2,5-Diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone (PAMDB000907)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000907
Identification
Name: 2,5-Diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone
Description:2,5-diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone is a nucleotide analog. It is involved in cofactor biosynthesis and riboflavin biosynthesis
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2,5-Diamino-4-hydroxy-6-(5-phosphoribosylamino)pyrimidine
  • 2,5-Diamino-6-(1-D-ribosylamino)pyrimidin-4(3H)-one 5'-phosphate
  • 2,5-diamino-6-(1-D-ribosylamino)Pyrimidin-4(3H)-one 5'-phosphoric acid
  • 2,5-Diamino-6-(D-ribosylamino)pyrimidin-4(3H)-one 5'-phosphate
  • 2,5-diamino-6-(D-ribosylamino)Pyrimidin-4(3H)-one 5'-phosphoric acid
  • 2,5-Diamino-6-(ribosylamino)-4-(3H)-pyrimidinone 5'-phosphate
  • 2,5-diamino-6-(ribosylamino)-4-(3H)-Pyrimidinone 5'-phosphoric acid
  • 2,5-Diamino-6-hydroxy-4-(5'-phosphoribosylamino)-pyrimidine
  • 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)-pyrimidine
  • 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine
  • DARP
Chemical Formula: C9H16N5O8P
Average Molecular Weight: 353.2258
Monoisotopic Molecular Weight: 353.073649025
InChI Key: OCLCLRXKNJCOJD-UMMCILCDSA-N
InChI:InChI=1S/C9H16N5O8P/c10-3-6(13-9(11)14-7(3)17)12-8-5(16)4(15)2(22-8)1-21-23(18,19)20/h2,4-5,8,15-16H,1,10H2,(H2,18,19,20)(H4,11,12,13,14,17)/t2-,4-,5-,8-/m1/s1
CAS number: Not Available
IUPAC Name:{[(2R,3S,4R,5R)-5-[(2,5-diamino-6-hydroxypyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name: [(2R,3S,4R,5R)-5-[(2,5-diamino-6-hydroxypyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
SMILES:NC1=NC(N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)=C(N)C(O)=N1
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether).
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent Glycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.65 mg/mLALOGPS
logP-1.4ALOGPS
logP-4.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)-4.1ChemAxon
pKa (Strongest Basic)6.25ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area226.53 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.44 m3·mol-1ChemAxon
Polarizability29.65 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Guanosine triphosphate + 3 Water > Formic acid + Pyrophosphate +2 Hydrogen ion + 2,5-Diamino-6-(5'-phosphoribosylamino)-4-pyrimidineone
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0913000000-01557e53570bef3b9be1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-f6658717f7c349876e0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-4900000000-73f7d2c81ed2acae2ca8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9x-5904000000-6f5576e606f7119b4f59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-d54a3ec0ad4389b73cc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8eb98271bc679458e166View 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
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID29114
HMDB IDNot Available
Pubchem Compound ID439480
Kegg IDC01304
ChemSpider ID388579
Wikipedia IDNot Available
BioCyc IDDIAMINO-OH-PHOSPHORIBOSYLAMINO-PYR
EcoCyc IDDIAMINO-OH-PHOSPHORIBOSYLAMINO-PYR