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1. Oxidoreductions of C40 psi,psi carotenoid (38) Aldehyde addition (3) Reaction center(s): C16 (3) CR00002 Tetradehydrolycopene + reduced acceptor + O2 = Tetradehydrolycopenal + acceptor + H2O (none -> 16-al) CR00003 Tetradehydrolycopenal = Tetradehydrolycopendial (none -> 16'-al) CR00004 Didehydrolycopene = Didehydrolycopenal (none -> 16-al) Cis isomeration and desaturation (9) Reaction center(s): C11,12 and C7 (1) CR00010 Asymmetric 9Z-ζ-carotene = 7,9-dicis-Neurosporene (11,12+H -> 7Z) Reaction center(s): C11, C12, C11', C12', and C15 (1) CR00450 15-cis-Phytoene <=> 9,9'-dicis-zeta-Carotene (15Z, 11,12+H, 11',12'+H -> 9Z, 9'Z) Reaction center(s): C7 and C7,8 (2) CR00011 9,9'-dicis-ζ-Carotene + a quinone = 7,9,9'-tricis-Neurosporene + a quinol CR00012 7,9,9'-tricis-Neurosporene + a quinone = 7,9,7',9'-tetracis-Lycopene + a quinol Reaction center(s): C7',8', C11,12, and C9 (1) CR00014 ζ-carotene = Asymmetric 9-cis-ζ-carotene (7',8'+H -> 9Z, 11,12+H) Reaction center(s): C9 and C11,12 (2) CR00015 15Z-Phytoene + 2 plastoquinone = 15,9'-dicis-Phytofluene + 2 plastoquinol (11',12'+H -> 9Z) CR00016 15,9'-dicis-Phytofluene + plastoquinone = 9,15,9'-tricis-ζ-Carotene + plastoquinol (11,12+H -> 9'Z) Reaction center(s): C15, C11,12, C7',8', and C11',12' (1) CR00458 15-cis-Phytoene + 3 Acceptor = all-trans-Neurosporene + 3 Reduced acceptor (15Z, 11,12+H, 7',8'+H, 11',12'+H -> none) Reaction center(s): C11,12 (1) CR00115 all-trans-Phytofluene + Acceptor = all-trans-ζ-Carotene + Reduced acceptor (11,12+H -> none) Desaturation (17) Reaction center(s): C11, C12, C11' and C12’ (1) CR00451 15-cis-Phytoene + 2 Plastoquinone = 9,15,9'-tricis-zeta-Carotene + 2 Plastoquinol (11,12+H, 11',12'+H -> 9Z, 9'Z) Reaction center(s): C7' and C8' (1) CR00448 9,9'-dicis-zeta-Carotene + 2 Quinone = 7,9,7',9'-tetracis-Lycopene + 2 Hydroquinone (7,8+H, 7',8'+H -> 7Z, 7'Z) Reaction center(s): C11 and C12 (1) CR00449 all-trans-Phytoene + Acceptor = all-trans-Phytofluene + Reduced acceptor (11',12'+H -> 15Z) Reaction center(s): C15,15' (1) CR00117 Lycopersene = Phytoene (15,15'+H -> none) Reaction center(s): C3,4 (8) CR00118 Chloroxanthin = Demethylspheroidene CR00119 Lycopene + Acceptor = 3,4-Didehydrolycopene + Reduced acceptor (none -> 3,4--H) CR00120 Rhodopin + Acceptor = 3,4-Dehydrorhodopin + Reduced acceptor (none -> 3,4--H) CR00121 Rhodovibrin = Hydroxyspirilloxanthin (none -> 3,4--H) CR00122 Didehydrolycopene = Tetradehydrolycopene (none -> 3',4'--H) CR00123 1'-Hydroxy-3,4-didehydrolycopene + Acceptor = 3,4,3',4'-Tetradehydrorhodopin + reduced acceptor (No fingerprints are given) CR00124 Dihydroxyneurosporene = OH-Demethylspheroidene (none -> 3,4--H) CR00125 1'-Hydroxy-3,4-didehydrolycopene + Acceptor = 3,4,3',4'-Tetradehydrorhodopin + Reduced acceptor (none -> 3,4--H) Reaction center(s): C3,4 and C3',4' (1) CR00128 3,4,3',4'-Tetrahydrospirilloxanthin = Spirilloxanthin (none -> 3,4--H, 3',4'--H) Reaction center(s): C7,8 (1) CR00132 all-trans-Neurosporene + Acceptor = Lycopene + Reduced acceptor Reaction center(s): C7,8 and C7',8' (1) CR00134 ζ-carotene = Lycopene Reaction center(s): C7,8, C11,12, C7',8', and C11',12' (1) CR00135 Phytoene = Lycopene (7,8+H, 11,12+H, 7',8'+H, 11',12'+H -> none) Reaction center(s): C7',8' (1) CR00136 all-trans-ζ-Carotene + Acceptor = all-trans-Neurosporene + Reduced acceptor (7',8'+H -> none) Cis isomerization and aldehyde addition (1) Reaction center(s): C13 and C20 (1) CR00018 1-Hydroxy-1,2-dihydrolycopene = Rhodopinal (none -> 13Z, 20-al) Cleavage and aldehyde addition (1) Reaction center(s): C4 (1) CR00071 3,4-Dehydrolycopene = Apo-4'-lycopenal (3,4--H -> 4'-apo, 4'-al) Cleavage, aldehyde addition, and cyclization from psi to beta (1) Reaction center(s): C4 (1) CR00077 3,4-Didehydrolycopene + O2 = β-apo-4'-carotenal + 3-methylbut-2-enal (3,4--H, psi -> 4'-apo, 4'-al, beta) Oxidative cleavage (3) Reaction center(s): C5 - C6 and C5' - C6' (3) CR00461 Violaxanthin di-myristate = Tobiraxanthin A1 (5,6+H, 5',6'+H, 5,6-Epoxy(Down), 5',6'-Epoxy(Down) -> 5,6-seco, 5',6'-seco, 5=O, 6=O, 5'=O, 6'=O) CR00462 Violaxanthin laurate myristate = Tobiraxanthin A2 (5',6'+H, 5,6+H, 5',6'-Epoxy(Down), 5,6-Epoxy(Down) -> 5,6-seco, 5',6'-seco, 5=O, 6=O, 5'=O, 6'=O) CR00463 Violaxanthin di-laurate = Tobiraxanthin A3 (5,6+H, 5',6'+H, 5,6-Epoxy(Down), 5',6'-Epoxy(Down) -> 5,6-seco, 5',6'-seco, 5=O, 6=O, 5'=O, 6'=O) Cleavage and ketolation (2) Reaction center(s): C9 (1) CR00097 Phytoene = Geranylacetone (11,12+H, 7',8'+H, 11',12'+H, psi' -> 10-apo, 9=O) Reaction center(s): C9 and C9' (1) CR00098 Lycopene = Pseudoionone (psi' -> 10-apo, 9=O) Cleavage, carboxylation, and cis isomerization (1) Reaction center(s): C6, C6', and C9 (1) CR00099 Lycopene = Norbixin (psi, psi' -> 9Z, 6-COOH, 6'-COOH, 6-apo, 6'-apo) 1. Oxidoreductions of C40 beta,psi carotenoid (15) Cleavage and aldehyde addition (5) Reaction center(s): C15 (4) CR00028 γ-Carotene + O2 = Retinal + Acycloretinal (psi' -> 15-al, 15-apo) CR00029 γ-Carotene + O2 = Acycloretinal + Retinal (beta' -> 15-apo, 15-al) CR00030 Torulene + O2 = Retinal + 3,4-didehydro-acycloretinal (3',4'--H, psi' -> 15-al, 15-apo) CR00031 Torulene + O2 = 3,4-didehydro-acycloretinal + Retinal (beta' -> 15-apo, 15-al) Reaction center(s): C3' and C4' (1) CR00036 Torulene + O2 = β-Apo-4'-carotenal Desaturation (2) Reaction center(s): C3,4 (1) CR00113 1'-Hydroxy-γ-carotene = 1'-Hydroxytorulene (none -> 3',4'--H) Reaction center(s): C3',4' (1) CR00114 γ-Carotene = Torulene (none -> 3',4'--H) Desaturation, demethylation, and methylation (reduction from beta to chi) (1) Reaction center(s): C1,2 and C3,4 (1) CR00152 Thiothece-474 = Okenone (beta -> chi) Desaturation, demethylation, and methylation (reduction from beta to phi) (1) Reaction center(s): C1,2 and C3,4 (1) CR00155 γ-Carotene = Chlorobactene (beta -> phi) Hydroxylation (6) Reaction center(s): C2(Dpwn) (1) CR00203 Myxol 2'-fucoside = 2-Hydroxymyxol 2'-fucoside (none -> 2-OH(Down)) Reaction center(s): C3(Up) (2) CR00204 (2'S)-Deoxymyxol 2'-(2,4-di-O-methyl-alpha-L-fucoside) = (3R,2'S)-Myxol 2'-(2,4-di-O-methyl-alpha-L-fucoside) (none -> 3-OH(Up)) CR00205 (2'S)-Deoxymyxol 2'-alpha-L-fucoside = (3R,2'S)-Myxol 2'-alpha-L-fucoside (none -> 3-OH(Up)) Reaction center(s): C4 (1) CR00206 Myxol 2'-fucoside = 4-Hydroxymyxol 2'-fucoside (none -> 4-OH) Reaction center(s): C4(Down) (1) CR00207 Myxol = (3S,4R,2'S)-4-Hydroxymyxol (2'-OH(Down) -> 4-OH, 4-OH(Down)) Reaction center(s): C4(Up) (1) CR00208 Myxol = (3S,4S,2'S)-4-Hydroxymyxol (2'-OH(Down) -> 4-OH, 4-OH(Up)) 1. Oxidoreductions of C40 beta,beta carotenoid (85) Cleavage and aldehyde addition (20) Reaction center(s): C10' (2) CR00021 β-Carotene = β-Apo-10'-carotenal CR00043 β-Cryptoxanthin + O2 = 10'-Apo-β-carotenal (3-OH(Up), beta' -> 10'-al, 10'-apo) Reaction center(s): C7 (1) CR00037 Zeaxanthin = Hydroxy-β-cyclocitral Reaction center(s): C10 (1) CR00040 9-cis-β-Carotene + O2 = 9-cis-10'-Apo-β-carotenal + β-Ionone (beta' -> 10'-apo, 10'-al) Reaction center(s): C10 and C10' (3) CR00041 β-Carotene = C14 aldehyde (beta, beta' -> 10-al, 10'-al, 10-apo, 10'-apo) CR00042 Violxanthin = C14 aldehyde (3-OH(Up), 3'-OH(Up), 5,6+H, 5',6'+H, 5,6-Epoxy(Down), 5',6'-Epoxy(Down), beta, beta' -> 10-al, 10'-al, 10-apo, 10'-apo) CR00059 Zeaxanthin = C14 aldehyde (3-OH(Up), 3'-OH(Up), beta, beta' -> 10-al, 10'-al, 10-apo, 10'-apo) Reaction center(s): C11 (2) CR00044 (9Z)-Violaxanthin + O2 = Xanthoxin + C25-Allenic-apo-aldehyde (6',7'--H, 5',6'+H, 3'-OH(Up), 5'-OH(Down), beta' -> 11-al, 11-apo) CR00045 (9Z)-Violaxanthin + O2 = Xanthoxin + (3S,5R,6S)-5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al (3'-OH(Up), 5',6'+H, 5',6'-Epoxy(Down), beta' -> 11-al, 11-apo) Reaction center(s): C12' (3) CR00046 (9'Z)-Neoxanthin + O2 = C25-Allenic-apo-aldehyde + Xanthoxin CR00047 (9Z)-Violxanthin = 5,6-epoxy-3-hydroxy-12'-apo-β-caroten-12'-al (No fingerprints are given) CR00048 (9Z)-Neoxanthn = 5,6-epoxy-3-hydroxy-12'-apo-β-caroten-12'-al + 3,5-dihydroxy-6,7- didehydro-12'-apo-β-caroten-12-al (No fingerprints are given) Reaction center(s): C14' (1) CR00049 β-Carotene + O2 = β-apo-14'-carotenonal (beta' -> 14'-al, 14'-apo) Reaction center(s): C15 (4) CR00050 β-Carotene + O2 = Retinal (Not capable by Nostoc) (beta' -> 15-al, 15-apo) CR00051 β-Cryptoxanthin + O2 = (all-E)-3-hydroxy-retinal (beta' -> 15-al, 15-apo) CR00052 Zeaxanthin + O2 = (3R)-11-cis-3-hydroxyretinal + (3R)-all-trans-3-hydroxyretinal (3'-OH(Up), beta' -> 15-al, 15-apo) CR00053 β-Cryptoxanthin + O2 = (all-E)-retinal (3-OH(Up), beta' -> 15-al, 15-apo) Reaction center(s): C8 (1) CR00055 Alloxanthin = 8'-Apoalloxanthinal (7',8'--H, 3'-OH(Up), beta' -> 8'-al, 8'-apo) Reaction center(s): C8 and C8' (1) CR00056 Zeaxanthin = Crocetin dialdehyde (3-OH(Up), 3'-OH(Up), beta, beta' -> 8-al, 8'-al, 8-apo, 8'-apo) Reaction center(s): C8' (1) CR00057 β-Carotene = β-Apo-8'-carotenal (beta' -> 8'-al, 8'-apo) Epoxidation (7) Reaction center(s): C5 and C6 (1) CR00471 Astaxanthin + superoxide anion radicals/hydroxyl radicals = Astaxanthin 5,6-epoxide (none -> 5,6-Epoxy) Reaction center(s): C5 and C8 (1) CR00472 Astaxanthin + superoxide anion radicals/hydroxyl radicals = Astaxanthin 5,8-epoxide (none -> 5,8-Epoxy) Reaction center(s): C5,6 (2) CR00157 β-Carotene = β-Carotene 5,6-epoxide (none -> 5,6+H, 5,6-Epoxy) CR00159 Antheraxanthin + NAD(P)H + H+ O2 = Violaxanthin + NAD(P)+ + H2O (none -> 5',6'+H, 5',6'-Epoxy(Down)) Reaction center(s): C5,6 and C5,8 (2) CR00161 Anthexraxanthin + HCL = Mutatoxanthin (5,6+H, 5,6-Epoxy(Down) -> 5,8+H, 5(Down),8-Epoxy) CR00162 β-Carotene 5,6-epoxide = Mutatochrome (5,6+H, 5,6-Epoxy -> 5,8+H, 5,8-Epoxy) Reaction center(s): C5,6 and C5',6' (1) CR00453 Zeaxanthin + 4 Reduced ferredoxin + 4 H+ + 2 Oxygen <=> Violaxanthin + 4 Oxidized ferredoxin + 2 H2O (none -> 5,6+H, 5',6'+H, 5,6-Epoxy(Down), 5',6'-Epoxy(Down)) Peroxidation (2) Reaction center(s): C5 and C6 (1) CR00473 Astaxanthin + singlet oxygens = Astaxanthin-5,6-peroxide (none -> 5,6-Peroxy) Reaction center(s): C5 and C8 (1) CR00474 Astaxanthin + singlet oxygen = Astaxanthin-5,8-peroxide (none -> 5,8-Peroxy) Nitration (1) Reaction center(s): C15 (1) CR00475 Astaxanthin + Peroxynitrite = Nitro-astaxanthin (none -> 15-NO2) Cleavage, aldehyde addition, and cis isomerization (4) Reaction center(s): C15 and C11 (2) CR00073 β-Carotene + O2 = (11Z)-retinal (beta' -> 11Z, 15-al, 15-apo) CR00074 β-Cryptoxanthin + O2 = (11Z)-retinal (3-OH(Up), beta' -> 11Z, 15-al, 15-apo) Reaction center(s): C15 and C13 (2) CR00075 β-Carotene + O2 = (13Z)-retinal (beta' -> 13Z, 15-al, 15-apo) CR00076 β-Cryptoxanthin + O2 = (11Z)-3-hydroxy-retinal (3-OH(Up), beta' -> 13Z, 15-al, 15-apo) Cleavage and ketolation (10) Reaction center(s): C10 and