Information on EC 1.14.16.4 - tryptophan 5-monooxygenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.16.4
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RECOMMENDED NAME
GeneOntology No.
tryptophan 5-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-tryptophan + tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
serotonin and melatonin biosynthesis
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Tryptophan metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
L-tryptophan,tetrahydrobiopterin:oxygen oxidoreductase (5-hydroxylating)
The active centre contains mononuclear iron(II). The enzyme is activated by phosphorylation, catalysed by a Ca2+-activated protein kinase. The 4a-hydroxytetrahydrobiopterin formed can dehydrate to 6,7-dihydrobiopterin, both spontaneously and by the action of EC 4.2.1.96, 4a-hydroxytetrahydrobiopterin dehydratase. The 6,7-dihydrobiopterin can be enzymically reduced back to tetrahydrobiopterin, by EC 1.5.1.34 (6,7-dihydropteridine reductase), or slowly rearranges into the more stable compound 7,8-dihydrobiopterin.
CAS REGISTRY NUMBER
COMMENTARY hide
9037-21-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
bat
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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1387186 A+, 1517939 A+, 1759369 A+, 1838840 A+, 1838894 A+, 1838917 A+, 1838918 A+, 1838933 A+, 1839004 A+, 1839292 A+, 1839337 A+, 1839362 A+, 1839369 A+, 1839370 A+, 2736380 A+, 2874318 A+, 2874421 A+, 2874496 A+, 2874558 A+, 2874585 A+, 2874607 A+, 2874617 A+, 2874678 A+, 2874682 A+, 2874684 A+, 2874697 A+, 1042936 A++, 1071741 A++, 1071762 A++, 1071770 A++, 1071774 A++, 1071874 A++, 1071875 A++, 1071881 A++, 1071883 A++, 1071887 A++, 1071892 A++, 1071920 A++, 1071921 A++, 1071925 A++, 1071927 A++, 1071972 A++, 1071992 A++, 1072047 A++, 1326258 A++, 1331634 A++, 1332139 A++, 1332241 A++, 1374595 A++, 1613802 A++, 1614278 A++, 1759490 A++, 1759955 A++, 1760592 A++, 1803639 A++, 1838839 A++, 1838899 A++, 1838937 A++, 1838940 A++, 1838958 A++, 1838998 A++, 1839005 A++, 1839010 A++, 1839012 A++, 1839016 A++, 1839017 A++, 1839027 A++, 1839067 A++, 1839091 A++, 1839127 A++, 1839136 A++, 1839173 A++, 1839183 A++, 1839298 A++, 1839315 A++, 2281425 A++, 2281452 A++, 2281453 A++, 2281456 A++, 2281462 A++, 2281521 A++, 2545453 A++, 2697867 A++, 2809186 A++, 2874311 A++, 2874312 A++, 2874329 A++, 2874359 A++, 2874376 A++, 2874393 A++, 2874394 A++, 2874400 A++, 2874412 A++, 2874427 A++, 2874429 A++, 2874495 A++, 2874511 A++, 2874519 A++, 2874546 A++, 2874649 A++, 657881 A++, 689230 A++, 1071763 A++, 1071769 A++, 1071853 A++, 1760352 A++, 1760457 A++, 1838857 A++, 1838932 A++, 1838994 A++, 1839062 A++, 1839142 A++, 2281438 A++, 2281448 A++, 2281451 A++, 2874345 A++, 2874406 A++, 2874490 A++
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
Mus musculus C57BL/6
C57/BL6 mice
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Manually annotated by BRENDA team
