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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
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MetaCyc Compound: 1,3-bisphospho-D-glycerate

Abbrev Name: 13-DPG

Synonyms: 3-phospho-D-glyceroyl-phosphate, 3-phosphoglyceroyl-P, P-glyceroyl-P, phosphoglyceroyl-P, 3-phosphoglyceroyl-phosphate, 3-P-glyceroyl-P, DPG, 13-DPG, glycerate 1,3-bisphosphate, 3-phosphonato-D-glyceroyl phosphate

Superclasses: a glycerate

Chemical Formula: C3H4O10P2

Molecular Weight: 262.01 Daltons

Monoisotopic Molecular Weight: 265.9592694978 Daltons

SMILES: C(C(O)C(OP(=O)([O-])[O-])=O)OP(=O)([O-])[O-]

InChI: InChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)/p-4/t2-/m1/s1

InChIKey: InChIKey=LJQLQCAXBUHEAZ-UWTATZPHSA-J

Unification Links: CAS:1981-49-3 , ChEBI:57604 , ChemSpider:19698372 , HMDB:HMDB01270 , IAF1260:34342 , KEGG:C00236 , MetaboLights:MTBLC57604 , PubChem:23405621

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -547.3985 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Calvin-Benson-Bassham cycle :
D-glyceraldehyde 3-phosphate + NADP+ + phosphate ← 1,3-bisphospho-D-glycerate + NADPH + H+

Rapoport-Luebering glycolytic shunt :
1,3-bisphospho-D-glycerate → 2,3-diphospho-D-glycerate + H+

Reactions known to both consume and produce the compound:

1-butanol autotrophic biosynthesis , Calvin-Benson-Bassham cycle :
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

Bifidobacterium shunt :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

formaldehyde assimilation III (dihydroxyacetone cycle) :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

gluconeogenesis I :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

gluconeogenesis III :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

glycerol degradation to butanol :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

glycolysis I (from glucose 6-phosphate) :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

glycolysis II (from fructose 6-phosphate) :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

glycolysis III (from glucose) :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

glycolysis IV (plant cytosol) :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

glycolysis VI (metazoan) :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

heterolactic fermentation :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

sucrose biosynthesis I (from photosynthesis) :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

superpathway of glucose and xylose degradation :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

Not in pathways:
D-glyceraldehyde 3-phosphate + NAD(P)+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NAD(P)H + H+

In Reactions of unknown directionality:

Not in pathways:
3-phospho-D-glycerate + GTP = 1,3-bisphospho-D-glycerate + GDP
1,3-bisphospho-D-glycerate + (polyphosphate)(n) = 3-phospho-D-glycerate + (polyphosphate)(n+1)
α-D-glucose 1-phosphate + 1,3-bisphospho-D-glycerate = α-glucose 1,6-bisphosphate + 3-phospho-D-glycerate + H+

Enzymes inhibited by 1,3-bisphospho-D-glycerate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: 6-phosphofructokinase [Turner03] , 6-phosphofructokinase [Turner03]

Credits:
Revised 28-Jul-2013 by Caspi R , SRI International


References

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

Turner03: Turner WL, Plaxton WC (2003). "Purification and characterization of pyrophosphate- and ATP-dependent phosphofructokinases from banana fruit." Planta 217(1);113-21. PMID: 12721855


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 21, 2014, BIOCYC14B.