Brand  (β version)

PDB ID: 4FAL

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Ligands
Code Name Style Show Link
0T0 3-(3,4-dihydroisoquinolin-2(1h)-ylsulfonyl)-N-methylbenzamide PoSSuM
EDO 1,2-ethanediol PoSSuM
NAP Nadp nicotinamide-adenine-dinucleotide phosphate PoSSuM
Non-standard Residues
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Structure summary

Code : 4FAL   PDBj   RCSB PDB   PDBe
Header : oxidoreductase/oxidoreductase inhibitor
Title : Crystal structure of human 17beta-hydroxysteroid dehydrogenase type 5 in complex with 3-((3,4-dihydroisoquinolin-2(1H)-yl)sulfonyl)-N-methylbenzamide (80)
Release Data : 2012-10-10
Compound :
mol_id molecule chains synonym
1 Aldo-keto reductase family 1 member C3 A 17-beta-hydroxysteroid dehydrogenase type 5, 17-beta-HSD 5, 3-alpha-HSD type II, brain, 3-alpha-hydroxysteroid dehydrogenase type 2, 3-alpha-HSD type 2, Chlordecone reductase homolog HAKRb, Dihydrodiol dehydrogenase 3, DD-3, DD3, Dihydrodiol dehydrogenase type I, HA1753, Indanol dehydrogenase, Prostaglandin F synthase, PGFS, Testosterone 17-beta-dehydrogenase 5, Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase
ec: 1.1.1.213, 1.1.1.112, 1.1.1.188, 1.1.1.63, 1.1.1.64, 1.3.1.20
Source :
mol_id organism_scientific organism_common expression_system
1 Homo sapiens  (taxid:9606) Human Escherichia coli  (taxid:469008)
gene: AKR1C3, DDH1, HSD17B5, KIAA0119, PGFS
expression_system_strain: BL21 DE3
expression_system_vector_type: PLASMID
expression_system_plasmid: pET21a
Authors : Turnbull, A.P., Jamieson, S.M.F., Brooke, D.G., Heinrich, D., Atwell, G.J., Silva, S., Hamilton, E.J., Rigoreau, L.J.M., Trivier, E., Soudy, C., Samlal, S.S., Owen, P.J., Schroeder, E., Raynham, T., Flanagan, J.U., Denny, W.A.
Keywords : aldo-keto reductase, oxidoreductase-oxidoreductase inhibitor complex
Exp. method : X-RAY DIFFRACTION ( 2.00 Å )
Citation :

3-(3,4-Dihydroisoquinolin-2(1H)-ylsulfonyl)benzoic acids; a New Class of Highly Potent and Selective Inhibitors of the Type 5 17-beta-hydroxysteroid Dehydrogenase AKR1C3

Jamieson, S.M.,Brooke, D.G.,Heinrich, D.  et al.
(2012)  J.Med.Chem.  55 : 7746 - 7758

PubMed: 22877157
DOI: 10.1021/jm3007867

Reaction

Chain : A
UniProt : P42330 (AK1C3_HUMAN)
Reaction: EC: Evidence:
Physiological Direction:
a 3alpha-hydroxysteroid + NADP(+) = a 3-oxosteroid + NADPH + H(+) 1.1.1.357 PubMed:11165022, PubMed:7650035, PubMed:9415401, PubMed:9927279
-
a 3alpha-hydroxysteroid + NAD(+) = a 3-oxosteroid + NADH + H(+) 1.1.1.357 PubMed:11165022, PubMed:7650035, PubMed:9415401, PubMed:9927279
-
prostaglandin F2alpha + NADP(+) = prostaglandin D2 + NADPH + H(+) 1.1.1.188 PubMed:10622721, PubMed:11165022, PubMed:7650035, PubMed:9415401, PubMed:9927279
-
prostaglandin F2alpha + NADP(+) = prostaglandin H2 + NADPH + H(+) - PubMed:15047184, PubMed:19010934
right-to-left
prostaglandin D2 + NADPH + H(+) = 11beta-prostaglandin F2 + NADP(+) - PubMed:10622721, PubMed:15047184, PubMed:20036328
right-to-left PubMed:10622721
prostaglandin D2-ethanolamide + NADPH + H(+) = 11beta- prostaglandin F2-ethanolamide + NADP(+) - PubMed:15047184
left-to-right
testosterone + NAD(+) = androst-4-ene-3,17-dione + NADH + H(+) 1.1.1.239 PubMed:10998348, PubMed:11165022, PubMed:9415401, PubMed:9927279
right-to-left PubMed:10998348
testosterone + NADP(+) = androst-4-ene-3,17-dione + NADPH + H(+) 1.1.1.64 PubMed:10998348, PubMed:11165022, PubMed:20036328, PubMed:9415401, PubMed:9927279
right-to-left PubMed:10998348, PubMed:20036328
17beta-estradiol + NADP(+) = estrone + NADPH + H(+) 1.1.1.62 PubMed:10998348, PubMed:11165022, PubMed:20036328
right-to-left PubMed:10998348, PubMed:20036328
17beta-estradiol + NAD(+) = estrone + NADH + H(+) 1.1.1.62 PubMed:10998348
right-to-left
(20S)-hydroxypregn-4-en-3-one + NADP(+) = progesterone + NADPH + H(+) - PubMed:10998348, PubMed:20036328
right-to-left
(20S)-hydroxypregn-4-en-3-one + NAD(+) = progesterone + NADH + H(+) - PubMed:10998348
right-to-left PubMed:10998348, PubMed:20036328
5alpha-androstane-3alpha,17beta-diol + NADP(+) = 17beta- hydroxy-5alpha-androstan-3-one + NADPH + H(+) - PubMed:10557352, PubMed:10998348, PubMed:11165022, PubMed:14672942, PubMed:7650035, PubMed:9415401
right-to-left PubMed:10998348, PubMed:14672942
5alpha-androstane-3alpha,17beta-diol + NAD(+) = 17beta- hydroxy-5alpha-androstan-3-one + NADH + H(+) 1.1.1.53 PubMed:10998348
right-to-left
androsterone + NADPH + H(+) = 5alpha-androstane-3alpha,17beta- diol + NADP(+) - PubMed:10557352, PubMed:10998348, PubMed:9415401
right-to-left PubMed:10998348
5alpha-androstane-3alpha,17beta-diol + NAD(+) = androsterone + NADH + H(+) - PubMed:10998348, PubMed:14672942, PubMed:9415401
left-to-right PubMed:10998348, PubMed:14672942
5alpha-androstane-3beta,17beta-diol + NADP(+) = 17beta- hydroxy-5alpha-androstan-3-one + NADPH + H(+) 1.1.1.210 PubMed:14672942
right-to-left
9-cis-retinol + NADP(+) = 9-cis-retinal + NADPH + H(+) - PubMed:21851338
right-to-left