Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:30 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0003073
Secondary Accession Numbers
  • HMDB03073
Metabolite Identification
Common Namegamma-Linolenic acid
Descriptiongamma-Linolenic acid, also known as 18:3n6 or GLA, belongs to the class of organic compounds known as linoleic acids and derivatives. These are derivatives of linoleic acid. Linoleic acid is a polyunsaturated omega-6 18-carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. gamma-Linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Linolenic acid is an omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted into dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1 (PubChem).
Structure
Data?1582752262
Synonyms
ValueSource
(6,9,12)-Linolenic acidChEBI
(6Z,9Z,12Z)-Octadecatrienoic acidChEBI
(Z,Z,Z)-6,9,12-Octadecatrienoic acidChEBI
18:3 (N-6)ChEBI
6,9,12-Octadecatrienoic acidChEBI
6-cis,9-cis,12-cis-Octadecatrienoic acidChEBI
all-cis-6,9,12-Octadecatrienoic acidChEBI
C18:3 (N-6)ChEBI
C18:3, N-6,9,12 all-cisChEBI
cis-Delta(6,9,12)-Octadecatrienoic acidChEBI
gamma-LinolensaeureChEBI
Gamoleic acidChEBI
Gamolenic acidChEBI
GLAChEBI
Octadeca-6,9,12-triensaeureChEBI
(6,9,12)-LinolenateGenerator
(6Z,9Z,12Z)-OctadecatrienoateGenerator
(Z,Z,Z)-6,9,12-OctadecatrienoateGenerator
6,9,12-OctadecatrienoateGenerator
6-cis,9-cis,12-cis-OctadecatrienoateGenerator
all-cis-6,9,12-OctadecatrienoateGenerator
cis-delta(6,9,12)-OctadecatrienoateGenerator
cis-Δ(6,9,12)-octadecatrienoateGenerator
cis-Δ(6,9,12)-octadecatrienoic acidGenerator
g-LinolensaeureGenerator
Γ-linolensaeureGenerator
GamoleateGenerator
GamolenateGenerator
g-LinolenateGenerator
g-Linolenic acidGenerator
gamma-LinolenateGenerator
Γ-linolenateGenerator
Γ-linolenic acidGenerator
6(Z),9(Z),12(Z)-OctadecatrienoateHMDB
6(Z),9(Z),12(Z)-Octadecatrienoic acidHMDB
6,9,12-all-cis-OctadecatrienoateHMDB
6,9,12-all-cis-Octadecatrienoic acidHMDB
6Z,9Z,12Z-OctadecatrienoateHMDB
6Z,9Z,12Z-Octadecatrienoic acidHMDB
gamma-Llnolenic acidHMDB
LiglaHMDB
Acid, gamma-linolenicHMDB
Acid, gamolenicHMDB
gamma Linolenic acidHMDB
FA(18:3(6Z,9Z,12Z))HMDB
FA(18:3n6)HMDB
LinolenateHMDB
gamma-Linolenic acidKEGG
(6Z,9Z,12Z)-6,9,12-Octadecatrienoic acidPhytoBank
(Z,Z,Z)-6,9,12-Octatrienoic acidPhytoBank
cis,cis,cis-6,9,12-Octadecatrienoic acidPhytoBank
cis-6,cis-9,cis-12-Octadecatrienoic acidPhytoBank
Chemical FormulaC18H30O2
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
IUPAC Name(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Traditional Namegamma linolenic acid
CAS Registry Number506-26-3
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O
InChI Identifier
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
InChI KeyVZCCETWTMQHEPK-QNEBEIHSSA-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
Not AvailableNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available173.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00000267
[M+H]+Not Available174.523http://allccs.zhulab.cn/database/detail?ID=AllCCS00000267
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00025 g/LALOGPS
logP6.59ALOGPS
logP6.06ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability33.8 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]+179.16931661259
DarkChem[M-H]-179.83831661259
DeepCCS[M+H]+175.11230932474
DeepCCS[M-H]-172.75430932474
DeepCCS[M-2H]-205.63930932474
DeepCCS[M+Na]+181.20530932474
AllCCS[M+H]+175.532859911
AllCCS[M+H-H2O]+172.432859911
AllCCS[M+NH4]+178.432859911
AllCCS[M+Na]+179.232859911
AllCCS[M-H]-176.832859911
AllCCS[M+Na-2H]-178.332859911
AllCCS[M+HCOO]-180.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
gamma-Linolenic acidCCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O3384.9Standard polar33892256
gamma-Linolenic acidCCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O2006.3Standard non polar33892256
gamma-Linolenic acidCCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O2130.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
gamma-Linolenic acid,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C2192.5Semi standard non polar33892256
