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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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: 399.20774031070005 Daltons

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

InChIKey: InChIKey=GPKJTRJOBQGKQK-UHFFFAOYSA-P

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

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 421.66763 Inferred 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]


References

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


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 18.5 on Thu Nov 27, 2014, BIOCYC14B.