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Showing Compound Steridonic acid (FDB004293)

Record Information
Version1.0
Creation date2010-04-08 22:06:10 UTC
Update date2020-09-17 15:33:13 UTC
Primary IDFDB004293
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSteridonic acid
DescriptionStearidonic acid, also known as SDA or stearidonate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Stearidonic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is biosynthesized from linolenic acid by the enzyme delta-6-desaturase. Natural sources of this fatty acid are in the blackcurrant and echium, and the cyanobacterium spirulina (a rich source of vitamins and minerals). Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) polyunsaturated fatty acids (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 eicosapentaenoic acid (EPA) content of human lipids and that combinations of gamma-linolenic acid and stearidonic 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 to influence cellular responses and functions in desirable ways (PMID: 15120716).
CAS Number20290-75-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity90.75 m³·mol⁻¹ChemAxon
Polarizability33.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H28O2
IUPAC name(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
InChI IdentifierInChI=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 KeyJIWBIWFOSCKQMA-LTKCOYKYSA-N
Isomeric SMILESCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O
Average Molecular Weight276.4137
Monoisotopic Molecular Weight276.20893014
Classification
Description 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
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSteridonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-9880000000-55228cb6c3a06a2fc9e6Spectrum
Predicted GC-MSSteridonic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9542000000-21c2332ba73d69ef8c6aSpectrum
Predicted GC-MSSteridonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0190000000-adcd1a052c188cb4e2922017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-004i-0090000000-a5d727e64a76416e19b92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-004i-1590000000-c31b6670486c2add88422020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-05ce-5920000000-97739d72e096d14b31732020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-06gm-9800000000-e3ef89b4b4086a02043d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-05ox-9300000000-e97626343f7e356e1b0c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, positivesplash10-05ox-9100000000-7d26fa860a4f5a50b5732020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-05r3-9100000000-c0fda9d6244f700113352020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-05r3-9000000000-05ef38b3be958b95c0662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 39V, positivesplash10-05r3-9000000000-0e7f4cff743f21c96f9d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 45V, positivesplash10-0v03-9000000000-1e7762f073fff0bbf25f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 54V, positivesplash10-0udi-9000000000-e29ae2d32138f06d4b672020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-08fs-0940000000-3ce59c1bcc6c938f80dd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-05gl-6900000000-e7b111913bb0b52b77322020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-004i-9000000000-829ac26a60349ce7dc652020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-00di-3900000000-d5e9c06ac391b2ed266c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-0006-9000000000-4afb061d75b952ae63972020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-0006-0890000000-2c1d0ecbce6768af6a662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-0072-0900000000-d1bd13cfc0f04540d6312020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0190000000-db9d40fa02eaf66224252016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05q9-4890000000-dacdea1487478325e7aa2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-069c-8930000000-57d8480196e2c8c768572016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-098cf1c00cd595f3355a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-74f3f2bf4ec73b4c14542016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-0bbf081c20a1f61dd3a12016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDSTERIDONIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).