1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide (ECMDB23195) (M2MDB003585)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
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
Description1-(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
MOLSDFPDBSMILESInChI
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub Class1-ribosyl-imidazolecarboxamides
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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity110.09 m³·mol⁻¹ChemAxon
Polarizability47.38 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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

Protein Details
1. Histidine biosynthesis bifunctional protein hisIE
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.
Protein Details
2. 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase
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.