Page last updated: 2024-12-04

2,3-diphosphoglycerate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2,3-Diphosphoglycerate (2,3-DPG) is a key regulator of oxygen delivery in red blood cells. It is synthesized from 1,3-diphosphoglycerate, an intermediate in glycolysis, by the enzyme 2,3-diphosphoglycerate mutase. 2,3-DPG binds to the deoxyhemoglobin form of hemoglobin, decreasing its affinity for oxygen and thus promoting the release of oxygen to tissues. 2,3-DPG levels are influenced by factors such as altitude, anemia, and pregnancy. Its importance lies in its role in maintaining adequate oxygen delivery to tissues under various physiological conditions. Research on 2,3-DPG focuses on understanding its role in oxygen transport, its regulation in different physiological states, and its potential therapeutic applications in conditions affecting oxygen delivery, such as anemia.'

2,3-Diphosphoglycerate: A highly anionic organic phosphate which is present in human red blood cells at about the same molar ratio as hemoglobin. It binds to deoxyhemoglobin but not the oxygenated form, therefore diminishing the oxygen affinity of hemoglobin. This is essential in enabling hemoglobin to unload oxygen in tissue capillaries. It is also an intermediate in the conversion of 3-phosphoglycerate to 2-phosphoglycerate by phosphoglycerate mutase (EC 5.4.2.1). (From Stryer Biochemistry, 4th ed, p160; Enzyme Nomenclature, 1992, p508) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2,3-bisphosphoglyceric acid : A bisphosphoglyceric acid that is glyceric acid carrying two phospho substituents at positions 2 and 3. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID61
CHEMBL ID144103
CHEBI ID28907
SCHEMBL ID80335
MeSH IDM0029370

Synonyms (37)

Synonym
138-81-8
2,3-diphosphoglyceric acid
2,3-bis(phosphonooxy)propanoic acid
CHEBI:28907 ,
2,3-diphosphoglycerate
propanoic acid, 2,3-bis(phosphonooxy)-, (r)-
glyceric acid, bis(dihydrogen phosphate) (8ci)
glycerate 2,3-diphosphate
2,3-diphospho-d-glyceric acid
2,3-dpg
diphosphoglyceric acid
glyceric acid, bis(dihydrogen phosphate), d- (8ci)
propanoic acid, 2,3-bis(phosphonooxy)- (9ci)
propanoic acid, 2,3-bis(phosphonooxy)-, (2r)- (9ci)
glyceric acid, diphosphate (6ci)
2,3-bisphosphoglycerate
greenwald ester
C03339
2,3-diphosphonooxypropanoic acid
2,3-bisphosphoglyceric acid
glyceric acid-2,3-diphosphate
D197673E-606F-4637-BB24-A390C435FB9F
CHEMBL144103
propanoic acid, 2,3-bis(phosphonooxy)-
tz4454o4yz ,
unii-tz4454o4yz
SCHEMBL80335
glyceric acid, bis(dihydrogen phosphate)
glyceric acid, diphosphate
XOHUEYCVLUUEJJ-UHFFFAOYSA-N
diphosphoglycerinsaure
2,3-bisphospho-glycerate
Q209155
2,3-bisphosphoglycericacid
CS-0059437
HY-113050
DTXSID10861801

Research Excerpts

Overview

2,3-Diphosphoglycerate is an inhibitor at physiological concentrations (Ki = 2 mM)

ExcerptReferenceRelevance
"2,3-Diphosphoglycerate is an inhibitor at physiological concentrations (Ki = 2 mM)."( Properties of a membrane-bound tyrosine kinase phosphorylating the cytosolic fragment of the red cell membrane band 3 protein.
Bertrand, O; Boivin, P; Galand, C, 1986
)
0.99

Effects

ExcerptReferenceRelevance
"2,3-Diphosphoglycerate (2,3-DPG) has been found to be the product of the enzymatic degradation of cyclic 2,3-diphosphoglycerate (cDPG) in the archaebacterium Methanobacterium thermoautotrophicum delta H. "( Enzymatic degradation of cyclic 2,3-diphosphoglycerate to 2,3-diphosphoglycerate in Methanobacterium thermoautotrophicum.
Moynihan, JA; Roberts, MF; Robertson, DE; Sastry, MV, 1992
)
2.01

Treatment

ExcerptReferenceRelevance
"2,3-Diphosphoglycerate levels of GV-treated blood significantly decreased from the 21st to the 28th day in relation to the control."( Metabolism and preservation of fresh and stored erythrocytes in blood treated with gentian violet.
Barretto, OC; Juliano, Y; Kerbauy, J; Moraes-Souza, H; Nonoyama, K; Pühler, GM, 1988
)
1

Toxicity

ExcerptReferenceRelevance
"5 LD50 and 1 LD50 doses in female rabbits resulted in significant changes in physiological, clinico-chemical and histological parameters."( Acute toxicity of methyl isocyanate, administered subcutaneously in rabbits: changes in physiological, clinico-chemical and histological parameters.
Jeevarathinam, K; Mukhopadhyay, S; Ray, US; Selvamurthy, W; Thakur, L, 1988
)
0.27

