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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:45:05 UTC
HMDB IDHMDB0001064
Secondary Accession Numbers
  • HMDB0060170
  • HMDB01064
  • HMDB60170
Metabolite Identification
Common NameLinoleoyl-CoA
DescriptionLinoleoyl-CoA is the acyl-CoA of linoleic acid found in the human body. It binds to and results in decreased activity of glutathione S-transferase1. It has been proposed that inhibition of mitochondrial adenine nucleotide translocator by long-chain acyl-CoA underlies the mechanism associating obesity and type 2 diabetes. Unsaturated fatty acids play an important role in the prevention of human diseases such as diabetes, obesity, cancer, and neurodegeneration. Their oxidation in vivo by acyl-CoA dehydrogenases (ACADs) catalyze the first step of each cycle of mitochondrial fatty acid beta-oxidation. ACAD-9 had maximal activity with long-chain unsaturated acyl-CoAs as substrates (PMID: 17184976 , 16020546 ).
Structure
Data?1594332729
Synonyms
ValueSource
(9Z,12Z)-Octadecadienoyl-CoAChEBI
Linoleoyl-coenzyme AHMDB
Linoleoyl-coenzyme A, (Z,Z)-isomerHMDB
(Z,Z)-9,12-Octadecadienoyl-CoAHMDB
CoA(18:2(9Z,12Z))HMDB
Linoleic coenzyme AHMDB
Linoleoyl coenzyme AHMDB
Linoleyl-CoAHMDB
Linoleyl-coenzyme AHMDB
(9Z,12Z)-Octadecadienoyl-coenzyme AHMDB
Linoleoyl-CoAHMDB
Chemical FormulaC39H66N7O17P3S
Average Molecular Weight1029.97
Monoisotopic Molecular Weight1029.344875861
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Namelinoleoyl-coa
CAS Registry Number6709-57-5
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-/t28-,32-,33-,34+,38-/m1/s1
InChI KeyYECLLIMZHNYFCK-RRNJGNTNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.86 g/LALOGPS
logP2.83ALOGPS
logP0.76ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity248.08 m³·mol⁻¹ChemAxon
Polarizability103.13 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+278.32730932474
DeepCCS[M-H]-276.43230932474
DeepCCS[M-2H]-311.31630932474
DeepCCS[M+Na]+286.0630932474
AllCCS[M+H]+296.832859911
AllCCS[M+H-H2O]+297.432859911
AllCCS[M+NH4]+296.332859911
AllCCS[M+Na]+296.132859911
AllCCS[M-H]-304.532859911
AllCCS[M+Na-2H]-310.732859911
AllCCS[M+HCOO]-317.432859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 123V, negative-QTOFsplash10-056r-1100903000-97979bc4426e696ca5002020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 133V, negative-QTOFsplash10-0a6r-2211903000-4df18afe923088dccc9d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 135V, negative-QTOFsplash10-0a6r-2311904000-084368125746db9a1a8d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 160V, negative-QTOFsplash10-056r-9834804000-ca985ff7e3a0a2cf068c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 168V, negative-QTOFsplash10-056r-9723402000-1ea9fba94f19b641305d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 185V, negative-QTOFsplash10-056r-9622100000-4bcd035304dec49a3add2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 199V, negative-QTOFsplash10-004i-9511000000-1f5c4a5c6b6d8b944e542020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 218V, negative-QTOFsplash10-004i-9410000000-cdcfa205f52edfcda7f12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 232V, negative-QTOFsplash10-004i-9400000000-678749dd0330558826572020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 253V, negative-QTOFsplash10-004i-9400000000-dcd823851fb7d4ad77a72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 273V, negative-QTOFsplash10-004i-9300000000-2e76dfce41f4d4f8fea52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 304V, negative-QTOFsplash10-004i-9300000000-6a4626bbeafb9da35d702020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA n/a 72V, negative-QTOFsplash10-001i-1000209003-f68430866c04428bfb902020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 47V, positive-QTOFsplash10-001i-9000200000-2cabae93047abe4a748d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 65V, positive-QTOFsplash10-00fr-3000970000-f399f99de6048f8887132020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 100V, positive-QTOFsplash10-00di-0100590000-9dc110d2f0daecf49e4d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 133V, positive-QTOFsplash10-00dr-1930160000-1caa8491ab78bfd3d5a92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 168V, positive-QTOFsplash10-000i-2920000000-c8b0b7ed0a3db1633f652020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 