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MetaCyc Compound: uroporphyrinogen-III

Synonyms: uroporphyrinogen III

Superclasses: a macrocycle a porphyrin

Summary:
Uroporphyrinogen-I and uroporphyrinogen-III are both naturally occurring isomers. The difference between the two is the relative positions of the acetyl and propanoyl side chains on only one of the rings. Where in uroporphyrinogen-I the side chains of all four rings have the same relative positions, in uroporphyrinogen-III the order is reversed on one of the rings.

While uroporphyrinogen-I can be formed spontaneously from hydroxymethylbilane, the formation of uroporphyrinogen-III requires a dedicated enzyme - EC 4.2.1.75, uroporphyrinogen-III synthase.

Both isomers are substrates for EC 4.1.1.37, uroporphyrinogen decarboxylase, although uroporphyrinogen-III is a better substrate [Cantoni84].

Chemical Formula: C40H36N4O16

Molecular Weight: 828.74 Daltons

Monoisotopic Molecular Weight: 836.2752313868 Daltons

SMILES: C(=O)([O-])CCC3(C(=C2(CC5(NC(CC4(NC(CC1(NC(=C(C=1CC(=O)[O-])CCC(=O)[O-])CC(N2)=3))=C(CC(=O)[O-])C=4CCC(=O)[O-]))=C(CC([O-])=O)C(CCC(=O)[O-])=5)))CC(=O)[O-])

InChI: InChI=1S/C40H44N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h41-44H,1-16H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/p-8

InChIKey: InChIKey=HUHWZXWWOFSFKF-UHFFFAOYSA-F

Unification Links: CAS:1976-85-8 , ChEBI:57308 , HMDB:HMDB01086 , IAF1260:36704 , KEGG:C01051 , MetaboLights:MTBLC57308 , PubChem:25202645

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -160.97144 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

chlorophyllide a biosynthesis I (aerobic, light-dependent) , chlorophyllide a biosynthesis II (anaerobic) , chlorophyllide a biosynthesis III (aerobic, light independent) , heme biosynthesis I (aerobic) , heme biosynthesis II (anaerobic) , superpathway of heme biosynthesis from uroporphyrinogen-III :
uroporphyrinogen-III + 4 H+ → coproporphyrinogen III + 4 CO2

cob(II)yrinate a,c-diamide biosynthesis I (early cobalt insertion) , cob(II)yrinate a,c-diamide biosynthesis II (late cobalt incorporation) , factor 430 biosynthesis , siroheme biosynthesis :
S-adenosyl-L-methionine + uroporphyrinogen-IIIS-adenosyl-L-homocysteine + precorrin-1 + H+

Not in pathways:
2 S-adenosyl-L-methionine + uroporphyrinogen-III → 2 S-adenosyl-L-homocysteine + precorrin-2 + H+

Reactions known to produce the compound:

tetrapyrrole biosynthesis I (from glutamate) , tetrapyrrole biosynthesis II (from glycine) :
hydroxymethylbilane → uroporphyrinogen-III + H2O

Enzymes inhibited by uroporphyrinogen-III, sorted by the type of inhibition, are:

Inhibitor (Allosteric) of: uroporphyrin-III (C2)-methyltransferase [Blanche89]

Credits:
Revised 21-Mar-2013 by Caspi R , SRI International


References

Blanche89: Blanche F, Debussche L, Thibaut D, Crouzet J, Cameron B (1989). "Purification and characterization of S-adenosyl-L-methionine: uroporphyrinogen III methyltransferase from Pseudomonas denitrificans." J Bacteriol 171(8);4222-31. PMID: 2546914

Cantoni84: Cantoni L, Dal Fiume D, Ruggieri R (1984). "Decarboxylation of uroporphyrinogen I and III in 2,3,7,8-tetrachlorodibenzo-p-dioxin induced porphyria in mice." Int J Biochem 16(5);561-5. PMID: 6724109

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


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 Fri Nov 28, 2014, BIOCYC14A.