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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:52:39 UTC
Update Date2019-07-23 07:14:02 UTC
HMDB IDHMDB0060313
Secondary Accession Numbers
  • HMDB60313
Metabolite Identification
Common Name(6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosahexa-6,9,12,15,18,21-enoyl-CoA
Description(6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosahexa-6,9,12,15,18,21-enoyl-CoA, also known as (6Z,9Z,12Z,15Z,18Z,21Z)-3-oxotetracosahexaenoyl-coenzyme A or 3-keto-tha-CoA, belongs to the class of organic compounds known as very-long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 22 carbon atoms or more. Thus, (6Z,9Z,12Z,15Z,18Z,21Z)-3-oxotetracosahexa-6,9,12,15,18,21-enoyl-CoA is considered to be a fatty ester lipid molecule (6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosahexa-6,9,12,15,18,21-enoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866042
Synonyms
ValueSource
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosa-6,9,12,15,18,21-hexaenoyl-CoAChEBI
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosa-6,9,12,15,18,21-hexaenoyl-coenzyme AChEBI
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosahexaenoyl-coenzyme AChEBI
1-(3-oxo-6Z,9Z,12Z,15Z,18Z,21Z-Tetracosahexaenoyl)-CoAChEBI
3-Keto-tha-CoAChEBI
3-oxo-C24:6(Omega-3)-CoAChEBI
CoA(24:6(6Z,9Z,12Z,15Z,18Z,21Z)(3Ke))ChEBI
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosahexa-6,9,12,15,18,21-enoyl-CoAChEBI
Chemical FormulaC45H68N7O18P3S
Average Molecular Weight1120.044
Monoisotopic Molecular Weight1119.355438633
IUPAC Name(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(6Z,9Z,12Z,15Z,18Z,21Z)-3-oxotetracosa-6,9,12,15,18,21-hexaenoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid
Traditional Name(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(6Z,9Z,12Z,15Z,18Z,21Z)-3-oxotetracosa-6,9,12,15,18,21-hexaenoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)CC(=O)SCCN=C(O)CCN=C(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=C(N)N=CN=C12
InChI Identifier
InChI=1S/C45H68N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-33(53)28-36(55)74-27-26-47-35(54)24-25-48-43(58)40(57)45(2,3)30-67-73(64,65)70-72(62,63)66-29-34-39(69-71(59,60)61)38(56)44(68-34)52-32-51-37-41(46)49-31-50-42(37)52/h5-6,8-9,11-12,14-15,17-18,20-21,31-32,34,38-40,44,56-57H,4,7,10,13,16,19,22-30H2,1-3H3,(H,47,54)(H,48,58)(H,62,63)(H,64,65)(H2,46,49,50)(H2,59,60,61)/b6-5-,9-8-,12-11-,15-14-,18-17-,21-20-/t34-,38-,39-,40+,44-/m1/s1
InChI KeyDNHDPAXPQGYGIJ-KWFBMMABSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as very-long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 22 carbon atoms or more.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentVery-long-chain 3-oxoacyl 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
  • 1,3-dicarbonyl compound
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Ketone
  • 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
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP3.99ALOGPS
logP2.91ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area387.68 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity281.89 m³·mol⁻¹ChemAxon
Polarizability109.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900700100-ffadbd155551bb0f8608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-1911701000-a2a237f24d7241ac5193Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900400000-ba7fcb8da3be6503b68aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fur-3904131300-ded81d2705ef4f807fa0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3901210100-bdb7fc7bdbf2a355be0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-d7a9c0af0bf9caa0f933Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDNot Available
KEGG Compound IDC16376
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70678653
PDB IDNot Available
ChEBI ID65131
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAA1
Uniprot ID:
P09110
Molecular weight:
34664.46
Reactions
Cervonyl coenzyme A + Acetyl-CoA → Coenzyme A + (6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosahexa-6,9,12,15,18,21-enoyl-CoAdetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA + NAD → (6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosahexa-6,9,12,15,18,21-enoyl-CoA + NADH + Hydrogen Iondetails