gamma-Linolenic acid,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C(C)(C)C2436.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - gamma-Linolenic acid GC-MS (1 TMS)splash10-005c-9800000000-7b6e7a36b048f5ed69bd2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - gamma-Linolenic acid GC-EI-TOF (Non-derivatized)splash10-00b9-9300000000-254ecb989081fdc719d22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - gamma-Linolenic acid GC-MS (Non-derivatized)splash10-005c-9800000000-7b6e7a36b048f5ed69bd2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Linolenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9650000000-eec5566c0f0f90bf00492017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Linolenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-007c-9431000000-b239852c91e5676687802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Linolenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Linolenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00nf-9200000000-cf911df79059a750cb2a2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 20V, Negative-QTOFsplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 30V, Negative-QTOFsplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 10V, Negative-QTOFsplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF , Negative-QTOFsplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 20V, Negative-QTOFsplash10-004i-0090000000-143e6ddfa05656a4c4da2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 30V, Negative-QTOFsplash10-004i-0090000000-0b9ba563ad074fe141e82017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0090000000-63bf7d731625d55779782017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0090000000-fbc4e202a8b26c91dc9e2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid ESI-TOF , Negative-QTOFsplash10-004i-0090000000-b56d00321ab0921fe7b72017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-QTOF , negative-QTOFsplash10-004i-0090000000-dcae4273443fd52bbb032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-143e6ddfa05656a4c4da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-0b9ba563ad074fe141e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-63bf7d731625d55779782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-QTOF 10V, positive-QTOFsplash10-004i-0090000000-370b301c8afc435a0ce12020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-QTOF 20V, positive-QTOFsplash10-003s-9850000000-54163d6f895368b9032c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid LC-ESI-QTOF 40V, positive-QTOFsplash10-001i-9000000000-e6cdb81ac5675944be822020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid 20V, Positive-QTOFsplash10-003s-9750000000-d1947011d4fc6a28a1352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid 30V, Positive-QTOFsplash10-004i-0090000000-0b9ba563ad074fe141e82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Linolenic acid 10V, Positive-QTOFsplash10-004i-0090000000-370b301c8afc435a0ce12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Linolenic acid 10V, Positive-QTOFsplash10-01t9-0190000000-6b136607b48b316678012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Linolenic acid 20V, Positive-QTOFsplash10-01q9-4790000000-5046458d5d3e3c2285182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Linolenic acid 40V, Positive-QTOFsplash10-05mo-8930000000-852d50a19eb0b0df729b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Linolenic acid 10V, Negative-QTOFsplash10-004i-0090000000-ab643cae783eb66bf1312016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Linolenic acid 20V, Negative-QTOFsplash10-0059-1090000000-abce276de392be9d7d3f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Linolenic acid 40V, Negative-QTOFsplash10-0a4i-9230000000-40a41feed498373e54d22016-08-04Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.08 +/- 1.5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.310 +/- 0.196 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified46.1 +/- 21.7 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified1.03 +/- 0.005 uMAdult (>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
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Lung cancer
details
