Record Information
Version2.0
Creation Date2012-07-30 14:54:47 -0600
Update Date2015-09-17 15:41:18 -0600
Secondary Accession Numbers
  • ECMDB21177
Identification
Name:5-Amino-6-(5'-phosphoribitylamino)uracil
Description5-Amino-6-(5'-phosphoribitylamino)uracil is an intermediate in Riboflavin metabolism. 5-Amino-6-(5'-phosphoribitylamino)uracil is the; 3rd to last step in the synthesis of 7-Hydroxy-6-methyl-8-ribityl lumazine and is converted from 5-Amino-6-(5'-phosphoribosylamino)uracil via the enzyme 5-amino-6-(5-phosphoribosylamino)uracil reductase (EC 1.1.1.193). It is then; converted to 4-(1-D-Ribitylamino)-5-amino-2,6-dihydroxypyrimidine via the enzyme Hydrolases (EC 3.1.3.- ).
Structure
Thumb
Synonyms:
  • 1-(5-Amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-ylamino)-1-deoxy-5-O-phosphono-D-ribitol
  • 1-(5-Amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-ylamino)-1-deoxy-D-ribitol 5-(dihydrogen phosphate)
  • 1-(5-amino-2,6-dioxo-1,2,3,6-Tetrahydropyrimidin-4-ylamino)-1-deoxy-D-ribitol 5-(dihydrogen phosphoric acid)
  • 1-[(5-Amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-1-deoxy-5-O-phosphono-D-ribitol
  • 5-Amino-2,6-dioxy-4-(5'-phospho-D-ribitylamino)pyrimidine
  • 5-Amino-2,6-dioxy-4-(5'-phosphoribitylamino)pyrimidine
  • 5-Amino-6-(5'-phospho-D-ribitylamino)uracil
  • 5-Amino-6-(5'-phosphoribitylamino)uracil
  • 5-Amino-6-(5-phospho-D-ribitylamino)uracil
  • 5-Amino-6-(5-phosphoribitylamino)uracil
  • 5-Amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 5'-phosphate
  • 5-amino-6-ribitylamino-2,4(1H,3H)-Pyrimidinedione 5'-phosphoric acid
  • 5A6-5'PRbAU
Chemical Formula:C9H17N4O9P
Weight:Average: 356.2264
Monoisotopic: 356.073314674
InChI Key:RQRINYISXYAZKL-UHFFFAOYSA-N
InChI:InChI=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)
CAS number:Not Available
IUPAC Name:{[(2R,3S,4S)-5-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-2,3,4-trihydroxypentyl]oxy}phosphonic acid
Traditional IUPAC Name:[(2R,3S,4S)-5-[(5-amino-2,6-dioxo-1,3-dihydropyrimidin-4-yl)amino]-2,3,4-trihydroxypentyl]oxyphosphonic acid
SMILES:NC1=C(NCC(O)C(O)C(O)COP(O)(O)=O)NC(=O)NC1=O
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
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Azacycle
  • Secondary amine
  • Primary amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.89 g/LALOGPS
logP-2.5ALOGPS
logP-4.5ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area223.7 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity82.36 m³·mol⁻¹ChemAxon
Polarizability30.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Flavin biosynthesisPW001971 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-7932000000-f99b2e65ef6ba20ea0f8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0249000000-aad1afed0b055e36f1f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-2932000000-8ce6cdef86c0d6904216View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9810000000-0889d500d98fdc446282View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mi-6926000000-99084eeb27c449bf8cafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9100000000-7df2c276c4edd1cadab5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c2c18ea089d342debbafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0039000000-29673935259424dca664View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-0490000000-f14bfba265a959aa7c3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6900000000-c2d4ad73928d0404741bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-8009000000-122c5a4319e344f1a64bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-77766ee562ec0704b879View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9100000000-4ea49ebd63ee36be8b96View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18247
HMDB IDHMDB03841
Pubchem Compound ID333
Kegg IDC04454
ChemSpider ID18921533
Wikipedia IDNot Available
BioCyc IDCPD-1086
EcoCyc IDCPD-1086

Enzymes

General function:
Involved in zinc ion binding
Specific function:
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:
ribD
Uniprot ID:
P25539
Molecular weight:
40338
Reactions
2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + H(2)O = 5-amino-6-(5-phosphoribosylamino)uracil + NH(3).
5-amino-6-(5-phospho-D-ribitylamino)uracil + NADP(+) = 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates FMN and beta-glucose 1-phosphate
Gene Name:
ybjI
Uniprot ID:
P75809
Molecular weight:
30196
General function:
riboflavin biosynthetic process
Specific function:
Catalyzes the dephosphorylation of 5-amino-6-(5-phospho-D-ribitylamino)uracil, and thus could be involved in the riboflavin biosynthesis pathway (PubMed:24123841). Is also able to dephosphorylate flavin mononucleotide (FMN) and other phosphoric acid esters (PubMed:16990279) (PubMed:24123841). YigB is important for the formation of dormant persister cells (PubMed:18519731).
Gene Name:
yigB
Uniprot ID:
P0ADP0
Molecular weight:
27121
Reactions
5-amino-6-(5-phospho-D-ribitylamino)uracil + H(2)O = 5-amino-6-(D-ribitylamino)uracil + phosphate