3-Phosphoglyceric acid (YMDB00341)

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Identification

YMDB ID

YMDB00341

Name

3-Phosphoglyceric acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

3-Phosphoglyceric acid, also known as glycerate 3-phosphate or 3-PG, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 3-Phosphoglyceric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Phosphoglyceric acid exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

3-(dihydrogen phosphate)Glycerate
3-(dihydrogen phosphate)Glyceric acid
3-Glycerophosphorate
3-Glycerophosphoric acid
3-P-D-glycerate
3-P-glycerate
3-pg
3-PGA
3-phospho-(R)-glycerate
3-phospho-D-glycerate
3-phospho-glycerate
3-phospho-glyceric acid
3-Phosphoglycerate
3-Phosphoglyceric acid
D-(-)-3-Phosphoglyceric acid
D-Glycerate 3-phosphate
G3P
Glycerate 3-phosphate
glycerate-3-P
Glyceric acid 3-phosphate
Phosphoglycerate
DL-Glycerate 3-phosphate
Glycerate 3-phosphates
3-(Dihydrogen phosphoric acid)glyceric acid
DL-Glyceric acid 3-phosphoric acid
Glyceric acid 3-phosphoric acid
Glyceric acid 3-phosphates
3-Phosphoglycerate, trisodium salt
3-Phosphoglycerate, (R)-isomer
3-Phosphoglycerate, monosodium salt

CAS number

820-11-1

Weight

Average: 186.0572
Monoisotopic: 185.99293909

InChI Key

OSJPPGNTCRNQQC-UHFFFAOYSA-N

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)

IUPAC Name

2-hydroxy-3-(phosphonooxy)propanoic acid

Traditional IUPAC Name

phosphoglycerate

Chemical Formula

C₃H₇O₇P

SMILES

[H]OC(=O)C([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Glyceric_acid
Monoalkyl phosphate
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetronic acid derivative (CHEBI:17050 )
monophosphoglyceric acid (CHEBI:17050 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	21 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-1.6	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	1.3	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.26 m³·mol⁻¹	ChemAxon
Polarizability	13.29 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Ethanol fermentation	PW002448
Glycerol metabolism	PW002407
Glycolysis I	PW002386
Starch and sucrose metabolism	PW002481
glycine metabolism	PW002398

KEGG Pathways

Starch and sucrose metabolism

ec00500

SMPDB Reactions

2,3-bisphospho-D-glyceric acid + water ↔ 3-Phosphoglyceric acid + phosphate

Glyceric acid 1,3-biphosphate + ADP → 3-Phosphoglyceric acid + Adenosine triphosphate

2,3-bisphospho-D-glyceric acid + water ↔ 3-Phosphoglyceric acid + phosphate

3-Phosphoglyceric acid ↔ 2-phospho-D-glyceric acid

3-Phosphoglyceric acid + NAD → NADH + hydron + Phosphohydroxypyruvic acid

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0974000000-41479250991be9cc1e07	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0974000000-41479250991be9cc1e07	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9200000000-2d6f0050126bbc72d771	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00fu-9081000000-487a9a33cdad68046ff3	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-002k-9300000000-4fafb3c93719c5a41327	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-004j-9000000000-c6bb9644e70a338c03be	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-004i-9000000000-9d164579c98406ad7c88	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a4i-0900000000-cea59554251398a27835	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0udi-0900000000-8a976aaa2f56f074d975	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a5c-9500000000-4bd264fcf029200c55c6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9100000000-1a020681f04042ff6966	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0900000000-cea59554251398a27835	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0900000000-8a976aaa2f56f074d975	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a5c-9600000000-4bd264fcf029200c55c6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9100000000-1a020681f04042ff6966	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0005-8900000000-bd4e0c8adef56968d87a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-9100000000-abd08e7a88ff6e65bc4b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9000000000-f8afa9e495e0f6c94717	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-9200000000-30ac9f237fd5b07a8ad8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9000000000-623d31045a6d2723a66b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0005-9800000000-592cc43b2d6718b5e805	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-75f21a1b3e228e0af7f2	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-3900000000-9d9dc94243143123d53b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kv-8900000000-b21c05dfded763ce62a0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c460ca316484eef90129	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-5900000000-653e5055531f19df4952	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-15195031d70847a75881	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-59550676899d259aeab5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004j-9000000000-0b41dc890757740bbb51	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Schwartz, J. M., Kanehisa, M. (2006). "Quantitative elementary mode analysis of metabolic pathways: the example of yeast glycolysis." BMC Bioinformatics 7:186.16584566
Takada, Y., Noguchi, T. (1985). "Characteristics of alanine: glyoxylate aminotransferase from Saccharomyces cerevisiae, a regulatory enzyme in the glyoxylate pathway of glycine and serine biosynthesis from tricarboxylic acid-cycle intermediates." Biochem J 231:157-163.3933486
Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Jakoby, Wm. B.; Brummond, Dewey O.; Ochoa, Severo. Formation of 3-phosphoglyceric acid by carbon dioxide fixation with spinach-leaf enzymes. Journal of Biological Chemistry (1956), 218 811-22.