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1071981 A+, 1071995 A+, 1072000 A+, 1072007 A+, 1072012 A+, 1072015 A+, 1072016 A+, 1072027 A+, 1072033 A+, 1072035 A+, 1072043 A+, 1072045 A+, 1072052 A+, 1113264 A+, 1284452 A+, 1613963 A+, 1761105 A+, 1761235 A+, 1838850 A+, 1838882 A+, 1838935 A+, 1838949 A+, 1838954 A+, 1839032 A+, 1839054 A+, 1839063 A+, 1839075 A+, 1839082 A+, 1839106 A+, 1839112 A+, 1839118 A+, 1839123 A+, 1839126 A+, 1839143 A+, 1839153 A+, 1839170 A+, 1839181 A+, 1839193 A+, 1839210 A+, 1839211 A+, 1839222 A+, 1839225 A+, 1839232 A+, 1839233 A+, 1839240 A+, 1839243 A+, 1839244 A+, 1839257 A+, 1839258 A+, 1839260 A+, 1839266 A+, 1839273 A+, 1839275 A+, 1839284 A+, 1839286 A+, 1839301 A+, 1839305 A+, 1839306 A+, 1839308 A+, 1839310 A+, 1839313 A+, 1839332 A+, 1839333 A+, 1839337 A+, 1839345 A+, 1839353 A+, 1839357 A+, 1839358 A+, 1839368 A+, 2281557 A+, 2281602 A+, 2325059 A+, 2326298 A+, 2468650 A+, 2771127 A+, 2775897 A+, 2811030 A+, 2811263 A+, 2874498 A+, 2874526 A+, 2874535 A+, 2874561 A+, 2874564 A+, 2874576 A+, 2874590 A+, 2874592 A+, 2874621 A+, 2874626 A+, 2874633 A+, 2874642 A+, 2874652 A+, 2874655 A+, 2874663 A+, 2874668 A+, 2874680 A+, 2874683 A+, 2874696 A+, 675539 A+, 684359 A+, 684813 A+, 688503 A+, 1043258 A++, 1071789 A++, 1071944 A++, 1071948 A++, 1071953 A++, 1071954 A++, 1071955 A++, 1071963 A++, 1072049 A++, 1072059 A++, 1326258 A++, 1331575 A++, 1613802 A++, 1759438 A++, 1759440 A++, 1760592 A++, 1838874 A++, 1838876 A++, 1838885 A++, 1838998 A++, 1839037 A++, 1839052 A++, 1839098 A++, 1839120 A++, 1839135 A++, 1839196 A++, 1839252 A++, 1839298 A++, 1839328 A++, 2246362 A++, 2281404 A++, 2281407 A++, 2281408 A++, 2281438 A++, 2281439 A++, 2281525 A++, 2697867 A++, 2874405 A++, 2874457 A++, 2874464 A++, 2874483 A++, 2874586 A++, 2874677 A++, 438678 A++, 657881 A++, 660505 A++, 675511 A++, 676184 A++, 715980 A++, 1043697 A++, 1071768 A++, 1071785 A++, 1071839 A++, 1071881 A++, 1071900 A++, 1071958 A++, 1072031 A++, 1298621 A++, 1331516 A++, 1760977 A++, 1768235 A++, 1838837 A++, 1838848 A++, 1838860 A++, 1838897 A++, 1838906 A++, 1838932 A++, 1838950 A++, 1838959 A++, 1838964 A++, 1839008 A++, 1839022 A++, 1839044 A++, 1839055 A++, 1839067 A++, 1839091 A++, 1839136 A++, 1839174 A++, 1839302 A++, 1839304 A++, 2281461 A++, 2281530 A++, 2281555 A++, 2749810 A++, 2874317 A++, 2874454 A++, 2874468 A++, 2874477 A++, 2874492 A++, 2874522 A++, 2874594 A++, 2874606 A++, 2874618 A++, 2874624 A++, 2874638 A++, 2874658 A++, 2874676 A++, 688946 A++, 689087 A++, 702962 A++, 1072011 A+++, 1072028 A+++, 1072030 A+++, 1072036 A+++, 1072054 A+++, 1071834 A++++, 1071852 A++++, 1071856 A++++
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Automatic Mining of ENzyme DAta
no activity in Rattus norvegicus
PC-12 cells
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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1031627 A+, 1042966 A+, 1044289 A+, 1071790 A+, 1071794 A+, 1071795 A+, 1071800 A+, 1071811 A+, 1071812 A+, 1071814 A+, 1071816 A+, 1071817 A+, 1071818 A+, 1071820 A+, 1071821 A+, 1071822 A+, 1071823 A+, 1071824 A+, 1071940 A+, 1071959 A+, 1071971 A+, 1072004 A+, 1072010 A+, 1072019 A+, 1072022 A+, 1072041 A+, 1072044 A+, 1072050 A+, 1072051 A+, 1207123 A+, 1326165 A+, 1328188 A+, 1331737 A+, 1332268 A+, 1340170 A+, 1455623 A+, 1759369 A+, 1759387 A+, 1759679 A+, 1759800 A+, 1761004 A+, 1761205 A+, 1768236 A+, 1838658 A+, 1838838 A+, 1838840 A+, 1838842 A+, 1838843 A+, 1838844 A+, 1838864 A+, 1838865 A+, 1838870 A+, 1838881 A+, 1838887 A+, 1838889 A+, 1838890 A+, 1838895 A+, 1838902 A+, 1838908 A+, 1838916 A+, 1838924 A+, 1838933 