BloodDetected and Quantified35.0 +/- 17.7 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
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
Lung Cancer
  1. Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
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 IDDB13854
Phenol Explorer Compound IDNot Available
FooDB IDFDB002943
KNApSAcK IDC00001226
Chemspider ID4444436
KEGG Compound IDC06426
BioCyc IDCPD-8117
BiGG ID48234
Wikipedia LinkGamma-Linolenic_acid
METLIN ID386
PubChem Compound5280933
PDB IDNot Available
ChEBI ID28661
Food Biomarker OntologyNot Available
VMH IDDLNLCGCRN
MarkerDB IDMDB00000409
Good Scents IDNot Available
References
Synthesis ReferenceGema H; Kavadia A; Dimou D; Tsagou V; Komaitis M; Aggelis G Production of gamma-linolenic acid by Cunninghamella echinulata cultivated on glucose and orange peel. Applied microbiology and biotechnology (2002), 58(3), 303-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Melnik BC, Plewig G: Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? J Am Acad Dermatol. 1989 Sep;21(3 Pt 1):557-63. [PubMed:2550526 ]
  2. Levy RJ, Lian JB: gamma-Carboxyglutamate excretion and warfarin therapy. Clin Pharmacol Ther. 1979 May;25(5 Pt 1):562-70. [PubMed:373941 ]
  3. Bolton-Smith C, Woodward M, Tavendale R: Evidence for age-related differences in the fatty acid composition of human adipose tissue, independent of diet. Eur J Clin Nutr. 1997 Sep;51(9):619-24. [PubMed:9306089 ]
  4. Purasiri P, Mckechnie A, Heys SD, Eremin O: Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids. Immunology. 1997 Oct;92(2):166-72. [PubMed:9415022 ]
  5. Ziboh VA, Miller CC, Cho Y: Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites. Am J Clin Nutr. 2000 Jan;71(1 Suppl):361S-6S. [PubMed:10617998 ]
  6. Magnusson G, Boberg M, Cederblad G, Meurling S: Plasma and tissue levels of lipids, fatty acids and plasma carnitine in neonates receiving a new fat emulsion. Acta Paediatr. 1997 Jun;86(6):638-44. [PubMed:9202801 ]
  7. Kankaanpaa PE, Salminen SJ, Isolauri E, Lee YK: The influence of polyunsaturated fatty acids on probiotic growth and adhesion. FEMS Microbiol Lett. 2001 Jan 15;194(2):149-53. [PubMed:11164299 ]
  8. Whitaker DK, Cilliers J, de Beer C: Evening primrose oil (Epogam) in the treatment of chronic hand dermatitis: disappointing therapeutic results. Dermatology. 1996;193(2):115-20. [PubMed:8884146 ]
  9. Kankaanpaa P, Nurmela K, Erkkila A, Kalliomaki M, Holmberg-Marttila D, Salminen S, Isolauri E: Polyunsaturated fatty acids in maternal diet, breast milk, and serum lipid fatty acids of infants in relation to atopy. Allergy. 2001 Jul;56(7):633-8. [PubMed:11421921 ]
  10. Koletzko B, Sauerwald U, Keicher U, Saule H, Wawatschek S, Bohles H, Bervoets K, Fleith M, Crozier-Willi G: Fatty acid profiles, antioxidant status, and growth of preterm infants fed diets without or with long-chain polyunsaturated fatty acids. A randomized clinical trial. Eur J Nutr. 2003 Oct;42(5):243-53. [PubMed:14569405 ]
  11. Leigh-Firbank EC, Minihane AM, Leake DS, Wright JW, Murphy MC, Griffin BA, Williams CM: Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses. Br J Nutr. 2002 May;87(5):435-45. [PubMed:12010583 ]
  12. 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 thiolester hydrolase activity
Specific function:
Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:
BAAT
Uniprot ID:
Q14032
Molecular weight:
46298.865
General function:
Lipid transport and metabolism
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:
ACOT7
Uniprot ID:
O00154
Molecular weight:
40454.945
Reactions
Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:
ACOT2
Uniprot ID:
P49753
Molecular weight:
53218.02
Reactions
Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Molecular weight:
46326.09
Reactions
Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic aciddetails
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:
ACOT8
Uniprot ID:
O14734
Molecular weight:
35914.02
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:
ACOT1
Uniprot ID:
Q86TX2
Molecular weight:
46276.96
Reactions
Gamma-linolenoyl-CoA + Water → Coenzyme A + gamma-Linolenic aciddetails