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CHEBI:16015 ChEBI C02739 KEGG Compound C04916 KEGG Compound 1.0 30572 ChemSpider PW000984 PathWhiz Histidinol dehydrogenase Histidine biosynthesis bifunctional protein hisIE 937 ChemSpider C9H15N4O8P 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide 338.06274 ATP phosphoribosyltransferase 144886 ChemSpider HMDB00250 HMDB CHEBI:16255 ChEBI 1012 PubChem-compound NADH 439153 PubChem-compound SMILES O Pyrophosphate 50 ChemSpider 1.0 1.0 CHEBI:15971 ChEBI HMDB00148 HMDB P60664 UniProt NAD 5961 PubChem-compound C4H6N4O 5-Aminoimidazole-4-carboxamide 126.05416 CHEBI:17111 ChEBI histidinal dehydrogenase / histidinol dehydrogenase histidinol-phosphate aminotransferase 1.0 SMILES OC1=CC(Cl)=CC=C1C1=CC=CC=C1 99979-59-6 CAS 51 PubChem-compound imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase 4836-52-6 CAS 559142 ChemSpider 1009 PubChem-compound imidazole glycerol phosphate synthase CHEBI:15846 ChEBI HMDB12236 HMDB HMDB12234 HMDB SMP01000 SMPDB P60757 UniProt 9679 PubChem-compound 5746 ChemSpider 1.0 6038 ChemSpider 5-Aminoimidazole-4-carboxamide 1038 PubChem-compound CHEBI:2030 ChEBI 7540-64-9 CAS HMDB59597 HMDB C5H6O5 Oxoglutaric acid 146.02153 HMDB00902 HMDB Secondary Metabolites: Histidine biosynthesis CHEBI:16908 ChEBI CPD-3762 BioCyc 6274 PubChem-compound HMDB12208 HMDB 30776608 ChemSpider O4P Phosphate 94.95342 SMILES N[C@H](CO)CC1=CN=CN1 1010 ChemSpider 30776607 ChemSpider HMDB03192 HMDB SMILES O[C@H](COP(O)(O)=O)[C@@H](O)C1=CNC=N1 PPI BioCyc 165271 PubChem-compound C00119 KEGG Compound Hydrogen Ion C5H10N2O3 L-Glutamine 146.06914 C15H23N5O14P2 Phosphoribosyl-AMP 559.07166 C15H26N5O20P4 Phosphoribosyl-ATP 720.01215 Imidazole glycerol phosphate synthase subunit hisF 71-00-1 CAS 1.0 Imidazole glycerol phosphate synthase subunit hisH C15H25N5O15P2 Phosphoribulosylformimino-AICAR-P 577.0822 C15H25N5O15P2 PhosphoribosylformiminoAICAR-phosphate 577.0822 58-68-4 CAS L-Glutamic acid C5H13O14P3 Phosphoribosyl pyrophosphate 389.9518 SMILES [O-]P([O-])([O-])=O SMILES OC(=O)CCC(=O)C(O)=O 1.0 HMDB00208 HMDB CHEBI:30915 ChEBI C00009 KEGG Compound 1.0 C00001 KEGG Compound PHOSPHORIBOSYL-FORMIMINO-AICAR-P BioCyc CHEBI:18361 ChEBI CHEBI:18367 ChEBI C00004 KEGG Compound 1032 ChemSpider C00003 KEGG Compound 792 PubChem-compound GLN BioCyc C04051 KEGG Compound HMDB01429 HMDB 1.0 GLT BioCyc 1.0 C21H28N7O14P2 NAD 664.11694 7339 PubChem-compound SMP00926 SMPDB C00135 KEGG Compound C00013 KEGG Compound O7P2 Pyrophosphate 173.91193 C21H29N7O14P2 NADH 665.12476 P10371 UniProt SMILES OP(O)(=O)OCC(=O)CC1=CNC=N1 SMILES NC(CC1=CNC=N1)C=O Phosphoribosyl pyrophosphate H Hydrogen Ion 1.007825 Phosphoribulosylformimino-AICAR-P L-Glutamine Phosphoribosyl-AMP SMILES N[C@@H](CC1=CN=CN1)C(O)=O PhosphoribosylformiminoAICAR-phosphate 53-84-9 CAS C00026 KEGG Compound 2.0 Phosphoribosyl-ATP 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide C00025 KEGG Compound 2.0 PHOSPHORIBOSYL-AMP BioCyc CHEBI:17805 ChEBI SubPathwayInteraction1729 SubPathwayReaction SubPathway1729Reaction 1.0 2.4.2.