You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00163
Name5-Amino-6-(5'-phosphoribosylamino)uracil
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Amino-6-(5'-phosphoribosylamino)uracil belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. 5-Amino-6-(5'-phosphoribosylamino)uracil is a strong basic compound (based on its pKa). 5-Amino-6-(5'-phosphoribosylamino)uracil exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • 5-Amino-6-(5-phosphoribosylamino)uracil
  • 5-Amino-6-(5'-phosphoribosylamino)uracil
  • 5-Amino-6-(ribosylamino)-2,4-(1H,3H)-pyrimidinedione 5'-phosphate
  • 5-Amino-6-(ribosylamino)-2,4-(1H,3H)-pyrimidinedione 5'-phosphoric acid
CAS numberNot Available
WeightAverage: 354.2106
Monoisotopic: 354.05766461
InChI KeyLZEXYCAGPMYXLX-UMMCILCDSA-N
InChIInChI=1S/C9H15N4O9P/c10-3-6(12-9(17)13-7(3)16)11-8-5(15)4(14)2(22-8)1-21-23(18,19)20/h2,4-5,8,14-15H,1,10H2,(H2,18,19,20)(H3,11,12,13,16,17)/t2-,4-,5-,8-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-5-[(5-amino-2,6-dioxo-1,3-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
Chemical FormulaC9H15N4O9P
SMILESNC1=C(N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)NC(=O)NC1=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Cyclitol or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.64 g/LALOGPS
logP-1.8ALOGPS
logP-5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)3.27ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area212.7 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.88 m³·mol⁻¹ChemAxon
Polarizability29.16 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Riboflavin metabolismPW002443 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Riboflavin metabolismec00740 Map00740
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18337
HMDB IDNot Available
Pubchem Compound ID439462
Kegg IDC01268
ChemSpider ID388566
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in zinc ion binding
Specific function:
Involved in riboflavin biosynthesis. Converts 2,5- diamino-6-(ribosylamino)-4(3H)-pyrimidinone 5'-phosphate into 5- amino-6-(ribosylamino)-2,4(1H,3H)-pyrimidinedione 5'-phosphate
Gene Name:
RIB2
Uniprot ID:
Q12362
Molecular weight:
67035.29688
Reactions
tRNA uridine → tRNA pseudouridine.
2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + H(2)O → 5-amino-6-(5-phosphoribosylamino)uracil + NH(3).
General function:
Involved in 5-amino-6-(5-phosphoribosylamino)uracil reductase activity
Specific function:
5-amino-6-(5-phosphoribitylamino)uracil + NADP(+) = 5-amino-6-(5-phosphoribosylamino)uracil + NADPH
Gene Name:
RIB7
Uniprot ID:
P33312
Molecular weight:
27116.0
Reactions
5-amino-6-(5-phospho-D-ribitylamino)uracil + NADP(+) → 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH.