2.0 2012-07-30 14:55:12 -0600 2015-10-15 16:13:56 -0600 ECMDB21279 M2MDB001686 Reduced riboflavin Reduced riboflavin is a member of the chemical class known as Quinoxalines. These are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring. Compared to riboflavin, reduced riboflavin has one extra hydrogen attached to an oxygen on its ring structure. Riboflavin, also known as vitamin B2, is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. As such, vitamin B2 is required for a wide variety of cellular processes. It plays a key role in energy metabolism, and for the metabolism of fats, ketone bodies, carbohydrates, and proteins. The reduced form, which occurs in metabolism along with the oxidized form, is colorless. (Wikipedia) 1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-1,3,4,5-tetrahydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol 4a,5-Dihydroriboflavine 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-4a,5-dihydroisoalloxazine 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-5,10-dihydrobenzo[g]pteridine-2,4(3H,4aH)-dione Reduced riboflavin C15H16N4O6 348.3107 348.106984264 10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione 10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-3H-benzo[g]pteridine-2,4-dione OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=CC=CC=C2N=C2C(=O)NC(=O)N=C12 InChI=1S/C15H16N4O6/c20-6-10(22)12(23)9(21)5-19-8-4-2-1-3-7(8)16-11-13(19)17-15(25)18-14(11)24/h1-4,9-10,12,20-23H,5-6H2,(H,18,24,25)/t9-,10-,12-/m1/s1 ATANIONNQLTUND-CKYFFXLPSA-N Cytosol logp -1.64 ALOGPS logs -2.86 ALOGPS solubility 4.76e-01 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 5.97 ChemAxon pka_strongest_basic -3 ChemAxon iupac 10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione ChemAxon average_mass 348.3107 ChemAxon mono_mass 348.106984264 ChemAxon smiles OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=CC=CC=C2N=C2C(=O)NC(=O)N=C12 ChemAxon formula C15H16N4O6 ChemAxon inchi InChI=1S/C15H16N4O6/c20-6-10(22)12(23)9(21)5-19-8-4-2-1-3-7(8)16-11-13(19)17-15(25)18-14(11)24/h1-4,9-10,12,20-23H,5-6H2,(H,18,24,25)/t9-,10-,12-/m1/s1 ChemAxon inchikey ATANIONNQLTUND-CKYFFXLPSA-N ChemAxon polar_surface_area 155.05 ChemAxon refractivity 86.19 ChemAxon polarizability 33.24 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 11922 Specdb::CMs 38126 Specdb::CMs 149200 Specdb::CMs 149201 Specdb::CMs 149203 Specdb::CMs 169852 Specdb::CMs 279715 Specdb::NmrOneD 336658 Specdb::NmrOneD 336659 Specdb::NmrOneD 336660 Specdb::NmrOneD 336661 Specdb::NmrOneD 336662 Specdb::NmrOneD 336663 Specdb::NmrOneD 336664 Specdb::NmrOneD 336665 Specdb::NmrOneD 336666 Specdb::NmrOneD 336667 Specdb::NmrOneD 336668 Specdb::NmrOneD 336669 Specdb::NmrOneD 336670 Specdb::NmrOneD 336671 Specdb::NmrOneD 336672 Specdb::NmrOneD 336673 Specdb::NmrOneD 336674 Specdb::NmrOneD 336675 Specdb::NmrOneD 336676 Specdb::NmrOneD 336677 Specdb::MsMs 292255 Specdb::MsMs 292256 Specdb::MsMs 292257 Specdb::MsMs 332407 Specdb::MsMs 332408 Specdb::MsMs 332409 Specdb::MsMs 3048857 Specdb::MsMs 3048858 Specdb::MsMs 3048859 Specdb::MsMs 3118603 Specdb::MsMs 3118604 Specdb::MsMs 3118605 11245895 26330553 C01007 17607 CPD-316 Riboflavin 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 Hydrogen ion + NADPH + Riboflavin > NADP + Reduced riboflavin NADPH-DEHYDROGENASE-FLAVIN-RXN Hydrogen ion + NADH + Riboflavin > NAD + Reduced riboflavin 2 Ferroxamine + Reduced riboflavin >2 Iron +2 ferroxamine minus Fe(3) +2 Hydrogen ion + Riboflavin Reduced riboflavin + NADP < Hydrogen ion + Riboflavin + NADPH NADPH-DEHYDROGENASE-FLAVIN-RXN Reduced riboflavin + NAD(P)⁺ Riboflavin + NAD(P)H + Hydrogen ion RXN-12445 Reduced riboflavin + NAD(P)(+) > Riboflavin + NAD(P)H