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Oxidized ferredoxin Reduced ferredoxin 1.0 HMDB00250 HMDB CHEBI:30314 ChEBI 1.0 C8H14O2S2 (R)-lipoic acid 206.04352 Lipoyl-AMP Reaction3559 false (R)-lipoic acid + Adenosine triphosphate + Hydrogen ion → Lipoyl-AMP + Pyrophosphate LEFT_TO_RIGHT 370 ChemSpider Pyrophosphate C10H14N5O7P Adenosine monophosphate 347.06308 1.0 2.0 H Hydrogen ion 1.007825 CHEBI:16027 ChEBI Protein N6-(octanoyl)lysine Protein N6-(lipoyl)lysine ATP BioCyc 6137 PubChem-compound (R)-lipoic acid C06423 KEGG Compound 62-46-4 CAS 1.0 559142 ChemSpider C16241 KEGG Compound C15H23N6O5S S-Adenosylmethionine 399.14505 439182 PubChem-compound 5742 ChemSpider 1038 PubChem-compound CPD-195 BioCyc 1.0 Octanoyl-[acyl-carrier protein] SMILES CSCC[C@H](N)C(O)=O GO:0005829 GENE ONTOLOGY HMDB59597 HMDB (R)-lipoic acid Adenosine monophosphate C16238 KEGG Compound C18H26N5O8PS2 Lipoyl-AMP 535.09607 5858 ChemSpider 379 PubChem-compound HMDB00482 HMDB 2.0 1010 ChemSpider HMDB01451 HMDB Reaction3564 false Protein N6-(octanoyl)lysine + 2 Reduced ferredoxin + 2 S-Adenosylmethionine + 2 a sulfurated [sulfur carrier]  → 2 5'-Deoxyadenosine + 2 L-Methionine + Oxidized ferredoxin + Protein N6-(lipoyl)lysine + an unsulfurated [sulfur carrier] LEFT_TO_RIGHT 2.7.7.63 false 2.7.7.63 Adenosine triphosphate + Caprylic acid + a [lipoyl-carrier protein]-L-lysine → Adenosine monophosphate + Hydrogen Ion + Protein N6-(octanoyl)lysine + Pyrophosphate LEFT_TO_RIGHT 2.3.1.40 false 2.3.1.40 Adenosine triphosphate + Caprylic acid + a holo-[acyl-carrier protein] → Adenosine monophosphate + Octanoyl-[acyl-carrier protein] + Pyrophosphate LEFT_TO_RIGHT 1.0 2.3.1.181 false 2.3.1.181 Octanoyl-[acyl-carrier protein] + a [lipoyl-carrier protein]-L-lysine → Hydrogen Ion + Protein N6-(octanoyl)lysine + a holo-[acyl-carrier protein] LEFT_TO_RIGHT 2.7.7.63 false 2.7.7.63 Lipoyl-AMP + a [lipoyl-carrier protein]-L-lysine → Adenosine monophosphate + Hydrogen Ion + Protein N6-(lipoyl)lysine LEFT_TO_RIGHT PPI BioCyc Octanoyltransferase Protein N6-(octanoyl)lysine 1.0 HMDB00696 HMDB Protein N6-(lipoyl)lysine 5886 ChemSpider Hydrogen Ion CHEBI:28837 ChEBI SMILES C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12 CH33ADO BioCyc Cytosol Adenosine triphosphate 388325 ChemSpider Oxidized ferredoxin an unsulfurated [sulfur carrier] a holo-[acyl-carrier protein] 4754-39-6 CAS PW000770 PathWhiz Reduced ferredoxin CHEBI:15414 ChEBI a [lipoyl-carrier protein]-L-lysine SMP00919 SMPDB 1.0 CHEBI:18361 ChEBI C00002 KEGG Compound 1.0 Bifunctional protein aas 23724672 PubChem-compound Caprylic acid 2.0 1.0 Hydrogen ion C00019 KEGG Compound 1.0 S-ADENOSYLMETHIONINE BioCyc Lipoate-protein ligase A fatty acid biosynthesis SubPathway C00013 KEGG Compound a holo-[acyl-carrier protein] O7P2 Pyrophosphate 173.91193 palmitate biosynthesis SubPathway 5957 PubChem-compound GO:0005620 GENE ONTOLOGY Lipoic