External Links:

Resource	Link
CHEBI ID	17050
HMDB ID	HMDB00807
Pubchem Compound ID	724
Kegg ID	C00597
ChemSpider ID	704
FOODB ID	FDB022255
Wikipedia	3-Phosphoglyceric_acid
BioCyc ID	G3P

Enzymes

Protein Details

1. D-3-phosphoglycerate dehydrogenase 2

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: 3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:: SER33
Uniprot ID:: P40510
Molecular weight:: 51187.80078

Reactions

3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.

Protein Details

2. Phosphoglycerate kinase

General function:: Involved in phosphoglycerate kinase activity
Specific function:: ATP + 3-phospho-D-glycerate = ADP + 3-phospho- D-glyceroyl phosphate
Gene Name:: PGK1
Uniprot ID:: P00560
Molecular weight:: 44738.0

Reactions

ATP + 3-phospho-D-glycerate → ADP + 3-phospho-D-glyceroyl phosphate.

Protein Details

3. Phosphoglucomutase YMR278W

General function:: Involved in intramolecular transferase activity, phosphotransferases
Specific function:: This enzyme participates in both the breakdown and synthesis of glucose
Gene Name:: Not Available
Uniprot ID:: Q03262
Molecular weight:: 71068.60156

Reactions

Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-phosphate.

Protein Details

4. Phosphoglycerate mutase 1

General function:: Involved in catalytic activity
Specific function:: Interconversion of 3- and 2-phosphoglycerate with 2,3- bisphosphoglycerate as the primer of the reaction. Can also Catalyze the reaction of EC 5.4.2.4 (synthase) and EC 3.1.3.13 (phosphatase), but with a reduced activity
Gene Name:: GPM1
Uniprot ID:: P00950
Molecular weight:: 27608.30078

Reactions

2-phospho-D-glycerate → 3-phospho-D-glycerate.

Protein Details

5. Putative phosphoglycerate mutase DET1

General function:: Involved in catalytic activity
Specific function:: Involved, either directly or indirectly, in the bidirectional transport of sterols between the endoplasmic reticulum and the plasma membrane
Gene Name:: DET1
Uniprot ID:: Q99288
Molecular weight:: 39171.80078

Reactions

2-phospho-D-glycerate → 3-phospho-D-glycerate.

Protein Details

6. Probable phosphoglycerate mutase YOR283W

General function:: Involved in catalytic activity
Specific function:: Catalyzes the interconversion of 2-phosphoglycerate and 3-phosphoglycerate
Gene Name:: Not Available
Uniprot ID:: Q12040
Molecular weight:: 26176.5

Reactions

2-phospho-D-glycerate → 3-phospho-D-glycerate.

Protein Details

7. Phosphoglycerate mutase 3

General function:: Involved in catalytic activity
Specific function:: Could be non-functional
Gene Name:: GPM3
Uniprot ID:: Q12326
Molecular weight:: 34863.19922

Reactions

2-phospho-D-glycerate → 3-phospho-D-glycerate.

Protein Details

8. Phosphoglycerate mutase 2

General function:: Involved in catalytic activity
Specific function:: Could be non-functional
Gene Name:: GPM2
Uniprot ID:: Q12008
Molecular weight:: 36072.80078

Reactions

2-phospho-D-glycerate → 3-phospho-D-glycerate.

Protein Details

9. D-3-phosphoglycerate dehydrogenase 1

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: 3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:: SER3
Uniprot ID:: P40054
Molecular weight:: 51192.80078

Reactions

3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.

Structure for #<Compound:0xab31ad70>

Enzymes

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