Information on EC 1.1.1.146 - 11beta-hydroxysteroid dehydrogenase

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

EC NUMBER
COMMENTARY hide
1.1.1.146
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RECOMMENDED NAME
GeneOntology No.
11beta-hydroxysteroid dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an 11beta-hydroxysteroid + NADP+ = an 11-oxosteroid + NADPH + H+
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
Steroid hormone biosynthesis
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Metabolism of xenobiotics by cytochrome P450
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
11beta-hydroxysteroid:NADP+ 11-oxidoreductase
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CAS REGISTRY NUMBER
COMMENTARY hide
9041-46-7
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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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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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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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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
dogfish
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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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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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1157078 A+, 1333796 A+, 1361204 A+, 1415136 A+, 1475225 A+, 1677930 A+, 1682823 A+, 1682901 A+, 1682937 A+, 1683019 A+, 1683068 A+, 2238601 A+, 2238633 A+, 2238639 A+, 2330074 A+, 2345348 A+, 2749648 A+, 2749649 A+, 2749688 A+, 686414 A+, 697563 A+, 736561 A+, 910168 A+, 990385 A+, 990428 A+, 990488 A+, 1157074 A++, 1157075 A++, 1157076 A++, 1157077 A++, 1333129 A++, 1333356 A++, 1682953 A++, 1682975 A++, 1682977 A++, 1682989 A++, 1682997 A++, 1683009 A++, 1683028 A++, 1683035 A++, 1683050 A++, 1683055 A++, 1683077 A++, 1683086 A++, 2238505 A++, 2238522 A++, 2238544 A++, 2238547 A++, 2238552 A++, 2238562 A++, 2238566 A++, 2238568 A++, 2238579 A++, 2238580 A++, 2238581 A++, 2238593 A++, 2238602 A++, 2238603 A++, 2238624 A++, 2238637 A++, 2238647 A++, 2749510 A++, 2749513 A++, 2749530 A++, 2749537 A++, 2749554 A++, 2749564 A++, 2749571 A++, 2749572 A++, 2749598 A++, 654196 A++, 669730 A++, 687317 A++, 690705 A++, 693002 A++, 990158 A++, 990177 A++, 990226 A++, 990259 A++, 990280 A++, 990284 A++, 990307 A++, 990340 A++, 990349 A++, 990360 A++, 990387 A++, 990403 A++, 990449 A++, 990478 A++, 990481 A++, 1241963 A++, 1241979 A++, 1333310 A++, 1614246 A++, 1682956 A++, 1682960 A++, 1683011 A++, 1683076 A++, 1683091 A++, 1683142 A++, 1683154 A++, 2238507 A++, 2238526 A++, 2238543 A++, 2238567 A++, 2238608 A++, 2238619 A++, 2238665 A++, 2468926 A++, 2667481 A++, 2749526 A++, 2749551 A++, 2749602 A++, 2749681 A++, 699469 A++, 712702 A++, 990337 A++, 990405 A++, 990482 A++, 711387 A+++, 711632 A+++, 782802 A+++, 990424 A+++, 990430 A+++, 990486 A+++, 693544 A++++, 990211 A++++, 990265 A++++, 990282 A++++, 990308 A++++, 990347 A++++, 990373 A++++, 990402 A++++, 990427 A++++, 990473 A++++
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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
no activity in frog
no activity for the oxidative direction in frog, toad, mud, puppy, shark and bird livers
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Manually annotated by BRENDA team
