MiMeDB: Showing metabocard for 2-Phosphoglyceric acid (MMDBc0030365)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:05:25 UTC

Update Date

2024-04-30 19:45:58 UTC

Metabolite ID

MMDBc0030365

Metabolite Identification

Common Name

2-Phosphoglyceric acid

Description

2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site. (PMID: 8994873 , Wikipedia )

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-2-(phosphonooxy)propanoic acid	ChEBI
3-Hydroxy-2-(phosphonooxy)propanoate	Generator
2-Phosphoglycerate	Generator
2-(Dihydrogen phosphate)glycerate	HMDB
2-(Dihydrogen phosphate)glyceric acid	HMDB
2-P-D-Glycerate	HMDB
2-P-D-Glyceric acid	HMDB
2-P-Glycerate	HMDB
2-P-Glyceric acid	HMDB
2-phospho-D-Glycerate	HMDB
2-phospho-DL-Glyceric acid	HMDB
3-Hydroxy-2-phosphonooxypropanoate	HMDB
3-Hydroxy-2-phosphonooxypropanoic acid	HMDB
DL-2-Phosphoglycerate	HMDB
Glycerate 2-phosphate	HMDB
Glyceric acid 2-phosphate	HMDB
Phosphoglycerate	HMDB
2-Phosphoglycerate, (+-)-isomer	MeSH, HMDB
2-Phosphoglycerate, (R)-isomer	MeSH, HMDB
2-Phosphoglycerate, (S)-isomer	MeSH, HMDB
2-Phosphoglycerate, monosodium salt	MeSH, HMDB
2-Phospho-DL-glyceric acid	HMDB
2-Phosphoglyceric acid	HMDB

Molecular Formula

C₃H₇O₇P

Average Mass

186.0572

Monoisotopic Mass

185.99293909

IUPAC Name

3-hydroxy-2-(phosphonooxy)propanoic acid

Traditional Name

2-phosphoglyceric acid

CAS Registry Number

2553-59-5

SMILES

OCC(OP(O)(O)=O)C(O)=O

InChI Identifier

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

InChI Key

GXIURPTVHJPJLF-UHFFFAOYSA-N

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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetronic acid derivative (CHEBI:24344 )
monophosphoglyceric acid (CHEBI:24344 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	20.3 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-1.6	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	0.81	ChemAxon
pKa (Strongest Basic)	-3.1	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	13.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9200000000-e2ebcf4711b384e44178	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9071000000-ee766df3166b5fd32cc6	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-91d2eb0c3d843dc23101	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-0d40ef3e26817734eb12	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-9a8f9f38b64222541995	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0pc0-8900000000-0ea2db58db10c9d65d8a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9100000000-5906d2344b35a6260d9a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9700000000-3c35d9442dbee0fecc88	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-9300000000-24ac9683b32428f58197	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9600000000-b12281d6d89eef904e6b	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-a07c4a51c820b32ec8bd	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4900000000-516a86a1a17689399892	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9500000000-b33f3e08e2e8b3d5aed5	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-07016cc3ecca7d5e323b	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9000000000-e2aa0f15a5d31307fa1e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-e1c96e130069d9cf375a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-91835bf01523e3aceb24	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-9000000000-d48b603841c58b435069	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cellular Cytoplasm

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191936	Bisphosphoglycerate mutase	Enzyme	P07738	Homo sapiens
MMDBp0191937	Phosphoglycerate mutase 2	Enzyme	P15259	Homo sapiens
MMDBp0191938	Probable phosphoglycerate mutase 4	Enzyme	Q8N0Y7	Homo sapiens
MMDBp0191939	Phosphoglycerate mutase 1	Enzyme	P18669	Homo sapiens
MMDBp0192416	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3	Enzyme	Q16875	Homo sapiens
MMDBp0192418	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4	Enzyme	Q16877	Homo sapiens
MMDBp0192419	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1	Enzyme	P16118	Homo sapiens
MMDBp0192424	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2	Enzyme	O60825	Homo sapiens
MMDBp0193063	Phosphoglycerate kinase 2	Enzyme	P07205	Homo sapiens
MMDBp0193084	Phosphoglycerate kinase 1	Enzyme	P00558	Homo sapiens
MMDBp0195873	Serine/threonine-protein phosphatase PGAM5, mitochondrial	Enzyme	Q96HS1	Homo sapiens
MMDBp0195874	Phosphoglycerate mutase	Enzyme	A4D2J6	Homo sapiens
MMDBp0195875	Phosphoglycerate mutase	Enzyme	Q0D2Q6	Homo sapiens
MMDBp0195876	Phosphoglycerate mutase	Enzyme	Q53G35	Homo sapiens
MMDBp0195877	Phosphoglycerate mutase	Enzyme	Q6FHU2	Homo sapiens
MMDBp0195878	Phosphoglycerate mutase	Enzyme	Q6P6D7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cellular cytoplasm	Detected and Quantified	14.0		9.0	19.0	uM	Adult (>18 years old)	Both	Normal	HMDB	15882454
Human Blood	Detected and Quantified	1.6	2.5			uM	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.