- false 2.4.2.- L-Glutamine + Phosphoribulosylformimino-AICAR-P → 5-Aminoimidazole-4-carboxamide + D-Erythro-imidazole-glycerol-phosphate + Hydrogen Ion + L-Glutamic acid LEFT_TO_RIGHT CPD-8587 BioCyc SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O 5682 ChemSpider 328-50-7 CAS SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O 439795 PubChem-compound Water PHOSPHORIBULOSYL-FORMIMINO-AICAR-P BioCyc 770 ChemSpider Reaction2867 false Phosphoribosyl-AMP + Water → 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide LEFT_TO_RIGHT 5.3.1.16 false 5.3.1.16 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide → PhosphoribosylformiminoAICAR-phosphate LEFT_TO_RIGHT 2.4.2.17 false 2.4.2.17 Hydrogen Ion + Phosphoribosyl pyrophosphate → Phosphoribosyl-ATP + Pyrophosphate LEFT_TO_RIGHT 3.5.4.19 false 3.5.4.19 Phosphoribosyl-ATP + Water → Hydrogen Ion + Phosphoribosyl-AMP + Pyrophosphate LEFT_TO_RIGHT SMILES [O-]P([O-])(=O)OP([O-])([O-])=O 14000-31-8 CAS 1.0 23784-15-8 CAS CHEBI:16426 ChEBI P06986 UniProt C6H11N3O L-Histidinol 141.09021 56-85-9 CAS 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase 7062 ChemSpider 1.0 D-Erythro-imidazole-glycerol-phosphate ReactionCatalysis2826 ACTIVATION ATP phosphoribosyltransferase C6H11N2O6P D-Erythro-imidazole-glycerol-phosphate 238.03548 P06989 UniProt P06988 UniProt D-ERYTHRO-IMIDAZOLE-GLYCEROL-P BioCyc P06987 UniProt Histidinol-phosphate aminotransferase Histidine biosynthesis bifunctional protein hisB ReactionCatalysis2828 ACTIVATION P60595 UniProt ReactionCatalysis2827 ACTIVATION L-Histidinol ReactionCatalysis2829 ACTIVATION 7732-18-5 CAS 388299 ChemSpider 1.0 C04896 KEGG Compound C01267 KEGG Compound ReactionCatalysis2831 ACTIVATION ReactionCatalysis2830 ACTIVATION ReactionCatalysis2833 ACTIVATION ReactionCatalysis2832 ACTIVATION ReactionCatalysis2835 ACTIVATION ReactionCatalysis2834 ACTIVATION 56-86-0 CAS 360-97-4 CAS 1.0 HIS BioCyc C5H9NO4 L-Glutamic acid 147.05316 33032 PubChem-compound 775 PubChem-compound HMDB00641 HMDB CHEBI:18263 ChEBI Histidine biosynthesis bifunctional protein hisIE SMILES NC(=O)C1=C(N)N=CN1 C04666 KEGG Compound C00064 KEGG Compound Histidinol dehydrogenase 1.0 1.0 C00860 KEGG Compound HISTIDINAL BioCyc 3.1.3.15 false 3.1.3.15 D-Erythro-imidazole-glycerol-phosphate → Imidazole acetol-phosphate + Water LEFT_TO_RIGHT 2.6.1.9 false 2.6.1.9 Imidazole acetol-phosphate + L-Glutamic acid → L-histidinol-phosphate + Oxoglutaric acid LEFT_TO_RIGHT C12H9ClO L-histidinol-phosphate 204.0342 440431 PubChem-compound CHEBI:6242 ChEBI L-histidinol-phosphate Reaction2874 false