P. aeruginosa Metabolome Database: Glyceric acid 1,3-biphosphate (PAMDB000317)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000317

Identification

Name:

Glyceric acid 1,3-biphosphate

Description:

1,3-Bisphosphogylcerate (1,3BPG), also known as PGAP, is a 3-carbon organic molecule present in most, if not all living creatures. It primarily exists as a metabolic intermediate in glycolysis during respiration.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

1,3-Biphosphoglycerate
1,3-Biphosphoglyceric acid
1,3-Bis-phosphoglycerate
1,3-Bis-phosphoglyceric acid
1,3-Bisphosphoglycerate
1,3-Bisphosphoglyceric acid
1,3-Diphosphateglycerate
1,3-Diphosphateglyceric acid
1,3-Diphosphoglycerate
1,3-Diphosphoglyceric acid
1,3-DPG
13-DPG
2-Hydroxy-3-(phosphonooxy)-Propanoate
2-Hydroxy-3-(phosphonooxy)-propanoate 1-anhydride with phosphate
2-Hydroxy-3-(phosphonooxy)-Propanoate 1-anhydride with phosphorate
2-Hydroxy-3-(phosphonooxy)-Propanoate 1-anhydride with phosphoric acid
2-Hydroxy-3-(phosphonooxy)-Propanoic acid
2-Hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphorate
2-Hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphoric acid
3-P-Glyceroyl-P
3-Phospho-D-glyceroyl phosphate
3-phospho-D-Glyceroyl phosphoric acid
3-Phospho-D-glyceroyl-phosphate
3-phospho-D-Glyceroyl-phosphoric acid
3-Phosphoglyceroyl phosphate
3-Phosphoglyceroyl phosphoric acid
3-Phosphoglyceroyl-P
3-Phosphoglyceroyl-phosphate
3-Phosphoglyceroyl-phosphoric acid
DPG
Glycerate 1,3-Biphosphate
Glycerate 1,3-bisphosphate
Glycerate 1,3-diphosphate
Glyceric acid 1,3-biphosphate
Glyceric acid 1,3-biphosphoric acid
Glyceric acid 1,3-bisphosphate
Glyceric acid 1,3-bisphosphoric acid
Glyceric acid 1,3-diphosphate
Glyceric acid 1,3-diphosphoric acid
P-Glyceroyl-P
Phosphoglyceroyl-P

Chemical Formula:

C₃H₈O₁₀P₂

Average Molecular Weight:

266.0371

Monoisotopic Molecular Weight:

265.9592695

InChI Key:

LJQLQCAXBUHEAZ-UHFFFAOYSA-N

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)

CAS number:

1981-49-3

IUPAC Name:

{[2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid

Traditional IUPAC Name:

1,3-bisphosphoglycerate

SMILES:

OC(COP(O)(O)=O)C(=O)OP(O)(O)=O

Chemical Taxonomy

Taxonomy Description

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

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Sugar acids and derivatives

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	9.64 mg/mL	ALOGPS
logP	-1.1	ALOGPS
logP	-2.3	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.01	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	42.42 m³·mol^-1	ChemAxon
Polarizability	18.04 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:

Cytoplasm

Reactions:

Pathways:

Glycolysis / Gluconeogenesis pae00010
Microbial metabolism in diverse environments pae01120

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1950000000-2cde7b5739871a882542	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014m-3910000000-72f2c46eab2036938056	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-9500000000-c835034f0ac11618922d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-6190000000-6f4870543fc6131d14a7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-d9d9c6d217a255d791fd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-1fef400a1ea8ca54c802	View in MoNA

References

References:

Carreras J, Bartrons R, Climent F, Cusso R: Bisphosphorylated metabolites of glycerate, glucose, and fructose: functions, metabolism and molecular pathology. Clin Biochem. 1986 Dec;19(6):348-58. Pubmed: 3555887
Fabry ME, Nagel RL: Heterogeneity of red cells in the sickler: a characteristic with practical clinical and pathophysiological implications. Blood Cells. 1982;8(1):9-15. Pubmed: 7115982
Flachner B, Varga A, Szabo J, Barna L, Hajdu I, Gyimesi G, Zavodszky P, Vas M: Substrate-assisted movement of the catalytic Lys 215 during domain closure: site-directed mutagenesis studies of human 3-phosphoglycerate kinase. Biochemistry. 2005 Dec 27;44(51):16853-65. Pubmed: 16363799
Fokina KV, Dainyak MB, Nagradova NK, Muronetz VI: A study on the complexes between human erythrocyte enzymes participating in the conversions of 1,3-diphosphoglycerate. Arch Biochem Biophys. 1997 Sep 15;345(2):185-92. Pubmed: 9308888
Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8. Pubmed: 8753225
Inoue H, Moriyasu M, Hamasaki N: Metabolism of 3-phosphoglyceroyl phosphate in phosphoenolpyruvate-enriched human erythrocytes. J Biol Chem. 1987 Jun 5;262(16):7635-8. Pubmed: 3584133
Joao HC, Williams RJ: The anatomy of a kinase and the control of phosphate transfer. Eur J Biochem. 1993 Aug 15;216(1):1-18. Pubmed: 8365395
Jovanovic S, Du Q, Crawford RM, Budas GR, Stagljar I, Jovanovic A: Glyceraldehyde 3-phosphate dehydrogenase serves as an accessory protein of the cardiac sarcolemmal K(ATP) channel. EMBO Rep. 2005 Sep;6(9):848-52. Pubmed: 16082386
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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(1):18. Pubmed: 15882454
Oimomi M, Yoshimura Y, Kubota S, Tanke G, Takagi K, Baba S: Effect of hydrocortisone on the synthesis of 2,3-diphosphoglycerate in human erythrocytes. Transfusion. 1982 Jul-Aug;22(4):266-8. Pubmed: 7101418
Sayed A, Matsuyama S, Inoue K, Alsina J, Cai F, Chen J, Inouye M: ATPase and GTPase activities copurifying with GTP-binding proteins in E. coli. J Mol Microbiol Biotechnol. 2000 Jul;2(3):261-3. Pubmed: 10937433
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	HMDB01270
Pubchem Compound ID	683
Kegg ID	C00236
ChemSpider ID	663
Wikipedia	1,3-Biphosphoglycerate
BioCyc ID	DPG
EcoCyc ID	DPG

Glyceric acid 1,3-biphosphate (PAMDB000317)

Structure for Glyceric acid 1,3-biphosphate (PAMDB000317)