External Links

HMDB ID

HMDB0062707

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023161

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Phosphoglyceric_acid

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

24344

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Tsujino S, Shanske S, Sakoda S, Toscano A, DiMauro S: Molecular genetic studies in muscle phosphoglycerate mutase (PGAM-M) deficiency. Muscle Nerve Suppl. 1995;3:S50-3. doi: 10.1002/mus.880181412. [PubMed:7603528 ]
Fujii H: [Red cell glycolytic intermediates]. Nihon Rinsho. 1995 Mar;53 Su Pt 2:234-8. [PubMed:8753225 ]
Reed GH, Poyner RR, Larsen TM, Wedekind JE, Rayment I: Structural and mechanistic studies of enolase. Curr Opin Struct Biol. 1996 Dec;6(6):736-43. doi: 10.1016/s0959-440x(96)80002-9. [PubMed:8994873 ]
Mulquiney PJ, Bubb WA, Kuchel PW: Model of 2,3-bisphosphoglycerate metabolism in the human erythrocyte based on detailed enzyme kinetic equations: in vivo kinetic characterization of 2,3-bisphosphoglycerate synthase/phosphatase using 13C and 31P NMR. Biochem J. 1999 Sep 15;342 Pt 3:567-80. [PubMed:10477268 ]
Comi GP, Fortunato F, Lucchiari S, Bordoni A, Prelle A, Jann S, Keller A, Ciscato P, Galbiati S, Chiveri L, Torrente Y, Scarlato G, Bresolin N: Beta-enolase deficiency, a new metabolic myopathy of distal glycolysis. Ann Neurol. 2001 Aug;50(2):202-7. doi: 10.1002/ana.1095. [PubMed:11506403 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. doi: 10.1186/1742-4682-2-18. [PubMed:15882454 ]
Wang Y, Wei Z, Liu L, Cheng Z, Lin Y, Ji F, Gong W: Crystal structure of human B-type phosphoglycerate mutase bound with citrate. Biochem Biophys Res Commun. 2005 Jun 17;331(4):1207-15. doi: 10.1016/j.bbrc.2005.03.243. [PubMed:15883004 ]
Hakobyan D, Nazaryan K: Investigation of interaction between enolase and phosphoglycerate mutase using molecular dynamics simulation. J Biomol Struct Dyn. 2006 Jun;23(6):625-34. doi: 10.1080/07391102.2006.10507087. [PubMed:16615808 ]
Reher M, Bott M, Schonheit P: Characterization of glycerate kinase (2-phosphoglycerate forming), a key enzyme of the nonphosphorylative Entner-Doudoroff pathway, from the thermoacidophilic euryarchaeon Picrophilus torridus. FEMS Microbiol Lett. 2006 Jun;259(1):113-9. doi: 10.1111/j.1574-6968.2006.00264.x. [PubMed:16684110 ]

Showing metabocard for 2-Phosphoglyceric acid (MMDBc0030365)

MOL for #<Metabolite:0x00007fec9d9995a8>

3D MOL for #<Metabolite:0x00007fec9d9995a8>

3D SDF for #<Metabolite:0x00007fec9d9995a8>

3D-SDF for #<Metabolite:0x00007fec9d9995a8>

PDB for #<Metabolite:0x00007fec9d9995a8>

3D PDB for #<Metabolite:0x00007fec9d9995a8>

SMILES for #<Metabolite:0x00007fec9d9995a8>

INCHI for #<Metabolite:0x00007fec9d9995a8>

Structure for #<Metabolite:0x00007fec9d9995a8>

3D Structure for #<Metabolite:0x00007fec9d9995a8>