A+, 1838963 A+, 1838967 A+, 1838974 A+, 1838996 A+, 1839001 A+, 1839006 A+, 1839007 A+, 1839013 A+, 1839025 A+, 1839058 A+, 1839064 A+, 1839138 A+, 1839150 A+, 1839152 A+, 1839171 A+, 1839172 A+, 1839190 A+, 1839191 A+, 1839195 A+, 1839226 A+, 1839235 A+, 1839238 A+, 1839251 A+, 1839265 A+, 1839271 A+, 1839282 A+, 1839284 A+, 1839292 A+, 1839294 A+, 1839309 A+, 1839316 A+, 1839321 A+, 1839338 A+, 1839347 A+, 1839356 A+, 1839362 A+, 1839364 A+, 1839369 A+, 2281576 A+, 2281577 A+, 2281590 A+, 2282079 A+, 2454712 A+, 2466303 A+, 2507102 A+, 2516250 A+, 2600112 A+, 2765984 A+, 2808992 A+, 2810695 A+, 2811240 A+, 2874315 A+, 2874320 A+, 2874334 A+, 2874336 A+, 2874337 A+, 2874346 A+, 2874347 A+, 2874349 A+, 2874350 A+, 2874354 A+, 2874399 A+, 2874425 A+, 2874469 A+, 2874472 A+, 2874496 A+, 2874508 A+, 2874549 A+, 2874555 A+, 2874559 A+, 2874585 A+, 2874607 A+, 2874610 A+, 2874630 A+, 2874634 A+, 2874688 A+, 2874692 A+, 686410 A+, 688062 A+, 781749 A+, 962019 A+, 987203 A+, 1041675 A++, 1071709 A++, 1071710 A++, 1071712 A++, 1071713 A++, 1071715 A++, 1071717 A++, 1071718 A++, 1071720 A++, 1071721 A++, 1071724 A++, 1071725 A++, 1071726 A++, 1071727 A++, 1071728 A++, 1071729 A++, 1071731 A++, 1071734 A++, 1071735 A++, 1071737 A++, 1071738 A++, 1071739 A++, 1071744 A++, 1071748 A++, 1071749 A++, 1071754 A++, 1071763 A++, 1071767 A++, 1071773 A++, 1071774 A++, 1071778 A++, 1071780 A++, 1071781 A++, 1071784 A++, 1071786 A++, 1071791 A++, 1071792 A++, 1071796 A++, 1071797 A++, 1071802 A++, 1071803 A++, 1071804 A++, 1071806 A++, 1071807 A++, 1071808 A++, 1071809 A++, 1071831 A++, 1071832 A++, 1071835 A++, 1071837 A++, 1071841 A++, 1071846 A++, 1071850 A++, 1071853 A++, 1071860 A++, 1071861 A++, 1071867 A++, 1071871 A++, 1071874 A++, 1071886 A++, 1071888 A++, 1071893 A++, 1071894 A++, 1071899 A++, 1071902 A++, 1071911 A++, 1071912 A++, 1071914 A++, 1071915 A++, 1071924 A++, 1071925 A++, 1071927 A++, 1071930 A++, 1071931 A++, 1071933 A++, 1071935 A++, 1071936 A++, 1071937 A++, 1071943 A++, 1071945 A++, 1071946 A++, 1071949 A++, 1071950 A++, 1071957 A++, 1071962 A++, 1071972 A++, 1073186 A++, 1129707 A++, 1331520 A++, 1331719 A++, 1331883 A++, 1332075 A++, 1584880 A++, 1759490 A++, 1759505 A++, 1759551 A++, 1768243 A++, 1798913 A++, 1837938 A++, 1838851 A++, 1838855 A++, 1838857 A++, 1838874 A++, 1838899 A++, 1838900 A++, 1838904 A++, 1838931 A++, 1838932 A++, 1838937 A++, 1838945 A++, 1838952 A++, 1838966 A++, 1838970 A++, 1838976 A++, 1838977 A++, 1838979 A++, 1838982 A++, 1838991 A++, 1838993 A++, 1839005 A++, 1839014 A++, 1839017 A++, 1839027 A++, 1839038 A++, 1839056 A++, 1839080 A++, 1839096 A++, 1839141 A++, 2127967 A++, 2222740 A++, 2281405 A++, 2281409 A++, 2281413 A++, 2281414 A++, 2281416 A++, 2281418 A++, 2281420 A++, 2281423 A++, 2281424 A++, 2281427 A++, 2281428 A++, 2281430 A++, 2281431 A++, 2281432 A++, 2281434 A++, 2281436 A++, 2281437 A++, 2281440 A++, 2281442 A++, 2281443 A++, 2281445 A++, 2281450 A++, 2281451 A++, 2281454 A++, 2281456 A++, 2281460 A++, 2281464 A++, 2281471 A++, 2281474 A++, 2281481 A++, 2281494 A++, 2281507 A++, 2281511 A++, 2464929 A++, 2468058 A++, 2468375 A++, 2468480 A++, 2468500 A++, 2470379 A++, 2874317 A++, 2874339 A++, 2874340 A++, 2874358 A++, 2874366 A++, 2874368 A++, 2874376 A++, 2874384 A++, 2874391 A++, 2874413 