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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-23 06:07:11 UTC
Update Date2018-05-16 23:27:17 UTC
HMDB IDHMDB0062758
Secondary Accession Numbers
  • HMDB62758
Metabolite Identification
Common Name3-phosphonato-D-glyceroyl Phosphate(4-)
DescriptionGlyceric acid 1,3-biphosphate, also known as 1,3-biphosphoglycerate or 3-phosphoglyceroyl 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 slightly soluble (in water) and a moderately acidic compound (based on its pKa). Glyceric acid 1,3-biphosphate has been primarily detected in blood. Within the cell, glyceric acid 1,3-biphosphate is primarily located in the cytoplasm. Glyceric acid 1,3-biphosphate exists in all eukaryotes, ranging from yeast to humans. Glyceric acid 1,3-biphosphate participates in a number of enzymatic reactions. In particular, Glyceric acid 1,3-biphosphate can be biosynthesized from D-glyceraldehyde 3-phosphate through the action of the enzyme glyceraldehyde-3-phosphate dehydrogenase. Furthermore, Glyceric acid 1,3-biphosphate can be converted into 2,3-diphosphoglyceric acid; which is catalyzed by the enzyme bisphosphoglycerate mutase. Furthermore, Glyceric acid 1,3-biphosphate can be biosynthesized from D-glyceraldehyde 3-phosphate through the action of the enzyme glyceraldehyde-3-phosphate dehydrogenase. Finally, Glyceric acid 1,3-biphosphate can be biosynthesized from 3-phosphoglyceric acid through its interaction with the enzyme pantothenate kinase 1. In humans, glyceric acid 1,3-biphosphate is involved in the glycogenosis, type ic pathway, the triosephosphate isomerase pathway, the glycogenosis, type ib pathway, and the glycolysis pathway. Glyceric acid 1,3-biphosphate is also involved in several metabolic disorders, some of which include glycogen synthetase deficiency, the glycogenosis, type iv. amylopectinosis, anderson disease pathway, the glycogenosis, type vii. tarui disease pathway, and the glycogenosis, type iii. cori disease, debrancher glycogenosis pathway.
Structure
Thumb
Synonyms
ValueSource
1,3-BiphosphoglycerateHMDB
1,3-Biphosphoglyceric acidHMDB
1,3-Bis-phosphoglycerateHMDB
1,3-BisphosphoglycerateHMDB
1,3-DiphosphateglycerateHMDB
1,3-DiphosphoglycerateHMDB
13-DPGHMDB
2-Hydroxy-3-(phosphonooxy)-propanoateHMDB
2-Hydroxy-3-(phosphonooxy)-propanoic acidHMDB
2-Hydroxy-3-(phosphonooxy)-propanoic acid 1-anhydride with phosphorateHMDB
2-Hydroxy-3-(phosphonooxy)-propanoic acid 1-anhydride with phosphoric acidHMDB
3-P-Glyceroyl-PHMDB
3-phospho-D-Glyceroyl phosphateHMDB
3-phospho-D-Glyceroyl-phosphateHMDB
3-Phosphoglyceroyl phosphateHMDB
3-Phosphoglyceroyl-PHMDB
3-Phosphoglyceroyl-phosphateHMDB
DPGHMDB
Glycerate 1,3-biphosphateHMDB
Glycerate 1,3-bisphosphateHMDB
Glycerate 1,3-diphosphateHMDB
P-Glyceroyl-PHMDB
Phosphoglyceroyl-PHMDB
Chemical FormulaC3H8O10P2
Average Molecular Weight266.0371
Monoisotopic Molecular Weight265.9592695
IUPAC Name{[2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
Traditional Name1,3-bisphosphoglycerate
CAS Registry NumberNot Available
SMILES
OC(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)
InChI KeyLJQLQCAXBUHEAZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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 DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility50.2 g/lALOGPS
LogP-1.25ALOGPS
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
Polarizability18.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
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 (1 TMS) - 70eV, Positivesplash10-0002-9230000000-4f86f41b27dd191408b9View in MoNA
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
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022524
KNApSAcK IDNot Available
Chemspider ID663
KEGG Compound IDC00236
BioCyc IDDPG
BiGG ID34342
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound683
PDB IDNot Available
ChEBI ID89363
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available