Record Information
Version2.0
Creation Date2012-05-31 13:59:00 -0600
Update Date2015-06-03 15:54:23 -0600
Secondary Accession Numbers
  • ECMDB03419
Identification
Name:Formyl-CoA
DescriptionFormyl-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
Thumb
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentCoenzyme A and derivatives
Alternative Parents
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-3.783PhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.92 g/LALOGPS
logP-0.44ALOGPS
logP-5.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area370.61 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity168.76 m³·mol⁻¹ChemAxon
Polarizability69.05 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f9i-0900000100-c4b2e70ff7f5bf63bf14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0910000000-b34aef96ad5be4d9e818View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9i-2900000000-9dfaa9af922995173949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003u-7920232800-56f45dbedfb76674c2e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3910100000-6e7607b201b621147860View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-86ef655bd0f41287a4fbView in MoNA
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
External Links:
ResourceLink
CHEBI ID15522
HMDB IDHMDB03419
Pubchem Compound ID439313
Kegg IDC00798
ChemSpider ID388444
Wikipedia IDAcyl-CoA
BioCyc IDFORMYL-COA
EcoCyc IDFORMYL-COA
Ligand ExpoFYN

Enzymes

General function:
Involved in oxalyl-CoA decarboxylase activity
Specific function:
Oxalyl-CoA = formyl-CoA + CO(2)
Gene Name:
oxc
Uniprot ID:
P0AFI0
Molecular weight:
60581
Reactions
Oxalyl-CoA = formyl-CoA + CO(2).
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of the CoA moiety from formyl-CoA to oxalate
Gene Name:
frc
Uniprot ID:
P69902
Molecular weight:
45828
Reactions
Formyl-CoA + oxalate = formate + oxalyl-CoA.