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Showing Compound 5'-phosphoribosyl-N-formylglycineamide (FDB030552)

Record Information
Version1.0
Creation date2015-05-07 19:29:23 UTC
Update date2025-11-19 03:01:31 UTC
Primary IDFDB030552
Secondary Accession Numbers
  • FDB022544
Chemical Information
FooDB Name5'-phosphoribosyl-N-formylglycineamide
Description5'-phosphoribosyl-n-formylglycinamide, also known as N-formyl-gar or N-formylglycinamide ribonucleotide, is a member of the class of 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. 5'-phosphoribosyl-n-formylglycinamide is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 5'-phosphoribosyl-n-formylglycinamide can be found in a number of food items such as rosemary, mexican groundcherry, common wheat, and bitter gourd, which makes 5'-phosphoribosyl-n-formylglycinamide a potential biomarker for the consumption of these food products. 5'-phosphoribosyl-n-formylglycinamide exists in all living species, ranging from bacteria to humans. In humans, 5'-phosphoribosyl-n-formylglycinamide is involved in few metabolic pathways, which include azathioprine action pathway, mercaptopurine action pathway, purine metabolism, and thioguanine action pathway. 5'-phosphoribosyl-n-formylglycinamide is also involved in several metabolic disorders, some of which include mitochondrial DNA depletion syndrome, aICA-Ribosiduria, molybdenum cofactor deficiency, and xanthinuria type I.
CAS Number349-34-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
N-Formyl-garKegg
N-Formylglycinamide ribonucleotideKegg
N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamideKegg
5'-p-Ribosyl-N-formylglycineamideHMDB
5'-Phosphoribosyl-formylglycinamideHMDB
5'-Phosphoribosyl-N-formylglycineamideHMDB
5-Phosphoribosyl-N-formalglycineamideHMDB
FGARHMDB
N(2)-Formyl-N(1)-(5-phospho-D-ribosyl)glycinamideHMDB
Formylglycinamide ribonucleotideHMDB
FormylglycineamideribotideHMDB
Phosphoribosyl-N-formylglycineamideHMDB
2-(Formylamino)-N-(5-O-phosphono-beta-D-ribofuranosyl)acetamideHMDB
2-(Formylamino)-N-(5-O-phosphono-β-D-ribofuranosyl)acetamideHMDB
5'-Phosphoribosyl-N-formylglycinamideHMDB
5’-Phosphoribosyl-N-formylglycinamideHMDB
Formylglycinamide ribotideHMDB
PhosphoribosylformylglycinamideHMDB
alpha-N-Formylglycinamide ribonucleotideHMDB
α-N-Formylglycinamide ribonucleotideHMDB
Predicted Properties
PropertyValueSource
Water Solubility6.52 g/LALOGPS
logP-2.3ALOGPS
logP-3.9ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area174.65 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.25 m³·mol⁻¹ChemAxon
Polarizability25.65 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H15N2O9P
IUPAC name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=1S/C8H15N2O9P/c11-3-9-1-5(12)10-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1
InChI KeyVDXLUNDMVKSKHO-XVFCMESISA-N
Isomeric SMILESO[C@H]1[C@@H](O)[C@H](NC(=O)CNC=O)O[C@@H]1COP(O)(O)=O
Average Molecular Weight314.1865
Monoisotopic Molecular Weight314.0515166
Classification
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassGlycinamide ribonucleotides
Sub ClassNot Available
Direct ParentGlycinamide ribonucleotides
Alternative Parents
Substituents
  • Glycinamide-ribonucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-formyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-formyl-alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Monosaccharide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Secondary carboxylic acid amide
  • 1,2-diol
  • Carboxamide group
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5'-Phosphoribosyl-N-formylglycinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9330000000-47bd3a51454a22349c16Spectrum
Predicted GC-MS5'-Phosphoribosyl-N-formylglycinamide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-5972200000-28cbe677e79c994d5692Spectrum
Predicted GC-MS5'-Phosphoribosyl-N-formylglycinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5'-Phosphoribosyl-N-formylglycinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9121000000-70e7f7e392d67c9062d72015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9110000000-24b14d3360fd37fa0b5a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-6c2f243f9e36f72670132015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01r6-8914000000-411b5cf47e3e7e5511fd2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-fc9464d8ad7b3b1ac8202015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ccc93e5e04249a7f14252015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0079000000-0c457b0a6a5c25c659622021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2920000000-569fd550eacc61a8bd6c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-32e3418d15835aba1b7b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-9036000000-b8480e9ce9f70df638e92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-14698f4417bb191539722021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-e93ac01407977ed807402021-09-24View Spectrum
NMRNot Available
ChemSpider ID115687
ChEMBL IDNot Available
KEGG Compound IDC04376
Pubchem Compound ID130805
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0001308
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00019642
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference