Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-05-31 13:54:38 -0600
Update Date	2015-06-03 15:54:12 -0600
Secondary Accession Numbers	ECMDB01567
Identification
Name:	Glycineamideribotide
Description	Glycinamidoribotide conversion to N-formylglycinamide ribonucleotide is the third reaction of the de novo purine biosynthesis, a reaction catalyzed by the enzyme glycinamide ribonucleotide transformylase (EC 2.1.2.2). Glycinamide ribonucleotide (GAR) synthetase catalyzes the conversion of phosphoribosylamine, glycine, and MgATP to glycinamide ribonucleotide. (PMID: 2182115)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaebf1644> Close
Synonyms:	5'-p-Ribosylglycinamide 5'-p-Ribosylglycineamide 5'-Phosphoribosyl-glycineamide 5'-Phosphoribosylglycinamide 5'-Phosphoribosylglycineamide GAR Glycinamide ribonucleotide Glycineamide ribonucleotide N(1)-(5-Phospho-D-ribosyl)glycinamide N-Glycyl-5-O-phosphono-D-ribofuranosylamine N1-(5-phospho-D-ribosyl)glycinamide
Chemical Formula:	C7H15N2O8P
Weight:	Average: 286.1764 Monoisotopic: 286.056601978
InChI Key:	OBQMLSFOUZUIOB-SHUUEZRQSA-N
InChI:	InChI=1S/C7H15N2O8P/c8-1-4(10)9-7-6(12)5(11)3(17-7)2-16-18(13,14)15/h3,5-7,11-12H,1-2,8H2,(H,9,10)(H2,13,14,15)/t3-,5-,6-,7-/m1/s1
CAS number:	10074-18-7
IUPAC Name:	{[(2R,3S,4R,5R)-5-(2-aminoacetamido)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:	glycineamide ribonucleotide
SMILES:	NCC(=O)N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as glycinamide ribonucleotides. Glycinamide ribonucleotides are compounds in which the amide N atom of glycineamide is linked to the C-1 of a ribosyl (or deoxyribosyl) moiety. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Glycinamide ribonucleotides
Sub Class	Not Available
Direct Parent	Glycinamide ribonucleotides
Alternative Parents	Pentose phosphates Alpha amino acid amides Monosaccharide phosphates Monoalkyl phosphates Tetrahydrofurans Secondary carboxylic acid amides Secondary alcohols 1,2-diols Oxacyclic compounds Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
Substituents	Glycinamide-ribonucleotide Pentose phosphate Pentose-5-phosphate Alpha-amino acid amide Alpha-amino acid or derivatives Monosaccharide phosphate Pentose monosaccharide Monoalkyl phosphate Monosaccharide Organic phosphoric acid derivative Phosphoric acid ester Alkyl phosphate Tetrahydrofuran Secondary carboxylic acid amide Secondary alcohol Amino acid or derivatives Carboxamide group 1,2-diol Organoheterocyclic compound Oxacycle Carboxylic acid derivative Organic nitrogen compound Organic oxide Primary aliphatic amine Organopnictogen compound Alcohol Organonitrogen compound Carbonyl group Organooxygen compound Amine Organic oxygen compound Hydrocarbon derivative Primary amine Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 14.6 g/L ALOGPS logP -2.4 ALOGPS logP -4.7 ChemAxon logS -1.3 ALOGPS pKa (Strongest Acidic) 1.23 ChemAxon pKa (Strongest Basic) 8.14 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 171.57 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 55.29 m³·mol⁻¹ ChemAxon Polarizability 23.68 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 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 + Formic acid + Glycineamideribotide > ADP + 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Phosphate N10-Formyl-THF + Glycineamideribotide <> 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid Adenosine triphosphate + Glycine + 5-Phosphoribosylamine <> ADP + Glycineamideribotide + Hydrogen ion + Phosphate Adenosine triphosphate + 5-Phosphoribosylamine + Glycine <> ADP + Phosphate + Glycineamideribotide N10-Formyl-THF + Glycineamideribotide <> Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide Glycineamideribotide + 5,10-Methenyltetrahydrofolate + Water <> 5'-Phosphoribosyl-N-formylglycineamide + Tetrahydrofolic acid Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > Water + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide + Glycineamideribotide Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > 10-Formyltetrahydrofolate + Glycineamideribotide + N10-Formyl-THF + Glycineamideribotide 5'-phosphoribosyl-a-N-formylglycineamidine + Tetrahydrofolic acid + Tetrahydrofolic acid > Water + Glycineamideribotide + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid Adenosine triphosphate + Glycine + 5 5-Phosphoribosylamine <> ADP + Glycineamideribotide + Hydrogen ion + Phosphate N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid
SMPDB Pathways:	One Carbon Pool by Folate I PW001735 One carbon pool by folate PW000773
KEGG Pathways:	Metabolic pathways eco01100 One carbon pool by folate ec00670 Purine metabolism ec00230
EcoCyc Pathways:	5-aminoimidazole ribonucleotide biosynthesis I PWY-6121 5-aminoimidazole ribonucleotide biosynthesis II PWY-6122 superpathway of 5-aminoimidazole ribonucleotide biosynthesis PWY-6277 tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate PWY-6613
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-000t-9420000000-d7fee78dd4657e2eba28 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00si-9541200000-4a23e3091baf72b01dc2 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-053i-9460000000-f71dc4d8ec0f4da03819 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0560-9120000000-4770933b45387be6728c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a59-9200000000-a6f2b9ab201fd0e69ee8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0170-9550000000-99520656892b8c415efb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-d6c860661b01956c80ac View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-c2f2b85e6ec9caaa4408 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-002r-2090000000-f6fcd99577c7e5d5d2ec View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9020000000-f5f361d4aef59382fc15 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-962cd48ee45a1c95e446 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0980000000-6a9e014a86b77c5ad3c3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001i-5920000000-cb0c5e3520ad275d3742 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-057j-9500000000-ab2ea8c5eb8a25044810 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:	Caperelli CA, Giroux EL: The human glycinamide ribonucleotide transformylase domain: purification, characterization, and kinetic mechanism. Arch Biochem Biophys. 1997 May 1;341(1):98-103. Pubmed: 9143358 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 McKerns KW: Gonadotropin regulation of nucleotide biosynthesis in corpus luteum. Biochemistry. 1973 Dec 4;12(25):5206-11. Pubmed: 4366083
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 18349 HMDB ID HMDB02022 Pubchem Compound ID 440137 Kegg ID C03838 ChemSpider ID 141370 Wikipedia ID Glycineamide ribonucleotide BioCyc ID 5-PHOSPHO-RIBOSYL-GLYCINEAMIDE EcoCyc ID 5-PHOSPHO-RIBOSYL-GLYCINEAMIDE Ligand Expo GAR

Enzymes