MetaCyc Compound: 3-phospho-D-glycerate

Synonyms: 3-phospho-(R)-glycerate, 3-phospho-D-glyceric acid, 3-P-D-glycerate, D-glycerate-3-P, D-glycerate 3-phosphate, 3-phosphoglycerate, D-3-phosphoglycerate

Superclasses: a glycerate 2/3-phospho-D-glycerate

Chemical Formula: C3H4O7P

Molecular Weight: 183.03 Daltons

Monoisotopic Molecular Weight: 185.9929390894 Daltons

3-phospho-D-glycerate compound structure

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

InChI: InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/p-3/t2-/m1/s1


Unification Links: CAS:820-11-1 , ChEBI:58272 , HMDB:HMDB60180 , IAF1260:34230 , KEGG:C00197 , MetaboLights:MTBLC58272 , PubChem:25245548

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -331.1141 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

glucosylglycerate biosynthesis I :
GDP-α-D-glucose + 3-phospho-D-glycerate → 2-O-(α-D-glucopyranosyl)-3-phospho-D-glycerate + GDP + H+

mannosylglucosylglycerate biosynthesis I :
UDP-α-D-glucose + 3-phospho-D-glycerate → 2-O-(α-D-glucopyranosyl)-3-phospho-D-glycerate + UDP + H+

mannosylglycerate biosynthesis I :
3-phospho-D-glycerate + GDP-α-D-mannose → mannosyl-3-phosphoglycerate + GDP + H+

phosphinothricin tripeptide biosynthesis :
CMP-5'-phosphonoformate + 3-phospho-D-glycerate + H2O → 2-phosphono-formylglycerate + CMP + phosphate + H+

Not in pathways:
3-phospho-D-glycerate + H2O → D-glycerate + phosphate

Reactions known to produce the compound:

Entner-Doudoroff pathway III (semi-phosphorylative) :
D-glyceraldehyde 3-phosphate + NAD+ + H2O → 3-phospho-D-glycerate + NADH + 2 H+

glycolate and glyoxylate degradation I , photorespiration :
D-glycerate + ATP → 3-phospho-D-glycerate + ADP + H+

glycolysis IV (plant cytosol) :
D-glyceraldehyde 3-phosphate + NADP+ + H2O → 3-phospho-D-glycerate + NADPH + 2 H+

Rapoport-Luebering glycolytic shunt :
2,3-diphospho-D-glycerate + H2O → 3-phospho-D-glycerate + phosphate

Reactions known to both consume and produce the compound:

1-butanol autotrophic biosynthesis :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

adenosine nucleotides degradation IV :
2 3-phospho-D-glycerate + 2 H+ ↔ D-ribulose-1,5-bisphosphate + CO2 + H2O

Bifidobacterium shunt :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

Calvin-Benson-Bassham cycle :
2 3-phospho-D-glycerate + 2 H+ ↔ D-ribulose-1,5-bisphosphate + CO2 + H2O
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

Entner-Doudoroff pathway III (semi-phosphorylative) , ethylene biosynthesis V (engineered) , photosynthetic 3-hydroxybutyrate biosynthesis (engineered) :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate

formaldehyde assimilation I (serine pathway) :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate

formaldehyde assimilation III (dihydroxyacetone cycle) , sucrose biosynthesis I (from photosynthesis) :
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

gluconeogenesis I :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

gluconeogenesis II (Methanobacterium thermoautotrophicum) :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
D-glyceraldehyde 3-phosphate + 2 an oxidized ferredoxin + H2O ↔ 3-phospho-D-glycerate + 2 a reduced ferredoxin + 3 H+

gluconeogenesis III :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

glycerol degradation to butanol :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

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

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

glycolysis III (from glucose) :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate

In Reactions of unknown directionality:

Not in pathways:
α-D-glucose 1-phosphate + 1,3-bisphospho-D-glycerate = α-glucose 1,6-bisphosphate + 3-phospho-D-glycerate + H+
1,3-bisphospho-D-glycerate + (polyphosphate)(n) = 3-phospho-D-glycerate + (polyphosphate)(n+1)
a [protein]-L-histidine + 2,3-diphospho-D-glycerate = a [protein]-Nπ-phospho-L-histidine + 3-phospho-D-glycerate
D-glyceraldehyde 3-phosphate + NAD(P)+ + H2O = 3-phospho-D-glycerate + NAD(P)H + 2 H+
an NDP-α-D-glucose + 3-phospho-D-glycerate = 2-O-(α-D-glucopyranosyl)-3-phospho-D-glycerate + a nucleoside diphosphate + H+
3-phospho-D-glycerate + GTP = 1,3-bisphospho-D-glycerate + GDP

Not in pathways:
a [protein]-Nπ-phospho-L-histidine + 2/3-phospho-D-glycerate = a [protein]-L-histidine + 2,3-diphospho-D-glycerate
a [protein]-L-histidine + 2,3-diphospho-D-glycerate = a [protein]-Nπ-phospho-L-histidine + 2/3-phospho-D-glycerate

Enzymes activated by 3-phospho-D-glycerate, sorted by the type of activation, are:

Activator (Allosteric) of: ADP-glucose pyrophosphorylase [Van96a] , ADP-glucose pyrophosphorylase [Kavakli02] , ADP-glucose pyrophosphorylase [Laughlin98]

