5-Amino-6-ribitylamino uracil (PAMDB000635)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000635
Identification
Name: 5-Amino-6-ribitylamino uracil
Description:5-Amino-6-ribitylamino uracil is an intermediate in riboflavin metabolism. It is converted from 5-Amino-6-(5'-phosphoribitylamino)uracil via dephosphorylation by the enzyme phosphohistidine phosphatase 1 (EC 3.1.3.-). (HMDB, KEGG)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
  • 5A6RbA2,4PD
  • 6-Ribitylamino-5-aminouracil
Chemical Formula: C9H16N4O6
Average Molecular Weight: 276.2465
Monoisotopic Molecular Weight: 276.106984264
InChI Key: XKQZIXVJVUPORE-UHFFFAOYSA-N
InChI:InChI=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)
CAS number: Not Available
IUPAC Name:5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional IUPAC Name: 5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,3-dihydropyrimidine-2,4-dione
SMILES:NC1=C(NCC(O)C(O)C(O)CO)NC(=O)NC1=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring,which bears a ketone. 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 Pyrimidones
Alternative Parents
Substituents
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Aminopyrimidine
  • Primary aromatic amine
  • Hydropyrimidine
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Urea
  • Secondary alcohol
  • Polyol
  • Lactam
  • 1,2-diol
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility14.3 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.48 m3·mol-1ChemAxon
Polarizability25.92 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
5-Amino-6-ribitylamino uracil + 3,4-Dihydroxy-2-butanone-4-P > 6,7-Dimethyl-8-(1-D-ribityl)lumazine +2 Water + Phosphate
2 6,7-Dimethyl-8-(1-D-ribityl)lumazine <> Riboflavin + 5-Amino-6-ribitylamino uracil
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1190000000-2514b630f375b2189bfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fu-9750000000-779ce19c1a0e6b0c6932View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9300000000-2f9fc8d8f57a4b3ca8c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01x0-5490000000-40e672b419cf2a89e723View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9210000000-e4e8a4b406ad4dfd459fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-0e769fc743b8cee3b542View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • WACKER H, HARVEY RA, WINESTOCK CH, PLAUT GW: 4-(1'-D-RIBITYLAMINO)-5-AMINO-2,6-DIHYDROXYPYRIMIDINE, THE SECOND PRODUCT OF THE RIBOFLAVIN SYNTHETASE REACTION. J Biol Chem. 1964 Oct;239:3493-7. Pubmed: 14245407
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15934
HMDB IDHMDB11106
Pubchem Compound ID221
Kegg IDC04732
ChemSpider ID216
Wikipedia IDNot Available
BioCyc IDNot Available