Histidinal + NAD + Water → 2 Hydrogen Ion + L-Histidine + NADH LEFT_TO_RIGHT Reaction2872 false L-histidinol-phosphate + Water → L-Histidinol + Phosphate LEFT_TO_RIGHT 1.1.1.23 false 1.1.1.23 L-Histidinol + NAD → Histidinal + Hydrogen Ion + NADH LEFT_TO_RIGHT 962 PubChem-compound HMDB00177 HMDB 2.0 2-KETOGLUTARATE BioCyc Phosphate 1.0 5893 PubChem-compound HMDB02111 HMDB 9298 ChemSpider C00080 KEGG Compound Oxoglutaric acid L-HISTIDINOL-P BioCyc SMILES N[C@@H](CCC(O)=O)C(O)=O C6H9N2O5P Imidazole acetol-phosphate 220.0249 C6H9N3O Histidinal 139.07455 CHEBI:15377 ChEBI CHEBI:15378 ChEBI SMILES [H+] 14265-44-2 CAS C6H9N3O2 L-Histidine 155.06947 CHEBI:18406 ChEBI 389372 ChemSpider 36244-87-8 CAS HMDB12276 HMDB 1.0 53481398 PubChem-compound 1.0 2.0 HMDB12278 HMDB HMDB12277 HMDB HMDB01487 HMDB 644102 PubChem-compound HMDB03665 HMDB 1.0 L-Histidine SMILES O[C@H](COP(=O)(O)O)[C@@H](O)C(=O)CN\C=N\C1=C(C(=O)N)N=CN1[C@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@@H]1O ATP phosphoribosyltransferase SMILES NC1=[N+](C=NC2=C1N=CN2C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O)C1OC(COP(O)(O)=O)C(O)C1O SMILES NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O SMILES N[C@@H](CCC(N)=O)C(O)=O SMILES O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN([C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C2=N 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase SMILES NC(=O)C1=C(\N=C\NC2OC(COP(O)(O)=O)C(O)C2O)N(C=N1)C1OC(COP(O)(O)=O)C(O)C1O PRPP BioCyc 754 ChemSpider CHEBI:18050 ChEBI H2O Water 18.010565 SMILES O[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O Imidazole acetol-phosphate Histidinal NADH BioCyc NAD BioCyc 2.0 1061 PubChem-compound HMDB00280 HMDB HMDB03431 HMDB 987 ChemSpider Imidazole glycerol phosphate synthase subunit hisH PRPP Biosynthesis SubPathway PW000909 PathWhiz 984 ChemSpider Imidazole glycerol phosphate synthase subunit hisF IMIDAZOLE-ACETOL-P BioCyc 1.0 Histidine biosynthesis bifunctional protein hisB Histidinol-phosphate aminotransferase ATP phosphoribosyltransferase Histidine biosynthesis bifunctional protein hisIE Histidine biosynthesis bifunctional protein hisIE 1-(5- phosphoribosyl)- 5-[(5- phosphoribosylamino)methylideneamino] imidazole-4- carboxamide isomerase Imidazole glycerol phosphate synthase subunit hisH Imidazole glycerol phosphate synthase subunit hisF Histidine biosynthesis bifunctional protein hisB Histidinol- phosphate aminotransferase Histidine biosynthesis bifunctional protein hisB Histidinol dehydrogenase Histidinol dehydrogenase Phosphoribosyl pyrophosphate H + PP i Phosphoribosyl- ATP H 2 O H + PP i Phosphoribosyl- AMP H 2 O 1-(5'- Phosphoribosyl)- 5-amino-4- imidazolecarboxamide PhosphoribosylformiminoAICAR- phosphate L-Glutamine L-Glutamic acid H + 5- Aminoimidazole- 4-carboxamide D-Erythro- imidazole- glycerol- phosphate H 2 O Imidazole acetol- phosphate L-Glutamic acid Oxoglutaric acid L-histidinol- phosphate H 2 O P i L-Histidinol NAD NADH H + Histidinal H 2 O NAD H + NADH L-Histidine PRPP Biosynthesis
