Flavin adenine dinucleotide

Flavin adenine dinucleotide

Identifiers
CAS Number	146-14-5 Y
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 Y
ChEMBL	ChEMBL1232653 N
DrugBank	DB03147 Y
ECHA InfoCard	100.005.149
EC Number	205-663-1
Gmelin Reference	108834
IUPHAR/BPS	5184
KEGG	C00016 N
MeSH	Flavin-Adenine+Dinucleotide
PubChem CID	643975
UNII	ZC44YTI8KK Y
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 Y[PubChem] Key: VWWQXMAJTJZDQX-UYBVJOGSSA-N Y[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). N verify (what is YN ?) 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.^[1] 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.^[2][3]