C9 (1) CR00082 9-cis-β-Carotene + O2 = 9-cis-10'-Apo-β-carotenal + β-Ionone (9Z, beta' -> 9=O, 9-apo) Reaction center(s): C13 (1) CR00083 β-Carotene + O2 = β-apo-13-carotenone (beta' -> 13=O, 13-apo) Reaction center(s): C9 (8) CR00084 (all-E)-β-Carotene + O2 = β-ionone + 10'-Apo-β-carotenal (beta' -> 9=O, 9-apo) CR00085 Zeaxanthin = 3-Hydroxy-β-Ionone CR00086 Canthaxanthin = 4-oxo-β-Ionone (4'=O, beta' -> 9=O, 9-apo) CR00087 Astaxanthin = 3-Hydroxy-4-oxo-β-Ionone (3'-OH(Up), 4'=O, beta' -> 9=O, 9-apo) CR00088 Neoxanthin = Grasshopper ketone (5',6'+H, 3'-OH(Up), 5',6'-Epoxy(Down), beta' -> 9=O, 9-apo, 8(Up)) CR00089 Violxanthin = 5,6-epoxy-3-hydroxy-9-apo-β-caroten-9-one (3'-OH(Up), 5',6'+H, 5',6'-Epoxy(Down), beta, beta' -> 9-apo, beta(Down), 9=O) CR00090 (9Z)-Violxanthin = 5,6-epoxy-3-hydroxy-9-apo-β-caroten-9-one (9Z, 3'-OH(Up), 5',6'+H, 5',6'-Epoxy(Down), beta, beta' -> 9-apo, beta(Down), 9=O) CR00091 (9Z)-Neoxanthn = Grasshopper ketone (9'Z, 5',6'+H, 3'-OH(Up), 5',6'-Epoxy(Down), beta' -> 9=O, 9-apo, 8(Up)) Cleavage, hydroxylation, hydration, and desaturation (1) Reaction center(s): C15 (1) CR00100 Anhydrolutein = 3-Dehydroretinol (3'-OH(Up), beta' -> 15-OH, 15-apo) Cleavage, ketolation, and epoxidation (1) Reaction center(s): C9 and C5,6 (1) CR00101 Neoxanthin = 5,6-Epoxy-3-hydroxy-β-Ionone (6,7--H, 5',6'+H, 3-OH(Up), 5-OH(Down), 3'-OH(Up), 5',6'-Epoxy(Down), beta' -> 9-apo, 3-OH, 5,6-Epoxy, 9=O) Conversion of double bond from beta to epsilon (2) Reaction center(s): C5 (2) CR00102 β-Carotene = α-Carotene (beta' -> epsilon') CR00104 Zeaxamthin = 3,3'-Diketo-epsilon-carotene (3-OH(Up), 3'-OH(Up), beta, beta' -> 3=O, 3'=O, epsilon, epsilon') Desaturation (acetylene bond forming out of allene bond) (3) Reaction center(s): C6,7 and C7,8 (2) CR00138 Fucoxanthinol = Halocynthiaxanthin (6',7'--H, 5',6'+H, 5'-OH(Down) -> 7',8'--H) CR00139 Peridinin = Pyrrhoxanthin (6',7'--H, 5',6'+H, 5'-OH(Down) -> 7',8'--H) Reaction center(s): C6,7 and C7',8' (1) CR00141 Neoxanthin = Diadinoxanthin (6',7'--H, 5',6'+H, 5'-OH(Down) -> 7',8'--H) Desaturation (acetylene bond forming) (2) Reaction center(s): C7,8 (1) CR00143 Zeaxanthin = Diatoxanthin (none -> 7,8--H) Reaction center(s): C7',8' (1) CR00144 Diatoxanthin = Alloxanthin (none -> 7',8'--H) Desaturation (keton forming) (2) Reaction center(s): C4 (2) CR00146 Pectenol = Pectenolone (4-OH(Up) -> 4=O) CR00147 4-Hydroxyalloxanthin = 4-Ketoalloxanthin (4-OH(Up) -> 4=O) Desaturation, demethylation, and methylation (reduction from beta to phi) (1) Reaction center(s): C1,2 and C3,4 (1) CR00153 β-Carotene = β-Isorenieratene (beta' -> phi') De-epoxidation (5) Reaction center(s): C5,6 (4) CR00166 Violaxanthin + Ascorbate = Antheraxanthin + Dehydroascorbate + H2O (5',6'+H, 5',6'-Epoxy(Down) -> none) CR00167 Antheraxanthin + Ascorbate = Zeaxanthin + Dehydroascorbate + H2O (5,6+H, 5,6-Epoxy(Down) -> none) CR00169 Pyrrhoxanthinol = Hydratopyrrhoxanthinol (5,6-Epoxy(Down) -> 5-OH(Down), 6-OH(Up)) CR00170 Diadinoxanthin = Heteroxanthin (5,6-Epoxy(Down) -> 5-OH(Up), 6-OH(Down)) Reaction center(s): C5,6 and C5',6' (1) CR00454 Violaxanthin + 2 Ascorbate <=> Zeaxanthin + 2 Dehydroascorbate + 2 H2O (5,6+H, 5',6'+H, 5,6-Epoxy(Down), 5',6'-Epoxy(Down) -> none) De-epoxidation and ketolation (epsilon end forming) (2) Reaction center(s): C5,6 and C3 (2) CR00173 Fucoxanthinol = Amarouciaxanthin A (5',6'+H, 3'-OH(Up), 5',6'-Epoxy(Down), beta' -> 6'-OH(Down), 3'=O, epsilon') CR00174 Halocynthiaxanthin = Amarouciaxanthin B (5',6'+H, 3'-OH(Up), 5',6'-Epoxy(Down), beta' -> 6'-OH(Down), 3'=O, epsilon') De-epoxidation, epoxidation, and