A++, 2874424 A++, 2874427 A++, 2874442 A++, 2874454 A++, 2874478 A++, 2874482 A++, 2874495 A++, 2874525 A++, 2874528 A++, 438656 A++, 438659 A++, 438663 A++, 438671 A++, 657701 A++, 660038 A++, 676184 A++, 688765 A++, 689230 A++, 1071836 A++, 1071901 A++, 1129785 A++, 1147281 A++, 1249937 A++, 1327020 A++, 1327197 A++, 1327485 A++, 1331522 A++, 1331571 A++, 1331572 A++, 1331634 A++, 1331787 A++, 1331856 A++, 1340360 A++, 1374595 A++, 1585334 A++, 1614278 A++, 1744638 A++, 1759500 A++, 1759969 A++, 1760352 A++, 1760429 A++, 1760592 A++, 1760962 A++, 1803639 A++, 1837967 A++, 1838833 A++, 1838839 A++, 1838841 A++, 1838847 A++, 1838852 A++, 1838854 A++, 1838861 A++, 1838866 A++, 1838867 A++, 1838871 A++, 1838873 A++, 1838875 A++, 1838877 A++, 1838888 A++, 1838893 A++, 1838901 A++, 1838907 A++, 1838909 A++, 1838910 A++, 1838911 A++, 1838919 A++, 1838920 A++, 1838922 A++, 1838925 A++, 1838934 A++, 1838943 A++, 1838944 A++, 1838946 A++, 1838958 A++, 1838961 A++, 1838962 A++, 1838973 A++, 1838987 A++, 1838990 A++, 1838998 A++, 1839034 A++, 1839035 A++, 1839037 A++, 1839043 A++, 1839059 A++, 1839062 A++, 1839078 A++, 1839084 A++, 1839089 A++, 1839095 A++, 1839107 A++, 1839108 A++, 1839127 A++, 1839134 A++, 1839140 A++, 1839162 A++, 1839163 A++, 1839182 A++, 1839183 A++, 1839208 A++, 1839221 A++, 1839315 A++, 2144061 A++, 2264471 A++, 2281406 A++, 2281408 A++, 2281410 A++, 2281412 A++, 2281417 A++, 2281425 A++, 2281426 A++, 2281429 A++, 2281433 A++, 2281441 A++, 2281444 A++, 2281446 A++, 2281447 A++, 2281449 A++, 2281452 A++, 2281455 A++, 2281458 A++, 2281463 A++, 2281466 A++, 2281489 A++, 2281490 A++, 2281505 A++, 2281509 A++, 2281510 A++, 2281547 A++, 2281604 A++, 2281609 A++, 2281611 A++, 2282381 A++, 2464603 A++, 2468416 A++, 2504010 A++, 2644084 A++, 2809438 A++, 2810814 A++, 2810822 A++, 2814372 A++, 2860073 A++, 2874312 A++, 2874314 A++, 2874319 A++, 2874325 A++, 2874327 A++, 2874331 A++, 2874333 A++, 2874335 A++, 2874341 A++, 2874345 A++, 2874355 A++, 2874361 A++, 2874364 A++, 2874371 A++, 2874374 A++, 2874375 A++, 2874387 A++, 2874393 A++, 2874396 A++, 2874398 A++, 2874400 A++, 2874407 A++, 2874408 A++, 2874410 A++, 2874411 A++, 2874412 A++, 2874417 A++, 2874418 A++, 2874429 A++, 2874434 A++, 2874439 A++, 2874449 A++, 2874461 A++, 2874477 A++, 2874510 A++, 2874511 A++, 2874523 A++, 2874539 A++, 2874649 A++, 438661 A++, 438670 A++, 5934 A++, 657881 A++, 685470 A++, 687604 A++, 688507 A++, 689991 A++, 781599 A++, 1071855 A+++, 1071980 A+++, 1071983 A+++, 1071984 A+++, 1071986 A+++, 1071989 A+++, 1071997 A+++, 1071998 A+++, 1071999 A+++, 1072003 A+++, 1072026 A+++, 1072037 A+++, 1072040 A+++, 1072053 A+++, 1072055 A+++, 689232 A+++, 1071722 A++++, 1071730 A++++, 1071733 A++++, 1071741 A++++, 1071742 A++++, 1071743 A++++, 1071747 A++++, 1071750 A++++, 1071755 A++++, 1071756 A++++, 1071757 A++++, 1071758 A++++, 1071759 A++++, 1071762 A++++, 1071764 A++++, 1071765 A++++, 1071766 A++++, 1071769 A++++, 1071770 A++++, 1071771 A++++, 1071772 A++++, 1071777 A++++, 1071779 A++++, 1071782 A++++, 1071783 A++++, 1071826 A++++, 1071833 A++++, 1071838 A++++, 1071842 A++++, 1071844 A++++, 1071845 A++++, 1071847 A++++, 1071849 A++++, 1071851 A++++, 1071857 A++++, 1071858 A++++, 1071859 A++++, 1071866 A++++, 1071869 A++++, 1071872 A++++, 1071875 A++++, 1071876 A++++, 1071877 A++++, 1071880 A++++, 1071882 A++++, 1071884 A++++, 1071885 A++++, 1071889 A++++, 1071890 A++++, 1071891 A++++, 1071892 A++++, 1071897 A++++, 1071905 A++++, 1071916 A++++, 1071934 A++++, 1071939 A++++, 1071942 A++++, 1071947 A++++, 1071966 A++++, 1071978 A++++, 1071992 A++++, 1071993 A++++, 438662 A++++, 438667 A++++, 781825 A++++
