Stearidonic acid (CHEM024973)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:03:08 UTC
Update Date2016-11-09 01:17:59 UTC
Accession NumberCHEM024973
Identification
Common NameStearidonic acid
ClassSmall Molecule
DescriptionAn octadecatetraenoic acid having four double bonds located at positions 6, 9, 12 and 15 (the all-cis-isomer). It has been isolated from Lithospermum officinale and fish oils.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(6Z,9Z,12Z,15Z)-Octadecatetraenoic acidChEBI
6,9,12,15-Octadecatetraenoic acidChEBI
SDAChEBI
6Z,9Z,12Z,15Z-Octadecatetraenoic acidKegg
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acidKegg
(6Z,9Z,12Z,15Z)-OctadecatetraenoateGenerator
6,9,12,15-OctadecatetraenoateGenerator
6Z,9Z,12Z,15Z-OctadecatetraenoateGenerator
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoateGenerator
StearidonateGenerator
Stearidonic acid C18:4HMDB
FA(18:4(6Z,9Z,12Z,15Z))HMDB
FA(18:4n3)HMDB
Moroctic acidHMDB
Chemical FormulaC18H28O2
Average Molecular Mass276.414 g/mol
Monoisotopic Mass276.209 g/mol
CAS Registry Number20290-75-9
IUPAC Name(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
Traditional Namestearidonic acid
SMILESCC\C=C\C\C=C/C\C=C\C\C=C\CCCCC(O)=O
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-DFARDDQGSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9880000000-55228cb6c3a06a2fc9e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9542000000-21c2332ba73d69ef8c6aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0190000000-adcd1a052c188cb4e292Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-004i-0090000000-a5d727e64a76416e19b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-004i-1590000000-c31b6670486c2add8842Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-05ce-5920000000-97739d72e096d14b3173Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-06gm-9800000000-e3ef89b4b4086a02043dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-05ox-9300000000-e97626343f7e356e1b0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 24V, positivesplash10-05ox-9100000000-7d26fa860a4f5a50b573Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-05r3-9100000000-c0fda9d6244f70011335Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-05r3-9000000000-05ef38b3be958b95c066Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 39V, positivesplash10-05r3-9000000000-0e7f4cff743f21c96f9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 45V, positivesplash10-0v03-9000000000-1e7762f073fff0bbf25fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, positivesplash10-0udi-9000000000-e29ae2d32138f06d4b67Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-08fs-0940000000-3ce59c1bcc6c938f80ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-05gl-6900000000-e7b111913bb0b52b7732Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-004i-9000000000-829ac26a60349ce7dc65Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-00di-3900000000-d5e9c06ac391b2ed266cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-0006-9000000000-4afb061d75b952ae6397Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-0006-0890000000-2c1d0ecbce6768af6a66Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-0072-0900000000-d1bd13cfc0f04540d631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0190000000-db9d40fa02eaf6622425Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05q9-4890000000-dacdea1487478325e7aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-069c-8930000000-57d8480196e2c8c76857Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-098cf1c00cd595f3355aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-74f3f2bf4ec73b4c1454Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-0bbf081c20a1f61dd3a1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006547
FooDB IDFDB004293
Phenol Explorer IDNot Available
KNApSAcK IDC00000405
BiGG ID2218006
BioCyc IDCPD-12653
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkStearidonic_acid
Chemspider ID4471933
ChEBI ID32389
PubChem Compound ID5312508
Kegg Compound IDC16300
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23932357
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24553695
3. 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.
4. 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.
5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.