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Record Information
Version	2.0
Creation Date	2012-05-31 13:51:14 -0600
Update Date	2015-09-13 12:56:11 -0600
Secondary Accession Numbers	ECMDB01373
Identification
Name:	Dephospho-CoA
Description	Dephospho-CoA is a substrate for Ectonucleotide pyrophosphatase/phosphodiesterase 1, Ectonucleotide pyrophosphatase/phosphodiesterase 3 and Ectonucleotide pyrophosphatase/phosphodiesterase 2.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x94f6fbf0> Close
Synonyms:	3'-dephospho-CoA 3'-dephospho-Coenzyme A 3'-O-Dephosphono-CoA 3'-O-Dephosphono-Coenzyme A 3-Dephospho-CoA DePCoA Dephospho-CoA Dephospho-Coenzyme A Dephosphocoenzyme a
Chemical Formula:	C21H35N7O13P2S
Weight:	Average: 687.554 Monoisotopic: 687.148877955
InChI Key:	KDTSHFARGAKYJN-DRCCLKDXSA-N
InChI:	InChI=1S/C21H35N7O13P2S/c1-21(2,16(32)19(33)24-4-3-12(29)23-5-6-44)8-39-43(36,37)41-42(34,35)38-7-11-14(30)15(31)20(40-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-32,44H,3-8H2,1-2H3,(H,23,29)(H,24,33)(H,34,35)(H,36,37)(H2,22,25,26)/t11-,14-,15-,16?,20-/m1/s1
CAS number:	3633-59-8
IUPAC Name:	[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid
Traditional IUPAC Name:	{[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy)phosphinic acid
SMILES:	CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCS
Chemical Taxonomy
Description	belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine ribonucleotides
Direct Parent	Purine ribonucleoside diphosphates
Alternative Parents	Purine ribonucleoside monophosphates Pentose phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Aminopyrimidines and derivatives Monoalkyl phosphates N-substituted imidazoles N-acyl amines Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary carboxylic acid amides Secondary alcohols Alkylthiols Azacyclic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Primary amines Organopnictogen compounds
Substituents	Purine ribonucleoside diphosphate Purine ribonucleoside monophosphate Pentose phosphate Pentose-5-phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound 6-aminopurine Pentose monosaccharide Monosaccharide phosphate Organic pyrophosphate Imidazopyrimidine Purine Aminopyrimidine Monoalkyl phosphate N-acyl-amine N-substituted imidazole Organic phosphoric acid derivative Pyrimidine Fatty amide Imidolactam Monosaccharide Fatty acyl Phosphoric acid ester Alkyl phosphate Azole Heteroaromatic compound Imidazole Tetrahydrofuran Secondary alcohol Secondary carboxylic acid amide Amino acid or derivatives Carboxamide group Organoheterocyclic compound Carboxylic acid derivative Alkylthiol Oxacycle Azacycle Organic oxide Organooxygen compound Organosulfur compound Carbonyl group Organopnictogen compound Organic nitrogen compound Organic oxygen compound Hydrocarbon derivative Alcohol Organonitrogen compound Primary amine Amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 2.56 g/L ALOGPS logP -0.98 ALOGPS logP -5.9 ChemAxon logS -2.4 ALOGPS pKa (Strongest Acidic) 1.86 ChemAxon pKa (Strongest Basic) 5 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 14 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 300.03 Ų ChemAxon Rotatable Bond Count 16 ChemAxon Refractivity 151.87 m³·mol⁻¹ ChemAxon Polarizability 62.51 ų ChemAxon Number of Rings 3 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 <> ADP + Coenzyme A + Hydrogen ion Adenosine triphosphate + Dephospho-CoA > 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + Adenine Adenosine triphosphate + Hydrogen ion + Pantetheine 4'-phosphate <> Dephospho-CoA + Pyrophosphate Adenosine triphosphate + Dephospho-CoA <> ADP + Coenzyme A Adenosine triphosphate + Pantetheine 4'-phosphate <> Pyrophosphate + Dephospho-CoA Hydrogen ion + Dephospho-CoA + Adenosine triphosphate > 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + Adenine Dephospho-CoA + Adenosine triphosphate > Hydrogen ion + Coenzyme A + ADP Adenosine triphosphate + Dephospho-CoA <> 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + Adenine Pantetheine 4'-phosphate + Adenosine triphosphate + pantotheine 4'-phosphate > Dephospho-CoA + Pyrophosphate Adenosine triphosphate + Dephospho-CoA > Adenosine diphosphate + Coenzyme A + ADP Dephospho-CoA + Water <> Pantetheine 4'-phosphate + Adenosine monophosphate + pantotheine 4'-phosphate 4'-phosphopantetheine + Adenosine triphosphate + Hydrogen ion + 4'-phosphopantetheine > Pyrophosphate + Dephospho-CoA Dephospho-CoA + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + Coenzyme A + ADP Adenosine triphosphate + Hydrogen ion + Pantetheine 4'-phosphate <> Dephospho-CoA + Pyrophosphate Adenosine triphosphate + Dephospho-CoA <> ADP + Coenzyme A + Hydrogen ion Adenosine triphosphate + Hydrogen ion + Pantetheine 4'-phosphate <> Dephospho-CoA + Pyrophosphate
SMPDB Pathways:	Citrate lyase activation PW002075 Pantothenate and CoA biosynthesis PW000828
KEGG Pathways:	Metabolic pathways eco01100 Pantothenate and CoA biosynthesis ec00770 Two-component system ec02020
EcoCyc Pathways:	2'-(5'-phosphoribosyl)-3'-dephospho-CoA biosynthesis I (citrate lyase) P2-PWY coenzyme A biosynthesis COA-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-03fr-1452933000-479a35a051c9c3fcda0d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-2930102000-19d2796dee5d14788e39 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-3930000000-d4541feacee9a6c7a4e3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-4900000000-1307cbce80b215d981b9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0040-2910618000-58e100b1447a771ecd7c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-1910200000-ba57f132dee9798389fa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a7i-3900000000-d382c7ac6874be7ea151 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:	Haugen HF, Skrede S: Nucleotide pyrophosphatase and phosphodiesterase I. Demonstration of activity in normal serum, and an increase in cholestatic liver disease. Scand J Gastroenterol. 1976;11(2):121-7. Pubmed: 4880 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 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)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 15468 HMDB ID HMDB01373 Pubchem Compound ID 444485 Kegg ID C00882 ChemSpider ID 388463 Wikipedia ID Not Available BioCyc ID DEPHOSPHO-COA EcoCyc ID DEPHOSPHO-COA

Enzymes