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Escherichia coli K-12 substr. MG1655 Compound: FAD

Synonyms: flavin adenine dinucleotide oxidized, flavin adenine dinucleotide, flavitan

Superclasses: an acceptora redox electron carrier
an organic heterocyclic compoundan organic heterobicyclic compounda pteridinea benzopteridinea flavinan oxidized flavin
an organic heterocyclic compoundan organonitrogen heterocyclic compounda pteridinea benzopteridinea flavinan oxidized flavin

Summary from MetaCyc:
Flavin adenine dinucleotide (FAD) is an important redox cofactor involved in many reactions in metabolism. The fully oxidized form, FAD, is converted to the reduced form, FADH2 by receiving two electrons and two protons. The reduced form can be oxidized to a semireduced form (semiquinone, FADH) by donating one electron and one proton. The semiquinone is then oxidized back to the fully oxidized form by losing a second electron and proton. Even though FAD has an aromatic ring system, FADH2 does not, making it significantly higher in energy.

Many proteins contain a flavin moiety, either in the form of FAD or FMN. They are known as flavoproteins.

Chemical Formula: C27H30N9O15P2

Molecular Weight: 782.53 Daltons

Monoisotopic Molecular Weight: 785.1571344575999 Daltons

FAD compound structure

SMILES: CC6(=C(C)C=C5(C(N=C1(C(=O)[N-]C(=O)N=C1N(CC(C(O)C(O)COP(OP([O-])(OCC4(C(O)C(O)C(N3(C=NC2(C(N)=NC=NC=23)))O4))=O)([O-])=O)O)5))=C6))

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,(H5,28,29,30,34,42,43,44,45,46,47)/p-3/t14-,15+,16+,19-,20+,21+,26+/m0/s1


Unification Links: CAS:146-14-5, ChEBI:57692, ChemSpider:13082029, HMDB:HMDB01248, IAF1260:33521, KEGG:C00016, PubChem:46906035, Wikipedia:Flavin_adenine_dinucleotide

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -646.338

Reactions known to produce the compound:

flavin biosynthesis I (bacteria and plants) :
ATP + FMN + H+FAD + diphosphate

In Reactions of unknown directionality:

Not in pathways:
NAD+ + FADH2 = NADH + FAD + 2 H+
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]

In Transport reactions:

Enzymes inhibited by FAD, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: FMN reductase [Louie02]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: glycerol-3-phosphate dehydrogenase, aerobic, aldehyde dehydrogenase, acetoin synthesis, glycerol-3-phosphate dehydrogenase, anaerobic, 5-aminomethyluridine-tRNA synthase, 5-carboxymethylaminomethyluridine-tRNA synthase, UDP-N-acetylenolpyruvoylglucosamine reductase, thioredoxin reductase, sulfite reductase, succinate:quinone oxidoreductase, N-methyltryptophan oxidase, pyruvate dehydrogenase, proline dehydrogenase, nitrite reductase - NADH dependent, NADH:ubiquinone oxidoreductase, L-aspartate oxidase, glyoxylate carboligase, glutathione reductase, L-glutamate:NADP+ oxidoreductase (transaminating), UDP-galactopyranose mutase, fumarate reductase, flavin reductase, L-aspartate oxidase, malate:quinone oxidoreductase, NADH cupric reductase, NADH oxidoreductase, alkyl hydroperoxide reductase, NADPH quinone reductase, dihydropteridine reductase, lipoate acetyltransferase N6-(dihydrolipoyl)lysine:NAD+ oxidoreductase, dihydrolipoate dehydrogenase, nitric oxide dioxygenase, pyruvate oxidase, D-lactate dehydrogenase, dihydropteridine reductase, D-alanine:quinone oxidoreductase (deaminating), D-amino-acid:quinone oxidoreductase (deaminating), acetohydroxybutanoate synthase, acetolactate synthase, 2-oxoglutarate dehydrogenase, ring 1,2-phenylacetyl-CoA epoxidase, L-2-hydroxyglutarate oxidase, isopentenyl-diphosphate:NAD(P)+ oxidoreductase, dimethylallyl-diphosphate:NAD(P)+ oxidoreductase, acetolactate synthase, acetohydroxybutanoate synthase, pyridine nucleotide transhydrogenase, crotonobetainyl-CoA reductase, acetohydroxybutanoate synthase, 5,10-methylenetetrahydrofolate reductase, flavodoxin NADP+ reductase, NADH:flavorubredoxin reductase, 2,4-dienoyl-CoA reductase, acetolactate synthase

This compound has been characterized as an alternative substrate of the following enzymes: flavin reductase, pyruvate:ferredoxin oxidoreductase, FMN reductase


Louie02: Louie TM, Yang H, Karnchanaphanurach P, Xie XS, Xun L (2002). "FAD is a preferred substrate and an inhibitor of Escherichia coli general NAD(P)H:flavin oxidoreductase." J Biol Chem 277(42);39450-5. PMID: 12177066

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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