Canmetcon
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Identification
YMDB IDYMDB00067
Name5-Phosphoribosylamine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Phosphoribosylamine is a substrate for amidophosphoribosyltransferase and trifunctional purine biosynthetic protein adenosine-3. It is an intermediate in purine metabolism and a precursor to IMP. It is generated from Phosphoribosyl pyrophosphate (PRPP). [Wikipedia]
Structure
Thumb
Synonyms
  • 5-P-beta-D-ribosyl-amine
  • 5-P-beta-delta-ribosyl-amine
  • 5-phospho-beta-D-ribosyl-amine
  • 5-phospho-beta-D-ribosylamine
  • 5-phospho-beta-delta-ribosyl-amine
  • 5-phospho-beta-delta-ribosylamine
  • 5-phospho-D-ribosylamine
  • 5-phospho-delta-ribosylamine
  • 5-phosphoribosylamine
  • PRA
  • 5-Phosphoribosyl-1-amine
  • 5-Phospho-b-D-ribosylamine
  • 5-Phospho-β-D-ribosylamine
CAS number14050-66-9
WeightAverage: 229.125
Monoisotopic: 229.035138255
InChI KeySKCBPEVYGOQGJN-TXICZTDVSA-N
InChIInChI=1S/C5H12NO7P/c6-5-4(8)3(7)2(13-5)1-12-14(9,10)11/h2-5,7-8H,1,6H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-amino-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name5-phospho-β-D-ribosylamine
Chemical FormulaC5H12NO7P
SMILES[H]O[C@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])N([H])[H])C([H])([H])OP(=O)(O[H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetrahydrofuran
  • Secondary alcohol
  • 1,2-diol
  • Hemiaminal
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility38.2 g/LALOGPS
logP-2.4ALOGPS
logP-3.5ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area142.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.49 m³·mol⁻¹ChemAxon
Polarizability18.66 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Purine metabolismec00230 Map00230
SMPDB Reactions
Phosphoribosyl pyrophosphate + water + L-Glutamine5-Phosphoribosylamine + L-Glutamic acid + Pyrophosphate
5-Phosphoribosylamine + Glycine + Adenosine triphosphateN1-(5-phospho-β-D-ribosyl)glycinamide + phosphate + ADP + hydron
KEGG Reactions
water + L-Glutamine + Phosphoribosyl pyrophosphatePyrophosphate + L-Glutamic acid + 5-Phosphoribosylamine
Adenosine triphosphate + Glycine + 5-Phosphoribosylaminephosphate + hydron + ADP + Glycineamideribotide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID37737
HMDB IDHMDB01128
Pubchem Compound ID150
Kegg IDC03090
ChemSpider ID388939
FOODB IDFDB030584
WikipediaPhosphoribosylamine
BioCyc ID5-P-BETA-D-RIBOSYL-AMINE

Enzymes

General function:
Involved in amidophosphoribosyltransferase activity
Specific function:
5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O
Gene Name:
ADE4
Uniprot ID:
P04046
Molecular weight:
56718.89844
Reactions
5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate → L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O.
General function:
Involved in catalytic activity
Specific function:
ATP + 5-phospho-D-ribosylamine + glycine = ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide
Gene Name:
ADE5
Uniprot ID:
P07244
Molecular weight:
86067.39844
Reactions
ATP + 5-phospho-D-ribosylamine + glycine → ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide.
ATP + 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine → ADP + phosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole.