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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-09-05 15:40:56 UTC
Update Date2022-11-30 19:02:48 UTC
HMDB IDHMDB0006729
Secondary Accession Numbers
  • HMDB06729
Metabolite Identification
Common NameCE(22:4(7Z,10Z,13Z,16Z))
DescriptionCholesteryl docosatetraenoic acid is a cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Docosatetraenoic acid is one of the main polyunsaturated fatty acids (PUFA) present in the brain, a lipid-rich organ containing mostly complex polar phospholipids, sphingolipids, gangliosides and cholesterol. Cholesteryl docosatetraenoic acid has been found in triglycerides-rich cells such as monocyte-derived macrophages. Docosatetraenoic acid is increased in plasma in children with protein-calorie malnutrition (PCM). (PMID: 17392137 , 10424250 , 9162758 ).
Structure
Data?1582752402
Synonyms
ValueSource
22:4 Cholesterol esterHMDB
Cholest-5-en-3beta-yl (7Z,10Z,13Z,16Z-docosatetraenoateHMDB
Cholest-5-en-3beta-yl (7Z,10Z,13Z,16Z-docosatetraenoic acidHMDB
Cholesteryl docosatetraenoateHMDB
Cholesteryl docosatetraenoic acidHMDB
1-Adrenoyl-cholesterolHMDB
Cholesteryl 1-adrenoic acidHMDB
Cholesteryl 1-adrenoateHMDB
Cholesteryl 1-(7Z,10Z,13Z,16Z-docosatetraenoic acid)HMDB
Cholesterol 1-adrenoic acidHMDB
Cholesteryl 1-(7Z,10Z,13Z,16Z-docosatetraenoate)HMDB
Cholesterol ester(22:4)HMDB
22:4(7Z,10Z,13Z,16Z) Cholesterol esterHMDB
Cholesterol 1-adrenoateHMDB
Cholesterol ester(22:4/0:0)HMDB
Cholesterol 1-(7Z,10Z,13Z,16Z-docosatetraenoic acid)HMDB
CE(22:4/0:0)HMDB
CE(22:4)HMDB
1-(7Z,10Z,13Z,16Z-Docosatetraenoyl)-cholesterolHMDB
Cholesterol 1-(7Z,10Z,13Z,16Z-docosatetraenoate)HMDB
CE(22:4(7Z,10Z,13Z,16Z))Lipid Annotator
(2R,5S,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acidGenerator
Chemical FormulaC49H80O2
Average Molecular Weight701.177
Monoisotopic Molecular Weight700.615831816
IUPAC Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoate
Traditional Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoate
CAS Registry Number14940-92-2
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C49H80O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-47(50)51-42-34-36-48(5)41(38-42)30-31-43-45-33-32-44(40(4)28-26-27-39(2)3)49(45,6)37-35-46(43)48/h11-12,14-15,17-18,20-21,30,39-40,42-46H,7-10,13,16,19,22-29,31-38H2,1-6H3/b12-11-,15-14-,18-17-,21-20-/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1
InChI KeyITGTXSFLBABXQA-IRNBNDQXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentCholesteryl esters
Alternative Parents
Substituents
  • Cholesteryl ester
  • Cholesterol
  • Cholestane-skeleton
  • Delta-5-steroid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
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 Solubility6.0e-06 g/LALOGPS
logP10.47ALOGPS
logP15.25ChemAxon
logS-8.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity226.28 m³·mol⁻¹ChemAxon
Polarizability91.65 ųChemAxon
Number of Rings4ChemAxon
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]+283.47630932474
DeepCCS[M-H]-281.51130932474
DeepCCS[M-2H]-314.75230932474
DeepCCS[M+Na]+289.21630932474
AllCCS[M+H]+273.432859911
AllCCS[M+H-H2O]+273.132859911
AllCCS[M+NH4]+273.732859911
AllCCS[M+Na]+273.832859911
AllCCS[M-H]-238.032859911
AllCCS[M+Na-2H]-244.832859911
AllCCS[M+HCOO]-252.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CE(22:4(7Z,10Z,13Z,16Z))CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C4899.0Standard polar33892256
CE(22:4(7Z,10Z,13Z,16Z))CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C5187.4Standard non polar33892256
CE(22:4(7Z,10Z,13Z,16Z))CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C4971.8Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 10V, Negative-QTOFsplash10-0002-0006009000-0925b5854c343ab5b39f2017-09-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 20V, Negative-QTOFsplash10-000i-0009002000-77e13fcb4d0714dcdc712017-09-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 40V, Negative-QTOFsplash10-00ku-2009000000-4e122eb60c28c6facfd32017-09-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 10V, Positive-QTOFsplash10-0uxr-1019014600-8244efae243bfbaa3a052017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 20V, Positive-QTOFsplash10-014r-3149012000-39acc63a5fcafe8e26cf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 40V, Positive-QTOFsplash10-0adi-4269003000-603d253fb8473b7243312017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 10V, Positive-QTOFsplash10-0gc0-4139001400-411feafb37c59305b2e82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 20V, Positive-QTOFsplash10-0aou-9121011000-4b6ebce89c61d657b1152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 40V, Positive-QTOFsplash10-05mo-9210002000-1523361cb1e65ce31c1d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 10V, Negative-QTOFsplash10-0002-0002009000-6e849b2deeef55a78f3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 20V, Negative-QTOFsplash10-0002-0005019000-b1f9a9182e6064722cd22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(22:4(7Z,10Z,13Z,16Z)) 40V, Negative-QTOFsplash10-0a4j-5003319000-ab1031720f024444090e2021-09-22Wishart 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 IDFDB024045
KNApSAcK IDNot Available
Chemspider ID17221005
KEGG Compound IDC02530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061341
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sinclair AJ, Begg D, Mathai M, Weisinger RS: Omega 3 fatty acids and the brain: review of studies in depression. Asia Pac J Clin Nutr. 2007;16 Suppl 1:391-7. [PubMed:17392137 ]
  2. Houssaini FZ, Foulon T, Iraqi MR, Payen N, Groslambert P: Lipids, lipoproteins, and fatty acids during infantile marasmus in the Fes area of Morocco. Biomed Pharmacother. 1999 Jun;53(5-6):278-83. [PubMed:10424250 ]
  3. Cullen P, Fobker M, Tegelkamp K, Meyer K, Kannenberg F, Cignarella A, Benninghoven A, Assmann G: An improved method for quantification of cholesterol and cholesteryl esters in human monocyte-derived macrophages by high performance liquid chromatography with identification of unassigned cholesteryl ester species by means of secondary ion mass spectrometry. J Lipid Res. 1997 Feb;38(2):401-9. [PubMed:9162758 ]

Enzymes

General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:
LCAT
Uniprot ID:
P04180
Molecular weight:
49577.545
General function:
Involved in lipid metabolic process
Specific function:
Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:
LIPA
Uniprot ID:
P38571
Molecular weight:
45418.71
General function:
Lipid transport and metabolism
Specific function:
Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
Gene Name:
CEL
Uniprot ID:
P19835
Molecular weight:
79666.385
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
General function:
Involved in acyl-CoA binding
Specific function:
Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase. May provide cholesteryl esters for lipoprotein secretion from hepatocytes and intestinal mucosa.
Gene Name:
SOAT2
Uniprot ID:
O75908
Molecular weight:
59895.735
General function:
Involved in acyl-CoA binding
Specific function:
Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:
SOAT1
Uniprot ID:
P35610
Molecular weight:
58130.665
General function:
Involved in cell adhesion
Specific function:
Receptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Probable receptor for HDL, located in particular region of the plasma membrane, called caveolae. Facilitates the flux of free and esterified cholesterol between the cell surface and extracellular donors and acceptors, such as HDL and to a lesser extent, apoB-containing lipoproteins and modified lipoproteins. Probably involved in the phagocytosis of apoptotic cells, via its phosphatidylserine binding activity. Receptor for hepatitis C virus glycoprotein E2. Binding between SCARB1 and E2 was found to be independent of the genotype of the viral isolate. Plays an important role in the uptake of HDL cholesteryl ester
Gene Name:
SCARB1
Uniprot ID:
Q8WTV0
Molecular weight:
60877.4
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes 2-acetyl monoalkylglycerol ether, the penultimate precursor of the pathway for de novo synthesis of platelet-activating factor. May be responsible for cholesterol ester hydrolysis in macrophages, thereby contributing to the development of atherosclerosis. Also involved in organ detoxification by hydrolyzing exogenous organophosphorus compounds. May contribute to cancer pathogenesis by promoting tumor cell migration
Gene Name:
NCEH1
Uniprot ID:
Q6PIU2
Molecular weight:
45807.4