5-Amino-6-(5'-phosphoribitylamino)uracil (PAMDB001586)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001586
Identification
Name: 5-Amino-6-(5'-phosphoribitylamino)uracil
Description:5-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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 356.2264
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Diazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct Parent Hydroxypyrimidines
Alternative Parents
Substituents
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.89 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity82.36 m3·mol-1ChemAxon
Polarizability30.11 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH > 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP
5-Amino-6-(5'-phosphoribitylamino)uracil + Water > 5-amino-6-(D-ribitylamino)uracil + Phosphate
5-Amino-6-(5'-phosphoribitylamino)uracil + NADP > 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
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