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Record Information
Version3.6
Creation Date2007-05-23 15:30:04 UTC
Update Date2016-02-11 01:07:35 UTC
HMDB IDHMDB06547
Secondary Accession NumbersNone
Metabolite Identification
Common NameStearidonic acid
DescriptionStearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) PUFA. These oils appear to possess hypotriglyceridemic properties typically associated with fish oils.(PMID: 15173404 ). Stearidonic acid may be used as a precursor to increase the EPA content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid eicosapentaenoic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition in order to influence cellular responses and functions in desirable ways. (PMID: 15120716 ).
Structure
Thumb
Synonyms
ValueSource
(6Z,9Z,12Z,15Z)-Octadecatetraenoic acidChEBI
6,9,12,15-Octadecatetraenoic acidChEBI
SDAChEBI
Stearidonic acidChEBI
(6Z,9Z,12Z,15Z)-OctadecatetraenoateGenerator
all-cis-Octadeca-6,9,12,15-tetraenoateGenerator
6,9,12,15-OctadecatetraenoateGenerator
StearidonateGenerator
Stearidonic acid C18:4HMDB
Chemical FormulaC18H28O2
Average Molecular Weight276.4137
Monoisotopic Molecular Weight276.20893014
IUPAC Name(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
Traditional Namestearidonic acid
CAS Registry Number20290-75-9
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O
InChI Identifier
InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-
InChI KeyInChIKey=JIWBIWFOSCKQMA-LTKCOYKYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassLineolic acids and derivatives
Sub ClassNot Available
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and 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 Solubility0.000502 mg/mLALOGPS
logP6.19ALOGPS
logP5.7ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)4.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity90.75 m3·mol-1ChemAxon
Polarizability33.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.408 +/- 0.4 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.016 +/- 0.001 uMAdult (>18 years old)BothNormal details
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 IDFDB002942
KNApSAcK IDNot Available
Chemspider ID4471933
KEGG Compound IDC16300
BioCyc IDNot Available
BiGG ID2218006
Wikipedia LinkStearidonic acid
NuGOwiki LinkHMDB06547
Metagene LinkHMDB06547
METLIN IDNot Available
PubChem Compound5312508
PDB IDNot Available
ChEBI ID32389
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Miles EA, Banerjee T, Calder PC: The influence of different combinations of gamma-linolenic, stearidonic and eicosapentaenoic acids on the fatty acid composition of blood lipids and mononuclear cells in human volunteers. Prostaglandins Leukot Essent Fatty Acids. 2004 Jun;70(6):529-38. [15120716 ]
  2. Surette ME, Edens M, Chilton FH, Tramposch KM: Dietary echium oil increases plasma and neutrophil long-chain (n-3) fatty acids and lowers serum triacylglycerols in hypertriglyceridemic humans. J Nutr. 2004 Jun;134(6):1406-11. [15173404 ]

Enzymes

General function:
Involved in heme binding
Specific function:
Component of a lipid metabolic pathway that catalyzes biosynthesis of highly unsaturated fatty acids (HUFA) from precursor essential polyunsaturated fatty acids (PUFA) linoleic acid (LA) (18:2n-6) and alpha-linolenic acid (ALA) (18:3n-3). Catalyzes the first and rate limiting step in this pathway which is the desaturation of LA (18:2n-6) and ALA (18:3n-3) into gamma- linoleic acid (GLA) (18:3n-6) and stearidonic acid (18:4n-3) respectively and other desaturation steps. Highly unsaturated fatty acids (HUFA) play pivotal roles in many biological functions. It catalizes as well the introduction of a cis double bond in palmitate to produce the mono-unsaturated fatty acid sapienate, the most abundant fatty acid in sebum
Gene Name:
FADS2
Uniprot ID:
O95864
Molecular weight:
52259.1