Acid Metabolism 6112 PubChem-compound H Hydrogen Ion 1.007825 P60720 UniProt SubPathwayInteraction1557 SubPathwayReaction SubPathway1557Reaction SubPathwayInteraction1559 SubPathway1559Reaction SubPathwayReaction 56-65-5 CAS 1.0 MET BioCyc C00020 KEGG Compound 1.0 SMP00818 SMPDB SMILES C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12 Octanoyltransferase SMILES CCCCCCCC(O)=O C5H11NO2S L-Methionine 149.05106 HMDB01983 HMDB Caprylic acid HMDB01185 HMDB AMP BioCyc Octanoyl-[acyl-carrier protein] SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O a sulfurated [sulfur carrier]  SMILES [O-]P([O-])(=O)OP([O-])([O-])=O 14000-31-8 CAS LIPOIC-ACID BioCyc 1.0 2.0 SMP00793 SMPDB HMDB00538 HMDB CHEBI:15422 ChEBI Bifunctional protein aas 61-19-8 CAS C05198 KEGG Compound SMILES NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1 SMILES OC(=O)CCCC[C@@H]1CCSS1 HMDB59635 HMDB 63-68-3 CAS 5907 ChemSpider CHEBI:16643 ChEBI C10H16N5O13P3 Adenosine triphosphate 506.99576 a sulfurated [sulfur carrier]  PW000797 PathWhiz Lipoate-protein ligase A (R)-lipoic acid L-Methionine C00073 KEGG Compound 1.0 31983 ChemSpider ReactionCatalysis3548 ACTIVATION C00080 KEGG Compound Periplasmic Space 1.0 ReactionCatalysis3549 ACTIVATION 1.0 1.0 CHEBI:15378 ChEBI SMILES [H+] CHEBI:17319 ChEBI SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O Caprylic acid C10H13N5O3 5'-Deoxyadenosine 251.10184 S-Adenosylmethionine 124-07-2 CAS C8H16O2 Caprylic acid 144.11504 ReactionCatalysis3550 ACTIVATION ReactionCatalysis3551 ACTIVATION P32099 UniProt ReactionCatalysis3552 ACTIVATION ReactionCatalysis3553 ACTIVATION 2.0 Transport451 false Caprylic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT Transport450 false (R)-lipoic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT 644102 PubChem-compound 6083 PubChem-compound P31119 UniProt 5'-Deoxyadenosine 29908-03-0 CAS a [lipoyl-carrier protein]-L-lysine HMDB00045 HMDB SMILES [H+] an unsulfurated [sulfur carrier] CHEBI:55451 ChEBI 26330628 ChemSpider 24762165 PubChem-compound 1.0 PW000900 PathWhiz Lipoate-protein ligase A Lipoate-protein ligase A Bifunctional protein aas Octanoyltransferase Lipoate-protein ligase A Lipoate-protein ligase A (R)-lipoic acid (R)-lipoic acid Caprylic acid Caprylic acid ATP Hydrogen ion PP i Lipoyl-AMP AMP H + ATP AMP PP i H + ATP H + PP i AMP S- Adenosylmethionine L-Methionine 5'- Deoxyadenosine Magnesium a [lipoyl-carrier protein]-L- lysine Protein N6- (lipoyl)lysine a holo-[acyl- carrier protein] Octanoyl- [acyl-carrier protein] a [lipoyl-carrier protein]-L- lysine a holo-[acyl- carrier protein] Protein N6- (octanoyl)lysine a [lipoyl-carrier protein]-L- lysine Protein N6- (octanoyl)lysine Reduced ferredoxin a sulfurated [sulfur carrier] Oxidized ferredoxin Protein N6- (lipoyl)lysine an unsulfurated [sulfur carrier] palmitate biosynthesis