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Automatic Mining of ENzyme DAta
squirrel
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Automatic Mining of ENzyme DAta
synthetic construct
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
toad
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Automatic Mining of ENzyme DAta
trout
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
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rate-limiting enzyme in the serotonin biosynthesis
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-azaisotryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-2-azaisotryptophan + 6-hydroxy-2-azaisotryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
4-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-4-azatryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
4-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-4-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
5-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxymethyltryptophan + 5-hydroxy-4-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
more than 99% 5-hydroxymethyltryptophan
?
6-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-6-azatryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
6-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-6-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
7-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-7-azatryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
7-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-7-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
L-methionine + ? + O2
?
show the reaction diagram
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relative high activity with pronase-treated PTMO
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?
L-phenylalanine + tetrahydropteridine + O2
L-tyrosine + dihydropteridine + H2O
show the reaction diagram
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purified PTMO shows no activity, relative high activity with pronase-treated PTMO
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?
L-phenylalanine + tetrahydropteridine + O2
tyrosine + dihydropteridine + H2O
show the reaction diagram
L-tryptophan + (6R)-L-erytho-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + ?
show the reaction diagram
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan
show the reaction diagram
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-
-
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?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + 6-methyl-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 6-methyl-4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + 6-methyl-tetrahydropterin + O2
5-hydroxy-L-tryptophan + 6-methyl-4a-hydroxytetrahydropterin
show the reaction diagram
L-tryptophan + tetrahydrobiopterin
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
show the reaction diagram
L-tyrosine + tetrahydropteridine + O2
?
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
tetrahydrobiopterin
additional information
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residue Y235 is involved in cofactor binding, residue is different from L-phenylalanine 4-hydroxylase
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(6R)-5,6,7,8-tetrahydrobiopterin
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(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
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TPH2, substrate inhibition
(7R)-5,6,7,8-tetrahydrobiopterin
-
recombinant pinal enzyme, 2.1 mM, 50% inhibition
1,10-phenanthroline
2,2'-dipyridyl
-
-
3,4-dihydroxyphenylalanine
-
-
3,4-Dihydroxyphenylethylamine
-
-
3,4-Dihydroxystyrene
-
-
3,4-methylenedioxymethamphetamine
-
inactivation of the enzyme
3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
-
-
3-amino-3-[4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenyl]propanoic acid
-
-
3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
-
-
3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
-
-
3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
-
-
4-(4-amino-6-[methyl[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
-
-
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-2-fluorophenylalanine
-
-
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-a-methylphenylalanine
-
-
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
4-(4-amino-6-[[(1S)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
-
-
4-(4-amino-6-[[(4'-methylbiphenyl-4-yl)methyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
-
-
4-(4-amino-6-[[4-(trifluoromethyl)benzyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(1-hydroxynaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(2'-methylbiphenyl-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(9-ethyl-9H-carbazol-3-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[3-(cyclopentyloxy)-4-methoxybenzyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-chloro-L-phenylalanine
4-Chlorophenylalanine
4-ethynylphenylalanine
-
-
4-Fluorotryptophan
-
-
4-[4-(methylamino)-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-(1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-(2,2,2-trifluoro-1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
4-[4-amino-6-(2,2,2-trifluoro-1-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]ethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-(benzylamino)-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-([[4'-(trifluoromethyl)biphenyl-4-yl]methyl]amino)-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(1-biphenyl-4-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(1-methyl-1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(1-naphthalen-2-ylpropyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(1-tricyclo[3.3.1.1(3,7)]dec-1-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(2,2,2-trifluoro-1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(2-methyl-1-naphthalen-2-ylpropyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(3,4-dimethylbenzyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(3-methyl-1-naphthalen-2-ylbutyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(4-phenoxybenzyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(biphenyl-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(biphenyl-3-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(biphenyl-4-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(cyclohexylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(naphthalen-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[2,2,2-trifluoro-1-(2-furan-2-ylphenyl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[2,2,2-trifluoro-1-(5-furan-2-ylthiophen-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-morpholin-4-yl-6-[(naphthalen-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-[(1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[5-[(3,4-dimethoxybenzyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(4-cyanobenzyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(biphenyl-4-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(cyclohexylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(furan-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(quinolin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
5-Fluorotryptophan
-
-
5-hydroxytryptophan
6-Fluorotryptophan
8-hydroxyquinoline
-
-
Aroclor 1254
-
-
citalopram
selective serotonin reuptake inhibitors, like citalopram, exert their activity enhancing the general serotonergic tone, citalopram is the most selective one with little or no affinity for a variety of receptor types, association between gene TPH1 A218C polymorphism and citalopram antidepressant response in a Korean population, overview
Co2+
-
80% inhibition at 0.1 mM
CoCl2
-
1 mM, complete inhibition
D,L-4-chlorophenylalanine
D-Dopa
-
noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
desferrioxamine
-
0.010 mM or higher, irreversible loss of activity
dithiothreitol
-
-
dopamine
H2O2
-
complete dependence on catalase in the absence of a mercaptan
Iron chelators
-
L-4-chlorophenylalanine
-
-
L-5-hydroxytryptophan
-
-
L-Dopa
-
noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
L-erythro-7,8-dihydrobiopterin
-
recombinant N-terminal truncated enzyme, competitive vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
L-p-Chlorophenylalanine
-
-
L-phenylalanine
L-tryptophan
L-tyrosine
-
noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
LP-533401
-
-
LP-615819
-
-
Mn2+
-
50% inhibition at 0.01 mM
nifedipine
-
reduces the enzyme activity by blocking the Ca2+-influx accompanied with a reduction of 5-hydroxytryptophan, serotonin, N-acetylserotonin and melatonin intracellular content, as well as a reduction of serotonin and melatonin secretion
phenylalanine
-
-
serotonin
-
1 mM, 7.5% inhibition, 10 mM, 70% inhibition
tryptophan
-
substrate inhibition of the catalytic domain of TPH1
ZnSO4
-
1 mM, 80% inhibition
additional information
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