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
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