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Identification
YMDB IDYMDB00300
Name5-Amino-6-(5'-phosphoribitylamino)uracil
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Amino-6-(5'-phosphoribitylamino)uracil is an intermediate in flavin biosynthesis pathway. Riboflavin (vitamin B2) is the precursor for the essential flavin cofactors FMN and FAD, which are used in a wide variety of redox reactions. [Biocyc PWY-6168]
Structure
Thumb
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 + hydron5-Amino-6-(5'-phosphoribitylamino)uracil + Ammonium
water + 5-Amino-6-(5'-phosphoribitylamino)uracil5-Amino-6-ribitylamino uracil + phosphate
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 ID18247
HMDB IDHMDB03841
Pubchem Compound ID333
Kegg IDC04454
ChemSpider ID326
FOODB IDFDB023235
Wikipedia IDNot Available
BioCyc IDCPD-1086

Enzymes

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.