Record Information
Version1.0
Creation Date2016-09-30 22:43:24 UTC
Update Date2020-05-21 16:29:05 UTC
BMDB IDBMDB0001270
Secondary Accession Numbers
  • BMDB01270
Metabolite Identification
Common NameGlyceric acid 1,3-biphosphate
DescriptionGlyceric acid 1,3-biphosphate, also known as 1,3-biphosphoglycerate or 3-phospho-D-glyceroyl phosphate, belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl. Glyceric acid 1,3-biphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceric acid 1,3-biphosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
(R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoic acidChEBI
1,3-Bisphospho-D-glycerateChEBI
3-Phospho-D-glyceroyl phosphateChEBI
D-Glycerate 1,3-diphosphateKegg
(R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoateGenerator
1,3-Bisphospho-D-glyceric acidGenerator
3-Phospho-D-glyceroyl phosphoric acidGenerator
D-Glyceric acid 1,3-diphosphoric acidGenerator
Glycerate 1,3-biphosphateGenerator
Glyceric acid 1,3-biphosphoric acidGenerator
3-Phospho-D-glyceroyl dihydrogen phosphoric acidHMDB
1,3-BiphosphoglycerateHMDB
1,3-BisphosphoglycerateHMDB
1,3-Bisphosphoglyceric acidHMDB
1,3-DiphosphoglycerateHMDB
1,3-Diphosphoglyceric acidHMDB
3-Phospho-D-glyceroyl-phosphateHMDB
3-Phosphoglyceroyl phosphateHMDB
3-Phosphoglyceroyl-pHMDB
3-Phosphoglyceroyl-phosphateHMDB
3-Phosphonato-D-glyceroyl phosphateHMDB
3-Phosphonatoglyceroyl phosphateHMDB
3-p-Glyceroyl-pHMDB
D-Glycerate 1,3-biphosphateHMDB
D-Glycerate 1,3-bisphosphateHMDB
D-Glyceric acid 1,3-biphosphateHMDB
D-Glyceric acid 1,3-bisphosphateHMDB
D-Glyceric acid 1,3-diphosphateHMDB
DPGHMDB
Glycerate 1,3-bisphosphateHMDB
Glycerate 1,3-diphosphateHMDB
Glyceric acid 1,3-bisphosphateHMDB
Glyceric acid 1,3-diphosphateHMDB
Phosphoglyceroyl-pHMDB
p-Glyceroyl-pHMDB
Glyceric acid 1,3-biphosphateHMDB
Chemical FormulaC3H8O10P2
Average Molecular Weight266.0371
Monoisotopic Molecular Weight265.9592695
IUPAC Name{[(2R)-2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
Traditional Name1,3-bisphospho-D-glycerate
CAS Registry Number1981-49-3
SMILES
O[C@H](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)/t2-/m1/s1
InChI KeyLJQLQCAXBUHEAZ-UWTATZPHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentAcyl monophosphates
Alternative Parents
Substituents
  • Acyl monophosphate
  • Glyceric_acid
  • Monoalkyl phosphate
  • Monosaccharide
  • Alkyl phosphate
  • Carboxylic acid salt
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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-1.1ALOGPS
logP-2.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.01ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.42 m³·mol⁻¹ChemAxon
Polarizability18.01 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, Positivesplash10-0002-9500000000-cb3071f9249ee92b7d2cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1950000000-2cde7b5739871a882542View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-3910000000-72f2c46eab2036938056View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9500000000-c835034f0ac11618922dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-6190000000-6f4870543fc6131d14a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d9d9c6d217a255d791fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1fef400a1ea8ca54c802View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0090000000-def40aa9bb3094302ce8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-9040000000-374a9ff8c866f10f2f3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4bf2b9a14f4e1c8fc62aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-1390000000-8fe62bbfc56bf59f28a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9410000000-e17767e21640a6f81532View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-c41dab2684b9d54afd31View in MoNA
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001270
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030188
KNApSAcK IDC00019552
Chemspider IDNot Available
KEGG Compound IDC00236
BioCyc IDDPG
BiGG IDNot Available
Wikipedia Link1,3-Bisphosphoglyceric acid
METLIN IDNot Available
PubChem Compound439191
PDB IDNot Available
ChEBI ID16001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Glyceraldehyde-3-phosphate dehydrogenase is a key enzyme in glycolysis that catalyzes the first step of the pathway by converting D-glyceraldehyde 3-phosphate (G3P) into 3-phospho-D-glyceroyl phosphate. Modulates the organization and assembly of the cytoskeleton. Facilitates the CHP1-dependent microtubule and membrane associations through its ability to stimulate the binding of CHP1 to microtubules. Also participates in nuclear events including transcription, RNA transport, DNA replication and apoptosis. Nuclear functions are probably due to the nitrosylase activity that mediates cysteine S-nitrosylation of nuclear target proteins such as SIRT1, HDAC2 and PRKDC. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma treatment assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation (By similarity).
Gene Name:
GAPDH
Uniprot ID:
P10096
Molecular weight:
35868.0
Reactions
D-Glyceraldehyde 3-phosphate + NAD + Hydrogen phosphate → Glyceric acid 1,3-biphosphate + NADHdetails
D-Glyceraldehyde 3-phosphate + NAD → Glyceric acid 1,3-biphosphate + Hydrogen phosphate + NADHdetails
General function:
Carbohydrate transport and metabolism
Specific function:
May play an important role in regulating the switch between different pathways for energy production during spermiogenesis and in the spermatozoon. Required for sperm motility and male fertility (By similarity).
Gene Name:
GAPDHS
Uniprot ID:
Q2KJE5
Molecular weight:
43288.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GAPDL17
Uniprot ID:
Q9XSN4
Molecular weight:
11514.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q862K5
Molecular weight:
15626.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GAPDH
Uniprot ID:
Q0QES8
Molecular weight:
24259.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
gapdh
Uniprot ID:
Q4H0Z3
Molecular weight:
10913.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GAPDH
Uniprot ID:
Q712W6
Molecular weight:
28755.0
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
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
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
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes one of the two ATP producing reactions in the glycolytic pathway via the reversible conversion of 1,3-diphosphoglycerate to 3-phosphoglycerate. In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein). May play a role in sperm motility.
Gene Name:
PGK1
Uniprot ID:
Q3T0P6
Molecular weight:
44538.0
Reactions
Glyceric acid 1,3-biphosphate + ADP → 3-Phosphoglyceric acid + Adenosine triphosphatedetails
General function:
Involved in ATP binding
Specific function:
Plays a role in the physiological regulation of coenzyme A (CoA) levels.
Gene Name:
PANK3
Uniprot ID:
Q08DA5
Molecular weight:
41117.0
Reactions
3-Phosphoglyceric acid + Adenosine triphosphate → Glyceric acid 1,3-biphosphate + ADPdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
PGM2L1
Uniprot ID:
A5PKH8
Molecular weight:
70419.0
Reactions
Glucose 1-phosphate + Glyceric acid 1,3-biphosphate → Alpha-D-Glucose 1,6-bisphosphate + 3-Phosphoglyceric aciddetails