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Record Information
Version	2.0
Creation Date	2012-05-31 13:59:00 -0600
Update Date	2015-06-03 15:54:23 -0600
Secondary Accession Numbers	ECMDB03419
Identification
Name:	Formyl-CoA
Description	Formyl-CoA is is an intermediate of glyoxylate and dicarboxylate metabolism. It is converted from oxalyl-CoA by oxalyl-CoA decarboxylase (EC:4.1.1.8) and converts to formate. (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaac4c214> Close
Synonyms:	Formyl coenzyme A
Chemical Formula:	C22H36N7O17P3S
Weight:	Average: 795.544 Monoisotopic: 795.110122987
InChI Key:	SXMOKYXNAPLNCW-GORZOVPNSA-N
InChI:	InChI=1S/C22H36N7O17P3S/c1-22(2,17(33)20(34)25-4-3-13(31)24-5-6-50-11-30)8-43-49(40,41)46-48(38,39)42-7-12-16(45-47(35,36)37)15(32)21(44-12)29-10-28-14-18(23)26-9-27-19(14)29/h9-12,15-17,21,32-33H,3-8H2,1-2H3,(H,24,31)(H,25,34)(H,38,39)(H,40,41)(H2,23,26,27)(H2,35,36,37)/t12-,15-,16-,17+,21-/m1/s1
CAS number:	13131-49-2
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)-N-(2-{[2-(formylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid
Traditional IUPAC 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]-N-(2-{[2-(formylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid
SMILES:	[H][C@](O)(C(O)=NCCC(O)=NCCSC=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 organic compounds known as coenzyme a and derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine ribonucleotides
Direct Parent	Coenzyme A and derivatives
Alternative Parents	Purine ribonucleoside diphosphates Ribonucleoside 3'-phosphates Pentose phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Aminopyrimidines and derivatives Monoalkyl phosphates Imidolactams N-acyl amines N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Thioesters Secondary carboxylic acid amides Carbothioic S-esters Azacyclic compounds Sulfenyl compounds Oxacyclic compounds Primary amines Hydrocarbon derivatives Carbonyl compounds Organic oxides Organopnictogen compounds
Substituents	Coenzyme a or derivatives Purine ribonucleoside diphosphate Pentose phosphate Pentose-5-phosphate Ribonucleoside 3'-phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound 6-aminopurine Pentose monosaccharide Organic pyrophosphate Monosaccharide phosphate Purine Imidazopyrimidine Aminopyrimidine Monoalkyl phosphate Monosaccharide N-acyl-amine N-substituted imidazole Organic phosphoric acid derivative Pyrimidine Imidolactam Phosphoric acid ester Fatty acyl Fatty amide Alkyl phosphate Tetrahydrofuran Heteroaromatic compound Imidazole Azole Carbothioic s-ester Thiocarboxylic acid ester Secondary carboxylic acid amide Secondary alcohol Carboxamide group Amino acid or derivatives Thiocarboxylic acid or derivatives Organoheterocyclic compound Azacycle Oxacycle Sulfenyl compound Carboxylic acid derivative Hydrocarbon derivative Alcohol Organic nitrogen compound Amine Organonitrogen compound Carbonyl group Organooxygen compound Organosulfur compound Organic oxygen compound Organopnictogen compound Primary amine Organic oxide Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	acyl-CoA (CHEBI:15522 )
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source LogP: -3.783 PhysProp
Predicted Properties	Property Value Source Water Solubility 5.92 g/L ALOGPS logP -0.44 ALOGPS logP -5.4 ChemAxon logS -2.1 ALOGPS pKa (Strongest Acidic) 0.83 ChemAxon pKa (Strongest Basic) 4.79 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 19 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 370.61 Ų ChemAxon Rotatable Bond Count 20 ChemAxon Refractivity 168.76 m³·mol⁻¹ ChemAxon Polarizability 69.05 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
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 GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0f9i-0900000100-c4b2e70ff7f5bf63bf14 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0f79-0910000000-b34aef96ad5be4d9e818 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0f9i-2900000000-9dfaa9af922995173949 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-003u-7920232800-56f45dbedfb76674c2e2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-3910100000-6e7607b201b621147860 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-6900000000-86ef655bd0f41287a4fb View in MoNA MS Mass Spectrum (Electron Ionization) 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 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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:	onsson, Stefan; Ricagno, Stefano; Lindqvist, Ylva; Richards, Nigel G. J. Kinetic and mechanistic characterization of the formyl-CoA transferase from Oxalobacter formigenes. Journal of Biological Chemistry (2004), 279(34), 36003-36012.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15522 HMDB ID HMDB03419 Pubchem Compound ID 439313 Kegg ID C00798 ChemSpider ID 388444 Wikipedia ID Acyl-CoA BioCyc ID FORMYL-COA EcoCyc ID FORMYL-COA Ligand Expo FYN

Enzymes