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Human Metabolome Database Version 3.5

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Showing metabocard for Glyceric acid 1,3-biphosphate (HMDB01270)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:13 -0700
HMDB ID HMDB01270
Secondary Accession Numbers None
Metabolite Identification
Common 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. 1,3BPG have been recognized as regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. 1,3BPG concentration in erythrocytes changes in a number of pathological conditions, such as Inherited Phosphoglycerate kinase deficiency in erythrocytes (involved in the synthesis and breakdown of 1,3 BPG). (PMID 3555887 Link_out). 1,3-bisphosphoglycerate is the anion form of bisphosphoglyceric acid. It is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ADP to form the energy storage molecule ATP.(wikipedia).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,3-Biphosphoglycerate
  2. 1,3-Biphosphoglyceric acid
  3. 1,3-Bis-phosphoglycerate
  4. 1,3-Bisphosphoglycerate
  5. 1,3-Diphosphateglycerate
  6. 1,3-Diphosphoglycerate
  7. 13-DPG
  8. 2-Hydroxy-3-(phosphonooxy)-Propanoate
  9. 2-Hydroxy-3-(phosphonooxy)-Propanoic acid
  10. 2-Hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphorate
  11. 2-Hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphoric acid
  12. 3-P-Glyceroyl-P
  13. 3-Phospho-D-glyceroyl phosphate
  14. 3-Phospho-D-glyceroyl-phosphate
  15. 3-Phosphoglyceroyl phosphate
  16. 3-Phosphoglyceroyl-P
  17. 3-Phosphoglyceroyl-phosphate
  18. DPG
  19. Glycerate 1,3-Biphosphate
  20. Glycerate 1,3-bisphosphate
  21. Glycerate 1,3-diphosphate
  22. Glyceric acid 1,3-biphosphate
  23. P-Glyceroyl-P
  24. Phosphoglyceroyl-P
Chemical Formula C3H8O10P2
Average Molecular Weight 266.0371
Monoisotopic Molecular Weight 265.9592695
IUPAC Name [2-hydroxy-3-oxo-3-(phosphonooxy)propoxy]phosphonic acid
Traditional IUPAC Name 2-hydroxy-3-oxo-3-(phosphonooxy)propoxyphosphonic acid
CAS Registry Number 1981-49-3
SMILES OC(COP(O)(O)=O)C(=O)OP(O)(O)=O
InChI Identifier 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)
InChI Key LJQLQCAXBUHEAZ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organophosphorus Compounds
Class Organic Phosphoric Acids and Derivatives
Sub Class Organophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organophosphate Esters
Substituents
  • Alpha Hydroxy Acid
  • Glyceric Acid
  • Organic Hypophosphite
  • Organic Phosphite
  • Secondary Alcohol
Direct Parent Acyl Phosphates
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 9.64 g/L ALOGPS
LogP -1.14 ALOGPS
LogP -2.3 ChemAxon
LogS -1.44 ALOGPS
pKa (strongest acidic) 1.01 ChemAxon
pKa (strongest basic) -4.2 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 170.82 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 42.42 ChemAxon
Polarizability 18.04 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Cellular Cytoplasm
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Glycolysis SMP00040 map00010 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Glycerol Phosphate Shuttle SMP00124 Not Available
Mitochondrial Electron Transport Chain SMP00355 map00190 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cellular Cytoplasm Detected and Quantified
Article_icon
0.4 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022524
KNApSAcK ID Not Available
Chemspider ID 663 Link_out
KEGG Compound ID C00236 Link_out
BioCyc ID DPG Link_out
BiGG ID 34342 Link_out
Wikipedia Link 1,3-Biphosphoglycerate Link_out
NuGOwiki Link HMDB01270 Link_out
Metagene Link HMDB01270 Link_out
METLIN ID Not Available
PubChem Compound 683 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8. Pubmed: 8753225 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
Enzymes
Name: Bisphosphoglycerate mutase
Reactions:
  • 3-phospho-D-glyceroyl phosphate = 2,3-bisphospho-D-glycerate [RN:R01662]
Gene Name: BPGM
Uniprot ID: P07738 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylphosphatase-1
Reactions:
  • an acylphosphate + H2O = a carboxylate + phosphate [RN:R00539]
Gene Name: ACYP1
Uniprot ID: P07311 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glyceraldehyde-3-phosphate dehydrogenase, testis-specific
Reactions:
  • D-glyceraldehyde 3-phosphate + phosphate + NAD+ = 3-phospho-D-glyceroyl phosphate + NADH + H+ [RN:R01061]
Gene Name: GAPDHS
Uniprot ID: O14556 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate kinase 1
Reactions:
  • ATP + 3-phospho-D-glycerate = ADP + 3-phospho-D-glyceroyl phosphate [RN:R01512]
Gene Name: PGK1
Uniprot ID: P00558 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA