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Escherichia coli K-12 substr. MG1655 Compound: o-phenanthroline

Synonyms: 1,10-phenanthroline, 1,10-fenanthroline, 1,10-o-phenanthroline, 2-phenanthroline, orthophenanthroline, β-phenanthroline

Chemical Formula: C12H8N2

Molecular Weight: 180.21 Daltons

Monoisotopic Molecular Weight: 180.06874826720002 Daltons

SMILES: C2(C=CC3(C=CC1(C=CC=NC=1C(N=2)=3)))

InChI: InChI=1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H

InChIKey: InChIKey=DGEZNRSVGBDHLK-UHFFFAOYSA-N

Unification Links: ChEBI:44975 , ChemSpider:1278 , DrugBank:DB02365 , KEGG:C00604 , PubChem:1318

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 43.782

Enzymes inhibited by o-phenanthroline, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: rhamnulose-1-phosphate aldolase [Chiu75]

Inhibitor (Mechanism unknown) of: aminopeptidase [Bhosale10] , quercetin 2,3-dioxygenase [Adams05] , guanosine-3',5'-bis(diphosphate) 3'-diphosphatase [Xiao91] , trimethylamine N-oxide reductase [Sagai73] , D-mannonate dehydratase [Dreyer87] , NADH:ubiquinone oxidoreductase [Finel94] , galactoside O-acetyltransferase [Musso73, Comment 1] , guanine deaminase [Maynes00] , L-serine deaminase [Newman80] , alanyl-tRNA synthetase [Miller91] , cytosine deaminase [Porter93] , D-glucuronate isomerase [Ashwell60] , D-galacturonate isomerase [Ashwell60] , deoxyuridine triphosphatase [Shlomai78, Comment 2] , glycerol dehydrogenase [Tang79] , peptide deformylase [Meinnel95]


References

Adams05: Adams M, Jia Z (2005). "Structural and biochemical analysis reveal pirins to possess quercetinase activity." J Biol Chem 280(31);28675-82. PMID: 15951572

Ashwell60: Ashwell G, Wahba AJ, Hickman J (1960). "Uronic acid metabolism in bacteria. I. Purification and properties of uronic acid isomerase in Escherichia coli." J Biol Chem 1960;235(6):1559-1565. PMID: 13794771

Bhosale10: Bhosale M, Pande S, Kumar A, Kairamkonda S, Nandi D (2010). "Characterization of two M17 family members in Escherichia coli, Peptidase A and Peptidase B." Biochem Biophys Res Commun 395(1);76-81. PMID: 20350528

Chiu75: Chiu TH, Evans KL, Feingold DS (1975). "L-Rhamnulose-1-phosphate aldosase." Methods Enzymol 1975;42;364-9. PMID: 237196

Dreyer87: Dreyer JL (1987). "The role of iron in the activation of mannonic and altronic acid hydratases, two Fe-requiring hydro-lyases." Eur J Biochem 166(3);623-30. PMID: 3038546

Finel94: Finel M, Majander A (1994). "Studies on the proton-translocating NADH:ubiquinone oxidoreductases of mitochondria and Escherichia coli using the inhibitor 1,10-phenanthroline." FEBS Lett 339(1-2);142-6. PMID: 8313963

Maynes00: Maynes JT, Yuan RG, Snyder FF (2000). "Identification, expression, and characterization of Escherichia coli guanine deaminase." J Bacteriol 182(16);4658-60. PMID: 10913105

Meinnel95: Meinnel T, Blanquet S (1995). "Enzymatic properties of Escherichia coli peptide deformylase." J Bacteriol 177(7);1883-7. PMID: 7896716

Miller91: Miller WT, Hill KA, Schimmel P (1991). "Evidence for a "cysteine-histidine box" metal-binding site in an Escherichia coli aminoacyl-tRNA synthetase." Biochemistry 30(28);6970-6. PMID: 1712632

Musso73: Musso RE, Zabin I (1973). "Substrate specificity and kinetic studies on thiogalactoside transacetylase." Biochemistry 1973;12(3);553-7. PMID: 4630409

Newman80: Newman EB, Kapoor V (1980). "In vitro studies on L-serine deaminase activity of Escherichia coli K12." Can J Biochem 1980;58(11);1292-7. PMID: 7011505

Porter93: Porter DJ, Austin EA (1993). "Cytosine deaminase. The roles of divalent metal ions in catalysis." J Biol Chem 1993;268(32);24005-11. PMID: 8226944

Sagai73: Sagai M, Ishimoto M (1973). "An enzyme reducing adenosine 1N-oxide in Escherichia coli, amine N-oxide reductase." J Biochem (Tokyo) 1973;73(4);843-59. PMID: 4578389

Shlomai78: Shlomai J, Kornberg A (1978). "Deoxyuridine triphosphatase of Escherichia coli. Purification, properties, and use as a reagent to reduce uracil incorporation into DNA." J Biol Chem 1978;253(9);3305-12. PMID: 346589

Tang79: Tang CT, Ruch FE, Lin CC (1979). "Purification and properties of a nicotinamide adenine dinucleotide-linked dehydrogenase that serves an Escherichia coli mutant for glycerol catabolism." J Bacteriol 1979;140(1);182-7. PMID: 40950

Xiao91: Xiao H, Kalman M, Ikehara K, Zemel S, Glaser G, Cashel M (1991). "Residual guanosine 3',5'-bispyrophosphate synthetic activity of relA null mutants can be eliminated by spoT null mutations." J Biol Chem 1991;266(9);5980-90. PMID: 2005134


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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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