ketolation (1) Reaction center(s): C4 and C3,6 (1) CR00175 Diadinoxanthin = Cyclodiadinoxanthin (3-OH(Up), 5,6-Epoxy(Down) -> 3,6-Epoxy(Up), 5-OH(Down)) Hydroxylation (17) Reaction center(s): C3 and C3' (2) CR00177 Canthaxanthin = Astaxanthin (none -> 3-OH(Up), 3'-OH(Up)) CR00459 beta-Carotene + 4 Reduced ferredoxin + 2 H+ + 2 Oxygen = Zeaxanthin + 4 Oxidized ferredoxin + 2 H2O (none -> 3-OH(Up), 3'-OH(Up)) Reaction center(s): C19 (1) CR00180 Neoxanthin = Vaucheriaxanthin (none -> 19'-OH) Reaction center(s): C2'(Down) (1) CR00181 Caloxanthin = Nostoxanthin (none -> 2'-OH(Down)) Reaction center(s): C2(Down) (1) CR00182 Zeaxanthin = Caloxanthin (none -> 2-OH(Down)) Reaction center(s): C3 (2) CR00183 Echinenone + NADH + H+ + O2 =3-Hydroxyechinenone + NAD+ + H2O (No fingerprints are given) CR00184 3'-Hydroxyechinenone + NADH + H+ + O2 = Adonixanthin + NAD+ + H2O (none -> 3-OH(Up)) Reaction center(s): C3(Up) (2) CR00185 Canthaxanthin + NADH + H+ + O2 = Phoenicoxanthin + NAD+ + H2O (none -> 3-OH(Up)) CR00192 β-Carotene + NADH + H + O2 = β-Cryptoxanthin + NAD+ + H2O (none -> 3-OH(Up)) Reaction center(s): C3' (3) CR00186 Echinenone + NADH + H+ + O2 = 3'-Hydroxyechinenone + NAD+ + H2O (none -> 3'-OH(Up)) CR00188 Thermocryptoxanthin-13 + NADH + H+ + O2 = Thermozeaxanthin-13 + NAD+ + H2O (3-b-Glc-10-methylundecanoyl(Up) -> 3'-OH(Up), 3-b-Glc-6-O-11-methyldodecanoyl(Up)) CR00189 Thermocryptoxanthin-15 + NADH + H+ + O2 = Thermozeaxanthin-15 + NAD+ + H2O (3-b-Glc-12-methyltridecanoyl(Up) -> 3'-OH(Up), 3-b-Glc-6-O-13-methyltetradecanoyl(Up)) Reaction center(s): C3'(Up) (3) CR00187 Phoenicoxanthin + NADH + H+ + O2 = Astaxanthin + NAD+ + H2O (none -> 3'-OH(Up)) CR00190 β-Cryptoxanthin + NADH + H+ + O2 = Zeaxanthin + NAD + H2O CR00191 3-Hydroxyechinenone + NADH + H+ + O2 = Adonixanthin + NAD+ + H2O (No fingerprints are given) Reaction center(s): C4(Up) (2) CR00193 Alloxanthin = 4-Hydroxyalloxanthin (none -> 4-OH(Up)) CR00194 Diatoxanthin = Pectenol (none -> 4-OH(Up)) Ketolation (4) Reaction center(s): C3' (1) CR00466 Diatoxanthin = Pectenolone ( -> ) Reaction center(s): C4 (3) CR00234 beta-Carotene + 2 Reduced acceptor + 2 Oxygen = Echinenone + 2 Acceptor + 3 H2O (none -> 4=O) CR00236 β-Cryptoxanthin = 3-Hydroxyechinenone (none -> 4=O) CR00237 Astaxanthin = Adonixanthin (4'=O -> none) 1. Oxidoreductions of C40 beta,epsilon carotenoid (33) Cleavage and aldehyde addition (6) Reaction center(s): C15 and C11 (1) CR00054 α-carotene + O2 = (11Z)-Retinal (epsilon' -> 11Z, 15-al, 15-apo) Reaction center(s): C10 and C10' (1) CR00058 Lutein = C14 aldehyde (3-OH(Up), 3'-OH(Down), beta, epsilon' -> 10-al, 10'-al, 10-apo, 10'-apo) Reaction center(s): C15 (4) CR00060 α-Carotene + O2 = Retinal (epsilon' -> 15-al, 15-apo) CR00061 α-Carotene + O2 = (all-E)-α-retinal (beta' -> 15-apo, 15-al) CR00062 Lutein + O2 = (all-E)-3-Hydroxy-retinal (3'-OH(Down), epsilon' -> 15-al, 15-apo) CR00063 Lutein + O2 = (all-E,3R)-3-Hydroxy-α-retinal (3'-OH(Up), beta' -> 15-apo, 15-al) Cleavage and ketolation (2) Reaction center(s): C9 (1) CR00092 Lutein = 3-Hydroxy-β-Ionone Reaction center(s): C9' (1) CR00093 Lutein = 3-Hydroxy-9-apo-ε-caroten-9-one (3'-OH(Up), beta' -> 9,10+H, 9=O, 9-apo) Conversion of double bond from beta to epsilon (1) Reaction center(s): C5 (1) CR00103 3'-Oxolutein = 3'-Hydroxy-ε-caroten-3-one (3'-OH(Up), beta' -> 3'-OH, epsilon') Conversion of double bond from beta to gamma, and hydroxylation (1) Reaction center(s): C5 and C6 (1) CR00105 Lutein = Prasinoxanthin (beta -> 7,8+H, 6-OH(Up), 8=O, gamma) Conversion of double bond from epsilon to beta (3) Reaction center(s): C4 (1) CR00106 α-Carotene = β-Carotene (epsilon' -> beta') Reaction center(s): C5 (2) CR00107 3'-Epilutein = Zeaxanthin (3'=O, epsilon' -> 3'-OH(Up), beta') CR00108 Lutein = meso-Zeaxanthin (epsilon' -> beta') Desaturation (1) Reaction center(s): C19 (1) CR00112 Micromonol = Micromonal (19'-OH -> 19'-al) Desaturation (acetylene bond forming out of allene bond) (1) Reaction center(s): C6,7 and C7,8 (1) CR00140 Amarouciaxanthin A = Amarouciaxanthin B (6,7--H, 5,6+H, 5-OH(Down) -> 7,8--H) Desaturation (keton forming) (2) Reaction center(s): C3' (2) CR00148 Uriolide = 3'-Dehydrouriolide (3'-OH(Down) -> 3'=O) CR00149 Lutein = 3'-Oxolutein (3'-OH(Down) -> 3'=O) Epoxidation (2) Reaction center(s): C5,6 (2) CR00163 Deepoxyuriolide = Uriolide (none -> 5,6+H, 5,6-Epoxy(Down)) CR00164 Lutein = Lutein epoxide (none -> 5,6+H, 5,6-Epoxy(Down)) Epoxidation (lactone forming) (1) Reaction center(s): C19',11' (1) CR00165 Micromonal = Deepoxyuriolide (19'-al -> 19',11'-olide) De-epoxidation (1) Reaction center(s): C5,6 (1) CR00168 Preprasinoxanthin = Prasinoxanthin (5,6+H, 5,6-Epoxy(Down), beta -> 6-OH(Up), gamma) Hydroxylation (8) Reaction center(s): C19 (2) CR00001 Dihydrolutein = Micromonol (none -> 19'-OH) CR00195 Lutein = Loroxanthin (none -> 19-OH) Reaction center(s): C3'(Down) (3) CR00196 Crocoxanthin = Monadoxanthin (none -> 3'-OH(Down)) CR00197 Zeinoxanthin + Reduced acceptor + O2 = Lutein + Acceptor + H20 (none -> 3'-OH(Down)) CR00198 alpha-Carotene Reduced acceptor + O2 = α-Cryptoxanthin Acceptor + H20 (none -> 3'-OH(Down)) Reaction center(s): C3(Up) (2) CR00199 α-Carotene + NADH+ + H+ + O2 = Zeinoxanthin + NAD+ + H2O (none -> 3-OH(Up)) CR00200 alpha-Cryptoxanthin + NADH + H+ + O2 = Lutein + NAD+ + H2O (none -> 3-OH(Up)) Reaction center(s): C6' (1) CR00201 Siphonaxanthin decenoate = 6-Hydroxysiphonaxanthin decenoate (3-OH(Up) 3'-OH(Down) -> 3-OH(Up), 3'-OH(Down), 6'-OH) De-hydroxylation and desaturation (3) Reaction center(s): C2',3' and C3' (2) CR00228 Uriolide = Anhydrouriolide (3'=O -> 2',3'--H) CR00230 Micromonal = Anhydromicromonal (3'-OH(Down) -> 2',3'--H) Reaction center(s): C3' (1) CR00231 Lutein = Anhydrolutein (3'-OH(Down), epsilon' -> 3',4'--H, beta') De-hydroxylation, desaturation, and saturation (1) Reaction center(s): C2',3' and C19' (1) CR00232 Micromonol = Anhydromicromonol (3'-OH(Down), 19'-al -> 2',3'--H, 19'-OH) 1. Oxidoreductions of C40 beta,kappa carotenoid (3) Desaturation (acetylene bond forming out of allene bond) (1) Reaction center(s): C6,7 and C7,8 (1) CR00142 Allenicmytilloxanthin = Mytiloxanthin (5-OH(Down), 6,7--H -> 7,8--H) Desaturation (keton forming) (1) Reaction center(s): C3 (1) CR00151 Mytiloxanthin = Mytiloxanthinone (3'-OH(Up) -> 3'=O) Epoxidation (1) Reaction center(s): C5,6 (1) CR00160 Capsanthin = Capsanthin 5,6-epoxide (none -> 5,6+H, 5,6-Epoxy(Down)) 1. Oxidoreductions of C40 beta,phi carotenoid (1) Desaturation, demethylation, and methylation (reduction from beta to phi) (1) Reaction center(s): C1,2 and C3,4 (1) CR00154 β-Isorenieratene = Isorenieratene (beta -> phi) 1. Oxidoreductions of C40 epsilon,psi carotenoid (2) Cleavage and ketolation (2) Reaction center(s): C9 (1) CR00095 δ-carotene = α-Ionone (psi' -> 9,10+H, 9=O, 9-apo) Reaction center(s): C9 and C9' (1) CR00096 δ-carotene = Pseudoionone (epsilon' -> 10-apo, 9=O) 1. Oxidoreductions of C40 epsilon,epsilon carotenoid (2) Cleavage and ketolation (1) Reaction center(s): C10 and C10' (1) CR00094 Lactucaxanthin = C14-aldehyde (3-OH(Down), 3'-OH(Down), epsilon, epsilon' -> 10-al, 10'-al, 10-apo, 10'-apo) Desaturation (keton forming) (1) Reaction center(s): C3' (1) CR00150 3'-Hydroxy-ε-caroten-3-one = epsilon-caroten-3,3-dione (3'-OH -> 3'=O) 1. Oxidoreductions of C40 gamma,epsilon carotenoid (0) 1. Oxidoreductions of C45 psi,psi carotenoid (0) 1. Oxidoreductions of C46 beta,psi carotenoid (0) 1. Oxidoreductions of C50 psi,psi carotenoid (3) Desaturation (1) Reaction center(s): C3',4' (1) CR00131 Dihydromonoanhydrobacterioruberin (DH-BABR) = Bisanhydrobacterioruberin (BABR) (none -> 3',4'--H) Hydroxylation (2) Reaction center(s): C3'' (1) CR00209 Bisanhydrobacterioruberin (BABR) = Monoanhydrobacterioruberin (MABR) (2-isoprene(Down), 2'-isoprene(Down) -> 2'-isoprene, 2-isoprene-3-OH) Reaction center(s): C3''' (1) CR00210 Monoanhydrobacterioruberin (MABR) = Bacterioruberin (BR) (1,2+H, 1',2'+H, 2'-isoprene, 2-isoprene-3-OH -> 2-isoprene-3-OH(Down), 2'-isoprene-3-OH(Down)) 1. Oxidoreductions of C35 psi,psi apocarotenoid (0) 1. Oxidoreductions of C35 beta,psi apocarotenoid (0) 1. Oxidoreductions of C30 psi,psi apocarotenoid (12) Aldehyde addition (4) Reaction center(s): C4 (2) CR00005 4,4'-Diapolycopene = 4,4'-diapolycopen-4-al (none -> 4-al) CR00006 4,4'-Diaponeurosporene + Proton-donor + O2 = 4,4'-Diaponeurosporene-4-al + Oxidized-proton-donor + H2O (none -> 4-al) Reaction center(s): C4 and C4' (1) CR00007 4,4'-Diapolycopene + 4 Reduced acceptors + 4 O2 = 4,4'-Diapolycopenedial + 4 Acceptor + 6 H2O (none -> 4-al, 4'-al) Reaction center(s): C4' (1) CR00008 4,4'-diapolycopen-4-al = 4,4'-diapolycopenedial (none -> 4'-al) Desaturation (2) Reaction center(s): C11,12 (1) CR00116 4,4'-Diapophytofluene + FAD = 4,4'-Diapo-ζ-carotene + FADH2 (11,12+H -> none) Reaction center(s): C7',8' (1) CR00137 4,4'-Diaponeurosporene + FAD = 4,4'-Diapolycopene + FADH2 (7,8+H -> none) Hydroxylation (aldehyde forming) (1) Reaction center(s): C4' (1) CR00211 Diaponeurosporenal = Hydroxy-diaponeurosporenal (none -> 4'-OH) Hydroxylation (carbonyl group forming) (5) Reaction center(s): C4 (3) CR00221 4,4'-Diaponeurosporene-4-al = 4,4'-Diaponeurosporene-4-oic acid CR00222 4,4'-diapolycopenedial = 4,4'-Diapocaroten-4'-al-4-oic acid (4-al -> 4-COOH) CR00223 4,4'-Diaponeurosporene + 3 Reduced acceptor + 3 O2 = 4,4'-Diaponeurosporenic acid + 3 Acceptor + 4H2O (none -> 4-COOH) Reaction center(s): C4 and C4' (1) CR00224 4,4'-Diapolycopenedial = 4,4'-Diaplycopene-4,4'-dioic acid (4-al, 4'-al -> 4-COOH, 4'-COOH) Reaction center(s): C4' (1) CR00227 4,4'-Diapocaroten-4'-al-4-oic acid = 4,4'-Diaplycopene-4,4'-dioic acid (4'-al -> 4'-COOH) 1. Oxidoreductions of C30 psi,- apocarotenoid (2) Cleavage and aldehyde addition (2) Reaction center(s): C15' (1) CR00069 Apo-8'-lycopenol + O2 = Apo-8',15'-carotenedial (8'-OH -> 8'-al, 15'-al, 15'-apo) Reaction center(s): C8 (1) CR00070 beta-apo-8'-lycopenal + 02 = crocetindial (psi -> 8-al, 8-apo) 1. Oxidoreductions of C30 beta,- apocarotenoid (1) Cleavage and ketolation (1) Reaction center(s): C9 (1) CR00081 β-apo-8'-carotenal = β-Ionone (8'-al, 8'-apo -> 9=O, 9-apo) 1. Oxidoreductions of C27 psi,- apocarotenoid (2) Cleavage and aldehyde addition (2) Reaction center(s): C15 (2) CR00067 Apo-10'-lycopenol + O2 = Acycloretinal (10'-OH, 10'-apo -> 15-apo, 15-al) CR00068 Apo-10'-lycopenal + O2 = Acycloretinal (10'-al, 10'-apo -> 15-apo, 15-al) 1. Oxidoreductions of C27 beta,- apocarotenoid (4) Cleavage and hydroxylation (1) Reaction center(s): C15 (1) CR00078 Anhydrolutein = 3-Hydroxy-retinol (3',4'--H, beta' -> 15-OH, 15-apo) Cleavage and ketolation (2) Reaction center(s): C13 (2) CR00079 3-OH-β-apo-10'-carotenal = 3-OH-β-apo-13-carotenone (10'-al, 