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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:08:28 UTC
Update Date2022-03-07 03:17:53 UTC
HMDB IDHMDB0062371
Secondary Accession Numbers
  • HMDB62371
Metabolite Identification
Common Name3-Oxohexacosanoyl-CoA
Description3-oxohexacosanoyl-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. 3-oxohexacosanoyl-CoA is a strong basic compound (based on its pKa).
Structure
Data?1563866302
Synonyms
ValueSource
3-Ketocerotoyl-CoA(4-)HMDB
3-Ketohexacosanoyl-CoA(4-)HMDB
3-Ketohexacosanoyl-coenzyme A(4-)HMDB
3-Oxocerotoyl-CoA(4-)HMDB
3-Oxohexacosanoyl-coenzyme A(4-)HMDB
[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-2-[[[[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[2-(3-oxohexacosanoylsulfanyl)ethylamino]propyl]amino]butoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphoric acidHMDB
[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-2-[[[[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[2-(3-oxohexacosanoylsulphanyl)ethylamino]propyl]amino]butoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphateHMDB
[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-2-[[[[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[2-(3-oxohexacosanoylsulphanyl)ethylamino]propyl]amino]butoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphoric acidHMDB
Chemical FormulaC47H84N7O18P3S
Average Molecular Weight1160.2
Monoisotopic Molecular Weight1159.480641061
IUPAC Name4-({[({[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-[(3-oxohexacosanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid
Traditional Name4-[({[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-[(3-oxohexacosanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(=O)CC(=O)SCCN=C(O)CCN=C(O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier
InChI=1S/C47H84N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-35(55)30-38(57)76-29-28-49-37(56)26-27-50-45(60)42(59)47(2,3)32-69-75(66,67)72-74(64,65)68-31-36-41(71-73(61,62)63)40(58)46(70-36)54-34-53-39-43(48)51-33-52-44(39)54/h33-34,36,40-42,46,58-59H,4-32H2,1-3H3,(H,49,56)(H,50,60)(H,64,65)(H,66,67)(H2,48,51,52)(H2,61,62,63)
InChI KeyVOMUIFOBQMYJPJ-UHFFFAOYSA-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
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • 1,3-dicarbonyl compound
  • Pyrimidine
  • Alkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Oxolane
  • Thiocarboxylic acid ester
  • Amino acid or derivatives
  • Secondary alcohol
  • Ketone
  • Carbothioic s-ester
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Oxacycle
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Primary amine
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.031 g/lALOGPS
LogP5.37ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.7ALOGPS
logP6.01ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area387.68 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity284.39 m³·mol⁻¹ChemAxon
Polarizability121.8 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-2H]-333.83630932474
DeepCCS[M+Na]+308.22730932474
AllCCS[M+H]+323.532859911
AllCCS[M+H-H2O]+323.932859911
AllCCS[M+NH4]+323.032859911
AllCCS[M+Na]+322.932859911
AllCCS[M-H]-289.032859911
AllCCS[M+Na-2H]-294.032859911
AllCCS[M+HCOO]-299.332859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 10V, Positive-QTOFsplash10-000i-1900330100-f3b05ada071edef1cdf72019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 20V, Positive-QTOFsplash10-000i-1901522000-367d76c92683abd84c5c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 40V, Positive-QTOFsplash10-000i-1900210000-8e3d596ac9294e99101d2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 10V, Negative-QTOFsplash10-05o3-2903131210-d2f59d48f9aa4d5610ba2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 20V, Negative-QTOFsplash10-001i-3901110000-4f08d4a1e2926636dbd92019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-3113848ce123c9e7552f2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 10V, Negative-QTOFsplash10-0a4i-0900000000-76e53cf02ce2a47843fe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 20V, Negative-QTOFsplash10-0a6r-5900301330-adb643ee6353d359b4222021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 40V, Negative-QTOFsplash10-00vu-6903300410-ab8fd731c83bd205db2d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 10V, Positive-QTOFsplash10-03dl-0900000000-4f072ffe3a5d318d81bb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 20V, Positive-QTOFsplash10-006x-2900200131-121ca9f2e192829eaea72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxohexacosanoyl-CoA 40V, Positive-QTOFsplash10-0udi-0000149000-042017611a29aa6390c32021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74441046
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.