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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:01:58 UTC
Update Date2022-03-07 03:17:40 UTC
HMDB IDHMDB0060181
Secondary Accession Numbers
  • HMDB60181
Metabolite Identification
Common Name3-Oxopristanoyl-CoA
Description3-Oxopristanoyl-CoA belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms. 3-Oxopristanoyl-CoA is a strong basic compound (based on its pKa).
Structure
Data?1563866025
SynonymsNot Available
Chemical FormulaC40H70N7O18P3S
Average Molecular Weight1062.006
Monoisotopic Molecular Weight1061.371088697
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-{[(2R,6R,10R)-2,6,10,14-tetramethyl-3-oxopentadecanoyl]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-{[(2R,6R,10R)-2,6,10,14-tetramethyl-3-oxopentadecanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid
CAS Registry NumberNot Available
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC(=O)[C@@H](C)C(=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/C40H70N7O18P3S/c1-24(2)10-8-11-25(3)12-9-13-26(4)14-15-28(48)27(5)39(53)69-19-18-42-30(49)16-17-43-37(52)34(51)40(6,7)21-62-68(59,60)65-67(57,58)61-20-29-33(64-66(54,55)56)32(50)38(63-29)47-23-46-31-35(41)44-22-45-36(31)47/h22-27,29,32-34,38,50-51H,8-21H2,1-7H3,(H,42,49)(H,43,52)(H,57,58)(H,59,60)(H2,41,44,45)(H2,54,55,56)/t25-,26-,27-,29-,32-,33-,34+,38-/m1/s1
InChI KeyNQFYRDGBRBDQQG-JJNGQNJBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated 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 3-oxoacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Diterpenoid
  • 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
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Imidolactam
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • 1,3-dicarbonyl compound
  • Imidazole
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Ketone
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Primary amine
  • Carbonyl group
  • Alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility2.16 g/LALOGPS
logP2.64ALOGPS
logP2.49ChemAxon
logS-2.7ALOGPS
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 Count33ChemAxon
Refractivity252 m³·mol⁻¹ChemAxon
Polarizability106.98 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]-314.0530932474
DeepCCS[M+Na]+288.48630932474
AllCCS[M+H]+307.132859911
AllCCS[M+H-H2O]+307.632859911
AllCCS[M+NH4]+306.632859911
AllCCS[M+Na]+306.532859911
AllCCS[M-H]-294.732859911
AllCCS[M+Na-2H]-301.032859911
AllCCS[M+HCOO]-307.732859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 10V, Positive-QTOFsplash10-000l-4905510200-08c92ef0635255f92d7f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 20V, Positive-QTOFsplash10-0079-1915210000-863ff9277507638d60522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 40V, Positive-QTOFsplash10-000i-1902200000-96fedc07b1e02e99c5072017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 10V, Negative-QTOFsplash10-00l7-9761332700-cf9bc59642c7663b7e2a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 20V, Negative-QTOFsplash10-001i-5920210100-0108296defbbcf2cf87c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-59f4fe6c1c6fb1be73282017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 10V, Positive-QTOFsplash10-03di-9000000003-2b3268e531fb6b7424632021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 20V, Positive-QTOFsplash10-0ue9-8000000019-45662e2d5debc112511e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 40V, Positive-QTOFsplash10-0a4i-0000390000-a17e59ee044667ed9cf72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 10V, Negative-QTOFsplash10-03di-9000000100-ed5b9eae7276929df7ad2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 20V, Negative-QTOFsplash10-01tl-9110101000-59e90eef089bd3541c2e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxopristanoyl-CoA 40V, Negative-QTOFsplash10-00n6-9003522501-62845a270817a19a92fe2021-10-12Wishart LabView Spectrum
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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769862
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. 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 ]
  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.