MetaCyc 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

<i>o</i>-phenanthroline compound structure

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


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

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 125.950966Inferred by computational analysis [Latendresse13]

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

Inhibitor (Competitive) of: rhamnulose-1-phosphate aldolase [Chiu75] Inhibitor (Noncompetitive) of: nitrite reductase [Lafferty74] Inhibitor (Mechanism unknown) of: D-galacturonate isomerase [Ashwell60], D-glucuronate isomerase [Ashwell60], D-mannonate dehydratase [Dreyer87], guanosine-3',5'-bis(diphosphate) 3'-diphosphatase [Xiao91], deoxyuridine triphosphatase [Shlomai78, Comment 1], guanine deaminase [Maynes00], alanyl-tRNA synthetase [Miller91], NADH:ubiquinone oxidoreductase (H+-transporting) [Finel94], L-serine deaminase [Newman80], peptide deformylase [Meinnel95], glycerol dehydrogenase [Tang79], dipeptidyl carboxypeptidase [Chen09, Henrich93], galactoside O-acetyltransferase [Musso73, Comment 2], aminopeptidase [Bhosale10], quercetin 2,3-dioxygenase [Adams05], cytosine deaminase [Porter93], mercaptosuccinate dioxygenase [Brandt14], 1,3,6,8-tetrahydroxynaphthalene monooxygenase (quinone-forming) [Funa05], gentisyl alcohol epoxidase [Priest89], synephrine dehydratase [Manne86], naringenin 4-reductase (cv sm) [Halbwirth03], eriodictyol 4-reductase (cv sm) [Halbwirth03], naringenin 4-reductase (cv Pirat) [Halbwirth03], eriodictyol 4-reductase (cv Pirat) [Halbwirth03], deoxycytidine deaminase [FaivreNitschke99], phenylalanine hydroxylase [Pribat10a], superoxide dismutase [Takenaka11], 1,2,4-trihydroxybenzene 1,2-dioxygenase [Takenaka03], 4-amino-3-hydroxy-benzoate 2,3-dioxygenase [Takenaka02], hydroquinone 1,2-dioxygenase [Moonen08], salicylate 1,2-dioxygenase [Hintner01], N-benzylformamide deformylase [Fukatsu04], cytidine deaminase [FaivreNitschke99], cytidine monophosphate-N-acetylneuraminate hydroxylase [Kawano94], norcoclaurine synthase [Minami07], parathion hydrolase [Dumas89], carbapenemase [Rossolini98], deacetoxycephalosporin C hydroxylase [Baker91], deacetoxycephalosporin C synthase [Dotzlaf89], deacetoxycephalosporin C hydroxylase [Dotzlaf87], deacetoxycephalosporin C synthase [Dotzlaf87], 6-hydroxynicotinate dehydrogenase [Hirschberg71], ethanolamine kinase [Macher76], (S)-canadine oxidase [Galneder88], mycothiol S-conjugate amidase [Newton02], 4-hydroxy-tetrahydrodipicolinate reductase [Kimura75], cysteine dioxygenase [Chai05], hexulose-6-phosphate synthase [Kato90], MtaC protein: coenzyme M methyltransferase [LeClerc96], phosphonoacetate hydrolase [McGrath95], berberine bridge enzyme [Steffens85], diamine oxidase [Suzuki96], nicotinate dehydrogenase [Hirschberg71], 2,5-dihydroxypyridine dioxygenase [Gauthier71], hydroxyproline 2-epimerase [Adams64], ribitol dehydrogenase [Taylor74], vellosimine reductase [Pfitzner84], acetyl-CoA:salutaridinol-7-O-acetyltransferase [Lenz95] Inhibitor (Other types) of: 1,5-anhydro-D-glucitol dehydrogenase [Yoshida03a], aldehyde decarbonylase [SchneiderBelhad00], hydroxymethylglutaryl-CoA lyase [Narasimhan92], androsta-1,4-diene-3,17-dione 9α-hydroxylase [Petrusma09], indole-3-carboxylate decarboxylase [Yoshida02a], hydroxylamine oxidoreductase [Hooper65], pyruvic oxime dioxygenase [Ono96], thiosulfate reductase [Aketagawa85], 1,2-dihydroxynaphthalene dioxygenase [Patel80]


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

Adams64: Adams E, Norton IL (1964). "Purification and properties of inducible hydroxyproline 2-epimerase from Pseudomonas." J Biol Chem 239;1525-35. PMID: 14189888

Aketagawa85: Aketagawa J, Kobayashi K, Ishimoto M (1985). "Purification and properties of thiosulfate reductase from Desulfovibrio vulgaris, Miyazaki F." J Biochem (Tokyo) 97(4);1025-32. PMID: 2993256

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. 235:1559-1565. PMID: 13794771

Baker91: Baker BJ, Dotzlaf JE, Yeh WK (1991). "Deacetoxycephalosporin C hydroxylase of Streptomyces clavuligerus. Purification, characterization, bifunctionality, and evolutionary implication." J Biol Chem 266(8);5087-93. PMID: 2002049

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

Brandt14: Brandt U, Schurmann M, Steinbuchel A (2014). "Mercaptosuccinate Dioxygenase, a Cysteine Dioxygenase Homologue, from Variovorax paradoxus Strain B4 Is the Key Enzyme of Mercaptosuccinate Degradation." J Biol Chem 289(44);30800-9. PMID: 25228698

Chai05: Chai SC, Jerkins AA, Banik JJ, Shalev I, Pinkham JL, Uden PC, Maroney MJ (2005). "Heterologous expression, purification, and characterization of recombinant rat cysteine dioxygenase." J Biol Chem 280(11);9865-9. PMID: 15623508

Chen09: Chen HL, Chang CT, Lin LL, Li TY, Lo HF (2009). "The dipeptidyl carboxypeptidase of Escherichia coli novablue: overproduction and molecular characterization of the recombinant enzyme." World Journal of Microbiology and Biotechnology 25(2);323-330.

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

Dotzlaf87: Dotzlaf JE, Yeh WK (1987). "Copurification and characterization of deacetoxycephalosporin C synthetase/hydroxylase from Cephalosporium acremonium." J Bacteriol 169(4);1611-8. PMID: 3558321

Dotzlaf89: Dotzlaf JE, Yeh WK (1989). "Purification and properties of deacetoxycephalosporin C synthase from recombinant Escherichia coli and its comparison with the native enzyme purified from Streptomyces clavuligerus." J Biol Chem 264(17);10219-27. PMID: 2656705

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

Dumas89: Dumas DP, Caldwell SR, Wild JR, Raushel FM (1989). "Purification and properties of the phosphotriesterase from Pseudomonas diminuta." J Biol Chem 264(33);19659-65. PMID: 2555328

FaivreNitschke99: Faivre-Nitschke SE, Grienenberger JM, Gualberto JM (1999). "A prokaryotic-type cytidine deaminase from Arabidopsis thaliana gene expression and functional characterization." Eur J Biochem 263(3);896-903. PMID: 10469156

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

Fukatsu04: Fukatsu H, Hashimoto Y, Goda M, Higashibata H, Kobayashi M (2004). "Amine-synthesizing enzyme N-substituted formamide deformylase: screening, purification, characterization, and gene cloning." Proc Natl Acad Sci U S A 101(38);13726-31. PMID: 15358859

Funa05: Funa N, Funabashi M, Yoshimura E, Horinouchi S (2005). "A novel quinone-forming monooxygenase family involved in modification of aromatic polyketides." J Biol Chem 280(15);14514-23. PMID: 15701630

Galneder88: Galneder E, Rueffer M, Wanner G, Tabata M, Zenk MH "Alternative final steps in berberine biosynthesis in Coptis japonica cell cultures." Plant Cell Report, 1988, 7:1-4.

Gauthier71: Gauthier JJ, Rittenberg SC (1971). "The metabolism of nicotinic acid. I. Purification and properties of 2,5-dihydroxypyridine oxygenase from Pseudomonas putida N-9." J Biol Chem 246(11);3737-42. PMID: 5578917

Halbwirth03: Halbwirth H, Martens S, Wienand U, Forkmann G, Stich K (2003). "Biochemical formation of anthocyanins in silk tissue of Zea mays

." Plant Science 164: 489-495.

Henrich93: Henrich B, Becker S, Schroeder U, Plapp R (1993). "dcp gene of Escherichia coli: cloning, sequencing, transcript mapping, and characterization of the gene product." J Bacteriol 175(22);7290-300. PMID: 8226676

Hintner01: Hintner JP, Lechner C, Riegert U, Kuhm AE, Storm T, Reemtsma T, Stolz A (2001). "Direct ring fission of salicylate by a salicylate 1,2-dioxygenase activity from Pseudaminobacter salicylatoxidans." J Bacteriol 183(23);6936-42. PMID: 11698383

Hirschberg71: Hirschberg R, Ensign JC (1971). "Oxidation of nicotinic acid by a Bacillus species: purification and properties of nicotinic acid and 6-hydroxynicotinic acid hydroxylases." J Bacteriol 108(2);751-6. PMID: 5128334

Hooper65: Hooper AB, Nason A (1965). "Characterization of hydroxylamine-cytochrome c reductase from the chemoautotrophs Nitrosomonas europaea and Nitrosocystis oceanus." J Biol Chem 240(10);4044-57. PMID: 5842070

Kato90: Kato N (1990). "3-Hexulose-6-phosphate synthase from Mycobacterium gastri MB19." Methods Enzymol 188;397-401. PMID: 2280712

Kawano94: Kawano T, Kozutsumi Y, Kawasaki T, Suzuki A (1994). "Biosynthesis of N-glycolylneuraminic acid-containing glycoconjugates. Purification and characterization of the key enzyme of the cytidine monophospho-N-acetylneuraminic acid hydroxylation system." J Biol Chem 269(12);9024-9. PMID: 8132639

Kimura75: Kimura K (1975). "A new flavin enzyme catalyzing the reduction of dihydrodipicolinate in sporulating Bacillus subtilis I. Purification and properties." J Biochem (Tokyo) 77(2);405-13. PMID: 236291

Lafferty74: Lafferty MA, Garrett RH (1974). "Purification and properties of the Neurospora crassa assimilatory nitrite reductase." J Biol Chem 249(23);7555-67. PMID: 4154942

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

LeClerc96: LeClerc GM, Grahame DA (1996). "Methylcobamide:coenzyme M methyltransferase isozymes from Methanosarcina barkeri. Physicochemical characterization, cloning, sequence analysis, and heterologous gene expression." J Biol Chem 1996;271(31);18725-31. PMID: 8702528

Lenz95: Lenz R, Zenk MH (1995). "Acetyl coenzyme A:salutaridinol-7-O-acetyltransferase from papaver somniferum plant cell cultures. The enzyme catalyzing the formation of thebaine in morphine biosynthesis." J Biol Chem 270(52);31091-6. PMID: 8537369

Macher76: Macher BA, Mudd JB (1976). "Partial purification and properties of ethanolamine kinase from spinach leaf." Arch Biochem Biophys 177(1);24-30. PMID: 187122

Manne86: Manne V, Kutty KR, Pillarisetti SR (1986). "Purification and properties of synephrinase from Arthrobacter synephrinum." Arch Biochem Biophys 248(1);324-34. PMID: 3729420

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

McGrath95: McGrath JW, Wisdom GB, McMullan G, Larkin MJ, Quinn JP (1995). "The purification and properties of phosphonoacetate hydrolase, a novel carbon-phosphorus bond-cleavage enzyme from Pseudomonas fluorescens 23F." Eur J Biochem 1995;234(1);225-30. PMID: 8529644

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

Minami07: Minami H, Dubouzet E, Iwasa K, Sato F (2007). "Functional analysis of norcoclaurine synthase in Coptis japonica." J Biol Chem 282(9);6274-82. PMID: 17204481

Moonen08: Moonen MJ, Synowsky SA, van den Berg WA, Westphal AH, Heck AJ, van den Heuvel RH, Fraaije MW, van Berkel WJ (2008). "Hydroquinone dioxygenase from pseudomonas fluorescens ACB: a novel member of the family of nonheme-iron(II)-dependent dioxygenases." J Bacteriol 190(15);5199-209. PMID: 18502867

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

Narasimhan92: Narasimhan C, Miziorko HM (1992). "Pseudomonas mevalonii 3-hydroxy-3-methylglutaryl-CoA lyase: characterization of the isolated recombinant protein and investigation of the enzyme's cation requirements." Biochemistry 31(45);11224-30. PMID: 1332752

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

Newton02: Newton GL, Fahey RC (2002). "Mycothiol biochemistry." Arch Microbiol 2002;178(6);388-94. PMID: 12420157

Ono96: Ono Y, Makino N, Hoshino Y, Shoji K, Yamanaka T (1996). "An iron dioxygenase from Alcaligenes faecalis catalyzing the oxidation of pyruvic oxime to nitrite." FEMS Microbiol Lett 139(2-3);103-8. PMID: 8674977

Patel80: Patel TR, Barnsley EA (1980). "Naphthalene metabolism by pseudomonads: purification and properties of 1,2-dihydroxynaphthalene oxygenase." J Bacteriol 143(2);668-73. PMID: 7204331

Petrusma09: Petrusma M, Dijkhuizen L, van der Geize R (2009). "Rhodococcus rhodochrous DSM 43269 3-ketosteroid 9alpha-hydroxylase, a two-component iron-sulfur-containing monooxygenase with subtle steroid substrate specificity." Appl Environ Microbiol 75(16);5300-7. PMID: 19561185

Pfitzner84: Pfitzner, Artur, Krausch, Brigitte, Stockigt, Joachim (1984). "Characterization of vellosimine reductase, a specific enzyme involved in the biosynthesis of the Rauvolfia alkaloid sarpagine." Tetrahetron, 40(10):1691-1699.

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

Pribat10a: Pribat A, Noiriel A, Morse AM, Davis JM, Fouquet R, Loizeau K, Ravanel S, Frank W, Haas R, Reski R, Bedair M, Sumner LW, Hanson AD (2010). "Nonflowering plants possess a unique folate-dependent phenylalanine hydroxylase that is localized in chloroplasts." Plant Cell 22(10);3410-22. PMID: 20959559

Priest89: Priest JW, Light RJ (1989). "Patulin biosynthesis: epoxidation of toluquinol and gentisyl alcohol by particulate preparations from Penicillium patulum." Biochemistry 28(23);9192-200. PMID: 2605253

Rossolini98: Rossolini GM, Franceschini N, Riccio ML, Mercuri PS, Perilli M, Galleni M, Frere JM, Amicosante G (1998). "Characterization and sequence of the Chryseobacterium (Flavobacterium) meningosepticum carbapenemase: a new molecular class B beta-lactamase showing a broad substrate profile." Biochem J 332 ( Pt 1);145-52. PMID: 9576862

SchneiderBelhad00: Schneider-Belhaddad F, Kolattukudy P (2000). "Solubilization, partial purification, and characterization of a fatty aldehyde decarbonylase from a higher plant, Pisum sativum." Arch Biochem Biophys 377(2);341-9. PMID: 10845712

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

Steffens85: Steffens, Paul, Nagakura, Naotaka, Zenk, Meinhart H. "Purification and characterization of the berberine bridge enzyme from Berberis beaniana cell culture." Phytochemistry, 1985, Vol 24 (11):2577-2583).

Suzuki96: Suzuki Y. "Purification and characterization of diamine oxidase from Triticum aesticum shoots." Phytochemistry (1996) 42(2) : 291-293.

Takenaka02: Takenaka S, Asami T, Orii C, Murakami S, Aoki K (2002). "A novel meta-cleavage dioxygenase that cleaves a carboxyl-group-substituted 2-aminophenol. Purification and characterization of 4-amino-3-hydroxybenzoate 2,3-dioxygenase from Bordetella sp. strain 10d." Eur J Biochem 269(23);5871-7. PMID: 12444975

Takenaka03: Takenaka S, Okugawa S, Kadowaki M, Murakami S, Aoki K (2003). "The metabolic pathway of 4-aminophenol in Burkholderia sp. strain AK-5 differs from that of aniline and aniline with C-4 substituents." Appl Environ Microbiol 69(9);5410-3. PMID: 12957929

Takenaka11: Takenaka S, Koshiya J, Okugawa S, Takata A, Murakami S, Aoki K (2011). "Fe-superoxide dismutase and 2-hydroxy-1,4-benzoquinone reductase preclude the auto-oxidation step in 4-aminophenol metabolism by Burkholderia sp. strain AK-5." Biodegradation 22(1);1-11. PMID: 20480210

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

Taylor74: Taylor SS, Rigby PW, Hartley BS (1974). "Ribitol dehydrogenase from Klebsiella aerogenes. Purification and subunit structure." Biochem J 141(3);693-700. PMID: 4618776

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

Yoshida02a: Yoshida T, Fujita K, Nagasawa T (2002). "Novel reversible indole-3-carboxylate decarboxylase catalyzing nonoxidative decarboxylation." Biosci Biotechnol Biochem 66(11);2388-94. PMID: 12506977

Yoshida03a: Yoshida N, Uchida E, Katsuragi T, Tani Y (2003). "A novel NAD-dependent dehydrogenase, highly specific for 1,5-anhydro-D-glucitol, from Trichoderma longibrachiatum strain 11-3." Appl Environ Microbiol 69(5);2603-7. PMID: 12732527

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.5 on Wed Nov 25, 2015, BIOCYC14A.