2.0 2012-05-31 13:46:17 -0600 2015-06-03 15:53:47 -0600 ECMDB01142 M2MDB000273 FMNH FMNH is a member of the chemical class known as Flavins. These are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, whose structure is characterized by an isoalloaxzine tricyclic ring. During their use in different catalytic cycles, the reversible interconversion of oxidized (FMN), semiquinone (FMNH FMNH2 Reduced flavin mononucleotide Reduced FMN C17H23N4O9P 458.3597 458.120264866 [(5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl)oxy]phosphonic acid (5-{7,8-dimethyl-2,4-dioxo-1H,3H,5H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl)oxyphosphonic acid CC1=CC2=C(C=C1C)N(CC(O)C(O)C(O)COP(O)(O)=O)C1=C(N2)C(=O)NC(=O)N1 InChI=1S/C17H23N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,18,22-24H,5-6H2,1-2H3,(H2,27,28,29)(H2,19,20,25,26) YTNIXZGTHTVJBW-UHFFFAOYSA-N Cytosol logp -0.17 ALOGPS logs -2.85 ALOGPS solubility 6.42e-01 g/l ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 1.5 ChemAxon pka_strongest_basic -0.52 ChemAxon iupac [(5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl)oxy]phosphonic acid ChemAxon average_mass 458.3597 ChemAxon mono_mass 458.120264866 ChemAxon smiles CC1=CC2=C(C=C1C)N(CC(O)C(O)C(O)COP(O)(O)=O)C1=C(N2)C(=O)NC(=O)N1 ChemAxon formula C17H23N4O9P ChemAxon inchi InChI=1S/C17H23N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,18,22-24H,5-6H2,1-2H3,(H2,27,28,29)(H2,19,20,25,26) ChemAxon inchikey YTNIXZGTHTVJBW-UHFFFAOYSA-N ChemAxon polar_surface_area 200.92 ChemAxon refractivity 118.51 ChemAxon polarizability 43.23 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 10 ChemAxon donor_count 8 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Pyrimidine metabolism The metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate. Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate. 1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate 4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate. PW000942 ec00240 Metabolic Sulfur metabolism The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. The alkyl sulfate is dehydrogenated and along with oxygen is converted to sulfite and an aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described. PW000922 ec00920 Metabolic Porphyrin and chlorophyll metabolism ec00860 Butirosin and neomycin biosynthesis ec00524 Riboflavin metabolism ec00740 Metabolic pathways eco01100 uracil degradation III PWY0-1471 two-component alkanesulfonate monooxygenase ALKANEMONOX-PWY Specdb::CMs 1083649 Specdb::NmrOneD 263688 Specdb::NmrOneD 263689 Specdb::NmrOneD 263690 Specdb::NmrOneD 263691 Specdb::NmrOneD 263692 Specdb::NmrOneD 263693 Specdb::NmrOneD 263694 Specdb::NmrOneD 263695 Specdb::NmrOneD 263696 Specdb::NmrOneD 263697 Specdb::NmrOneD 263698 Specdb::NmrOneD 263699 Specdb::NmrOneD 263700 Specdb::NmrOneD 263701 Specdb::NmrOneD 263702 Specdb::NmrOneD 263703 Specdb::NmrOneD 263704 Specdb::NmrOneD 263705 Specdb::NmrOneD 263706 Specdb::NmrOneD 263707 Specdb::MsMs 29525 Specdb::MsMs 29526 Specdb::MsMs 29527 Specdb::MsMs 36083 Specdb::MsMs 36084 Specdb::MsMs 36085 HMDB01142 691 C01847 FMNH2 FMNH Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 NAD(P)H-flavin reductase P0AEN1 FRE_ECOLI fre http://ecmdb.ca/proteins/P0AEN1.xml Sulfite reductase [NADPH] hemoprotein beta-component P17846 CYSI_ECOLI cysI http://ecmdb.ca/proteins/P17846.xml Sulfite reductase [NADPH] flavoprotein alpha-component P38038 CYSJ_ECOLI cysJ http://ecmdb.ca/proteins/P38038.xml Ferric iron reductase protein fhuF P39405 FHUF_ECOLI fhuF http://ecmdb.ca/proteins/P39405.xml FMN reductase P80644 SSUE_ECOLI ssuE http://ecmdb.ca/proteins/P80644.xml Alkanesulfonate monooxygenase P80645 SSUD_ECOLI ssuD http://ecmdb.ca/proteins/P80645.xml Putative flavin reductase rutF P75893 RUTF_ECOLI rutF http://ecmdb.ca/proteins/P75893.xml Putative monooxygenase rutA P75898 RUTA_ECOLI rutA http://ecmdb.ca/proteins/P75898.xml Flavin Mononucleotide + Hydrogen ion + NADH > FMNH + NAD R05705 Flavin Mononucleotide + Hydrogen ion + NADPH <> FMNH + NADP R05706 RXN-12444 FMNH + Oxygen + Sulfoacetate > Flavin Mononucleotide + Glyoxylic acid + Hydrogen ion + Water + Sulfite FMNH + Isethionic acid + Oxygen > Flavin Mononucleotide + Glycolaldehyde + Hydrogen ion + Water + Sulfite RXN-13418 FMNH + Methanesulfonate + Oxygen > Formaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite Butanesulfonate + FMNH + Oxygen > Butanal + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite RXN0-6973 Ethanesulfonate + FMNH + Oxygen > Acetaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite 2 Ferroxamine + FMNH >2 Iron +2 ferroxamine minus Fe(3) + Flavin Mononucleotide +2 Hydrogen ion FMNH + NAD <> Flavin Mononucleotide + NADH + Hydrogen ion R05705 FMNH + NADP <> Flavin Mononucleotide + NADPH + Hydrogen ion R05706 Uracil + FMNH + Oxygen <> Ureidoacrylate peracid + Flavin Mononucleotide R09936 RXN0-6444 NAD(P)⁺ + FMNH <> NAD(P)H + Flavin Mononucleotide + Hydrogen ion FMNREDUCT-RXN FMNH + NADP < Flavin Mononucleotide + NADPH + Hydrogen ion RXN-12444 Thymine + Oxygen + FMNH > (<i>Z</i>)-2-methylureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion RXN-12886 an alkanesulfonate + Oxygen + FMNH > an aldehyde + Sulfite + Water + Flavin Mononucleotide + Hydrogen ion RXN0-280 Uracil + Oxygen + FMNH > Hydrogen ion + Ureidoacrylate peracid + Flavin Mononucleotide RXN0-6444 Butanesulfonate + Oxygen + FMNH > Butanal + Sulfite + Water + Flavin Mononucleotide + Hydrogen ion RXN0-6973 Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + Water R07210 Uracil + FMNH + Oxygen + Thymine <> Ureidoacrylate peracid + Flavin Mononucleotide + (Z)-2-Methyl-ureidoacrylate peracid R09936 Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + Water Flavin Mononucleotide + Hydrogen ion + NADH > FMNH + NAD Flavin Mononucleotide + Hydrogen ion + NADH > FMNH + NAD