247V, positive-QTOFsplash10-000i-4900000000-70e58b576b80fd6196af2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoleoyl-CoA n/a 72V, positive-QTOFsplash10-00di-0000490000-7f3332450575be86b2d12020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl-CoA 10V, Positive-QTOFsplash10-001i-9000000000-08cf5e6d7b995d0cb8cd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl-CoA 20V, Positive-QTOFsplash10-01p9-7900200548-53d677114eea1a3495ee2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl-CoA 40V, Positive-QTOFsplash10-00di-0200890000-1142d1b46c49361093612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl-CoA 10V, Negative-QTOFsplash10-004i-9000000000-47a1be0b9f32d430c2812021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl-CoA 20V, Negative-QTOFsplash10-004i-9010201300-d0da1a5320d13a306df82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4593690
KEGG Compound IDC02050
BioCyc IDCPD-18
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5497112
PDB IDNot Available
ChEBI ID15530
Food Biomarker OntologyNot Available
VMH IDLNLCCOA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKawaguchi, Akihiko; Yoshimura, Tsutomu; Okuda, Shigenobu. A new method for the preparation of acyl-CoA thioesters. Journal of Biochemistry (Tokyo, Japan) (1981), 89(2), 337-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ramsay RR, Mancinelli G, Arduini A: Carnitine palmitoyltransferase in human erythrocyte membrane. Properties and malonyl-CoA sensitivity. Biochem J. 1991 May 1;275 ( Pt 3):685-8. [PubMed:2039446 ]
  2. Domergue F, Abbadi A, Ott C, Zank TK, Zahringer U, Heinz E: Acyl carriers used as substrates by the desaturases and elongases involved in very long-chain polyunsaturated fatty acids biosynthesis reconstituted in yeast. J Biol Chem. 2003 Sep 12;278(37):35115-26. Epub 2003 Jun 30. [PubMed:12835316 ]
  3. Kawasaki T, Snyder F: Synthesis of a novel acetylated neutral lipid related to platelet-activating factor by acyl-CoA:1-O-alkyl-2-acetyl-sn-glycerol acyltransferase in HL-60 cells. J Biol Chem. 1988 Feb 25;263(6):2593-6. [PubMed:3422635 ]
  4. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  5. Ensenauer R, He M, Willard JM, Goetzman ES, Corydon TJ, Vandahl BB, Mohsen AW, Isaya G, Vockley J: Human acyl-CoA dehydrogenase-9 plays a novel role in the mitochondrial beta-oxidation of unsaturated fatty acids. J Biol Chem. 2005 Sep 16;280(37):32309-16. Epub 2005 Jul 14. [PubMed:16020546 ]
  6. Ciapaite J, Bakker SJ, Van Eikenhorst G, Wagner MJ, Teerlink T, Schalkwijk CG, Fodor M, Ouwens DM, Diamant M, Heine RJ, Westerhoff HV, Krab K: Functioning of oxidative phosphorylation in liver mitochondria of high-fat diet fed rats. Biochim Biophys Acta. 2007 Mar;1772(3):307-16. Epub 2006 Nov 10. [PubMed:17184976 ]
  7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  8. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  9. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  10. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  11. (). Silva C, Loyola G, Valenzuela R, García-Huidobro T, Monasterio O, Bronfman M. High-affinity binding of fatty acyl-CoAs and peroxisome proliferator-CoA esters to glutathione S-transferases effect on enzymatic activity. Eur J Biochem. 1999 Nov;266(1):143-50.. .
  12. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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
Linoleoyl-CoA + Water → Coenzyme A + Linoleic 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
Linoleoyl-CoA + Water → Coenzyme A + Linoleic 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
Linoleoyl-CoA + Water → Coenzyme A + Linoleic 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 acyltransferase activity
Specific function:
Acyl-CoA:lysocardiolipin acyltransferase. Possesses both lysophosphatidylinositol acyltransferase (LPIAT) and lysophosphatidylglycerol acyltransferase (LPGAT) activities. Recognizes both monolysocardiolipin and dilysocardiolipin as substrates with a preference for linoleoyl-CoA and oleoyl-CoA as acyl donors. Acts as a remodeling enzyme for cardiolipin, a major membrane polyglycerophospholipid. Converts lysophosphatidic acid (LPA) into phosphatidic acid (PA) with a relatively low activity. Required for establishment of the hematopoietic and endothelial lineages.
Gene Name:
LCLAT1
Uniprot ID:
Q6UWP7
Molecular weight:
44560.815
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
Linoleoyl-CoA + Water → Coenzyme A + Linoleic aciddetails