MetaCyc 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

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 Change Formation (ΔfG in kcal/mol): -305.61398Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

4,4'-diapolycopenedioate biosynthesis :
all-trans-4,4'-diaponeurosporene + FAD + H+all-trans-4,4'-diapolycopene + FADH2
all-trans-4,4'-diapo-ζ-carotene + FAD + H+all-trans-4,4'-diaponeurosporene + FADH2
all-trans-4,4'-diapophytofluene + FAD + H+all-trans-4,4'-diapo-ζ-carotene + FADH2
15-cis-4,4'-diapophytoene + FAD + H+all-trans-4,4'-diapophytofluene + FADH2

cytokinins degradation :
isopentenyl adenosine + FAD + H2O + H+ → adenosine + 3-methyl-2-butenal + FADH2
trans-zeatin riboside + FAD + H2O + H+ → adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2
trans-zeatin + FAD + H2O + H+ → adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2
N6-dimethylallyladenine + FAD + H2O + H+ → 3-methyl-2-butenal + adenine + FADH2
cis-zeatin + FAD + H2O + H+ → 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2

guadinomine B biosynthesis :
a 2-aminomalonyl semialdehyde-[seryl-carrier protein] + FAD + H2O → an aminomalonyl-[seryl-carrier protein] + FADH2

L-valine degradation I :
isobutanoyl-CoA + FAD + H+ → methylacrylyl-CoA + FADH2

methylthiopropanoate degradation I (cleavage) :
3-(methylthio)propionyl-CoA + FAD + H+ → 3-(methylthio)acryloyl-CoA + FADH2

mycolyl-arabinogalactan-peptidoglycan complex biosynthesis :
trans,octacis-decaprenylphospho-β-D-ribofuranose + FAD + H+trans,octacis-decaprenylphospho-β-D-erythro-pentofuranosid-2-ulose + FADH2

quinoxaline-2-carboxylate biosynthesis :
(R)-β-hydroxy-L-kynurenine + FAD + H2O → (2S,3R)-2-[(2-aminophenyl)amino]-3-carboxy-3-hydroxypropanoate + FADH2 + H+

spinosyn A biosynthesis :
spinosyn macrolactone + FAD + H+ → 15-oxo spinosyn macrolactone + FADH2

staphyloxanthin biosynthesis :
all-trans-4,4'-diapo-ζ-carotene + FAD + H+all-trans-4,4'-diaponeurosporene + FADH2
all-trans-4,4'-diapophytofluene + FAD + H+all-trans-4,4'-diapo-ζ-carotene + FADH2
15-cis-4,4'-diapophytoene + FAD + H+all-trans-4,4'-diapophytofluene + FADH2

zwittermicin A biosynthesis :
a 2-aminomalonyl semialdehyde-[seryl-carrier protein] + FAD + H2O → an aminomalonyl-[seryl-carrier protein] + FADH2
a (2R)-2-hydroxy-3-oxopropanoyl-[acp] + FAD + H2O → a (2R)-2-hydroxymalonyl-[acp] + FADH2

Not in pathways:
1'-carboxy-chondrochloren B + FAD + 2 H+ → chondrochloren B + CO2 + FADH2
1'-carboxy-chondrochloren A + FAD + 2 H+ → chondrochloren A + CO2 + FADH2

Reactions known to produce the compound:

2,4,5-trichlorophenoxyacetate degradation :
2,5-dichloro-p-quinol + FADH2 + oxygen → 5-chlorohydroxyquinone + chloride + FAD + H2O + 3 H+
2,4,5-trichlorophenol + FADH2 + oxygen → 2,5-dichloro-p-quinone + chloride + FAD + H2O + H+

2,4,6-trichlorophenol degradation :
2,6-dichloro-p-hydroquinone + 2 FADH2 + oxygen → 6-chlorohydroxyquinol + chloride + 2 FAD + H2O + 2 H+
2,4,6-trichlorophenol + 2 FADH2 + oxygen → 2,6-dichloro-p-hydroquinone + chloride + 2 FAD + H2O + 3 H+

3,5,6-trichloro-2-pyridinol degradation :
3,5,6-trichloro-2-pyridinol + FADH2 + oxygen + 2 H2O → 3,6-dihydroxypyridine-2,5-dione + 3 chloride + FAD + H2O + 4 H+

4-hydroxyphenylacetate degradation , aromatic biogenic amine degradation (bacteria) :
4-hydroxyphenylacetate + FADH2 + oxygen → 3,4-dihydroxyphenylacetate + FAD + H+ + H2O

anthranilate degradation IV (aerobic) :
anthranilate + FADH2 + oxygen → 3-hydroxyanthranilate + FAD + H+ + H2O

coumarins biosynthesis (engineered) :
4-coumarate + FADH2 + oxygen → trans-caffeate + FAD + H2O + H+
L-tyrosine + FADH2 + oxygen → L-dopa + FAD + H2O + H+

flavin biosynthesis I (bacteria and plants) , flavin biosynthesis II (archaea) , flavin biosynthesis III (fungi) , flavin biosynthesis IV (mammalian) :
ATP + FMN + H+FAD + diphosphate

griseofulvin biosynthesis :
griseophenone C + chloride + FADH2 + oxygen → griseophenone B + FAD + 2 H2O

hopanoid biosynthesis (bacteria) :
squalene + FAD + H2O + H+ ← hydroxysqualene + FADH2

pyrrolnitrin biosynthesis , rebeccamycin biosynthesis :
L-tryptophan + chloride + FADH2 + oxygen → 7-chloro-L-tryptophan + FAD + 2 H2O

styrene degradation :
styrene + FADH2 + oxygen → (S)-2-phenyloxirane + FAD + H+ + H2O

Not in pathways:
8-demethylnovobiocic acid + chloride + FADH2 + oxygen → clorobiocic acid + FAD + 2 H2O
4-tyrosol + FADH2 + oxygen → 3-hydroxytyrosol + FAD + H2O + H+
(S)-β-tyrosyl-[SgcC2] + chloride + FADH2 + oxygen → (S)-3-chloro-β-tyrosyl-[SgcC2] + FAD + 2 H2O
(S)-3-chloro-β-tyrosyl-[SgcC2] + FADH2 + oxygen → (S)-3-chloro-5-hydroxy-β-tyrosyl-[SgcC2] + FAD + H2O + H+
3,5,6-trichloro-2-pyridinol + FADH2 + oxygen → 3,6-dichloropyridine-2,5-dione + chloride + FAD + H2O + 2 H+
deoxycholate + FAD + H+ + H2O ← cholate + FADH2
lithocholate + FAD + H+ + H2O ← chenodeoxycholate + FADH2

Not in pathways:
2-methylpropanamine + a reduced flavin + oxygen → N-(2-methylpropyl)hydroxylamine + an oxidized flavin + H2O + H+

Reactions known to both consume and produce the compound:

2,4,5-trichlorophenoxyacetate degradation :
5-chlorohydroxyquinol + FAD ↔ 5-chlorohydroxyquinone + FADH2
2,5-dichloro-p-quinol + FAD + H+ → 2,5-dichloro-p-quinone + FADH2

In Reactions of unknown directionality:

Not in pathways:
NAD+ + FADH2 = NADH + FAD + 2 H+
FADH2 + NAD(P)+ = FAD + NAD(P)H + 2 H+
a 5,10-methylene-tetrahydrofolate + a uracil54 in tRNA + FADH2 = a tetrahydrofolate + a 5-methyluracil54 in tRNA + FAD + H+
15-cis-4,4'-diapophytoene + 3 FAD + 3 H+ = all-trans-4,4'-diaponeurosporene + 3 FADH2
a [protein]-L-threonine + FAD = a [protein]-FMN-L-threonine + AMP
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
15-cis-4,4'-diapophytoene + 4 FAD + 4 H+ = all-trans-4,4'-diapolycopene + 4 FADH2
isovaleryl-CoA + FAD + H+ = 3-methylcrotonyl-CoA + FADH2
D-gluconate + FAD + H+ = 2-keto-D-gluconate + FADH2
2-hydroxyglutarate + FAD + H+ = 2-oxoglutarate + FADH2
a decanoyl-HmqF protein + FAD + H+ = a 2,3-dehydro-decanoyl-HmqF + FADH2
L-tryptophan + chloride + FAD + 2 H+ = 5-chloro-L-tryptophan + FADH2
FAD = AMP + riboflavin cyclic-4',5'-phosphate
FAD + H2O = AMP + FMN + 2 H+

Not in pathways:
a reduced flavin + NAD+ = an oxidized flavin + NADH + H+

In Transport reactions:

In Redox half-reactions:
FAD[in] + 3 H+[in] + 2 e-[membrane] → FADH2[in]

Enzymes activated by FAD, sorted by the type of activation, are:

Activator (Allosteric) of: benzene 1,2-dioxygenase [Axcell75] Activator (Mechanism unknown) of: hydrogenase [Ma00], (S)-2-hydroxypropylphosphonate epoxidase [Liu01], 2-pyrazoline synthase [Brown90a], pyrazolidine synthase [Brown90a], pyrazole synthase [Brown90a]

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

Inhibitor (Competitive) of: FMN reductase [Louie02] Inhibitor (Mechanism unknown) of: isopenicillin N epimerase [Usui89] Inhibitor (Other types) of: sulfur oxygenase reductase [Kletzin89]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: glycerol-3-phosphate dehydrogenase, anaerobic, glycerol-3-phosphate dehydrogenase, aerobic, glyoxylate carboligase, UDP-N-acetylenolpyruvoylglucosamine reductase, D-lactate dehydrogenase, isopentenyl-diphosphate:NAD(P)+ oxidoreductase, dimethylallyl-diphosphate:NAD(P)+ oxidoreductase, lipoate acetyltransferase N6-(dihydrolipoyl)lysine:NAD+ oxidoreductase, 2-oxoglutarate dehydrogenase, succinate:quinone oxidoreductase, malate:quinone oxidoreductase, ring 1,2-phenylacetyl-CoA epoxidase, acetolactate synthase, acetohydroxybutanoate synthase, acetolactate synthase, acetohydroxybutanoate synthase, acetohydroxybutanoate synthase, acetolactate synthase, UDP-galactopyranose mutase, fumarate reductase, 5,10-methylenetetrahydrofolate reductase, dihydrolipoate dehydrogenase, pyruvate dehydrogenase, thioredoxin reductase, glutathione reductase, proline dehydrogenase, L-glutamate:NADP+ oxidoreductase (transaminating), flavin reductase, sulfite reductase, NADH cupric reductase, NADH:ubiquinone oxidoreductase, L-aspartate oxidase, L-aspartate oxidase, L-2-hydroxyglutarate oxidase, aldehyde dehydrogenase, D-alanine:quinone oxidoreductase (deaminating), D-amino-acid:quinone oxidoreductase (deaminating), NADH oxidoreductase, alkyl hydroperoxide reductase, 2,4-dienoyl-CoA reductase, 5-aminomethyluridine-tRNA synthase, 5-carboxymethylaminomethyluridine-tRNA synthase, NADPH quinone reductase, nitrite reductase - NADH dependent, dihydropteridine reductase, acetoin synthesis, pyruvate oxidase, pyridine nucleotide transhydrogenase, dihydropteridine reductase, nitric oxide dioxygenase, flavodoxin NADP+ reductase, N-methyltryptophan oxidase, phenazine-1-carboxylate 1-monooxygenase, triostin A dithiol oxidase, L-gulono-1,4-lactone dehydrogenase, hydroxysqualene dehydroxylase, (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoA oxidase, (6Z,9Z,12Z,15Z,18Z)-tetracosapentaenoyl-CoA oxidase, demethylphylloquinone dehydrogenase, demethylphylloquinone dehydrogenase, 4-hydroxyisophthalate monooxygenase, 4-hydroxy-3-methylbenzyl alcohol dehydrogenase, 2,4-xylenol methylhydroxylase, 4-hydroxybenzyl alcohol dehydrogenase, 4-methylphenol methylhydroxylase, 3-hydroxy-5-methylbenzoate 6-hydroxylase, 3-hydroxy-4-methylbenzoate 6-hydroxylase, 2-aminomalonyl semialdehyde-[pcp] hydroxylase, tirandamycin F 10-dehydrogenase, tirandamycin E 10-dehydrogenase, holomycin dithiol oxidase, holothin dithiol oxidase, 3-methylorcinaldehyde monooxygenase, 2-chloro-6-nitrotoluene 1,2-dioxygenase, 2-chloro-4-nitrotoluene 1,2-dioxygenase, 1,4-dinitrobenzene 1,2-dioxygenase, 1,3-dinitrobenzene 1,2-dioxygenase, 3,4-dinitrotoluene 1,2-dioxygenase, 2,6-dinitrotoluene 1,2-dioxygenase, 4-nitrotoluene 1,2-dioxygenase, 2-nitrotoluene 1,2-dioxygenase, 2,4-dinitrotoluene 1,2-dioxygenase, 2,3-dinitrotoluene 1,2-dioxygenase, 2-dihydro-NADP oxidase, 6-dihydro-NADP oxidase, 6-dihydro-NAD oxidase, 2-dihydro-NAD oxidase, 3-oxocholest-4-en-26-oyl-CoA dehydrogenase, 6-hydroxy-3-succinoyl-pyridine hydroxylase, (S)-6-hydroxynicotine oxidase, nicotine dehydrogenase, (2S)-methylsuccinyl-CoA dehydrogenase, medicarpin 1α-hydroxylase, maackiain 1α-hydroxylase, UDP-galactopyranose mutase, maackiain 1α-hydroxylase, medicarpin 1α-hydroxylase, epoxyfarnesyl-5,7-dihydroxy-4,6-dimethylphthalide synthase, 2,5-bis-hydroxymethylfuran oxidase, 2-carboxy-5-(dihydroxymethyl)furan oxidase, 2-(dihydroxymethyl)-5-formylfuran oxidase, 5-hydroxymethylfurfural oxidase, asperlicin C monooxygenase, 3-benzyl-3,6 -dithio-6-(hydroxymethyl)-diketopiperazine oxidase, 2-methyl-3-n-amyl-dihydropyrrole oxidase, L-prolyl-S-peptidyl-carrier protein dehydrogenase, methylene tetrahydrofolate reductase, (S)-2-acetolactate synthase, 71-hydroxychlorophyll a reductase, NADPH-cytochrome P540 reductase, 4-sulfoacetophenone monooxygenase, choline oxidase, betaine aldehyde oxidase, choline oxidase, trimethyluric acid monooxygenase, tetracenomycin A2 C4,C4A,C12A hydroxylase, carnitine monooxygenase, 3-sulfinopropionyl-CoA desulfinase, NADPH-cytochrome P450 reductase, dihydropterin oxidase, 3-oxochol-4-en-24-oyl-CoA dehydrogenase, vancosamine nitrososynthase, vancosamine nitrososynthase, indole 2,3-dioxygenase, indole 2,3-dioxygenase, indole 2,3-dioxygenase, tylosin reductase, aurachin C monooxygenase, cyclohexane-1-carbonyl-CoA dehydrogenase, benzoyl-CoA reductase, cyclohex-1-ene-1-carbonyl-CoA dehydrogenase, desmosterol reductase, 2-naphthoyl-CoA reductase, dihydrolipoyl dehydrogenase, fumarate reductase, glycine oxidase/deaminase, 2-iminoacetate deaminase, FAD-dependent urate hydroxylase, aclacinomycin N oxidase, aclacinomycin A oxidase, aklavinone 12-hydroxylase, NAD(P)H sulfur oxidoreductase, cis-4-hydroxy-D-proline dehydrogenase, glucose dehydrogenase (quinone), bis-γ-glutamylcystine reductase, 2,3-di-O-geranylgeranyl-sn-glycerol 1-phosphate reductase [NAD(P)H], 2,3-di-O-geranylgeranyl-sn-glycerol 1-phosphate reductase, urocanate reductase, D-glyceraldehyde dehydrogenase, sulfide dehydrogenase, peroxisomal acyl-coenzyme A oxidase, branched chain fatty acyl-CoA oxidase, fatty acyl-CoA oxidase, ornithine N-hydroxylase, spinosyn cyclic macrolactone flavin-dependent oxidase, indole-3-pyruvate monooxygenase, protoporphyrinogen oxidase, chanoclavine-I synthase oxidoreductase, 4-nitrocatechol 4-monooxygenas, 4-nitrophenol 2-monooxygenase, 4-nitrocatechol 4-monooxygenase, very-long-chain acyl-CoA dehydrogenase, short-chain acyl-CoA dehydrogenase, short-chain acyl-CoA dehydrogenase, butanoyl-CoA dehydrogenase, medium-chain acyl-CoA dehydrogenase, long-chain-acyl-CoA dehydrogenase, premithramycin B monooxygenase, all-trans-3-hydroxyretinol epimerase, protoviolaceinate synthase, deoxyviolaceinate synthase, violaceinate synthase, L-tryptophan oxidase, glutaconyl-CoA decarboxylase, 2-hydroxybiphenyl-3-monooxygenase, 2,2'-hydroxybiphenyl monooxygenase, 2,2',3-trihydroxybiphenyl monooxygenase, 2-isopropylphenol monooxygenase, 2-propylphenol monooxygenase, paromamine 6'-oxidase, 6'''-hydroxyneomycin C 6'-oxidase, 4-hydroxyacetophenone monooxygenase, 4-hydroxyacetophenone monooxygenase, pesudooxynicotine oxidase, 6-hydroxy-3-succinoyl-pyridine hydroxylase, 4-methylaminobutanoate oxidase, 4-methylaminobutyrate oxidase (demethylating), 2,6-dihydroxypyridine 3-monooxygenase, nicotine dehydrogenase, pyruvate dehydrogenase (NADP+), trimethylamine monooxygenase, cholesterol oxidase, styrene monooxygenase, 1-hydroxy-2-naphthoate hydroxylase, androsta-1,4-diene-3,17-dione 9α-hydroxylase, 1,4-androstadiene-3,17-dione 9α-hydroxylase, cholesterol oxidase, 1-deoxy-11-oxopentalenate monooxygenase (neopentalenolactone D producing), glycine oxidase, tRNA-dihydrouridine20 synthase, tRNA-dihydrouridine17 synthase, tRNA-dihydrouridine16 synthase, dopamine oxidase, serotonin oxidase, NADH-dependent cytochrome b5 reductase, squalene,NADPH:oxygen oxidoreductase (2,3-epoxidizing), rubredoxin--NAD(P)+ reductase, malate:quinone oxidoreductase, glycerol-3-phosphate dehydrogenase, rubredoxin NAD+ reductase, 2-oxopropyl-CoM reductase (carboxylating), anthranilate dioxygenase, sulfite reductase, sucrose 3-dehydrogenase, glutaryl-CoA dehydrogenase, nitrobenzene dioxygenase, lactose 3-dehydrogenase, cob(II)yrinate a,c-diamide reductase, mercury(II) reductase, rubredoxin-NAD+ reductase, 6-hydroxypseudooxynicotine dehydrogenase, cyclohexanone monooxygenase, (R)-6-hydroxynicotine oxidase, adenylylsulfate reductase, 2-oxo-Δ3-4,5,5-trimethylcyclopentenyl acetyl coA 1,2-monooxygenase, 3-hydroxybenzoate 6-hydroxylase, thioredoxin reductase, butyryl-CoA dehydrogenase, pentachlorophenol hydroxylase, benzoate,NADH:oxygen oxidoreductase (1,2-hydroxylating), 2,4-dichlorophenol 6-monooxygenase, 4-hydroxybutyryl-CoA dehydratase, vinylacetyl-CoA Δ 3-Δ 2-isomerase, 4-hydroxybutyryl-CoA dehydratase, 4-methyl-5-nitrocatechol monooxygenase, 2-nitrotoluene dioxygenase, 3-nitrotoluene 1,2-dioxygenase, naphthalene 1,2-dioxygenase, trypanothione reductase, L-gulono-γ-lactone oxidase, alcohol oxidase, 2-methyl-3-hydroxypyridine-5-carboxylate oxygenase, pyridoxine 4-oxidase, xanthine dehydrogenase, hypoxanthine hydroxylase, xanthine:NAD+ oxidoreductase, D-lactate dehydrogenase (cytochrome), factor F420-reducing hydrogenase, ethylnitronate monooxygenase, adenylylsulfate reductase, APS reductase, 2-methylbutanoyl-CoA dehydrogenase, sulfide dehydrogenase, L-lysine monooxygenase, F420H2 dehydrogenase, glutaryl-CoA dehydrogenase, nucleoside oxidase, arginine oxidase, toluene 1,2-dioxygenase, sarcosine oxidase, glutathione amide reductase, phytofluene desaturase, pyrrole-2-carboxylate monooxygenase, pyrrole-2-carboxylate monooxygenase, thiol oxidase, dimethylglycine dehydrogenase, sarcosine dehydrogenase, electron transfer flavoprotein-ubiquinone oxidoreductase, L-saccharopine oxidase, prejadomycin monooxygenase/dehydratase, 4-nitrophenol 4-monooxygenase, isovaleryl-CoA dehydrogenase, citronellyl-CoA dehydrogenase, 5-methylphenazine-1-carboxylate 1-monooxygenase, xanthine oxidase, monoamine oxidase, farnesylcysteine lyase, flavin-dependent thymidylate synthase, flavin-dependent thymidylate synthase, flavin-dependent thymidylate synthase, flavin-dependent thymidylate synthase, lactose 3-dehydrogenase, proline dehydrogenase, proline dehydrogenase, limonene hydroxylase, phytoene desaturase, 6-hydroxynicotinate 3-monooxygenase, spermidine oxidase, spermine oxidase, dihydrothymine dehydrogenase, dihydrouracil dehydrogenase, D-proline dehydrogenase, D-amino acid dehydrogenase, D-arginine dehydrogenase, FAD-dependent urate hydroxylase, D-proline dehydrogenase, tryptophan 5-halogenase, decaprenylphospho-β-D-ribofuranose 2-dehydrogenase, UDP-galactopyranose mutase, thioredoxin reductase, xanthine oxidase, hypoxanthine dehydrogenase, xanthine dehydrogenase, flavin dependent hydroxylase, StaC monooxygenase, arcyriaflavin A synthase, phenylethylamine oxidase, 7-chloro-L-tryptophan oxidase, tryptophan 7-halogenase, sulfide:quinone oxidoreductase, (6-4)DNA photolyase, spermine oxidase, N1-acetylspermine oxidase, norspermine oxidase, kynurenine 3-monooxygenase, tryptamine oxidase, methoxyneurosporene desaturase, hydroxyneurosporene desaturase, phytoene desaturase, phytofluene desaturase, ζ-carotene desaturase, dihydrolipoyl dehydrogenase, dihydrolipoyl dehydrogenase, cob(II)yrinate a,c-diamide reductase, precorrin 3B synthase, 2-fluorobenzoate 1,2-dioxygenase, 2,4,5-trichlorophenol-4-monooxygenase, 2,5-dichloro-p-quinol 2-monooxygenase, 2,4,5-trichlorophenoxyacetate hydroxylase, phenol,NADPH:oxygen oxidoreductase (2-hydroxylating), phenol 2-monooxygenase, D-aspartate oxidase, D-amino acid oxidase, N1-acetylspermidine oxidase, N1-acetylspermine oxidase, dihydroorotate dehydrogenase, xylitol oxidase, alditol oxidase, 2-amninobenzoyl-CoA monooxygenase/reductase, squalene,NADPH:oxygen oxidoreductase (2,3-epoxidizing), pyranose oxidase, (25S)-3α,7α,12α-trihydroxy-5β-cholestanoyl-CoA dehydrogenase, adrenodoxin-NADP+ reductase, NADPH-cytochrome P450 reductase, NADPH-cytochrome