Activator (Mechanism unknown) of: phosphoglycerate kinase , isocitrate dehydrogenase phosphatase [Miller00] , ADP-glucose pyrophosphorylase [Iglesias94] , pyruvate kinase [Singh98] , L-lactate dehydrogenase [Davies72]

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

Inhibitor (Competitive) of: glycerol-3-phosphate dehydrogenase, aerobic [Schryvers78] , isocitrate lyase [Comment 1] , triose phosphate isomerase [Tomlinson79]

Inhibitor (Noncompetitive) of: α-ketoglutarate reductase [Zhao96]

Inhibitor (Mechanism unknown) of: methylglyoxal synthase [Hopper71, Hopper72, Comment 2] , isocitrate dehydrogenase kinase [Miller00] , glutamine synthetase adenylyltransferase [Ebner70, Comment 3] , 6-phosphofructokinase [Garland80a] , 6-phosphofructokinase [Knowles90]

This compound has been characterized as an alternative substrate of the following enzymes: erythronate-4-phosphate dehydrogenase , phosphoglycolate phosphatase


Davies72: Davies DD, Davies S (1972). "Purification and properties of L(+)-lactate dehydrogenase from potato tubers." Biochem J 129(4);831-9. PMID: 4144124

Ebner70: Ebner E, Wolf D, Gancedo C, Elsasser S, Holzer H (1970). "ATP: glutamine synthetase adenylyltransferase from Escherichia coli B. Purification and properties." Eur J Biochem 1970;14(3);535-44. PMID: 4920894

Garland80a: Garland WJ, Dennis DT (1980). "Plastid and cytosolic phosphofructokinases from the developing endosperm of Ricinus communis. II. Comparison of the kinetic and regulatory properties of the isoenzymes." Arch Biochem Biophys 204(1);310-7. PMID: 6448584

Hopper71: Hopper DJ, Cooper RA (1971). "The regulation of Escherichia coli methylglyoxal synthase; a new control site in glycolysis?." FEBS Lett 13(4);213-216. PMID: 11945670

Hopper72: Hopper DJ, Cooper RA (1972). "The purification and properties of Escherichia coli methylglyoxal synthase." Biochem J 1972;128(2);321-9. PMID: 4563643

Iglesias94: Iglesias AA, Charng YY, Ball S, Preiss J (1994). "Characterization of the kinetic, regulatory, and structural properties of ADP-glucose pyrophosphorylase from Chlamydomonas reinhardtii." Plant Physiol 104(4);1287-94. PMID: 8016263

Kavakli02: Kavakli IH, Kato C, Choi SB, Kim KH, Salamone PR, Ito H, Okita TW (2002). "Generation, characterization, and heterologous expression of wild-type and up-regulated forms of Arabidopsis thaliana leaf ADP-glucose pyrophosphorylase." Planta 2002;215(3);430-9. PMID: 12111225

Knowles90: Knowles VL, Greyson MF, Dennis DT (1990). "Characterization of ATP-Dependent Fructose 6-Phosphate 1-Phosphotransferase Isozymes from Leaf and Endosperm Tissues of Ricinus communis." Plant Physiol 92(1);155-159. PMID: 16667239

Ko89: Ko YH, Vanni P, McFadden BA (1989). "The interaction of 3-phosphoglycerate and other substrate analogs with the glyoxylate- and succinate-binding sites of isocitrate lyase." Arch Biochem Biophys 1989;274(1);155-60. PMID: 2673042

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

Laughlin98: Laughlin MJ, Chantler SE, Okita TW (1998). "N- and C-terminal peptide sequences are essential for enzyme assembly, allosteric, and/or catalytic properties of ADP-glucose pyrophosphorylase." Plant J 1998;14(2);159-68. PMID: 9628013

Miller00: Miller SP, Chen R, Karschnia EJ, Romfo C, Dean A, LaPorte DC (2000). "Locations of the regulatory sites for isocitrate dehydrogenase kinase/phosphatase." J Biol Chem 275(2);833-9. PMID: 10625615

Schryvers78: Schryvers A, Lohmeier E, Weiner JH (1978). "Chemical and functional properties of the native and reconstituted forms of the membrane-bound, aerobic glycerol-3-phosphate dehydrogenase of Escherichia coli." J Biol Chem 253(3);783-8. PMID: 340460

Singh98: Singh DK, Malhotra SP, Singh R (1998). "Purification and characterizaton of plastidic pyruvate kinase from developing seeds of Brassica campestris L." Indian J Biochem Biophys 35(6);346-52. PMID: 10412228

Tomlinson79: Tomlinson J.D., Turner J.F. "Pea seed triose phosphate isomerase." Phytochemistry (1979) 18:1959-1962.

Van96a: Van den Koornhuyse N, Libessart N, Delrue B, Zabawinski C, Decq A, Iglesias A, Carton A, Preiss J, Ball S (1996). "Control of starch composition and structure through substrate supply in the monocellular alga Chlamydomonas reinhardtii." J Biol Chem 271(27);16281-7. PMID: 8663144

Zhao96: Zhao G, Winkler ME (1996). "A novel alpha-ketoglutarate reductase activity of the serA-encoded 3-phosphoglycerate dehydrogenase of Escherichia coli K-12 and its possible implications for human 2-hydroxyglutaric aciduria." J Bacteriol 1996;178(1);232-9. PMID: 8550422

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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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