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Record Information
Version	2.0
Creation Date	2012-05-31 14:31:51 -0600
Update Date	2015-06-03 17:19:28 -0600
Secondary Accession Numbers	ECMDB20182
Identification
Name:	Oxalyl-CoA
Description	Oxalyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. Oxalyl CoA is invovled in the catabolism of toxic compound oxalate. Oxalyl coenzyme A (CoA) decarboxylase (Oxc) is a key enzyme in the catabolism of the highly toxic compound oxalate, catalyzing the decarboxylation of oxalyl-CoA to formyl-CoA. (PMID 15345383) Oxalyl-coenzyme A decarboxylase is a thiamin diphosphate dependent enzyme active in the catabolism of the highly toxic compound oxalate. (PMID 16198641)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xafa758b4> Close
Synonyms:	CoA-oxalate CoA-oxalic acid Oxalyl-coenzyme a
Chemical Formula:	C23H36N7O19P3S
Weight:	Average: 839.554 Monoisotopic: 839.099952231
InChI Key:	QVXMZFTWJVBUHP-IBOSZNHHSA-N
InChI:	InChI=1S/C23H36N7O19P3S/c1-23(2,16(33)19(34)26-4-3-12(31)25-5-6-53-22(37)21(35)36)8-46-52(43,44)49-51(41,42)45-7-11-15(48-50(38,39)40)14(32)20(47-11)30-10-29-13-17(24)27-9-28-18(13)30/h9-11,14-16,20,32-33H,3-8H2,1-2H3,(H,25,31)(H,26,34)(H,35,36)(H,41,42)(H,43,44)(H2,24,27,28)(H2,38,39,40)/t11-,14-,15-,16+,20-/m1/s1
CAS number:	Not Available
IUPAC Name:	2-({2-[(3-{[(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)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-oxoacetic acid
Traditional IUPAC Name:	({2-[(3-{[(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]-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)(oxo)acetic acid
SMILES:	[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)C(O)=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
Chemical Taxonomy
Description	belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'.
Kingdom	Inorganic compounds
Super Class	Homogeneous non-metal compounds
Class	Homogeneous other non-metal compounds
Sub Class	Not Available
Direct Parent	Homogeneous other non-metal compounds
Alternative Parents	Not Available
Substituents	Homogeneous other non metal
Molecular Framework	Not Available
External Descriptors	oxygen hydride (CHEBI:15377 ) mononuclear parent hydride (CHEBI:15377 ) inorganic hydroxy compound (CHEBI:15377 ) a small molecule (WATER )
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 5.54 g/L ALOGPS logP -0.42 ALOGPS logP -4.1 ChemAxon logS -2.2 ALOGPS pKa (Strongest Acidic) 0.81 ChemAxon pKa (Strongest Basic) 4.8 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 21 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 407.91 Ų ChemAxon Rotatable Bond Count 21 ChemAxon Refractivity 175.05 m³·mol⁻¹ ChemAxon Polarizability 72.11 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:	Hydrogen ion + Oxalyl-CoA <> Carbon dioxide + Formyl-CoA Formyl-CoA + Oxalic acid <> Formic acid + Oxalyl-CoA Oxalyl-CoA <> Formyl-CoA + Carbon dioxide Hydrogen ion + Oxalyl-CoA Carbon dioxide + Formyl-CoA Formyl-CoA + Oxalic acid Formic acid + Oxalyl-CoA Formyl-CoA + Oxalic acid > Formic acid + Oxalyl-CoA Oxalyl-CoA > Formyl-CoA + Carbon dioxide Acetyl-CoA + Oxalic acid <> Acetic acid + Oxalyl-CoA
SMPDB Pathways:	Not Available
KEGG Pathways:	Glyoxylate and dicarboxylate metabolism ec00630 Metabolic pathways eco01100
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00ks-0931000110-22ded9fe531730449923 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000j-0911000000-19e3e76082c9e7682f2c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00ks-1920000000-2d4244f1d0638760c091 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0040-4930142370-1fa4f6902014b005941c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-3910200000-c7b620c7bb31afb999d7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-5900100000-c407c65037998edc22bc View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer
References
References:	Berthold, C. L., Sidhu, H., Ricagno, S., Richards, N. G., Lindqvist, Y. (2006). "Detection and characterization of merohedral twinning in crystals of oxalyl-coenzyme A decarboxylase from Oxalobacter formigenes." Biochim Biophys Acta 1764:122-128. Pubmed: 16198641 Federici, F., Vitali, B., Gotti, R., Pasca, M. R., Gobbi, S., Peck, A. B., Brigidi, P. (2004). "Characterization and heterologous expression of the oxalyl coenzyme A decarboxylase gene from Bifidobacterium lactis." Appl Environ Microbiol 70:5066-5073. Pubmed: 15345383 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)	Not Available
Links
External Links:	Resource Link CHEBI ID 15535 HMDB ID Not Available Pubchem Compound ID 439206 Kegg ID C00313 ChemSpider ID 388346 Wikipedia ID Not Available BioCyc ID OXALYL-COA EcoCyc ID OXALYL-COA Ligand Expo OXK

Enzymes