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5-Amino-6-(5'-phosphoribitylamino)uracil (YMDB00300)

Identification
YMDB IDYMDB00300
Name5-Amino-6-(5'-phosphoribitylamino)uracil
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Amino-6-(5'-phosphoribitylamino)uracil belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. 5-Amino-6-(5'-phosphoribitylamino)uracil is a very strong basic compound (based on its pKa). 5-Amino-6-(5'-phosphoribitylamino)uracil exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 5-Amino-2,6-dioxy-4-(5'-phosphoribitylamino)pyrimidine
  • 5-Amino-6-(5-phosphoribitylamino)uracil
CAS numberNot Available
WeightAverage: 356.2264
Monoisotopic: 356.073314674
InChI KeyRQRINYISXYAZKL-UHFFFAOYSA-N
InChIInChI=1S/C9H17N4O9P/c10-5-7(12-9(18)13-8(5)17)11-1-3(14)6(16)4(15)2-22-23(19,20)21/h3-4,6,14-16H,1-2,10H2,(H2,19,20,21)(H3,11,12,13,17,18)
IUPAC Name({5-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-2,3,4-trihydroxypentyl}oxy)phosphonic acid
Traditional IUPAC Name{5-[(5-amino-2,6-dioxo-1,3-dihydropyrimidin-4-yl)amino]-2,3,4-trihydroxypentyl}oxyphosphonic acid
Chemical FormulaC9H17N4O9P
SMILES[H]OC([H])(C([H])([H])OP(=O)(O[H])O[H])C([H])(O[H])C([H])(O[H])C([H])([H])N([H])C1=C(N([H])[H])C(=O)N([H])C(=O)N1[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Urea
  • Lactam
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Polyol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Alcohol
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.89 g/LALOGPS
logP-2.5ALOGPS
logP-5.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)6.52ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area223.7 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity82.36 m³·mol⁻¹ChemAxon
Polarizability30.26 ųChemAxon
Number of Rings1ChemAxon
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 Reactions
2,5-Diamino-6-(5-phosphono)ribitylamino-4(3H)-pyrimidinone + water + hydron → 5-Amino-6-(5'-phosphoribitylamino)uracil + Ammonium
water + 5-Amino-6-(5'-phosphoribitylamino)uracil → 5-Amino-6-ribitylamino uracil + phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-7932000000-f99b2e65ef6ba20ea0f8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fdk-7905640000-c9a3d0310f1af6d7c4faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0249000000-5a3bec4a17c34777337dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-2932000000-215c4b7565ae7b5e0bd9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-8910000000-e297079a225fff6f9041JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mi-5927000000-436a23030b9f7f3801bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9100000000-3731c088773859710badJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6686c1b8596958b9ba6bJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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 ID18247
HMDB IDHMDB03841
Pubchem Compound ID333
Kegg IDC04454
ChemSpider ID326
FOODB IDFDB023235
Wikipedia IDNot Available
BioCyc IDCPD-1086

Enzymes

Protein Details
1. 5-amino-6-(5-phosphoribosylamino)uracil reductase
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.