Canmetcon
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Identification
YMDB IDYMDB00171
Name5-Amino-6-ribitylamino uracil
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Amino-6-(D-ribitylamino)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
  • 1-[(5-amino-2,6-dihydroxypyrimidin-4-yl)amino]-1-deoxy-D-ribitol
  • 1-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-1-deoxy-D-ribitol
  • 4-(1-D-Ribitylamino)-5-amino-2,6 dihydroxypyrimidine
  • 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
  • 4-(1-D-Ribitylamino)-5-aminouracil
  • 5-amino-6-(2,3,4,5-tetrahydroxypentylamino)-1H-pyrimidine-2,4-dione
  • 6-Ribitylamino-5-aminouracil
CAS numberNot Available
WeightAverage: 276.2465
Monoisotopic: 276.106984264
InChI KeyXKQZIXVJVUPORE-UHFFFAOYSA-N
InChIInChI=1S/C9H16N4O6/c10-5-7(12-9(19)13-8(5)18)11-1-3(15)6(17)4(16)2-14/h3-4,6,14-17H,1-2,10H2,(H3,11,12,13,18,19)
IUPAC Name5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional IUPAC Name5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,3-dihydropyrimidine-2,4-dione
Chemical FormulaC9H16N4O6
SMILES[H]OC([H])([H])C([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 pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Hydropyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Secondary alcohol
  • Polyol
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP-2.4ALOGPS
logP-4.4ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)4.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area177.17 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.48 m³·mol⁻¹ChemAxon
Polarizability25.92 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
Riboflavin metabolismPW002443 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Methane metabolismec00680 Map00680
Riboflavin metabolismec00740 Map00740
SMPDB Reactions
2-Hydroxy-3-oxobutyl phosphate + 5-Amino-6-ribitylamino uracil6,7-Dimethyl-8-(1-D-ribityl)lumazine
6,7-Dimethyl-8-(1-D-ribityl)lumazineRiboflavin + 5-Amino-6-ribitylamino uracil
KEGG Reactions
water + 5-Amino-6-(5'-phosphoribitylamino)uracil5-Amino-6-ribitylamino uracil + phosphate
5-Amino-6-ribitylamino uracil + 2-Hydroxy-3-oxobutyl phosphatewater + 6,7-Dimethyl-8-(1-D-ribityl)lumazine + phosphate
6,7-Dimethyl-8-(1-D-ribityl)lumazineRiboflavin + 5-Amino-6-ribitylamino uracil
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 ID15934
HMDB IDHMDB11106
Pubchem Compound ID221
Kegg IDC04732
ChemSpider ID216
FOODB IDFDB027889
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in riboflavin biosynthetic process
Specific function:
Condensation of 5-amino-6-(1'-D)-ribityl-amino- 2,4(1H,3H)-pyrimidinedione with L-3,4-dihydroxy-2-butanone 4- phosphate to produce 6,7-dimethyl-8-(1-D-ribityl)lumazine
Gene Name:
RIB4
Uniprot ID:
P50861
Molecular weight:
18555.40039
Reactions
2 6,7-dimethyl-8-(1-D-ribityl)lumazine → riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine.
General function:
Involved in riboflavin synthase activity
Specific function:
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
Gene Name:
RIB5
Uniprot ID:
P38145
Molecular weight:
26195.59961
Reactions
2 6,7-dimethyl-8-(1-D-ribityl)lumazine → riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine.