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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: FAD

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

Superclasses: a redox electron carrier
an organic heterocyclic compound an organic heterobicyclic compound a pteridine a benzopteridine a flavin an oxidized flavin
an organic heterocyclic compound an organonitrogen heterocyclic compound a pteridine a benzopteridine a flavin an oxidized flavin

Chemical Formula: C27H30N9O15P2

Molecular Weight: 782.53 Daltons

Monoisotopic Molecular Weight: 785.1571344575999 Daltons

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

InChIKey: InChIKey=IMGVNJNCCGXBHD-UYBVJOGSSA-K

Unification Links: CAS:146-14-5 , ChEBI:4956 , ChemSpider:13082029 , HMDB:HMDB01248 , IAF1260:33521 , KEGG:C00016 , PubChem:15938970

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -305.61398 Inferred by computational analysis [Latendresse, 2013]

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

methylthiopropionate degradation I (cleavage) :
3-(methylthio)propionyl-CoA + FAD + H+ → methylthioacryloyl-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

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

valine degradation I :
isobutanoyl-CoA + FAD + H+ → methylacrylyl-CoA + 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 :
2,4,6-trichlorophenol + FADH2 + oxygen → 2,6-dichloro-p-hydroquinone + chloride + FAD + H2O
2,6-dichloro-p-hydroquinone + FADH2 + oxygen + H+ → 6-chlorohydroxyquinol + chloride + FAD + H2O

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

phloridzin biosynthesis :
4-coumaryl-CoA + NADPH + FADH2 → 4-dihydrocoumaroyl-CoA + NADP+ + FAD + 2 H+

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+


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+
(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+
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[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
myristoyl-CoA + FAD + H+ = 2-trans-tetradecenoyl-CoA + FADH2
lithocholate + FAD + H+ + H2O = chenodeoxycholate + FADH2
15-cis-4,4'-diapophytoene + 4 FAD + 4 H+ = all-trans-4,4'-diapolycopene + 4 FADH2
hexanoyl-CoA + FAD + H+ = trans-hex-2-enoyl-CoA + FADH2
isovaleryl-CoA + FAD + H+ = 3-methylcrotonyl-CoA + FADH2
lauroyl-CoA + FAD + H+ = 2-trans-dodecenoyl-CoA + FADH2
octanoyl-CoA + FAD + H+ = trans-oct-2-enoyl-CoA + FADH2
D-gluconate + FAD + H+ = 2-keto-D-gluconate + FADH2
palmitoyl-CoA + FAD + H+ = trans-hexadec-2-enoyl-CoA + FADH2
butanoyl-CoA + FAD + H+ = crotonyl-CoA + FADH2
decanoyl-CoA + FAD + H+ = trans-Δ2-decenoyl-CoA + 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
deoxycholate + FAD + H+ + H2O = cholate + FADH2
FAD = AMP + riboflavin cyclic-4',5'-phosphate
FAD + H2O = AMP + FMN + 2 H+


a reduced flavin + NAD+ = an oxidized flavin + NADH + H+

In Redox half-reactions:
FAD[in] + 2 H+[in] + 2 e- → 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 [Liu01b] , 2-pyrazoline synthase [Brown90a] , pyrazolidine synthase [Brown90a] , pyrazole synthase [Brown90a]

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

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: aldehyde dehydrogenase , acetolactate synthase , acetohydroxybutanoate synthase , acetolactate synthase , acetohydroxybutanoate synthase , acetohydroxybutanoate synthase , acetolactate synthase , L-glutamate:NADP+ oxidoreductase (transaminating) , glyoxylate carboligase , glycerol-3-phosphate dehydrogenase, anaerobic , succinate:quinone oxidoreductase , malate:quinone oxidoreductase , UDP-N-acetylenolpyruvoylglucosamine reductase , UDP-galactopyranose mutase , ring 1,2-phenylacetyl-CoA epoxidase , 5,10-methylenetetrahydrofolate reductase , isopentenyl-diphosphate:NAD(P)+ oxidoreductase , dimethylallyl-diphosphate:NAD(P)+ oxidoreductase , dihydrolipoate dehydrogenase , lipoate acetyltransferase N6-(dihydrolipoyl)lysine:NAD+ oxidoreductase , 2-oxoglutarate dehydrogenase , pyruvate dehydrogenase , fumarate reductase , thioredoxin reductase , glutathione reductase , D-lactate dehydrogenase , proline dehydrogenase , L-2-hydroxyglutarate oxidase , flavin reductase , sulfite reductase , L-aspartate oxidase , L-aspartate oxidase , 2,4-dienoyl-CoA reductase , NADPH quinone reductase , dihydropteridine reductase , dihydropteridine reductase , nitric oxide dioxygenase , 5-aminomethyluridine-tRNA synthase , 5-carboxymethylaminomethyluridine-tRNA synthase , acetoin synthesis , pyruvate oxidase , D-alanine:quinone oxidoreductase (deaminating) , D-amino-acid:quinone oxidoreductase (deaminating) , pyridine nucleotide transhydrogenase , N-methyltryptophan oxidase , NADH oxidoreductase , nitrite reductase , flavodoxin NADP+ reductase , NADH cupric reductase , NADH:ubiquinone oxidoreductase , alkylhydroperoxide reductase , 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 , pyocyanin hydroxylase , 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 oxygenase , 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


References

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

Brown90a: Brown, E.G., Diffin, F.M. (1990). "Biosynthesis and metabolism of pyrazole by Cucumis sativus: enzymic cyclization and dehydrogenation of 1,3-diaminopropane." Phytochemistry, 1990, 29(2):469-478.

Kletzin89: Kletzin A (1989). "Coupled enzymatic production of sulfite, thiosulfate, and hydrogen sulfide from sulfur: purification and properties of a sulfur oxygenase reductase from the facultatively anaerobic archaebacterium Desulfurolobus ambivalens." J Bacteriol 171(3);1638-43. PMID: 2493451

Latendresse, 2013: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Liu01b: Liu P, Murakami K, Seki T, He X, Yeung SM, Kuzuyama T, Seto H, Liu H (2001). "Protein purification and function assignment of the epoxidase catalyzing the formation of fosfomycin." J Am Chem Soc 123(19);4619-20. PMID: 11457256

Ma00: Ma K, Weiss R, Adams MW (2000). "Characterization of hydrogenase II from the hyperthermophilic archaeon Pyrococcus furiosus and assessment of its role in sulfur reduction." J Bacteriol 182(7);1864-71. PMID: 10714990

Usui89: Usui S, Yu CA (1989). "Purification and properties of isopenicillin N epimerase from Streptomyces clavuligerus." Biochim Biophys Acta 999(1);78-85. PMID: 2804141


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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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