no activity in Necturus maculosus
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Manually annotated by BRENDA team
no activity in shark
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Manually annotated by BRENDA team
no activity in toad
no activity for the oxidative direction in frog, toad, mud, puppy, shark and bird livers
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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
plant
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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1001107 A+, 1241996 A+, 1251136 A+, 1562303 A+, 1647684 A+, 1678405 A+, 1682813 A+, 1682817 A+, 1682829 A+, 1682837 A+, 1682841 A+, 1682851 A+, 1682853 A+, 1682854 A+, 1682860 A+, 1682866 A+, 1682867 A+, 1682868 A+, 1682876 A+, 1682879 A+, 1682885 A+, 1682888 A+, 1682889 A+, 1682895 A+, 1682917 A+, 1682941 A+, 1682974 A+, 1682979 A+, 1682998 A+, 1683023 A+, 1683040 A+, 1683042 A+, 1683092 A+, 1683099 A+, 1683110 A+, 1683112 A+, 1683149 A+, 1683160 A+, 1683163 A+, 1683165 A+, 1683167 A+, 2238465 A+, 2238631 A+, 2238634 A+, 2238659 A+, 2384505 A+, 2487934 A+, 2538277 A+, 2745801 A+, 2749411 A+, 2749461 A+, 2749467 A+, 2749484 A+, 2749525 A+, 2749563 A+, 2749662 A+, 2749677 A+, 2749687 A+, 389380 A+, 655347 A+, 697286 A+, 711907 A+, 712594 A+, 938222 A+, 988242 A+, 990070 A+, 990074 A+, 990085 A+, 990100 A+, 990102 A+, 990103 A+, 990104 A+, 990105 A+, 990108 A+, 990110 A+, 990118 A+, 990120 A+, 990121 A+, 990122 A+, 990123 A+, 990124 A+, 990125 A+, 990127 A+, 990128 A+, 990131 A+, 990138 A+, 990144 A+, 990150 A+, 990341 A+, 990342 A+, 990442 A+, 990445 A+, 990456 A+, 990457 A+, 990479 A+, 990487 A+, 990491 A+, 990492 A+, 990497 A+, 990498 A+, 990499 A+, 991087 A+, 1241819 A++, 1241916 A++, 1241922 A++, 1241924 A++, 1241965 A++, 1241988 A++, 1293696 A++, 1333319 A++, 1348818 A++, 1468717 A++, 1560016 A++, 1582302 A++, 1582801 A++, 1654378 A++, 1656862 A++, 1657590 A++, 1662404 A++, 1677790 A++, 1682847 A++, 1682916 A++, 1682930 A++, 1682934 A++, 1682946 A++, 1682958 A++, 1682968 A++, 1682970 A++, 1682992 A++, 1683002 A++, 1683012 A++, 1683014 A++, 1683027 A++, 1683032 A++, 1683036 A++, 1683069 A++, 1683079 A++, 1683115 A++, 1683144 A++, 1683152 A++, 2158847 A++, 2238477 A++, 2238480 A++, 2238489 A++, 2238490 A++, 2238492 A++, 2238494 A++, 2238495 A++, 2238499 A++, 2238502 A++, 2238504 A++, 2238535 A++, 2238542 A++, 2238550 A++, 2238557 A++, 2238561 A++, 2238606 A++, 2238620 A++, 2238621 A++, 2238638 A++, 2238665 A++, 2401747 A++, 2401749 A++, 2401766 A++, 2411987 A++, 2657609 A++, 2657940 A++, 2658275 A++, 2745749 A++, 2749478 A++, 2749482 A++, 2749487 A++, 2749491 A++, 2749492 A++, 2749512 A++, 2749524 A++, 2749555 A++, 2749557 A++, 2749565 A++, 2749600 A++, 2749607 A++, 2749618 A++, 2749620 A++, 2749623 A++, 2749625 A++, 285961 A++, 669504 A++, 670263 A++, 688225 A++, 692078 A++, 693880 A++, 695089 A++, 990149 A++, 990214 A++, 990244 A++, 990261 A++, 990304 A++, 990318 A++, 990371 A++, 1241820 A++, 1241854 A++, 1562379 A++, 1682848 A++, 1682897 A++, 1682913 A++, 1682922 A++, 1682939 A++, 1682944 A++, 1682945 A++, 1682955 A++, 1682982 A++, 1682988 A++, 1682991 A++, 1682997 A++, 1683035 A++, 1683039 A++, 1683052 A++, 1683058 A++, 1683088 A++, 1683120 A++, 2163424 A++, 2238487 A++, 2238488 A++, 2238511 A++, 2238512 A++, 2238515 A++, 2238516 A++, 2238518 A++, 2238523 A++, 2238530 A++, 2238536 A++, 2238539 A++, 2238547 A++, 2238555 A++, 2238570 A++, 2238571 A++, 2238594 A++, 2238595 A++, 2238645 A++, 2238652 A++, 2279122 A++, 2328550 A++, 2401667 A++, 2401762 A++, 2401765 A++, 2567819 A++, 2747706 A++, 2749462 A++, 2749486 A++, 2749489 A++, 2749496 A++, 2749516 A++, 2749558 A++, 2749560 A++, 2749624 A++, 654171 A++, 655349 A++, 657253 A++, 667148 A++, 669907 A++, 670261 A++, 687317 A++, 693785 A++, 695409 A++, 697625 A++, 782567 A++, 990002 A++, 990094 A++, 990154 A++, 990157 A++, 990165 A++, 990175 A++, 990179 A++, 990183 A++, 990184 A++, 990201 A++, 990204 A++, 990217 A++, 990220 A++, 990227 A++, 990228 A++, 990231 A++, 990234 A++, 990236 A++, 990238 A++, 990239 A++, 990251 A++, 990253 A++, 990262 A++, 990287 A++, 990308 A++, 990319 A++, 990361 A++, 990366 A++, 990367 A++, 990418 A++, 990432 A++, 990475 A++, 990482 A++, 699841 A+++, 990073 A+++, 990075 A+++, 990077 A+++, 990083 A+++, 990119 A+++, 990137 A+++, 990155 A+++, 990278 A+++, 990298 A+++, 990311 A+++, 990379 A+++, 990446 A+++, 990450 A+++, 990460 A+++, 990461 A+++, 656215 A++++, 668126 A++++, 670034 A++++, 686419 A++++, 990160 A++++, 990163 A++++, 990166 A++++, 990167 A++++, 990168 A++++, 990172 A++++, 990182 A++++, 990185 A++++, 990188 A++++, 990194 A++++, 990196 A++++, 990203 A++++, 990207 A++++, 990218 A++++, 990219 A++++, 990224 A++++, 990226 A++++, 990229 A++++, 990243 A++++, 990255 A++++, 990257 A++++, 990264 A++++, 990266 A++++, 990277 A++++, 990285 A++++, 990286 A++++, 990303 A++++, 990320 A++++, 990325 A++++, 990326 A++++, 990329 A++++, 990330 A++++, 990338 A++++, 990346 A++++, 990352 A++++, 990357 A++++, 990378 A++++, 990401 A++++, 990406 A++++, 990407 A++++, 990410 A++++, 990415 A++++, 990417 A++++, 990420 A++++, 990426 A++++, 990438 A++++, 990451 A++++, 990467 A++++, 990468 A++++, 990470 A++++, 990495 A++++
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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
salmon
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
squirrel
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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
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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the two reactions 11beta-HSD1-dehydrogenase, EC 1.1.1146, and 17beta-HSD3, EC 1.1.1.64, which utilize NADPH are competing for NADPH from the same cofactor pool. 11beta-HSD1-dehydrogenase serves as a NADPH-regenerating system that is tightly coupled in regulating 17beta-HSD3 reaction synthesizing testosterone. A cycle can exist whereby the NADPH produced by 11beta-HSD1 dehydrogenase can drive the reductase activity of 17beta-HSD3 and the NADP+ produced by 17beta-HSD3 and other enzymes involved in testosterone biosynthesis can drive the dehydrogenase activity of 11beta-HSD1
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2-dehydrocortisol + NADP+
1,2-dehydrocortisone + NADPH
show the reaction diagram
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r
1,2-dehydrocortisone + NADPH
1,2-dehydrocortisol + NADP+
show the reaction diagram
11-dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
11-dehydrocorticosterone + NADPH + H+
corticosterone + NADP+
show the reaction diagram
11-oxo-progesterone + NADPH + H+
11beta-hydroxyprogesterone + NADP+
show the reaction diagram
11alpha-hydroxy-pregn-4-ene-3,20-dione + ?
pregn-4-ene-3,11,20-trione + ?
show the reaction diagram
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + ?
