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Record Information
Version	2.0
Creation Date	2012-05-31 14:33:57 -0600
Update Date	2015-06-04 17:06:03 -0600
Secondary Accession Numbers	ECMDB20223
Identification
Name:	2'-(5-Triphosphoribosyl)-3'-dephospho-CoA
Description	2'-(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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x95612200> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Organic phosphoric acids and derivatives
Sub Class	Phosphate esters
Direct Parent	Monoalkyl phosphates
Alternative Parents	Carboximidic acids Alkylthiols Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Organic anions
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 Framework	Aliphatic acyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-5
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 18.3 g/L ALOGPS logP -0.2 ALOGPS logP -3.7 ChemAxon logS -1.8 ALOGPS pKa (Strongest Acidic) 0.85 ChemAxon Physiological Charge -5 ChemAxon Hydrogen Acceptor Count 26 ChemAxon Hydrogen Donor Count 14 ChemAxon Polar Surface Area 505.52 Ų ChemAxon Rotatable Bond Count 25 ChemAxon Refractivity 211.98 m³·mol⁻¹ ChemAxon Polarizability 87.74 ų ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Adenosine triphosphate + Dephospho-CoA > 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + Adenine Hydrogen ion + Dephospho-CoA + Adenosine triphosphate > 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + Adenine 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + citrate lyase apo-[acyl-carrier-protein] > citrate lyase holo-[acyl-carrier-protein] + Pyrophosphate Adenosine triphosphate + Dephospho-CoA <> 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + Adenine 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA <> Pyrophosphate 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + [an apo citrate-lyase acyl-carrier protein] > Pyrophosphate + Hydrogen ion + [a holo citrate lyase acyl-carrier protein]
SMPDB Pathways:	Citrate lyase activation PW002075 Pantothenate and CoA biosynthesis PW000828
KEGG Pathways:	Pantothenate and CoA biosynthesis ec00770 Two-component system ec02020
EcoCyc Pathways:	2'-(5'-phosphoribosyl)-3'-dephospho-CoA biosynthesis I (citrate lyase) P2-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-002s-6910001000-f4f861f346fb75cca342 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01ti-7930000000-695461e8bfd161ed5316 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-004s-9810000000-6addae9cde79098e0b87 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-053r-9731214201-22f57ed038436902e62b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-003r-7930201100-8d23cd24997eafa3b68b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a70-6951200000-5f6342661b613623c853 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 25203684 Kegg ID C19771 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID 2-5-TRIPHOSPHORIBOSYL-3-DEPHOSPHO- EcoCyc ID 2-5-TRIPHOSPHORIBOSYL-3-DEPHOSPHO-

Enzymes