CHEBI:16015 ChEBI C02739 KEGG Compound C04916 KEGG Compound 1.0 30572 ChemSpider PW000984 PathWhiz Histidinol dehydrogenase Histidine biosynthesis bifunctional protein hisIE 937 ChemSpider C9H15N4O8P 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide 338.06274 ATP phosphoribosyltransferase 144886 ChemSpider HMDB00250 HMDB CHEBI:16255 ChEBI 1012 PubChem-compound NADH 439153 PubChem-compound SMILES O Pyrophosphate 50 ChemSpider 1.0 1.0 CHEBI:15971 ChEBI HMDB00148 HMDB P60664 UniProt NAD 5961 PubChem-compound C4H6N4O 5-Aminoimidazole-4-carboxamide 126.05416 CHEBI:17111 ChEBI histidinal dehydrogenase / histidinol dehydrogenase histidinol-phosphate aminotransferase 1.0 SMILES OC1=CC(Cl)=CC=C1C1=CC=CC=C1 99979-59-6 CAS 51 PubChem-compound imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase 4836-52-6 CAS 559142 ChemSpider 1009 PubChem-compound imidazole glycerol phosphate synthase CHEBI:15846 ChEBI HMDB12236 HMDB HMDB12234 HMDB http://identifiers.org/smpdb/SMP01000 SMPDB P60757 UniProt 9679 PubChem-compound 5746 ChemSpider 1.0 6038 ChemSpider 5-Aminoimidazole-4-carboxamide 1038 PubChem-compound CHEBI:2030 ChEBI 7540-64-9 CAS HMDB59597 HMDB C5H6O5 Oxoglutaric acid 146.02153 HMDB00902 HMDB Secondary Metabolites: Histidine biosynthesis CHEBI:16908 ChEBI CPD-3762 BioCyc 6274 PubChem-compound HMDB12208 HMDB 30776608 ChemSpider O4P Phosphate 94.95342 SMILES N[C@H](CO)CC1=CN=CN1 1010 ChemSpider 30776607 ChemSpider HMDB03192 HMDB SMILES O[C@H](COP(O)(O)=O)[C@@H](O)C1=CNC=N1 PPI BioCyc 165271 PubChem-compound C00119 KEGG Compound Hydrogen Ion C5H10N2O3 L-Glutamine 146.06914 C15H23N5O14P2 Phosphoribosyl-AMP 559.07166 C15H26N5O20P4 Phosphoribosyl-ATP 720.01215 Imidazole glycerol phosphate synthase subunit hisF 71-00-1 CAS 1.0 Imidazole glycerol phosphate synthase subunit hisH C15H25N5O15P2 Phosphoribulosylformimino-AICAR-P 577.0822 C15H25N5O15P2 PhosphoribosylformiminoAICAR-phosphate 577.0822 58-68-4 CAS L-Glutamic acid C5H13O14P3 Phosphoribosyl pyrophosphate 389.9518 SMILES [O-]P([O-])([O-])=O SMILES OC(=O)CCC(=O)C(O)=O 1.0 HMDB00208 HMDB CHEBI:30915 ChEBI C00009 KEGG Compound 1.0 C00001 KEGG Compound PHOSPHORIBOSYL-FORMIMINO-AICAR-P BioCyc CHEBI:18361 ChEBI CHEBI:18367 ChEBI C00004 KEGG Compound 1032 ChemSpider C00003 KEGG Compound 792 PubChem-compound GLN BioCyc C04051 KEGG Compound HMDB01429 HMDB 1.0 GLT BioCyc 1.0 C21H28N7O14P2 NAD 664.11694 7339 PubChem-compound http://identifiers.org/smpdb/SMP00926 SMPDB C00135 KEGG Compound C00013 KEGG Compound O7P2 Pyrophosphate 173.91193 C21H29N7O14P2 NADH 665.12476 P10371 UniProt SMILES OP(O)(=O)OCC(=O)CC1=CNC=N1 SMILES NC(CC1=CNC=N1)C=O Phosphoribosyl