Showing Compound Card for Stearidonic acid (CDB000375)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:33:44 UTC
Updated at2020-12-07 19:07:24 UTC
CannabisDB IDCDB000375
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameStearidonic 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 the seed oils of hemp, 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 ).
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 Weight276.41
Monoisotopic Molecular Weight276.2089
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 KeyJIWBIWFOSCKQMA-LTKCOYKYSA-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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSStearidonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-9880000000-55228cb6c3a06a2fc9e6Spectrum
Predicted GC-MSStearidonic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9542000000-21c2332ba73d69ef8c6aSpectrum
Predicted GC-MSStearidonic 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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Fatty acid desaturase 2FADS211q12.2O95864 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Fatty acid desaturase 2FADS211q12.2O95864 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006547
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004293
KNApSAcK IDC00000405
Chemspider ID4471933
KEGG Compound IDC16300
BioCyc IDCPD-12653
BiGG ID2218006
Wikipedia LinkStearidonic_acid
METLIN IDNot Available
PubChem Compound5312508
PDB IDNot Available
ChEBI ID32389
References
General References
  1. 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. doi: 10.1093/jn/134.6.1406. [PubMed:15173404 ]
  2. 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. doi: 10.1016/j.plefa.2003.11.008. [PubMed:15120716 ]

Enzymes

Enzyme Details
1. Fatty acid desaturase 2
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