Showing Compound Card for 2,3-Diphosphoglyceric acid (CDB004905)

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Record Information
Version1.0
Created at2020-04-17 18:49:00 UTC
Updated at2020-11-18 16:38:58 UTC
CannabisDB IDCDB004905
Secondary Accession NumbersNot Available
Cannabis Compound 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. The D-enantiomer of 2,3-bisphosphoglyceric acid. 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. Within humans, 2,3-diphosphoglyceric acid participates in a number of enzymatic reactions. In particular, 2,3-diphosphoglyceric acid can be biosynthesized from glyceric acid 1,3-biphosphate; which is catalyzed by the enzyme bisphosphoglycerate mutase. In addition, 2,3-diphosphoglyceric acid can be converted into 3-phosphoglyceric acid; which is catalyzed by the enzyme bisphosphoglycerate mutase. In humans, 2,3-diphosphoglyceric acid is involved in the metabolic disorder called the glycogen storage disease type 1A (gsd1a) or von gierke disease pathway. 2,3-Diphosphoglyceric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight266.04
Monoisotopic Molecular Weight265.9593
IUPAC Name(2R)-2,3-bis(phosphonooxy)propanoic acid
Traditional Namediphosphoglycerate
CAS Registry Number14438-19-8
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
Disposition

Source:

Biological location:

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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,3-Diphosphoglyceric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9320000000-fbd8c78fd88d592fab56Spectrum
Predicted GC-MS2,3-Diphosphoglyceric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006t-9410000000-ea4c253779009c08e1bdSpectrum
Predicted GC-MS2,3-Diphosphoglyceric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0930000000-5127f7f7568a961a80782012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-e9e3c8a32ece4b7f9fce2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006t-9300000000-e09861cf36df495519f62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0090000000-4a9ded352d59128107412012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-066r-1960000000-0d244402e55e5ef9de1d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0ar0-5960000000-1d5a4352115c6c5eb82f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9330000000-70ae76c58e470fe3b5942012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9100000000-6cacbc2756ef980dc5a22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0uxr-1490000000-ddf502cfcfd4ff0bca0b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00xr-6910000000-871a376b75658c914a1e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00xr-9200000000-ab1b55ce1ad971f1b3f82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-016r-9100000000-2af5a77daca9f7cef8522012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9100000000-1d6a9786ab78002b7ac22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0090000000-4a9ded352d59128107412017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-066r-1960000000-fcab8021959f67dc5a442017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ar0-5960000000-1d5a4352115c6c5eb82f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9330000000-70ae76c58e470fe3b5942017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-37f228e9721638e332122017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uxr-1490000000-ddf502cfcfd4ff0bca0b2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1930000000-6b2743652b0e2aa819602016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r2-8890000000-64b460dbcc7be6d3e8202016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-6900000000-7cbb7d86341bbdc1500a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-5090000000-73e5bca24796a45bebaf2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-a07defbdfd47a3f232252016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9f9abb79cd423f7b15f02016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Bisphosphoglycerate mutaseBPGM7q33P07738 details
Phosphoglycerate mutase 2PGAM27p13-p12P15259 details
Probable phosphoglycerate mutase 4PGAM4Xq13Q8N0Y7 details
Phosphoglycerate mutase 1PGAM110q25.3P18669 details
Multiple inositol polyphosphate phosphatase 1MINPP110q23Q9UNW1 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001294
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

Enzyme Details
1. Bisphosphoglycerate mutase
General function:
Involved in catalytic activity
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 5.4.2.1) and phosphatase (EC 3.1.3.13) activities.
Gene Name:
BPGM
Uniprot ID:
P07738
Molecular weight:
30004.98
Enzyme Details
2. Phosphoglycerate mutase 2
General function:
Involved in catalytic activity
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) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
Gene Name:
PGAM2
Uniprot ID:
P15259
Molecular weight:
28765.96
Enzyme Details
3. Probable phosphoglycerate mutase 4
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
Molecular weight:
28776.605
Enzyme Details
4. Phosphoglycerate mutase 1
General function:
Involved in catalytic activity
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) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
Gene Name:
PGAM1
Uniprot ID:
P18669
Molecular weight:
28803.675
Enzyme Details
5. Multiple inositol polyphosphate phosphatase 1
General function:
Involved in acid phosphatase activity
Specific function:
Acts as a phosphoinositide 5- and phosphoinositide 6-phosphatase and regulates cellular levels of inositol pentakisphosphate (InsP5) and inositol hexakisphosphate (InsP6). Also acts as a 2,3-bisphosphoglycerate 3-phosphatase, by mediating the dephosphorylation of 2,3-bisphosphoglycerate (2,3-BPG) to produce phospho-D-glycerate without formation of 3-phosphoglycerate. May play a role in bone development (endochondral ossification).
Gene Name:
MINPP1
Uniprot ID:
Q9UNW1
Molecular weight:
34660.555