Flavin adenine dinucleotide

Flavin adenine dinucleotide
Identifiers
CAS Number	146-14-5 ;
3D model (JSmol)	quinone form: Interactive image; semiquinone form: Interactive image; hydroquinone form: Interactive image; flavin-N(5)-oxide form: Interactive image;
3DMet	B04792;
Beilstein Reference	1208946
ChEBI	CHEBI:16238 ;
ChEMBL	ChEMBL1232653 ;
DrugBank	DB03147 ;
ECHA InfoCard	100.005.149
EC Number	205-663-1;
Gmelin Reference	108834
IUPHAR/BPS	5184;
KEGG	C00016 ;
MeSH	Flavin-Adenine+Dinucleotide
PubChem CID	643975;
UNII	ZC44YTI8KK ;
CompTox Dashboard (EPA)	DTXSID4048307 ;
	InChI 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 [PubChem] Key: VWWQXMAJTJZDQX-UYBVJOGSSA-N [PubChem];
	SMILES quinone form: 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; semiquinone form: 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; hydroquinone form: 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; flavin-N(5)-oxide form: 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;
Properties
Chemical formula	C27H33N9O15P2
Molar mass	785.557 g·mol−1
Appearance	White, vitreous crystals
log P	-1.336
Acidity (pKa)	1.128
Basicity (pKb)	12.8689
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 can exist in four redox states, which are the flavin-N(5)-oxide, quinone, semiquinone, and hydroquinone. FAD is converted between these states by accepting or donating electrons. FAD, in its fully oxidized form, or quinone form, accepts two electrons and two protons to become FADH₂ (hydroquinone form). 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 superoxidized form of the flavin cofactor, the flavin-N(5)-oxide.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.