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MetaCyc Compound: precorrin-3A

Superclasses: an organic heterocyclic compoundan organonitrogen heterocyclic compounda polypyrrolecyclic polypyrrolea cyclic tetrapyrrolea corrinoida precorrin

Summary:
The intermediates of the pathway between uroporphyrinogen-III and cobyrinate are termed precorrin-n, where n refers to the number of methyl groups that have been added to the uroporphyrinogen-III framework. They include precorrin-1, precorrin-2, precorrin-3A, precorrin-3B, precorrin-4, precorrin-5, precorrin-6A, precorrin-6B, precorrin-7 and precorrin-8x.

Chemical Formula: C43H43N4O16

Molecular Weight: 871.83 Daltons

Monoisotopic Molecular Weight: 879.3300066115 Daltons

precorrin-3A compound structure

SMILES: CC1(=C5([N+]C(=CC4(=NC(=CC3(NC(CC2(NC1=C(CC(=O)[O-])C(CCC(=O)[O-])=2))=C(CCC(=O)[O-])C(CC(=O)[O-])=3))C(CCC(=O)[O-])C(C)(CC(=O)[O-])4))C(CCC(=O)[O-])C(C)(CC(=O)[O-])5))

InChI: InChI=1S/C43H50N4O16/c1-19-40-23(13-37(58)59)21(5-9-33(50)51)27(46-40)14-26-20(4-8-32(48)49)22(12-36(56)57)28(44-26)15-29-24(6-10-34(52)53)42(2,17-38(60)61)31(45-29)16-30-25(7-11-35(54)55)43(3,18-39(62)63)41(19)47-30/h15-16,24-25,44,46-47H,4-14,17-18H2,1-3H3,(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)(H,62,63)/p-7/b29-15-,30-16-,41-19-/t24-,25-,42+,43+/m1/s1

InChIKey: InChIKey=AILJETHLKULYHE-IHDLTXBCSA-G

Unification Links: ChEBI:58561, KEGG:C05772, PubChem:25245613

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -74.60272Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

cob(II)yrinate a,c-diamide biosynthesis II (late cobalt incorporation) :
precorrin-3A + NADH + oxygen + H+ → precorrin-3B + NAD+ + H2O

Reactions known to produce the compound:

cob(II)yrinate a,c-diamide biosynthesis II (late cobalt incorporation) :
precorrin-2 + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + precorrin-3A + H+

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: tetrachloroethene reductive dehalogenase, corrinoid protein:5-methyltetrahydrosarcinapterin methyltransferase

Credits:
Revised 16-Oct-2012 by Caspi R, SRI International


References

Hagemeier06: Hagemeier CH, Krer M, Thauer RK, Warkentin E, Ermler U (2006). "Insight into the mechanism of biological methanol activation based on the crystal structure of the methanol-cobalamin methyltransferase complex." Proc Natl Acad Sci U S A 103(50);18917-22. PMID: 17142327

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

Neumann02: Neumann A, Siebert A, Trescher T, Reinhardt S, Wohlfarth G, Diekert G (2002). "Tetrachloroethene reductive dehalogenase of Dehalospirillum multivorans: substrate specificity of the native enzyme and its corrinoid cofactor." Arch Microbiol 177(5);420-6. PMID: 11976751

Paul96: Paul L, Krzycki JA (1996). "Sequence and transcript analysis of a novel Methanosarcina barkeri methyltransferase II homolog and its associated corrinoid protein homologous to methionine synthase." J Bacteriol 178(22);6599-607. PMID: 8932317

Tallant96: Tallant TC, Krzycki JA (1996). "Coenzyme M methylase activity of the 480-kilodalton corrinoid protein from Methanosarcina barkeri." J Bacteriol 178(5);1295-301. PMID: 8631705


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 Feb 10, 2016, BIOCYC11A.