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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-23 15:30:04 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006547
Secondary Accession Numbers
  • HMDB06547
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
Data?1582752390
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 Weight276.4137
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 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

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point382.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.037 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.890 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.67831661259
DarkChem[M-H]-174.74931661259
DeepCCS[M+H]+171.07730932474
DeepCCS[M-H]-168.71930932474
DeepCCS[M-2H]-201.60530932474
DeepCCS[M+Na]+177.1730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Stearidonic acidCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O3524.8Standard polar33892256
Stearidonic acidCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O1970.7Standard non polar33892256
Stearidonic acidCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O2134.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Stearidonic acid,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C2188.5Semi standard non polar33892256
Stearidonic acid,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C(C)(C)C2430.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Stearidonic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9880000000-55228cb6c3a06a2fc9e62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stearidonic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9542000000-21c2332ba73d69ef8c6a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stearidonic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid LC-ESI-IT , negative-QTOFsplash10-001i-0190000000-adcd1a052c188cb4e2922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 6V, positive-QTOFsplash10-004i-0090000000-a5d727e64a76416e19b92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 8V, positive-QTOFsplash10-004i-1590000000-c31b6670486c2add88422020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 12V, positive-QTOFsplash10-05ce-5920000000-97739d72e096d14b31732020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 14V, positive-QTOFsplash10-06gm-9800000000-e3ef89b4b4086a02043d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 19V, positive-QTOFsplash10-05ox-9300000000-e97626343f7e356e1b0c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 24V, positive-QTOFsplash10-05ox-9100000000-7d26fa860a4f5a50b5732020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 28V, positive-QTOFsplash10-05r3-9100000000-c0fda9d6244f700113352020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 33V, positive-QTOFsplash10-05r3-9000000000-05ef38b3be958b95c0662020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 39V, positive-QTOFsplash10-05r3-9000000000-0e7f4cff743f21c96f9d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 45V, positive-QTOFsplash10-0v03-9000000000-1e7762f073fff0bbf25f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid Orbitrap 54V, positive-QTOFsplash10-0udi-9000000000-e29ae2d32138f06d4b672020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOFsplash10-08fs-0940000000-3ce59c1bcc6c938f80dd2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOFsplash10-05gl-6900000000-e7b111913bb0b52b77322020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOFsplash10-004i-9000000000-829ac26a60349ce7dc652020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOFsplash10-00di-3900000000-d5e9c06ac391b2ed266c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOFsplash10-0006-9000000000-4afb061d75b952ae63972020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOFsplash10-0006-0890000000-2c1d0ecbce6768af6a662020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Stearidonic acid n/a 19V, positive-QTOFsplash10-0072-0900000000-d1bd13cfc0f04540d6312020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearidonic acid 10V, Positive-QTOFsplash10-056r-0190000000-db9d40fa02eaf66224252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearidonic acid 20V, Positive-QTOFsplash10-05q9-4890000000-dacdea1487478325e7aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearidonic acid 40V, Positive-QTOFsplash10-069c-8930000000-57d8480196e2c8c768572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearidonic acid 10V, Negative-QTOFsplash10-004i-0090000000-098cf1c00cd595f3355a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearidonic acid 20V, Negative-QTOFsplash10-0059-1090000000-74f3f2bf4ec73b4c14542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stearidonic acid 40V, Negative-QTOFsplash10-0a4i-9230000000-0bbf081c20a1f61dd3a12016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.408 +/- 0.4 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.016 +/- 0.001 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDSTRDNC
MarkerDB IDNot Available
Good Scents IDrw1680171
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. [PubMed: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. [PubMed:15173404 ]
  3. 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. [PubMed:32033212 ]

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