2.0 2012-10-10 12:21:34 -0600 2015-06-03 17:26:08 -0600 ECMDB23195 M2MDB003585 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide 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 (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 C15H21N5O15P2 573.2993 573.050938051 [(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 [(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 [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 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 QOUSHGMTBIIAHR-KEOHHSTQSA-J logp -1.91 ALOGPS logs -1.91 ALOGPS solubility 7.95e+00 g/l ALOGPS logp -5.5 ChemAxon pka_strongest_acidic 1.21 ChemAxon pka_strongest_basic 6.75 ChemAxon iupac [(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 ChemAxon average_mass 573.2993 ChemAxon mono_mass 573.050938051 ChemAxon 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 ChemAxon formula C15H21N5O15P2 ChemAxon 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 ChemAxon inchikey QOUSHGMTBIIAHR-KEOHHSTQSA-J ChemAxon polar_surface_area 329.52 ChemAxon refractivity 110.09 ChemAxon polarizability 47.38 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 16 ChemAxon donor_count 6 ChemAxon physiological_charge -4 ChemAxon formal_charge -4 ChemAxon Specdb::NmrOneD 312601 Specdb::NmrOneD 312602 Specdb::NmrOneD 312603 Specdb::NmrOneD 312604 Specdb::NmrOneD 312605 Specdb::NmrOneD 312606 Specdb::NmrOneD 312607 Specdb::NmrOneD 312608 Specdb::NmrOneD 312609 Specdb::NmrOneD 312610 Specdb::NmrOneD 312611 Specdb::NmrOneD 312612 Specdb::NmrOneD 312613 Specdb::NmrOneD 312614 Specdb::NmrOneD 312615 Specdb::NmrOneD 312616 Specdb::NmrOneD 312617 Specdb::NmrOneD 312618 Specdb::NmrOneD 312619 Specdb::NmrOneD 312620 Specdb::MsMs 27932 Specdb::MsMs 27933 Specdb::MsMs 27934 Specdb::MsMs 34490 Specdb::MsMs 34491 Specdb::MsMs 34492 45266644 58435 Histidine biosynthesis bifunctional protein hisIE P06989 HIS2_ECOLI hisI http://ecmdb.ca/proteins/P06989.xml 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase P10371 HIS4_ECOLI hisA http://ecmdb.ca/proteins/P10371.xml 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