Showing metabocard for 2,3-Diphosphoglyceric acid (BMDB0001294)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:43:42 UTC
Update Date2020-05-19 22:01:13 UTC
BMDB IDBMDB0001294
Secondary Accession Numbers
  • BMDB01294
Metabolite Identification
Common Name2,3-Diphosphoglyceric acid
Description2,3-Diphosphoglyceric acid, also known as 2,3-disphospho-D-glycerate or DPG, 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. 2,3-Diphosphoglyceric acid is an extremely strong acidic compound (based on its pKa). 2,3-Diphosphoglyceric acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3-Bisphospho-D-glycerateChEBI
2,3-Bisphosphoglyceric acidChEBI
2,3-BPGChEBI
2,3-Disphospho-D-glycerateChEBI
D-Greenwald esterChEBI
DPGChEBI
Glyceric acid bis(dihydrogen phosphate)ChEBI
Glyceric acid diphosphateChEBI
2,3-Bisphospho-D-glyceric acidGenerator
2,3-BisphosphoglycerateGenerator
2,3-Disphospho-D-glyceric acidGenerator
Glycerate bis(dihydrogen phosphate)Generator
Glyceric acid bis(dihydrogen phosphoric acid)Generator
Glycerate diphosphateGenerator
Glyceric acid diphosphoric acidGenerator
2,3-DiphosphoglycerateGenerator
(2R)-2,3-Bis(phosphonooxy)-propanoateHMDB
(2R)-2,3-Bis(phosphonooxy)-propanoic acidHMDB
(R)-2,3-Bis(phosphonooxy)-propanoateHMDB
(R)-2,3-Bis(phosphonooxy)-propanoic acidHMDB
2,3-Bis(phosphonooxy)-propanoateHMDB
2,3-Bis(phosphonooxy)-propanoic acidHMDB
2,3-Diphospho-D-glycerateHMDB
2,3-Diphospho-D-glyceric acidHMDB
2,3-Diphospho-D-glyceric acid pentasodium saltHMDB
D-Glyceric acid bisHMDB
D-Glyceric acid bis(dihydrogen phosphate)HMDB
DiphosphoglycerateHMDB
Diphosphoglyceric acidHMDB
Glycerate 2,3-diphosphateHMDB
2,3 Diphosphoglyceric acidHMDB
2,3 BisphosphoglycerateHMDB
2,3 DiphosphoglycerateHMDB
2,3-DPGHMDB
2,3-Diphosphoglycerate, (D)-isomerHMDB
Glycerate 2,3-bisphosphateHMDB
2,3-Bisphosphate, glycerateHMDB
(2R)-2,3-Bis(phosphonooxy)propanoic acidHMDB
(2R)-2,3-Bis(phosphonooxy)propionic acidHMDB
2,3-Bis(phosphonooxy)propanoic acidHMDB
2,3-Bis(phosphonooxy)propionic acidHMDB
2,3-Diphosphoglyceric acidHMDB
2,3-Diphosphonooxypropanoic acidHMDB
2,3-Diphosphonooxypropionic acidHMDB
Chemical FormulaC3H8O10P2
Average Molecular Weight266.0371
Monoisotopic Molecular Weight265.9592695
IUPAC Name(2R)-2,3-bis(phosphonooxy)propanoic acid
Traditional Namediphosphoglycerate
CAS Registry Number138-81-8
SMILES
OC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C3H8O10P2/c4-3(5)2(13-15(9,10)11)1-12-14(6,7)8/h2H,1H2,(H,4,5)(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1
InChI KeyXOHUEYCVLUUEJJ-UWTATZPHSA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Glyceric_acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-1.8ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)0.48ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.13 m³·mol⁻¹ChemAxon
Polarizability17.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9320000000-fbd8c78fd88d592fab56View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9410000000-ea4c253779009c08e1bdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0930000000-5127f7f7568a961a8078View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-e9e3c8a32ece4b7f9fceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006t-9300000000-e09861cf36df495519f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0090000000-4a9ded352d5912810741View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-066r-1960000000-0d244402e55e5ef9de1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0ar0-5960000000-1d5a4352115c6c5eb82fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9330000000-70ae76c58e470fe3b594View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9100000000-6cacbc2756ef980dc5a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0uxr-1490000000-ddf502cfcfd4ff0bca0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00xr-6910000000-871a376b75658c914a1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00xr-9200000000-ab1b55ce1ad971f1b3f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-016r-9100000000-2af5a77daca9f7cef852View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9100000000-1d6a9786ab78002b7ac2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0090000000-4a9ded352d5912810741View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-066r-1960000000-fcab8021959f67dc5a44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ar0-5960000000-1d5a4352115c6c5eb82fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9330000000-70ae76c58e470fe3b594View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-37f228e9721638e33212View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uxr-1490000000-ddf502cfcfd4ff0bca0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1930000000-6b2743652b0e2aa81960View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r2-8890000000-64b460dbcc7be6d3e820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-6900000000-7cbb7d86341bbdc1500aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-5090000000-73e5bca24796a45bebafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-a07defbdfd47a3f23225View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9f9abb79cd423f7b15f0View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Myelin sheath
Biospecimen Locations
  • Erythrocyte
  • Neuron
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001294
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022538
KNApSAcK IDNot Available
Chemspider ID161681
KEGG Compound IDC01159
BioCyc ID23-DIPHOSPHOGLYCERATE
BiGG ID1315507
Wikipedia Link2,3-Bisphosphoglyceric acid
METLIN ID153
PubChem Compound186004
PDB IDNot Available
ChEBI ID17720
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphoglycerate mutase 2
General function:
Carbohydrate transport and metabolism
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), but with a reduced activity.
Gene Name:
PGAM2
Uniprot ID:
Q32KV0
Molecular weight:
28685.0
Enzyme Details
2. Bisphosphoglycerate mutase
General function:
Carbohydrate transport and metabolism
Specific function:
Plays a major role in regulating hemoglobin oxygen affinity by controlling the levels of its allosteric effector 2,3-bisphosphoglycerate (2,3-BPG). Also exhibits mutase (EC 5.4.2.11) activity.
Gene Name:
BPGM
Uniprot ID:
Q3T014
Molecular weight:
30061.0
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
Enzyme Details
3. Phosphoglycerate mutase 1
General function:
Carbohydrate transport and metabolism
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), but with a reduced activity.
Gene Name:
PGAM1
Uniprot ID:
Q3SZ62
Molecular weight:
28852.0
Reactions
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Hydrogen phosphatedetails