10'-apo -> 13=O, 13-apo) CR00080 (all-E)-10'-apo-beta-carotenal + O2 = β-apo-13-carotenone + C9-aldehyde (10'-al, 10'-apo -> 13=O, 13-apo) Cyclization (lactone forming) (1) Reaction center(s): C10 and C14 (1) CR00109 9-cis-10'-apo-β-carotenal + 2 O2 = carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal (9Z, 10'-apo, 10'-al -> 10-apo, 10-methyl-furanone-OH) 1. Oxidoreductions of C25 beta,- apocarotenoid (0) 1. Oxidoreductions of C24 -,- apocarotenoid (0) 1. Oxidoreductions of C20 psi,- apocarotenoid (0) 1. Oxidoreductions of C20 beta,- apocarotenoid (2) Cis isomeration and desaturation (1) Reaction center(s): C15 and C11 (1) CR00009 All-trans-Retinol + NAD+ + H2O = (11Z)-Retinaldehyde + NADH + H+ + O2 (15-OH -> 11Z, 15-al) Desaturation (1) Reaction center(s): C15 (1) CR00111 (11Z)-Retinol = (11Z)-Retinylaldehyde 1. Oxidoreductions of C20 -,- apocarotenoid (0) 1. Oxidoreductions of C19 beta,- apocarotenoid (1) Cyclization (lactone forming) (1) Reaction center(s): (1) CR00110 Carlactone = Strigol (No fingerprints are given) 1. Oxidoreductions of C15 epsilon,- apocarotenoid (0) 1. Oxidoreductions of C15 beta,- apocarotenoid (0) 1. Oxidoreductions of C14 -,- apocarotenoid (0) 1. Oxidoreductions of C37 beta,beta norcarotenoid (0) 1. Oxidoreductions of C39 beta,beta norcarotenoid (0) 2. Transfer reactions of C40 psi,psi intermediate carotenoid (0) 2. Transfer reactions of C40 psi,psi carotenoid (0) 2. Transfer reactions of C40 beta,psi carotenoid (0) 2. Transfer reactions of C40 beta,beta carotenoid (0) 2. Transfer reactions of C40 phi,psi carotenoid (0) 2. Transfer reactions of C40 beta,epsilon carotenoid (0) 2. Transfer reactions of C45 psi,psi carotenoid (0) 2. Transfer reactions of C50 gamma,gamma carotenoid (0) 2. Transfer reactions of C39 beta,beta norcarotenoid (0) 2. Transfer reactions of C37 beta,beta norcarotenoid (0) 2. Transfer reactions of C30 psi,psi apocarotenoid (0) 2. Transfer reactions of C24 -,- apocarotenoid (0) 2. Transfer reactions of C20 beta,- apocarotenoid (0) 2. Transfer reactions of C20 -,- apocarotenoid (0) 2. Transfer reactions of C19 beta,- apocarotenoid (0) 2. Transfer reactions of C15 epsilon,- apocarotenoid (0) 2. Transfer reactions of C13 epsilon,- apocarotenoid (0) 2. Transfer reactions of C10 beta,- apocarotenoid (0) 3. Hydrations of C36 beta,- apocarotenoid (0) 3. Hydrations of C21 epsilon,- apocarotenoid (0) 3. Hydrations of C20 beta,- apocarotenoid (0) 3. Hydrations of C16 beta,- apocarotenoid (0) 4. Lyase reactions of C40 psi,psi carotenoid (1) 4. Lyase reactions of C40 psi,psi carotenoid - potentially defined (0) 4. Lyase reactions of C40 beta,beta carotenoid - potentially defined (0) 4. Lyase reactions of C40 beta,psi carotenoid (0) 4. Lyase reactions of C40 phi,psi carotenoid (0) 4. Lyase reactions of C50 psi,psi carotenoid (0) 5. Isomerizations of C40 psi,psi carotenoid (0) 5. Isomerizations of C40 beta,psi carotenoid (0) 5. Isomerizations of C40 epsilon,psi carotenoid (0) 5. Isomerizations of C40 beta,kappa carotenoid (0) 5. Isomerizations of C40 beta,beta carotenoid (0) 5. Isomerizations - potentially defined of C40 beta,beta carotenoid (0) 5. Isomerizations of C50 psi,psi carotenoid (0) 5. Isomerizations of C35 psi,psi apocarotenoid (0) 5. Isomerizations of C19 beta,- apocarotenoid (0) 5. Isomerizations of C15 epsilon,- apocarotenoid (0) Photoisomerization of C20 beta,- apocarotenoid (0) Dark reaction of C20 beta,- apocarotenoid (0) Heatisomerization of C40 beta,beta carotenoid (0) Aldol condensation of C30 beta,- apocarotenoid (0) |
Since June 15th, 2015 by Junko Yabuzaki. |