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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0001270
Secondary Accession Numbers
  • HMDB0062758
  • HMDB01270
  • HMDB62758
Metabolite Identification
Common NameGlyceric acid 1,3-biphosphate
DescriptionGlyceric acid 1,3-biphosphate (CAS: 1981-49-3), also known as 1,3-bisphosphoglycerate (1,3BPG) or PGAP, is a 3-carbon organic molecule present in most, if not all living creatures. It primarily exists as a metabolic intermediate in glycolysis during respiration. 1,3BPG has been recognized as regulatory signal implicated in the control of metabolism, oxygen affinity of red cells, and other cellular functions. 1,3BPG concentration in erythrocytes changes in a number of pathological conditions, such as inherited phosphoglycerate kinase deficiency in erythrocytes (involved in the synthesis and breakdown of 1,3BPG) (PMID: 3555887 ). Glyceric acid 1,3-biphosphate is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ADP to form the energy storage molecule ATP (Wikipedia ).
Structure
Thumb
Synonyms
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 Number38168-82-0
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
Physiological effectNot Available
Disposition
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified0.4 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH ID13DPG
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References

Only showing the first 10 proteins. There are 11 proteins in total.

Enzymes

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
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
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
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
Molecular weight:
28776.605
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
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
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP2
Uniprot ID:
P14621
Molecular weight:
11139.52
Reactions
Glyceric acid 1,3-biphosphate + Water → 3-Phosphoglyceric acid + Phosphatedetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP1
Uniprot ID:
P07311
Molecular weight:
11260.84
Reactions
Glyceric acid 1,3-biphosphate + Water → 3-Phosphoglyceric acid + Phosphatedetails
General function:
Involved in glyceraldehyde-3-phosphate dehydrogenase activity
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:
O14556
Molecular weight:
44500.835
Reactions
Glyceraldehyde 3-phosphate + Phosphate + NAD → Glyceric acid 1,3-biphosphate + NADHdetails
Glyceraldehyde 3-phosphate + Phosphate + NAD → Glyceric acid 1,3-biphosphate + NADH + Hydrogen Iondetails
General function:
Involved in glyceraldehyde-3-phosphate dehydrogenase activity
Specific function:
Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. 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. 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 (By similarity). 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. 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.
Gene Name:
GAPDH
Uniprot ID:
P04406
Molecular weight:
31547.76
Reactions
Glyceraldehyde 3-phosphate + Phosphate + NAD → Glyceric acid 1,3-biphosphate + NADHdetails
Glyceraldehyde 3-phosphate + Phosphate + NAD → Glyceric acid 1,3-biphosphate + NADH + Hydrogen Iondetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PGK2
Uniprot ID:
P07205
Molecular weight:
44795.79
Reactions
Adenosine triphosphate + 3-Phosphoglyceric acid → ADP + Glyceric acid 1,3-biphosphatedetails
General function:
Involved in phosphoglycerate kinase activity
Specific function:
In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein).
Gene Name:
PGK1
Uniprot ID:
P00558
Molecular weight:
44614.36
Reactions
Adenosine triphosphate + 3-Phosphoglyceric acid → ADP + Glyceric acid 1,3-biphosphatedetails

Only showing the first 10 proteins. There are 11 proteins in total.