Search Results - FAD

Flavin adenine dinucleotide

| ImageSize = 150 | ImageName = Stereo, Kekulé, skeletal formula of FAD | ImageClass = skin-invert-image | ImageFile2 = FAD_Raswin.png | ImageFile2_Ref = | ImageSize2 = 244 | ImageName2 = Spacefill model of FAD |Section1= | PubChem = 643975 | ChemSpiderID = 559059 | ChemSpiderID_Ref = | UNII = ZC44YTI8KK | UNII_Ref = | EINECS = 205-663-1 | DrugBank = DB03147 | DrugBank_Ref = | KEGG = C00016 | KEGG_Ref = | MeSHName = Flavin-Adenine+Dinucleotide | ChEBI = 16238 | ChEBI_Ref = | ChEMBL = 1232653 | ChEMBL_Ref = | Beilstein = 1208946 | Gmelin = 108834 | SMILES = c12cc(C)c(C)cc1N=C3C(=O)NC(=O)N=C3N2C[C@H](O)[C@H](O)[C@H](O)COP(=O)(O)OP(=O)(O)OC[C@@H]4[C@@H](O)[C@@H](O)[C@@H](O4)n5cnc6c5ncnc6N | SMILES_Comment = quinone form | SMILES1 = c12cc(C)c(C)cc1N[C]3C(=O)NC(=O)N=C3N2C[C@H](O)[C@H](O)[C@H](O)COP(=O)([O-])OP(=O)([O-])OC[C@@H]4[C@@H](O)[C@@H](O)[C@@H](O4)n5cnc6c5ncnc6N | SMILES1_Comment = semiquinone form | SMILES2 = c12cc(C)c(C)cc1NC=3C(=O)NC(=O)NC=3N2C[C@H](O)[C@H](O)[C@H](O)COP(=O)([O-])OP(=O)([O-])OC[C@@H]4[C@@H](O)[C@@H](O)[C@@H](O4)n5cnc6c5ncnc6N | SMILES2_Comment = hydroquinone form | SMILES3 = c12cc(C)c(C)cc1[N+]([O-])=C3C(=O)NC(=O)N=C3N2C[C@H](O)[C@H](O)[C@H](O)COP(=O)(O)OP(=O)(O)OC[C@@H]4[C@@H](O)[C@@H](O)[C@@H](O4)n5cnc6c5ncnc6N | SMILES3_Comment = flavin-N(5)-oxide form | InChI_Ref = | InChI = 1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1 | InChIKey = VWWQXMAJTJZDQX-UYBVJOGSSA-N | InChIKey_Ref = }} |Section2= }}

In biochemistry, flavin adenine dinucleotide (FAD) is a redox-active coenzyme associated with various proteins, which is involved with several enzymatic reactions in metabolism. A flavoprotein is a protein that contains a flavin group, which may be in the form of FAD or flavin mononucleotide (FMN). Many flavoproteins are known: components of the succinate dehydrogenase complex, α-ketoglutarate dehydrogenase, and a component of the pyruvate dehydrogenase complex.

FAD exists in two common oxidation states, the fully oxidized form (FAD) and the fully reduced, dihydrogenated form, FADH₂. Other oxidation states also exist, including the N-oxide and semiquinone states. FAD, in its fully oxidized form, accepts two electrons and two protons to become FADH₂. The semiquinone (FADH^·) can be formed by either reduction of FAD or oxidation of FADH₂ by accepting or donating one electron and one proton, respectively. Some proteins, however, generate and maintain a super oxidized form of the flavin cofactor, the flavin-N(5)-oxide. Provided by Wikipedia