P450 reductase, methanesulfonate monooxygenase, xanthine oxidase, ferredoxin-NADP oxidoreductase, (-)-(4S)-limonene 1,2-monooxygenase, (+)-(4R)-limonene 1,2-monooxygenase, (-)-dihydrocarvone monooxygenase, (1S,4R)-iso-dihydrocarvone monooxygenase, (1R,4S)-iso-dihydrocarvone monooxygenase, (1R,4R)-dihydrocarvone monooxygenase, (1R,4S)-1-hydroxy-2-oxolimonene monooxygenase, (1S,4R)-1-hydroxy-2-oxolimonene monooxygenase, 4,4'-diapophytofluene desaturase, 4,4'-diapo-ζ-carotene desaturase, dehydrosqualene desaturase, methylenetetrahydrofolate reductase, protoporphyrinogen oxidase, CDP-4-dehydro-6-deoxyglucose reductase, 4-hydroxybutyryl-CoA dehydratase, L-sorbose dehydrogenase, spermine oxidase, nitrate reductase, squalene,hydrogen-donor:oxygen oxidoreductase (2,3-epoxidizing), hypotaurine dehydrogenase, glutamate synthase, glutamate synthase, naphthalene 1,2-dioxygenase, salicylate hydroxylase, acryloyl-CoA reductase, nitroalkane oxidase, nitrite reductase, L-lysine α-oxidase, pipecolate oxidase, berberine bridge enzyme, UDP-N-acetylenolpyruvoylglucosamine reductase, p-hydroxyphenylpyruvate oxidase, acyl-CoA oxidase, Δ9-tetrahydrocannabinolate synthase, butanoyl-CoA dehydrogenase, 6-hydroxynicotinate dehydrogenase, betaine aldehyde oxidase, spermidine oxidase, benzoyl-CoA 2,3-epoxidase, mycothione reductase, benzylsuccinyl-CoA dehydrogenase, nitrate reductase, spermidine oxidase, cresol ortho-monooxygenase, toluene ortho-monooxygenase, nitrate reductase, quinoline 2-oxidoreductase, resorcinol hydroxylase, nicotine dehydrogenase, p-hydroxybenzoate hydroxylase, glutathione reductase, nitric-oxide synthase, nitric oxide synthase, nitric-oxide synthase, proline dehydrogenase, p-hydroxybenzoate hydroxylase, orcinol hydroxylase, (S)-6-hydroxynicotine oxidase, monodehydroascorbate reductase, 5,10-methylenetetrahydrofolate reductase, isethionate dehydrogenase, tryptophan 2-monooxygenase, sarcosine oxidase, spermine oxidase, spermine oxidase, nicotinate hydroxylase, isobutyryl-CoA:FAD oxidoreductase, lipoate acetyltransferase N6-(dihydrolipoyl)lysine:NAD+ oxidoreductase, 4-imidazolone-5-propionate oxidase, nicotinate dehydrogenase, 6-hydroxynicotinate 3-monooxygenase, L-lysine 6-monooxygenase, arginine 2-monooxygenase, putrescine oxidase, N-acetylputrescine oxidase

This compound has been characterized as an alternative substrate of the following enzymes: thiol oxidase, flavin reductase, flavin:NADH reductase, pyruvate-ferredoxin oxidoreductase, pyruvate:ferredoxin oxidoreductase, FMN reductase (NADH), NAD pyrophosphatase, FMN reductase (NADH), hydrogenase, FMN reductase

Revised 04-Nov-2014 by Caspi R, SRI International


Axcell75: Axcell BC, Geary PJ (1975). "Purification and some properties of a soluble benzene-oxidizing system from a strain of Pseudomonas." Biochem J 146(1);173-83. PMID: 167712

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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