pyrophosphate H Hydrogen Ion 1.007825 Phosphoribulosylformimino-AICAR-P L-Glutamine Phosphoribosyl-AMP SMILES N[C@@H](CC1=CN=CN1)C(O)=O PhosphoribosylformiminoAICAR-phosphate 53-84-9 CAS C00026 KEGG Compound 2.0 Phosphoribosyl-ATP 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide C00025 KEGG Compound 2.0 PHOSPHORIBOSYL-AMP BioCyc CHEBI:17805 ChEBI SubPathwayInteraction1729 SubPathwayReaction SubPathway1729Reaction 1.0 2.4.2.- false 2.4.2.- L-Glutamine + Phosphoribulosylformimino-AICAR-P → 5-Aminoimidazole-4-carboxamide + D-Erythro-imidazole-glycerol-phosphate + Hydrogen Ion + L-Glutamic acid LEFT_TO_RIGHT CPD-8587 BioCyc SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O 5682 ChemSpider 328-50-7 CAS SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O 439795 PubChem-compound Water PHOSPHORIBULOSYL-FORMIMINO-AICAR-P BioCyc 770 ChemSpider Reaction2867 false Phosphoribosyl-AMP + Water → 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide LEFT_TO_RIGHT 5.3.1.16 false 5.3.1.16 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide → PhosphoribosylformiminoAICAR-phosphate LEFT_TO_RIGHT 2.4.2.17 false 2.4.2.17 Hydrogen Ion + Phosphoribosyl pyrophosphate → Phosphoribosyl-ATP + Pyrophosphate LEFT_TO_RIGHT 3.5.4.19 false 3.5.4.19 Phosphoribosyl-ATP + Water → Hydrogen Ion + Phosphoribosyl-AMP + Pyrophosphate LEFT_TO_RIGHT SMILES [O-]P([O-])(=O)OP([O-])([O-])=O 14000-31-8 CAS 1.0 23784-15-8 CAS CHEBI:16426 ChEBI P06986 UniProt C6H11N3O L-Histidinol 141.09021 56-85-9 CAS 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase 7062 ChemSpider 1.0 D-Erythro-imidazole-glycerol-phosphate ReactionCatalysis2826 ACTIVATION ATP phosphoribosyltransferase C6H11N2O6P D-Erythro-imidazole-glycerol-phosphate 238.03548 P06989 UniProt P06988 UniProt D-ERYTHRO-IMIDAZOLE-GLYCEROL-P BioCyc P06987 UniProt Histidinol-phosphate aminotransferase Histidine biosynthesis bifunctional protein hisB ReactionCatalysis2828 ACTIVATION P60595 UniProt ReactionCatalysis2827 ACTIVATION L-Histidinol ReactionCatalysis2829 ACTIVATION 7732-18-5 CAS 388299 ChemSpider 1.0 C04896 KEGG Compound C01267 KEGG Compound ReactionCatalysis2831 ACTIVATION ReactionCatalysis2830 ACTIVATION ReactionCatalysis2833 ACTIVATION ReactionCatalysis2832 ACTIVATION ReactionCatalysis2835 ACTIVATION ReactionCatalysis2834 ACTIVATION 56-86-0 CAS 360-97-4 CAS 1.0 HIS BioCyc C5H9NO4 L-Glutamic acid 147.05316 33032 PubChem-compound 775 PubChem-compound HMDB00641 HMDB CHEBI:18263 ChEBI Histidine biosynthesis bifunctional protein hisIE SMILES NC(=O)C1=C(N)N=CN1 C04666 KEGG Compound C00064 KEGG Compound Histidinol dehydrogenase 1.0 1.0 C00860 KEGG Compound HISTIDINAL BioCyc 3.1.3.15 false 3.1.3.15 D-Erythro-imidazole-glycerol-phosphate → Imidazole acetol-phosphate + Water LEFT_TO_RIGHT 2.6.1.9 false 2.6.1.9 Imidazole acetol-phosphate + L-Glutamic acid → L-histidinol-phosphate + Oxoglutaric acid LEFT_TO_RIGHT C12H9ClO L-histidinol-phosphate 204.0342 440431 PubChem-compound CHEBI:6242 ChEBI L-histidinol-phosphate Reaction2874 false Histidinal + NAD + Water → 2 Hydrogen Ion + L-Histidine + NADH LEFT_TO_RIGHT Reaction2872 false L-histidinol-phosphate + Water → L-Histidinol + Phosphate LEFT_TO_RIGHT 1.1.1.23 false 1.1.1.23 L-Histidinol + NAD → Histidinal + Hydrogen Ion + NADH LEFT_TO_RIGHT 962 PubChem-compound HMDB00177 HMDB 2.0 2-KETOGLUTARATE BioCyc Phosphate 1.0 5893 PubChem-compound HMDB02111 HMDB 9298 ChemSpider C00080 KEGG Compound Oxoglutaric acid L-HISTIDINOL-P BioCyc SMILES N[C@@H](CCC(O)=O)C(O)=O C6H9N2O5P Imidazole acetol-phosphate 220.0249 C6H9N3O Histidinal 139.07455 CHEBI:15377 ChEBI CHEBI:15378 ChEBI SMILES [H+] 14265-44-2 CAS C6H9N3O2 L-Histidine 155.06947 CHEBI:18406 ChEBI 389372 ChemSpider 36244-87-8 CAS HMDB12276 HMDB 1.0 53481398 PubChem-compound 1.0 2.0 HMDB12278 HMDB HMDB12277 HMDB HMDB01487 HMDB 644102 PubChem-compound HMDB03665 HMDB 1.0 L-Histidine SMILES O[C@H](COP(=O)(O)O)[C@@H](O)C(=O)CN\C=N\C1=C(C(=O)N)N=CN1[C@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@@H]1O ATP phosphoribosyltransferase SMILES NC1=[N+](C=NC2=C1N=CN2C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O)C1OC(COP(O)(O)=O)C(O)C1O SMILES NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O SMILES N[C@@H](CCC(N)=O)C(O)=O SMILES O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN([C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C2=N 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase SMILES NC(=O)C1=C(\N=C\NC2OC(COP(O)(O)=O)C(O)C2O)N(C=N1)C1OC(COP(O)(O)=O)C(O)C1O PRPP BioCyc 754 ChemSpider CHEBI:18050 ChEBI H2O Water 18.010565 SMILES O[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O Imidazole acetol-phosphate Histidinal NADH BioCyc NAD BioCyc 2.0 1061 PubChem-compound HMDB00280 HMDB PRPP Biosynthesis SubPathway HMDB03431 HMDB 987 ChemSpider Imidazole glycerol phosphate synthase subunit hisH PW000909 PathWhiz 984 ChemSpider Imidazole glycerol phosphate synthase subunit hisF IMIDAZOLE-ACETOL-P BioCyc 1.0 Histidine biosynthesis bifunctional protein hisB Histidinol-phosphate aminotransferase hisG hisI hisI hisA hisH hisF hisB hisC hisB hisD hisD Phosphoribosyl pyrophosphate Hydrogen Ion Pyrophosphate Phosphoribosyl- ATP Water Hydrogen Ion Pyrophosphate Phosphoribosyl- AMP Water 1-(5'- Phosphoribosyl)- 5-amino-4- imidazolecarboxamide PhosphoribosylformiminoAICAR- phosphate L-Glutamine L-Glutamic acid Hydrogen Ion 5- Aminoimidazole- 4-carboxamide D-Erythro- imidazole- glycerol- phosphate Water Imidazole acetol- phosphate L-Glutamic acid Oxoglutaric acid L-histidinol- phosphate Water Phosphate L-Histidinol NAD NADH Hydrogen Ion Histidinal Water NAD Hydrogen Ion NADH L-Histidine PRPP Biosynthesis