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + ?
show the reaction diagram
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i.e. cortisol
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?
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NADP+
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADPH
show the reaction diagram
11beta,17beta-dihydroxyandrost-4-ene-3-one + ?
17beta-hydroxyandrost-4-ene-3,11-dione + ?
show the reaction diagram
11beta,20alpha-dihydroxypregn-4-ene-3-one + ?
20alpha-hydroxypregn-4-ene-3,11-dione + ?
show the reaction diagram
11beta,20beta-dihydroxypregn-4-ene-3-one + ?
20beta-hydroxypregn-4-ene-3,11-dione + ?
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + ?
11-dehydro,21-hydroxy-pregn-4-en-3,20-dione + ?
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NAD+
21-hydroxy-pregn-4-en-3,11,20-trione + NADH + H+
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NADP+
21-hydroxy-pregn-4-en-3,11,20-trione + NADPH
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NADP+
21-hydroxy-pregn-4-en-3,11,20-trione + NADPH + H+
show the reaction diagram
11beta-hydroxy-pregn-4-ene-3,20-dione + ?
pregn-4-ene-3,11,20-trione + ?
show the reaction diagram
11beta-hydroxyandrost-4-ene-3,17-dione + ?
androst-4-ene-3,11,17-trione + ?
show the reaction diagram
11beta-hydroxytestosterone + NAD+
11-oxotestosterone + NADH + H+
show the reaction diagram
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?
12alpha-fluoro-11-dehydrocorticosterone + NADPH
12alpha-fluoro-corticosterone + NADP+
show the reaction diagram
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ir
15-deoxy-D12,14-prostaglandin J2 + NADPH
?
show the reaction diagram
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isozyme 11beta-HSD1
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?
16alpha-methyl-1,2-dehydrocortisone + NADPH
16alpha-methyl-1,2-dehydrocortisol + NADP+
show the reaction diagram
16alpha-methylcortisol + NADP+
16alpha-methylcortisone + NADPH
show the reaction diagram
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16alpha-methylcortisone + NADPH
16alpha-methylcortisol + NADP+
show the reaction diagram
16beta-methylcortisol + NADP+
16beta-methylcortisone + NADPH
show the reaction diagram
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-
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17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADPH
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NADP+
show the reaction diagram
17alpha,21-dihydroxypregna-1,4-diene-3,11,20-trione + NADPH
11beta,17alpha,21-trihydroxypregna-1,4-diene-3,20-dione + NADP+
show the reaction diagram
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i.e. prednisone
i.e. prednisolone
?
2,3-benzoylphenyl-propanoic acid + NADPH
2,3-benzoylphenyl-propanol + NADP+
show the reaction diagram
20alpha-hydroxypregn-4-ene-3-one + ?
20alpha-hydroxypregn-4-ene-3,11-dione + ?
show the reaction diagram
21-hydroxy-pregn-4-en-3,11,20-trione + NADPH
11beta,21-dihydroxypregn-4-en-3,20-dione + NADP+
show the reaction diagram
4-methylnitrosamine-1-(3-pyridiyl)-1-butanone + NADPH
4-methylnitrosamine-1-(3-pyridiyl)-1-butanol + NADP+
show the reaction diagram
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-
-
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?
4-methylnitrosamino-1-(3-pyridyl)-1-butanone + NADPH
4-methylnitrosamino-1-(3-pyridyl)-1-butanol + NADP+
show the reaction diagram
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i.e. NNK, genotoxic compound from tobacco smoke, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184
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r
5,5-dimethyl-3-(3-fluorphenyl)-4-(4-methylsulfonyl)phenyl-2-(5H-furanone)-lactol + NADP+
5,5-dimethyl-3-(3-fluorphenyl)-4-(4-methylsulfonyl)phenyl-2-(5H-furanone)-lactone + NADPH
show the reaction diagram
5alpha-androstane-3beta,7alpha,17beta-triol + NADP+
5alpha-androstane-3beta,7beta,17beta-triol + NADPH
show the reaction diagram
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interconversion of 7alpha to 7beta isoform, ratio Vmax/Km is 2 pmol min-1 microgramm-1/microMol
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r
5alpha-androstane-3beta,7beta,17beta-triol + NADP+
5alpha-androstane-3beta,7alpha,17beta-triol + NADP
show the reaction diagram
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interconversion of 7beta to 7alpha isoform, ratio Vmax/Km is 0.5 pmol min-1 microgramm-1/microMol
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r
6-[2-(2-hydroxy-ethylamino)-ethyl]-6H-indeno[1,2-c]isoquinoline-5,11-dione + NADPH
(+)-6-[2-(2-hydroxyethyl)aminoethyl]-5-oxo-11-hydroxy-5,6-dihydro-11H-indeno[1,2-c]isoquinoline + NADP+
show the reaction diagram
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trivial name oracin, cytostatic drug, 11beta-HSD 1 exhibits enzyme cooperativity for the formation of both hydroxy-enantiomers
24% (+)-stereoisomer
-
?
6-[2-(2-hydroxy-ethylamino)-ethyl]-6H-indeno[1,2-c]isoquinoline-5,11-dione + NADPH + H+
(-)-6-[2-(2-hydroxyethyl)aminoethyl]-5-oxo-11-hydroxy-5,6-dihydro-11H-indeno[1,2-c]isoquinoline + NADP+
show the reaction diagram
-
trivial name oracin, cytostatic drug
76% (-)-stereoisomer
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?
7-ketodehydroepiandrosterone + 2 NADPH + 2 H+
7alpha-hydroxydehydroepiandrosterone + 7beta-hydroxydehydroepiandrosterone + 2 NADP+
show the reaction diagram
-
-
formation of alpha- and beta-product in almost equal amounts. In presence of hexose-6-phosphate dehydrogenase, the 7keto-substrate is almost fully metabolized and the 7beta-product is preferentially formed
-
?
7-oxo-5alpha-androstane-3beta,17beta-diol + NADPH
5alpha-androstane-3beta,7alpha,17beta-triol + 5alpha-androstane-3beta,7alpha,17beta-triol + NADP+
show the reaction diagram
-
-
-
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r
7-oxocholesterol + NADPH
7beta-hydroxycholesterol + 7alpha-hydroxycholesterol + NADPH
show the reaction diagram
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40% and 60%, respectively, in lysates of HEK-293 cells and intact HEK-293 cells expressing 11beta-HSD1
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r
7-oxocholesterol + NADPH
7beta-hydroxycholesterol + NADP+
show the reaction diagram
7alpha-hydroxycholesterol + NADP+
7-oxocholesterol + NADPH
show the reaction diagram
in lysates of HEK-293 cells expressing 11beta-HSD1, no oxidation in intact HEK293 cells expressing 11beta-HSD1
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r
7alpha-hydroxydehydroepiandrosterone + NADP+
7beta-hydroxydehydroepiandrosterone + 7-ketodehydroepiandrosterone + NADPH
show the reaction diagram
-
-
in presence of hexose-6-phosphate dehydrogenase, less substrate is metabolized and accumulation of 7-ketodehydroepiandrosterone is abolished
-
?
