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Inhibitor Report for: thio-NAD

PlaB shows concentration-dependent phospholipase inactivation by tetramerization which may be a mechanism for self-protection. (See Papers Bender et al. 2009 and Kuhle et al. 2014.). The tetramer is a dimer of identical dimers. Diwo et al. found in the structure eight NAD(H) molecules at the dimer/dimer interface, suggesting that these molecules stabilize the tetramer leading to enzyme inactivation


General
Type Sulfur Compound, Nicotinamide, Organophosphate, Pyridine, Purine
Chemical_Nomenclature [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl][[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamothioylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Canonical SMILES C1=CC(=C[N+](=C1)C2C(C(C(O2)COP(=O)([O-])OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O)C(=S)N
InChI InChI=1S/C21H27N7O13P2S/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(40-21)6-38-43(35,36)41-42(33,34)37-5-10-13(29)15(31)20(39-10)27-3-1-2-9(4-27)18(23)44/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,44)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChIKey UQYPZLRUJKCREN-NNYOXOHSSA-N
Other name(s) Thionicotinamide-adenine-dinucleotide ; J-700249 ; SND ; DB03893 ; [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamothioylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
________________________________________________________________________________________________
MW|679.5
Formula|C21H27N7O13P2S
CAS_number|
PubChem|5289382
UniChem|UQYPZLRUJKCREN-NNYOXOHSSA-N
IUPHAR|
Wikipedia|

Target
Families | thio-NAD ligand of proteins in family: PlaB
Stucture | 1 structure: 6ZTI: Phospholipase PlaB from Legionella pneumophila in complex with thio-NAD
Protein | legpn-i7i328

References:
Search PubMed for references concerning: thio-NAD
    Title: NAD(H)-mediated tetramerization controls the activity of Legionella pneumophila phospholipase PlaB
    Diwo M, Michel W, Aurass P, Kuhle-Keindorf K, Pippel J, Krausze J, Wamp S, Lang C, Blankenfeldt W, Flieger A
    Ref: Proc Natl Acad Sci U S A, 118:, 2021 : PubMed