Compound-Compound Interactions

ExcerptReferenceRelevance
" Here, we investigated the killing effect of cisplatin combined with hyperthermia on human hepatocarcinoma (HepG2) cells and erythrocytes from IBS in vitro."( Cisplatin combined with hyperthermia kills HepG2 cells in intraoperative blood salvage but preserves the function of erythrocytes.
Liu, YQ; Tang, LH; Wang, LJ; Wang, Y; Yan, M; Yang, JT; Zhang, FJ, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
", in factors involved in the bioavailability of oxygen (oxygen transport activity and RBC deformability)."( Experimental approach of activity and mechanism(s) of action of drugs used in cerebral metabolic insufficiency. Application to 1-eburnamonine.
Gueguen, M; Hollands, MA; Le Polles, JB; Linee, P; Quiniou, P, 1981
)
0.26
" I hypothesize that NO may suppress BPG production by (1) inhibiting glyceraldehyde-3-phosphate dehydrogenase (G3PDH), the most critical glycolytic enzyme for the bioavailability of 1,3-bisphosphoglycerate; and to a lesser extent by (2) associated pH changes in the deoxy-Hb-catalyzed depletion of nitrite, a metabolic reservoir of NO."( Nitric oxide-mediated suppression of 2,3-bisphosphoglycerate synthesis: therapeutic relevance for environmental hypoxia and sickle cell disease.
Bertrand, R, 2012
)
0.38

Dosage Studied

ExcerptRelevanceReference
" An in vivo rejuvenating technique, employing fructose-1,6-diphosphate (FDP) at a mean dosage of 1 mmol kg-1 day-1 of phosphate, to increase the DPG circulating level in multi-transfused patients is proposed."( Restoration of blood 2,3-diphosphoglycerate levels in multi-transfused patients: effect of organic and inorganic phosphate.
Franzosi, MG; Iapichino, G; Pallavicini, FB; Radrizzani, D; Scherini, A; Solca, M; Spina, G,
)
0.45
" Also, in vitro analysis of the effects of the catecholamines, oxygen tension, lactate and adenosine may be helpful in understanding the dose-response relationship between these variables and 2,3-BPG concentration."( The effects of acute exercise on levels of erythrocyte 2,3-bisphosphoglycerate: a brief review.
Brown, SP; Keith, WB, 1993
)
0.29
"03) sampled just before dialysis correlated significantly and positively with the total weekly dosage of erythropoietin given to the patients."( Oxygen and 2,3 biphosphoglycerate (2,3-BPG) during haemodialysis.
Andersen, EM; Jensen, HA; Jørgensen, LG; Nielsen, AL, 1998
)
0.3
"The two basic aims of this study were to add to the limited literature concerning Inosine as an ergogenic aid, and to determine the effects of Inosine supplementation over a period of 5 and 10 days, at a dosage of 10,000 mg."( Inosine supplementation has no effect on aerobic or anaerobic cycling performance.
Dalton, B; McNaughton, L; Tarr, J, 1999
)
0.3
" Dose-response curves indicate small chloride effects and pronounced and differentiated phosphate effects, DPG < ATP < GTP < IHP."( Isohemoglobin differentiation in the bimodal-breathing amazon catfish Hoplosternum littorale.
Bang, A; Dewilde, S; Fago, A; Moens, L; Val, AL; Van Hauwaert, ML; Weber, RE; Zal, F, 2000
)
0.31
" Whilst there is evidence to support the ergogenic benefits of sodium phosphate, many studies researching this substance differ in terms of the administered dose and dosing protocol, the washout period employed and the fitness level of the participants recruited."( Sodium phosphate as an ergogenic aid.
Buck, CL; Dawson, B; Guelfi, KJ; Wallman, KE, 2013
)
0.39
" After daily dosing of etavopivat over 5 consecutive days in NHPs, ATP was increased by 38% from baseline."( Etavopivat, a Pyruvate Kinase Activator in Red Blood Cells, for the Treatment of Sickle Cell Disease.
Drake, A; Fessler, R; Forsyth, S; Fulzele, K; Guichard, S; Kalfa, TA; Konstantinidis, DG; Marshall, CG; Ribadeneira, MD; Schroeder, P; Seu, KG; Wilker, E, 2022
)
0.72
" When animals lacking 2,3-DPG were dosed with a compound designed to increase hemoglobin oxygen affinity, oxygen delivery related toxicity was observed."( Effects of 2,3-DPG knockout on SCD phenotype in Townes SCD model mice.
Ahn, Y; Barakat, A; Field, D; Jasuja, R; Kapinos, B; Knee, KM; Lintner, N; Pagan, V; Petterson, BA; Ramaiah, L; Sawant, A; Tomlinson, L; Wenzel, Z, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
bisphosphoglyceric acidA glyceric acid phosphate in which both of the hydroxy groups have been phosphorylated.
tetronic acid derivativeAn aldonic acid derivative that is formally obtained from a tetronic acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID92761Tested for binding affinity against human erythrocyte 5-phosphatase1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Synthesis of selective non-Ca(2+)-mobilizing inhibitors of D-myo-inositol 1,4,5-trisphosphate 5-phosphatase.
AID221770Effective concentration to activate gammadelta T cells2002Journal of medicinal chemistry, Oct-24, Volume: 45, Issue:22
Quantitative structure--activity relations for gammadelta T cell activation by phosphoantigens.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,306)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990637 (48.77)18.7374
1990's368 (28.18)18.2507
2000's168 (12.86)29.6817
2010's111 (8.50)24.3611
2020's22 (1.68)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 64.36

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index64.36 (24.57)
Research Supply Index7.28 (2.92)
Research Growth Index4.29 (4.65)
Search Engine Demand Index112.82 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (64.36)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials39 (2.75%)5.53%
Reviews71 (5.01%)6.00%
Case Studies28 (1.97%)4.05%
Observational1 (0.07%)0.25%
Other1,279 (90.20%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]