2.0 2012-10-10 12:21:08 -0600 2015-06-03 17:26:07 -0600 ECMDB23187 M2MDB003577 FMNH(2) FMNH2 is the reduced form of flavin mononucleotide. It is a substrate of the enzyme FMN reductase (EC 1.5.1.29), an enzyme that catalyzes the chemical reaction FMNH2 + NAD(P)+ <=> FMN + NAD(P)H + H+. Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase. During a catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH•) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-1,5-dihydrobenzogpteridin-10-yl)-2,3,4-trihydroxypentyl phosphate (2R,3S,4S)-5-(7,8-Dimethyl-2,4-dioxo-1,5-dihydrobenzogpteridin-10-yl)-2,3,4-trihydroxypentyl phosphoric acid 1,5-dihydroriboflavin 5'-phosphate 1,5-Dihydroriboflavin 5'-phosphoric acid 1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-1,3,4,5-tetrahydrobenzogpteridin-10(2H)-yl)-5-O-phosphonato-D-ribitol FMNH2 FMNH2 dianion Reduced flavin mononucleotide Reduced flavin mononucleotide dianion Reduced FMN Reduced FMN dianion Reduced FMN(2-) C17H21N4O9P 456.3438 456.104614802 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4-trihydroxy-5-(phosphonooxy)pentyl]-5H,10H-benzo[g]pteridine-2,4-bis(olate) 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4-trihydroxy-5-(phosphonooxy)pentyl]-5H-benzo[g]pteridine-2,4-bis(olate) 5666-16-0 [H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)[C@@]([H])(O)CN1C2=C(NC3=C1N=C([O-])N=C3[O-])C=C(C)C(C)=C2 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)/p-2/t11-,12+,14-/m0/s1 YTNIXZGTHTVJBW-SCRDCRAPSA-L Solid Cytoplasm (Predicted from LogP) logp 0.17 ALOGPS logs -2.15 ALOGPS solubility 3.51e+00 g/l ALOGPS logp 0.76 ChemAxon pka_strongest_acidic 1.49 ChemAxon pka_strongest_basic -1.1 ChemAxon iupac 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4-trihydroxy-5-(phosphonooxy)pentyl]-5H,10H-benzo[g]pteridine-2,4-bis(olate) ChemAxon average_mass 456.3438 ChemAxon mono_mass 456.104614802 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)[C@@]([H])(O)CN1C2=C(NC3=C1N=C([O-])N=C3[O-])C=C(C)C(C)=C2 ChemAxon formula C17H21N4O9P 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)/p-2/t11-,12+,14-/m0/s1 ChemAxon inchikey YTNIXZGTHTVJBW-SCRDCRAPSA-L ChemAxon polar_surface_area 214.62 ChemAxon refractivity 129.3 ChemAxon polarizability 42.14 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 12 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Specdb::NmrOneD 300585 Specdb::NmrOneD 300586 Specdb::NmrOneD 300587 Specdb::NmrOneD 300588 Specdb::NmrOneD 300589 Specdb::NmrOneD 300590 Specdb::NmrOneD 300591 Specdb::NmrOneD 300592 Specdb::NmrOneD 300593 Specdb::NmrOneD 300594 Specdb::NmrOneD 300595 Specdb::NmrOneD 300596 Specdb::NmrOneD 300597 Specdb::NmrOneD 300598 Specdb::NmrOneD 300599 Specdb::NmrOneD 300600 Specdb::NmrOneD 300601 Specdb::NmrOneD 300602 Specdb::NmrOneD 300603 Specdb::NmrOneD 300604 Specdb::MsMs 27428 Specdb::MsMs 27429 Specdb::MsMs 27430 Specdb::MsMs 33986 Specdb::MsMs 33987 Specdb::MsMs 33988 HMDB01142 445395 C01847 16048 FMNH2 FMNH FDB022449 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 Uracil + FMNH(2) + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Water Thymine + FMNH(2) + Oxygen > (Z)-2-Methyl-ureidoacrylate peracid + Flavin Mononucleotide + Water FMNH(2) + NAD > Flavin Mononucleotide + NADH An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + Oxygen > an aldehyde (R-CHO) + Flavin Mononucleotide + Sulfite + Water FMNH(2) + NADP > Flavin Mononucleotide + NADPH