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Record Information
Version	2.0
Creation Date	2012-05-31 14:03:35 -0600
Update Date	2015-06-03 15:54:41 -0600
Secondary Accession Numbers	ECMDB04052
Identification
Name:	2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine
Description	2,5-Diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine or DARP, is an intermediate in flavin biosynthesis. It is a substrate for diaminohydroxyphosphoribosylaminopyrimidine deaminase, which catalyzes the reaction 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine + H2O = 5-amino-6-(5-phospho-D-ribosylamino)uracil + NH3
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaff8b2cc> Close
Synonyms:	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-(5'-phosphoribosylamino)-4-pyrimidineone 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 2,5DA6RA4P5P DARP
Chemical Formula:	C9H16N5O8P
Weight:	Average: 353.2258 Monoisotopic: 353.073649025
InChI Key:	CIEXRWBOBYOQGW-DOAYSINJSA-N
InChI:	InChI=1S/C9H16N5O8P/c10-1-5(13-9(11)14-6(1)17)12-7-3(16)2(15)4(22-7)8(18)23(19,20)21/h2-4,7-8,15-16,18H,10H2,(H2,19,20,21)(H4,11,12,13,14,17)/t2-,3+,4-,7?,8?/m0/s1
CAS number:	Not Available
IUPAC Name:	{[(2S,3S,4R)-5-[(5-amino-6-hydroxy-2-imino-2,3-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl](hydroxy)methyl}phosphonic acid
Traditional IUPAC Name:	[(2S,3S,4R)-5-[(5-amino-6-hydroxy-2-imino-3H-pyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl](hydroxy)methylphosphonic acid
SMILES:	[H]C(O)([C@@]1([H])OC([H])(NC2=C(N)C(O)=NC(=N)N2)[C@]([H])(O)[C@]1([H])O)P(O)(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as glycosylamines. Glycosylamines 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 Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Glycosylamines
Alternative Parents	Pentoses Secondary alkylarylamines Pyrimidones Aminopyrimidines and derivatives Hydropyrimidines Vinylogous amides Tetrahydrofurans Organic phosphonic acids Heteroaromatic compounds Secondary alcohols 1,2-diols Oxacyclic compounds Azacyclic compounds Primary amines Organopnictogen compounds Organophosphorus compounds Organic oxides Hydrocarbon derivatives
Substituents	N-glycosyl compound Pentose monosaccharide Secondary aliphatic/aromatic amine Pyrimidone Aminopyrimidine Pyrimidine Monosaccharide Hydropyrimidine Heteroaromatic compound Vinylogous amide Tetrahydrofuran Organophosphonic acid derivative Organophosphonic acid Secondary alcohol 1,2-diol Oxacycle Azacycle Organoheterocyclic compound Secondary amine Organic nitrogen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Primary amine Organophosphorus compound Organonitrogen compound Amine Alcohol Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 6.36 g/L ALOGPS logP -2.6 ALOGPS logP -4.4 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) 1.25 ChemAxon pKa (Strongest Basic) 21.89 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 233.97 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 92.41 m³·mol⁻¹ ChemAxon Polarizability 30.01 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Hydrogen ion + Water > 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonium Guanosine triphosphate + 3 Water <> 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Formic acid +2 Hydrogen ion + Pyrophosphate + 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine Guanosine triphosphate + 3 Water <> Formic acid + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Pyrophosphate 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Water + 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine <> 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonia Water + Guanosine triphosphate > Hydrogen ion + Pyrophosphate + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Formic acid Water + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine > 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonia Guanosine triphosphate + 3 Water > Formic acid + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Pyrophosphate Guanosine triphosphate + Water > 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Hydrogen ion + Formic acid + Pyrophosphate Guanosine triphosphate + 3 Water <>2 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Formic acid +2 Hydrogen ion + Pyrophosphate +2 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine
SMPDB Pathways:	Flavin biosynthesis PW001971
KEGG Pathways:	Riboflavin metabolism ec00740
EcoCyc Pathways:	flavin biosynthesis I (bacteria and plants) RIBOSYN2-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0006-0903000000-d54583fd9a311884312f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-3900000000-53208a77172da4a83d20 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-002f-3900000000-612947fc7c218d0e9df5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f7o-4914000000-54a4bb0b18b52d646bf8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000x-9521000000-806330d4617413a810b5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-001l-9400000000-4b19cb6e4b769db39582 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
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 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 29114 HMDB ID Not Available Pubchem Compound ID 25244331 Kegg ID C01304 ChemSpider ID 26331269 Wikipedia ID 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine BioCyc ID DIAMINO-OH-PHOSPHORIBOSYLAMINO-PYR EcoCyc ID DIAMINO-OH-PHOSPHORIBOSYLAMINO-PYR

Enzymes