7beta-hydroxycholesterol + NADP+
7-oxocholesterol + NADPH
show the reaction diagram
7beta-hydroxydehydroepiandrosterone + NADP+
7alpha-hydroxydehydroepiandrosterone + 7-ketodehydroepiandrosterone + NADPH
show the reaction diagram
-
-
formation of products in almost equal amounts. In presence of hexose-6-phosphate dehydrogenase, less substrate is metabolized and accumulation of 7-ketodehydroepiandrosterone is abolished
-
?
9alpha-fluoro-11-oxoprogesterone + NADPH
9alpha-fluoro-11beta-hydroxyprogesterone + NADP+
show the reaction diagram
-
-
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ir
9alpha-fluorocortisone + NADPH
9alpha-fluorocortisol + NADP+
show the reaction diagram
androst-4-ene-3,11,17-trione + NADPH
11beta-hydroxyandrost-4-ene-3,17-dione + NADP+
show the reaction diagram
androst-4-ene-3,11,17-trione + NADPH
11beta-hydroxyandrost-4-ene-3,17-one + NADP+
show the reaction diagram
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
corticosterone + NADP+
11-dehydrocorticosterone + NADPH
show the reaction diagram
corticosterone + NADP+
11-dehydrocorticosterone + NADPH + H+
show the reaction diagram
corticosterone + NADP+
?
show the reaction diagram
-
-
-
-
?
corticosterone + NADPH
corticosterol + NADP+
show the reaction diagram
-
-
-
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r
corticosterone + NADPH + H+
corticosterol + NADP+
show the reaction diagram
cortisol + NAD+
cortisone + NADH
show the reaction diagram
cortisol + NAD+
cortisone + NADH + H+
show the reaction diagram
cortisol + NADP+
cortisone + NADPH
show the reaction diagram
cortisone + NAD(P)H
cortisol + NAD(P)+
show the reaction diagram
cortisone + NADPH
cortisol + NADP+
show the reaction diagram
cortisone + NADPH
cortisol + NADP+ + H+
show the reaction diagram
cortisone + NADPH
cortisole + NADP+
show the reaction diagram
-
-
-
-
?
cortisone + NADPH + H+
cortisol + NADP+
show the reaction diagram
dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
dexamethasone + NADP+
11-dehydromethasone + NADPH
show the reaction diagram
metyrapone + NADPH
? + NADP+
show the reaction diagram
-
-
-
r
oracin + NADPH + H+
11-dihydrooracin + NADP+
show the reaction diagram
oracin + NADPH + H+
dihydrooracin + NADP+
show the reaction diagram
-
a cytostatic drug, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184, stereochemical ratio of 3:1 for R:S enantiomers of the pro-chiral carbonyl centre of oracin, inactivation of the anti-cancer drug
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r
pregn-4-ene-3,11,20-trione + NADPH
11beta-hydroxy-pregn-4-ene-3,20-dione + NADP+
show the reaction diagram
additional information
?
-
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
1,2-dehydrocortisol + NADP+
1,2-dehydrocortisone + NADPH
show the reaction diagram
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-
-
-
r
11-dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
11alpha-hydroxy-pregn-4-ene-3,20-dione + ?
pregn-4-ene-3,11,20-trione + ?
show the reaction diagram
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + ?
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + ?
show the reaction diagram
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i.e. cortisol
-
?
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NADP+
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADPH
show the reaction diagram
11beta,17beta-dihydroxyandrost-4-ene-3-one + ?
17beta-hydroxyandrost-4-ene-3,11-dione + ?
show the reaction diagram
11beta,20alpha-dihydroxypregn-4-ene-3-one + ?
20alpha-hydroxypregn-4-ene-3,11-dione + ?
show the reaction diagram
11beta,20beta-dihydroxypregn-4-ene-3-one + ?
20beta-hydroxypregn-4-ene-3,11-dione + ?
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + ?
11-dehydro,21-hydroxy-pregn-4-en-3,20-dione + ?
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NAD+
21-hydroxy-pregn-4-en-3,11,20-trione + NADH + H+
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NADP+
21-hydroxy-pregn-4-en-3,11,20-trione + NADPH
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NADP+
21-hydroxy-pregn-4-en-3,11,20-trione + NADPH + H+
show the reaction diagram
11beta-hydroxy-pregn-4-ene-3,20-dione + ?
pregn-4-ene-3,11,20-trione + ?
show the reaction diagram
11beta-hydroxyandrost-4-ene-3,17-dione + ?
androst-4-ene-3,11,17-trione + ?
show the reaction diagram
11beta-hydroxytestosterone + NAD+
11-oxotestosterone + NADH + H+
show the reaction diagram
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-
-
-
?
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADPH
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NADP+
show the reaction diagram
17alpha,21-dihydroxypregna-1,4-diene-3,11,20-trione + NADPH
11beta,17alpha,21-trihydroxypregna-1,4-diene-3,20-dione + NADP+
show the reaction diagram
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i.e. prednisone
i.e. prednisolone
?
21-hydroxy-pregn-4-en-3,11,20-trione + NADPH
11beta,21-dihydroxypregn-4-en-3,20-dione + NADP+
show the reaction diagram
4-methylnitrosamino-1-(3-pyridyl)-1-butanone + NADPH
4-methylnitrosamino-1-(3-pyridyl)-1-butanol + NADP+
show the reaction diagram
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i.e. NNK, genotoxic compound from tobacco smoke, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184
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-
r
7beta-hydroxycholesterol + NADP+
7-oxocholesterol + NADPH
show the reaction diagram
androst-4-ene-3,11,17-trione + NADPH
11beta-hydroxyandrost-4-ene-3,17-one + NADP+
show the reaction diagram
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
the two reactions 11beta-HSD1-dehydrogenase, EC 1.1.1146, and 17beta-HSD3, EC 1.1.1.64, which utilize NADPH are competing for NADPH from the same cofactor pool. 11beta-HSD1-dehydrogenase serves as a NADPH-regenerating system that is tightly coupled in regulating 17beta-HSD3 reaction synthesizing testosterone. A cycle can exist whereby the NADPH produced by 11beta-HSD1 dehydrogenase can drive the reductase activity of 17beta-HSD3 and the NADP+ produced by 17beta-HSD3 and other enzymes involved in testosterone biosynthesis can drive the dehydrogenase activity of 11beta-HSD1
i.e. 4-androsten-17beta-ol-3-one
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?
corticosterone + NADP+
11-dehydrocorticosterone + NADPH
show the reaction diagram
corticosterone + NADP+
11-dehydrocorticosterone + NADPH + H+
show the reaction diagram
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bidirectional in vitro, believed to predominantly function as an oxidoreductase in vivo
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-
r
cortisol + NAD+
cortisone + NADH
show the reaction diagram
P50172, P51661
isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+
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-
ir
cortisol + NADP+
cortisone + NADPH
show the reaction diagram
cortisone + NAD(P)H
cortisol + NAD(P)+
show the reaction diagram
cortisone + NADPH
cortisol + NADP+
show the reaction diagram
cortisone + NADPH
cortisol + NADP+ + H+
show the reaction diagram
cortisone + NADPH
cortisole + NADP+
show the reaction diagram
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-
-
-
?
dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
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isozyme 11beta-HSD1, 11beta-hydroxysteroid dehydrogenase activity, EC 1.1.1.146
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-
r
oracin + NADPH + H+
dihydrooracin + NADP+
show the reaction diagram
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a cytostatic drug, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184, stereochemical ratio of 3:1 for R:S enantiomers of the pro-chiral carbonyl centre of oracin, inactivation of the anti-cancer drug
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-
r
pregn-4-ene-3,11,20-trione + NADPH
11beta-hydroxy-pregn-4-ene-3,20-dione + NADP+
show the reaction diagram
additional information
?
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