Record Information
Version2.0
Creation Date2012-10-10 12:21:34 -0600
Update Date2015-06-03 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
Thumb
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
DescriptionThis compound belongs to the class of chemical entities known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassImidazole ribonucleosides and ribonucleotides
Direct Parent1-ribosyl-imidazolecarboxamides
Alternative Parents
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.95 mg/mLALOGPS
logP-1.9ALOGPS
logP-5.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area329.52 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity110.09 m3·mol-1ChemAxon
Polarizability47.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-2fad1b9d7b9af5cb200fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0000090000-650c453631ebf914e44aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9434810000-8b35471c1d38e7f1907aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000090000-12b5745255550f27fed1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2000090000-7daea325e825cf6ed2acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005a-9011000000-d828b3df227622e4a8efView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID58435
HMDB IDNot Available
Pubchem Compound ID45266644
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in phosphoribosyl-AMP cyclohydrolase activity
Specific function:
1-(5-phosphoribosyl)-ATP + H(2)O = 1-(5- phosphoribosyl)-AMP + diphosphate
Gene Name:
hisI
Uniprot ID:
P06989
Molecular weight:
22756
Reactions
1-(5-phosphoribosyl)-ATP + H(2)O = 1-(5-phosphoribosyl)-AMP + diphosphate.
1-(5-phosphoribosyl)-AMP + H(2)O = 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide.
General function:
Involved in catalytic activity
Specific function:
1-(5-phosphoribosyl)-5-((5- phosphoribosylamino)methylideneamino)imidazole-4-carboxamide = 5- ((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5- phosphoribosyl)imidazole-4-carboxamide
Gene Name:
hisA
Uniprot ID:
P10371
Molecular weight:
26033
Reactions
1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide = 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide.