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MetaCyc Compound: atabrine

Synonyms: quinacrine mustard, mepacrine, chinacrin, atebrin, acrichine, quinacrine

Chemical Formula: C23H32N3OCl

Molecular Weight: 401.98 Daltons

Monoisotopic Molecular Weight: 401.2233903749 Daltons

atabrine compound structure

SMILES: CC[N+](CCCC(NC2(C3(C([N+]=C1(C=CC(=CC1=2)OC))=CC(=CC=3)Cl)))C)CC

InChI: InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)/p+2


Unification Links: CAS:83-89-6, ChEBI:8711, ChemSpider:10296089, DrugBank:DB01103, HMDB:HMDB15235, KEGG:C07339, PubChem:15329120

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 421.66763Inferred by computational analysis [Latendresse13]

Enzymes activated by atabrine, sorted by the type of activation, are:

Activator (Mechanism unknown) of: hydroxylamine oxidoreductase [Hooper65], sucrose 3-dehydrogenase [Hayano67]

Enzymes inhibited by atabrine, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: biotin sulfoxide reductase [Comment 1], 6-hydroxynicotinate dehydrogenase [Hirschberg71], 4-imidazolone-5-propionate oxidase [Hassall68], nicotinate dehydrogenase [Hirschberg71], cis-4-hydroxy-D-proline dehydrogenase [Yoneya61], hydroxyproline 2-epimerase [Adams64] Inhibitor (Other types) of: indole 2,3-dioxygenase [Divakar79], indole 2,3-dioxygenase [Nair64]


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

Del79: Del Campillo-Campbell, A, Dykhuizen, D, Cleary, PP "Enzymatic reduction of d-biotin d-sulfoxide to d-biotin." Methods in Enzymology 62:379-385 (1979).

Divakar79: Divakar, N.G., Subramanian, V., Sugumaran, M., Vaidyanathan, C.S. (1979). "Indole oxygenase from the leaves of Jasminum grandiflorum." Plant Sci. Lett. 1:177-181.

Hassall68: Hassall H, Greenberg DM (1968). "Studies on the enzymic decomposition of urocanic acid. VI. Properties of the enzyme catalyzing the oxidation of 4(5)-imidazolone-5(4)-propionic acid to L-hydantoin-5-propionic acid." Arch Biochem Biophys 125(1);278-85. PMID: 4967723

Hayano67: Hayano K, Fukui S (1967). "Purification and properties of 3-ketosucrose-forming enzyme from the cells of Agrobacterium tumefaciens." J Biol Chem 242(16);3655-72. PMID: 6038493

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

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

Nair64: Nair PM, Vaidyanathan CS (1964). "An indole oxidase isolated from the leaves of Tecoma stans." Biochim Biophys Acta 81;496-506. PMID: 14170321

Yoneya61: Yoneya T, Adams E (1961). "Hydroxyproline metabolism. V. Inducible allohydroxy-D-proline oxidase of Pseudomonas." J Biol Chem 236;3272-9. PMID: 14009182

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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