Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-10-10 12:21:34 -0600
Update Date	2015-06-03 17:26:08 -0600
Secondary Accession Numbers	ECMDB23195
Identification
Name:	1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide
Description	1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide is an intermediate in the histidine biosynthesis pathway. It is a substrate for the enzyme 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase which catalyzes the reaction 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide = 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa20b9328> Close
Synonyms:	(2R,3S,4R,5R)-5-(E)-5-carbamoyl-3-(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonatooxymethyl)oxolan-2-ylimidazol-4-ylaminomethylideneamino-3,4-dihydroxyoxolan-2-ylmethyl phosphate (2R,3S,4R,5R)-5-(e)-5-Carbamoyl-3-(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonatooxymethyl)oxolan-2-ylimidazol-4-ylaminomethylideneamino-3,4-dihydroxyoxolan-2-ylmethyl phosphoric acid (2R,3S,4R,5R)-5-4-carbamoyl-5-(E)-(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonatooxymethyl)tetrahydrofuran-2-ylaminomethyleneaminoimidazol-1-yl-3,4-dihydroxy-tetrahydrofuran-2-ylmethyl phosphate (2R,3S,4R,5R)-5-4-Carbamoyl-5-(e)-(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonatooxymethyl)tetrahydrofuran-2-ylaminomethyleneaminoimidazol-1-yl-3,4-dihydroxy-tetrahydrofuran-2-ylmethyl phosphoric acid 1-(5-phospho-D-ribosyl)-5-(5-phospho-D-ribosylamino)methylideneaminoimidazole-4-carboxamide tetraanion
Chemical Formula:	C15H21N5O15P2
Weight:	Average: 573.2993 Monoisotopic: 573.050938051
InChI Key:	QOUSHGMTBIIAHR-KEOHHSTQSA-J
InChI:	InChI=1S/C15H25N5O15P2/c16-12(25)7-13(17-3-18-14-10(23)8(21)5(34-14)1-32-36(26,27)28)20(4-19-7)15-11(24)9(22)6(35-15)2-33-37(29,30)31/h3-6,8-11,14-15,21-24H,1-2H2,(H2,16,25)(H,17,18)(H2,26,27,28)(H2,29,30,31)/p-4/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1
CAS number:	Not Available
IUPAC Name:	[(2R,3S,4R,5R)-5-(N'-{4-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}imidamido)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Traditional IUPAC Name:	[(2R,3S,4R,5R)-5-(N'-{5-carbamoyl-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]imidazol-4-yl}imidamido)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
SMILES:	[H][C@]1(COP([O-])([O-])=O)O[C@@]([H])(NC=NC2=C(N=CN2[C@]2([H])O[C@]([H])(COP([O-])([O-])=O)[C@@]([H])(O)[C@@]2([H])O)C(N)=O)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Imidazole ribonucleosides and ribonucleotides
Sub Class	1-ribosyl-imidazolecarboxamides
Direct Parent	1-ribosyl-imidazolecarboxamides
Alternative Parents	Pentose phosphates Glycosylamines Monosaccharide phosphates 2-heteroaryl carboxamides Carbonylimidazoles Alkyl phosphates N-substituted imidazoles Vinylogous amides Heteroaromatic compounds Tetrahydrofurans Primary carboxylic acid amides Secondary alcohols Formamidines Carboxamidines Azacyclic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives Organopnictogen compounds Organic anions
Substituents	1-ribosyl-imidazolecarboxamide Pentose phosphate Pentose-5-phosphate Glycosyl compound N-glycosyl compound Monosaccharide phosphate 2-heteroaryl carboxamide Imidazole-4-carbonyl group Alkyl phosphate Phosphoric acid ester Monosaccharide N-substituted imidazole Organic phosphoric acid derivative Azole Heteroaromatic compound Imidazole Vinylogous amide Tetrahydrofuran Carboxamide group Secondary alcohol Primary carboxylic acid amide Amidine Carboxylic acid amidine Oxacycle Carboxylic acid derivative Azacycle Organoheterocyclic compound Formamidine Organic oxide Organic oxygen compound Alcohol Hydrocarbon derivative Organopnictogen compound Organic nitrogen compound Organooxygen compound Organonitrogen compound Organic anion Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	organophosphate oxoanion (CHEBI:58435 )
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 7.95 g/L ALOGPS logP -1.9 ALOGPS logP -5.5 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 1.21 ChemAxon pKa (Strongest Basic) 6.75 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 329.52 Ų ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 110.09 m³·mol⁻¹ ChemAxon Polarizability 47.38 ų ChemAxon Number of Rings 3 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:	1-(5-phosphoribosyl)-AMP + Water > 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide > 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00di-0000090000-2fad1b9d7b9af5cb200f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fk9-0000090000-650c453631ebf914e44a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0596-9434810000-8b35471c1d38e7f1907a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00di-0000090000-12b5745255550f27fed1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00di-2000090000-7daea325e825cf6ed2ac View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-005a-9011000000-d828b3df227622e4a8ef 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:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 58435 HMDB ID Not Available Pubchem Compound ID 45266644 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

Enzymes