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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 03:11:59 UTC
Update Date2022-03-07 03:17:56 UTC
HMDB IDHMDB0062535
Secondary Accession Numbers
  • HMDB62535
Metabolite Identification
Common Nametrans-2,3-dehydropristanoyl-CoA
Description(E)-2,3-didehydropristanoyl-CoA belongs to the class of organic compounds known as 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives. Thus, (e)-2,3-didehydropristanoyl-CoA is considered to be a fatty ester lipid molecule. A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (E)-2,3-didehydropristanic acid (E)-2,3-didehydropristanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866325
Synonyms
ValueSource
trans-2,3-Dehydropristanoyl-CoAChEBI
trans-2,3-Didehydropristanoyl-CoAChEBI
Chemical FormulaC40H70N7O17P3S
Average Molecular Weight1046.01
Monoisotopic Molecular Weight1045.37617599
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-{[(2E)-2,6,10,14-tetramethylpentadec-2-enoyl]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-{[(2E)-2,6,10,14-tetramethylpentadec-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCC([H])(C)CCCC([H])(C)CCCC(C)C)=C(\C)C(=O)SCCN=C(O)CCN=C(O)[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
InChI Identifier
InChI=1S/C40H70N7O17P3S/c1-25(2)11-8-12-26(3)13-9-14-27(4)15-10-16-28(5)39(52)68-20-19-42-30(48)17-18-43-37(51)34(50)40(6,7)22-61-67(58,59)64-66(56,57)60-21-29-33(63-65(53,54)55)32(49)38(62-29)47-24-46-31-35(41)44-23-45-36(31)47/h16,23-27,29,32-34,38,49-50H,8-15,17-22H2,1-7H3,(H,42,48)(H,43,51)(H,56,57)(H,58,59)(H2,41,44,45)(H2,53,54,55)/b28-16+/t26?,27?,29-,32-,33-,34+,38-/m1/s1
InChI KeyWLOASZHRLIOYIA-TXRROMTDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class5'-deoxyribonucleosides
Sub ClassNot Available
Direct Parent5'-deoxyribonucleosides
Alternative Parents
Substituents
  • 5'-deoxyribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Pentose monosaccharide
  • 6-aminopurine
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Azole
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Selenoether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary amine
  • Organoselenium compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.97 g/lALOGPS
LogP2.71ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.07ALOGPS
logP3.28ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area370.61 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity252.19 m³·mol⁻¹ChemAxon
Polarizability103.39 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]-322.78530932474
DeepCCS[M+Na]+296.39630932474
AllCCS[M+H]+307.332859911
AllCCS[M+H-H2O]+307.732859911
AllCCS[M+NH4]+306.832859911
AllCCS[M+Na]+306.732859911
AllCCS[M-H]-294.532859911
AllCCS[M+Na-2H]-300.832859911
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 - trans-2,3-dehydropristanoyl-CoA 10V, Positive-QTOFsplash10-002r-4906510200-b8869cad0134b6d203202017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 20V, Positive-QTOFsplash10-000i-1915210000-c2348c12a6e3fb0dd4232017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 40V, Positive-QTOFsplash10-000i-1912200000-b46746d80b68fda466612017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 10V, Negative-QTOFsplash10-0059-9751332600-da51082bb80d8f5c69122017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 20V, Negative-QTOFsplash10-003r-5920210000-ada2071309d2c9133a062017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 40V, Negative-QTOFsplash10-057i-5900000000-56877c69a35897b12f4e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 10V, Negative-QTOFsplash10-0006-9000000000-98d325ef7163e719f5b52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 20V, Negative-QTOFsplash10-004l-9031103300-43c231971a0bae08e6832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 40V, Negative-QTOFsplash10-00p0-8003522902-150301604a930652c8ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 10V, Positive-QTOFsplash10-0002-9000000005-e2f3ecd149ec1307810d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 20V, Positive-QTOFsplash10-001i-4000000339-1b75471468a57ec568f22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2,3-dehydropristanoyl-CoA 40V, Positive-QTOFsplash10-000i-0000790000-b9b29c1933086d4bc9202021-09-24Wishart 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 Compound56927963
PDB IDNot Available
ChEBI ID63803
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.