMDB
beta-Hydroxymyristic acidHMDB
beta-Hydroxytetradecanoic acidHMDB
D-(-)-beta-Hydroxymyristic acidHMDB
(-)-3-HydroxymyristateHMDB
(3R)-HydroxymyristateHMDB
(R)-(-)-3-HydroxytetradecanoateHMDB
(R)-3-HydroxymyristateHMDB
b-HydroxymyristateHMDB
b-Hydroxymyristic acidHMDB
beta-HydroxymyristateHMDB
Β-hydroxymyristateHMDB
Β-hydroxymyristic acidHMDB
b-HydroxytetradecanoateHMDB
b-Hydroxytetradecanoic acidHMDB
beta-HydroxytetradecanoateHMDB
Β-hydroxytetradecanoateHMDB
Β-hydroxytetradecanoic acidHMDB
D-(-)-b-HydroxymyristateHMDB
D-(-)-b-Hydroxymyristic acidHMDB
D-(-)-beta-HydroxymyristateHMDB
D-(-)-Β-hydroxymyristateHMDB
D-(-)-Β-hydroxymyristic acidHMDB
(R)-3-Hydroxytetradecanoic acidHMDB
(R)-3-HydroxytetradecanoateHMDB
Chemical FormulaC14H28O3
Average Molecular Weight244.3703
Monoisotopic Molecular Weight244.203844762
IUPAC Name(3R)-3-hydroxytetradecanoic acid
Traditional Name3-hydroxy-tetradecanoic acid
CAS Registry Number28715-21-1
SMILES
[H][C@@](O)(CCCCCCCCCCC)CC(O)=O
InChI Identifier
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m1/s1
InChI KeyATRNZOYKSNPPBF-CYBMUJFWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • 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
logP4.69ALOGPS
logP4.14ChemAxon
logS-3.9ALOGPS
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 Count12ChemAxon
Refractivity69.4 m³·mol⁻¹ChemAxon
Polarizability30.86 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-d3837d6527b09790d09eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-9142000000-2b802003b701914b13b7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0290000000-3cbad25621cd84dd55dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057j-4960000000-28121e72e39700d4f373View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-77f13667a638fc0db127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1490000000-041e325e3e96f0f26837View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5d-4950000000-ceff7e67442b0ca855abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9600000000-2a651411e77e87c314c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1090000000-576941859c2295d4cb14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9110000000-be27ca1efc0330f18073View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9110000000-b5cfa3eff2f2e135cf70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-4390000000-0cbb960da18db3e0e662View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-9310000000-0ff6d44ab8d422fb3b9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-29ad8b4130f67f29eb80View in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Mammary Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010731
DrugBank IDDB02767
Phenol Explorer Compound IDNot Available
FooDB IDFDB027878
KNApSAcK IDNot Available
Chemspider ID4450466
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5288266
PDB IDFTT
ChEBI ID42539
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-Oxotetradecanoic acid → (R)-3-Hydroxy-tetradecanoic aciddetails
(R)-3-Hydroxy-tetradecanoic acid → trans-Tetra-dec-2-enoic aciddetails