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Escherichia coli K-12 substr. MG1655 Compound Class: NADHX

Superclasses: an acceptora redox electron carrier

NADHX is a hydrated form of NADH, where the hydroxyl group is attached at position 6 of the nicotinamide moiety.

Studies in the 1950's have shown that glyceraldehyde 3-phosphate dehydrogenase slowly catalyzes the formation of NADHX from NADH [Rafter54]. The equilibrium of this hydration reaction is in favor (100/1) of the hydrated form [Acheson88], making the reaction virtually irreversible.

NADHX and NADPHX are inhibitors of several dehydrogenases [Prabhakar98] and it is thus important to eliminate them. Reconversion of NADHX to NADH is catalyzed by an ATP-dependent dehydratase [Yoshida75, Marbaix11].

NADHX compound structure

Chemical Formula: C21H29N7O15P2


Molecular Weight: 681.44 Daltons

Monoisotopic Molecular Weight: 683.1353363829999 Daltons

SMILES: C1(=C(CCC(O)N1C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5))C(N)=O)

InChI: InChI=1S/C21H31N7O15P2/c22-17-12-19(25-6-24-17)28(7-26-12)21-16(33)14(31)10(42-21)5-40-45(37,38)43-44(35,36)39-4-9-13(30)15(32)20(41-9)27-3-8(18(23)34)1-2-11(27)29/h3,6-7,9-11,13-16,20-21,29-33H,1-2,4-5H2,(H2,23,34)(H,35,36)(H,37,38)(H2,22,24,25)/p-2/t9-,10-,11?,13-,14-,15-,16-,20-,21-/m1/s1


Created 18-Oct-2011 by Keseler I, SRI International


Acheson88: Acheson SA, Kirkman HN, Wolfenden R (1988). "Equilibrium of 5,6-hydration of NADH and mechanism of ATP-dependent dehydration." Biochemistry 27(19);7371-5. PMID: 3061454

Marbaix11: Marbaix AY, Noel G, Detroux AM, Vertommen D, Van Schaftingen E, Linster CL (2011). "Extremely Conserved ATP- or ADP-dependent Enzymatic System for Nicotinamide Nucleotide Repair." J Biol Chem 286(48);41246-52. PMID: 21994945

Prabhakar98: Prabhakar P, Laboy JI, Wang J, Budker T, Din ZZ, Chobanian M, Fahien LA (1998). "Effect of NADH-X on cytosolic glycerol-3-phosphate dehydrogenase." Arch Biochem Biophys 360(2);195-205. PMID: 9851831

Rafter54: Rafter, G. W., Chaykin, S., Krebs, E. G. (1954). "The action of glyceraldehyde-3-phosphate dehydrogenase on reduced diphosphopyridine nucleotide." J. Biol. Chem. 208: 799-812. PMID: 13174589

Yoshida75: Yoshida A, Dave V (1975). "Inhibition of NADP-dependent dehydrogenases by modified products of NADPH." Arch Biochem Biophys 169(1);298-303. PMID: 239637

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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