Record Information
Version2.0
Creation Date2012-05-31 14:33:57 -0600
Update Date2015-06-04 17:06:03 -0600
Secondary Accession Numbers
  • ECMDB20223
Identification
Name:2'-(5-Triphosphoribosyl)-3'-dephospho-CoA
Description2'-(5-triphosphoribosyl)-3'-dephospho-CoA is a member of the chemical class known as Purine Ribonucleoside Triphosphates. These are purine ribobucleotides with triphosphate group linked to the ribose moiety.
Structure
Thumb
Synonyms:
  • 2'-(5''-Triphosphoribosyl)-3'-dephospho-CoA
  • 2-5-TRIPHOSPHORIBOSYL-3-DEPHOSPHO-
  • 2-5-Triphosphoribosyl-3-dephospho-CoA
Chemical Formula:C26H46N7O26P5S
Weight:Average: 1059.609
Monoisotopic: 1059.090127929
InChI Key:NFWZJXFBUKDGOX-JIRKQKIOSA-N
InChI:InChI=1S/C26H46N7O26P5S/c1-26(2,20(38)23(39)29-4-3-14(34)28-5-6-65)9-53-63(47,48)58-61(43,44)52-8-13-17(36)19(24(54-13)33-11-32-15-21(27)30-10-31-22(15)33)56-25-18(37)16(35)12(55-25)7-51-62(45,46)59-64(49,50)57-60(40,41)42/h10-13,16-20,24-25,35-38,65H,3-9H2,1-2H3,(H,28,34)(H,29,39)(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H2,27,30,31)(H2,40,41,42)/t12-,13-,16-,17-,18-,19-,20+,24-,25+/m1/s1
CAS number:Not Available
IUPAC Name:(2R)-4-({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-2-yl]oxy}-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-sulfanylethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid
Traditional IUPAC Name:(2R)-4-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-2-yl]oxy}-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-{2-[(2-sulfanylethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid
SMILES:[H][C@](O)(C(O)=NCCC(O)=NCCS)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@]2([H])O[C@]([H])(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@]([H])(O)[C@@]2([H])O)[C@]1([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Carboximidic acid derivative
  • Carboximidic acid
  • Alkylthiol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-5
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility18.3 g/LALOGPS
logP-0.2ALOGPS
logP-3.7ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.85ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area505.52 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity211.98 m³·mol⁻¹ChemAxon
Polarizability87.74 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Citrate lyase activationPW002075 ThumbThumb?image type=greyscaleThumb?image type=simple
Pantothenate and CoA biosynthesisPW000828 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • 2'-(5'-phosphoribosyl)-3'-dephospho-CoA biosynthesis I (citrate lyase) P2-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002s-6910001000-f4f861f346fb75cca342View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ti-7930000000-695461e8bfd161ed5316View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004s-9810000000-6addae9cde79098e0b87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-9731214201-22f57ed038436902e62bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-7930201100-8d23cd24997eafa3b68bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-6951200000-5f6342661b613623c853View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25203684
Kegg IDC19771
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc ID2-5-TRIPHOSPHORIBOSYL-3-DEPHOSPHO-
EcoCyc ID2-5-TRIPHOSPHORIBOSYL-3-DEPHOSPHO-

Enzymes

General function:
Involved in prosthetic group biosynthetic process
Specific function:
Transfers 2-(5''-triphosphoribosyl)-3'- dephosphocoenzyme-A on a serine residue to the apo-acyl carrier protein (gamma chain) of the citrate lyase to yield holo-acyl carrier protein
Gene Name:
citX
Uniprot ID:
P0A6G5
Molecular weight:
20270
Reactions
2'-(5-triphosphoribosyl)-3'-dephospho-CoA + citrate lyase apo-[acyl-carrier-protein] = citrate lyase holo-[acyl-carrier-protein] + diphosphate.
General function:
Involved in ATP binding
Specific function:
Catalyzes the formation of 2-(5''-triphosphoribosyl)-3'- dephosphocoenzyme-A, the precursor of the prosthetic group of the holo-acyl carrier protein (gamma chain) of citrate lyase, from ATP and dephospho-CoA
Gene Name:
citG
Uniprot ID:
P77231
Molecular weight:
31644
Reactions
ATP + 3-dephospho-CoA = 2'-(5-triphosphoribosyl)-3'-dephospho-CoA + adenine.