Oxidized ferredoxin Reduced ferredoxin 1.0 HMDB00250 HMDB CHEBI:30314 ChEBI 1.0 C8H14O2S2 (R)-lipoic acid 206.04352 Lipoyl-AMP Reaction3559 false (R)-lipoic acid + Adenosine triphosphate + Hydrogen ion → Lipoyl-AMP + Pyrophosphate LEFT_TO_RIGHT 370 ChemSpider Pyrophosphate C10H14N5O7P Adenosine monophosphate 347.06308 1.0 2.0 H Hydrogen ion 1.007825 CHEBI:16027 ChEBI Protein N6-(octanoyl)lysine Protein N6-(lipoyl)lysine ATP BioCyc 6137 PubChem-compound (R)-lipoic acid C06423 KEGG Compound 62-46-4 CAS 1.0 559142 ChemSpider C16241 KEGG Compound C15H23N6O5S S-Adenosylmethionine 399.14505 439182 PubChem-compound 5742 ChemSpider 1038 PubChem-compound CPD-195 BioCyc 1.0 Octanoyl-[acyl-carrier protein] SMILES CSCC[C@H](N)C(O)=O GO:0005829 GENE ONTOLOGY HMDB59597 HMDB (R)-lipoic acid Adenosine monophosphate C16238 KEGG Compound C18H26N5O8PS2 Lipoyl-AMP 535.09607 5858 ChemSpider 379 PubChem-compound HMDB00482 HMDB 2.0 1010 ChemSpider HMDB01451 HMDB Reaction3564 false Protein N6-(octanoyl)lysine + 2 Reduced ferredoxin + 2 S-Adenosylmethionine + 2 a sulfurated [sulfur carrier]  → 2 5'-Deoxyadenosine + 2 L-Methionine + Oxidized ferredoxin + Protein N6-(lipoyl)lysine + an unsulfurated [sulfur carrier] LEFT_TO_RIGHT 2.7.7.63 false 2.7.7.63 Adenosine triphosphate + Caprylic acid + a [lipoyl-carrier protein]-L-lysine → Adenosine monophosphate + Hydrogen Ion + Protein N6-(octanoyl)lysine + Pyrophosphate LEFT_TO_RIGHT 2.3.1.40 false 2.3.1.40 Adenosine triphosphate + Caprylic acid + a holo-[acyl-carrier protein] → Adenosine monophosphate + Octanoyl-[acyl-carrier protein] + Pyrophosphate LEFT_TO_RIGHT 1.0 2.3.1.181 false 2.3.1.181 Octanoyl-[acyl-carrier protein] + a [lipoyl-carrier protein]-L-lysine → Hydrogen Ion + Protein N6-(octanoyl)lysine + a holo-[acyl-carrier protein] LEFT_TO_RIGHT 2.7.7.63 false 2.7.7.63 Lipoyl-AMP + a [lipoyl-carrier protein]-L-lysine → Adenosine monophosphate + Hydrogen Ion + Protein N6-(lipoyl)lysine LEFT_TO_RIGHT PPI BioCyc Octanoyltransferase Protein N6-(octanoyl)lysine 1.0 HMDB00696 HMDB Protein N6-(lipoyl)lysine 5886 ChemSpider Hydrogen Ion CHEBI:28837 ChEBI SMILES C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12 CH33ADO BioCyc Cytosol Adenosine triphosphate 388325 ChemSpider Oxidized ferredoxin an unsulfurated [sulfur carrier] a holo-[acyl-carrier protein] 4754-39-6 CAS PW000770 PathWhiz Reduced ferredoxin CHEBI:15414 ChEBI a [lipoyl-carrier protein]-L-lysine http://identifiers.org/smpdb/SMP00919 SMPDB 1.0 CHEBI:18361 ChEBI C00002 KEGG Compound 1.0 Bifunctional protein aas 23724672 PubChem-compound Caprylic acid 2.0 1.0 Hydrogen ion C00019 KEGG Compound 1.0 S-ADENOSYLMETHIONINE BioCyc Lipoate-protein ligase A C00013 KEGG Compound a holo-[acyl-carrier protein] O7P2 Pyrophosphate 173.91193 5957 PubChem-compound GO:0005620 GENE ONTOLOGY Lipoic Acid Metabolism 6112 PubChem-compound H Hydrogen Ion 1.007825 P60720 UniProt SubPathwayInteraction1557 SubPathwayReaction SubPathway1557Reaction SubPathwayInteraction1559 SubPathway1559Reaction SubPathwayReaction 56-65-5 CAS 1.0 MET BioCyc C00020 KEGG Compound 1.0 http://identifiers.org/smpdb/SMP00818 SMPDB SMILES C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12 Octanoyltransferase SMILES CCCCCCCC(O)=O C5H11NO2S L-Methionine 149.05106 HMDB01983 HMDB Caprylic acid HMDB01185 HMDB AMP BioCyc Octanoyl-[acyl-carrier protein] SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O a sulfurated [sulfur carrier]  SMILES [O-]P([O-])(=O)OP([O-])([O-])=O 14000-31-8 CAS LIPOIC-ACID BioCyc 1.0 2.0 http://identifiers.org/smpdb/SMP00793 SMPDB HMDB00538 HMDB CHEBI:15422 ChEBI Bifunctional protein aas 61-19-8 CAS C05198 KEGG Compound SMILES NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1 SMILES OC(=O)CCCC[C@@H]1CCSS1 HMDB59635 HMDB 63-68-3 CAS 5907 ChemSpider CHEBI:16643 ChEBI C10H16N5O13P3 Adenosine triphosphate 506.99576 a sulfurated [sulfur carrier]  PW000797 PathWhiz Lipoate-protein ligase A (R)-lipoic acid L-Methionine C00073 KEGG Compound 1.0 31983 ChemSpider ReactionCatalysis3548 ACTIVATION C00080 KEGG Compound Periplasmic Space 1.0 ReactionCatalysis3549 ACTIVATION 1.0 1.0 palmitate biosynthesis SubPathway CHEBI:15378 ChEBI SMILES [H+] CHEBI:17319 ChEBI SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O Caprylic acid C10H13N5O3 5'-Deoxyadenosine 251.10184 S-Adenosylmethionine 124-07-2 CAS C8H16O2 Caprylic acid 144.11504 ReactionCatalysis3550 ACTIVATION ReactionCatalysis3551 ACTIVATION P32099 UniProt ReactionCatalysis3552 ACTIVATION ReactionCatalysis3553 ACTIVATION 2.0 Transport451 false Caprylic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT Transport450 false (R)-lipoic acid (→) Transport: Escherichia coli, Periplasmic Space to Escherichia coli, Cytosol LEFT_TO_RIGHT 644102 PubChem-compound 6083 PubChem-compound P31119 UniProt 5'-Deoxyadenosine 29908-03-0 CAS a [lipoyl-carrier protein]-L-lysine HMDB00045 HMDB SMILES [H+] an unsulfurated [sulfur carrier] fatty acid biosynthesis SubPathway CHEBI:55451 ChEBI 26330628 ChemSpider 24762165 PubChem-compound 1.0 PW000900 PathWhiz lplA lplA aas lipB lplA lplA (R)-lipoic acid (R)-lipoic acid Caprylic acid Caprylic acid Adenosine triphosphate Hydrogen ion Pyrophosphate Lipoyl-AMP Adenosine monophosphate Hydrogen Ion Adenosine triphosphate Adenosine monophosphate Pyrophosphate Hydrogen Ion Adenosine triphosphate Hydrogen Ion Pyrophosphate Adenosine monophosphate S- Adenosylmethionine L-Methionine 5'- Deoxyadenosine a [lipoyl-carrier protein]-L- lysine Protein N6- (lipoyl)lysine a holo-[acyl- carrier protein] Octanoyl- [acyl-carrier protein] a [lipoyl-carrier protein]-L- lysine a holo-[acyl- carrier protein] Protein N6- (octanoyl)lysine a [lipoyl-carrier protein]-L- lysine Protein N6- (octanoyl)lysine Reduced ferredoxin a sulfurated [sulfur carrier] Oxidized ferredoxin Protein N6- (lipoyl)lysine an unsulfurated [sulfur carrier] palmitate biosynthesis