2,3-Bisphospho-D-glycerate (BioCAD00000002898)
Metabolite Card
Formula: C3H8O10P2 (265.9593)
SMILES: OC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O
Synonyms [en]
2,3-bisphospho-D-glycerate; D-greenwald ester; Glyceric acid bis(dihydrogen phosphate); DPG; Glyceric acid diphosphate; 2,3-BPG
Last reviewed on 2024-06-28.
Cite this Page
2,3-Bisphospho-D-glycerate. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000002898). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
2,3-Bisphosphoglycerate (CAS: 138-81-8), also known as 2,3-BPG or 2,3-diphosphoglycerate, is a three-carbon isomer of the glycolytic intermediate 1,3-bisphosphoglycerate and is present at high levels in the human red blood cell (RBC; erythrocyte) at the same molar concentration as hemoglobin. It is notable because it binds to deoxygenated hemoglobin in RBCs. In doing so, it allosterically upregulates the ability of RBCs to release oxygen near tissues that need it most. Its function was discovered in 1967 by Reinhold Benesch and Ruth Benesch.
DBLinks
- CAS Registry Number: 14438-19-8
- PubChem CID: 186004
- ChEBI: 17720
- HMDB: HMDB0001294
- LipidMaps:
- KEGG: C01159
- BioCyc: 23-DIPHOSPHOGLYCERATE
- NCBI MeSH:
- Wikipedia: 2,3-Bisphosphoglyceric acid
Other DBLinks
- CAS Registry Number: 138-81-8
- CAS Registry Number: 14438-19-8
- PubChem: 186004
- ChEBI: ChEBI:17720
- HMDB: HMDB0001294
- KEGG: C01159
- KEGG: C03339
- BioCyc: 23-DIPHOSPHOGLYCERATE
- Wikipedia: 2,3-Bisphosphoglyceric acid
- RefMet: RM0030628
- MoNA: HMDB0001294_ms_ms_1504
- MoNA: HMDB0001294_ms_ms_1505
- MoNA: HMDB0001294_ms_ms_1506
- MoNA: KO000559
- MoNA: KO000560
- MoNA: KO000561
- MoNA: KO000562
- MoNA: KO000563
- MoNA: KO002642
- MoNA: KO002643
- MoNA: KO002644
- MoNA: KO002645
- MoNA: KO002646
- Metlin: METLIN_153
- Metlin: METLIN_63126
- Coconut NaturalProduct: CNP0221489.1
Class / Ontology
- WishartLab ClassyFire: [Carbohydrates and carbohydrate conjugates] Carbohydrates and carbohydrate conjugates
- RefMet: [Sugar acids] Sugar acids
- ChEBI: [CHEBI:17720] 2,3-bisphospho-D-glyceric acid
| ID | EC Number | Name |
|---|---|---|
| KEGG:R01516 | 5.4.2.11 | 2,3-bisphospho-D-glycerate 2-phosphohydrolase |
| KEGG:R01662 | 5.4.2.4 | 3-phospho-D-glycerate 1,2-phosphomutase |
| KEGG:R02664 | 2.7.2.16 | C00631 + C00002<=>C01159 + C00008 |
| KEGG:R03298 | 6.5.1.9 | (2R)-2,3-bisphosphoglycerate ligase (cyclizing) |
| KEGG:R09532 | 3.1.3.80 | 2,3-bisphospho-D-glycerate 3-phosphohydrolase |
| BioCyc:RXN-15512 | Protein-pi-phospho-L-histidines + CPD-16758<=>Protein-Histidines + 23-DIPHOSPHOGLYCERATE | |
| BioCyc:RXN-15511 | Protein-Histidines + 23-DIPHOSPHOGLYCERATE<=>Protein-pi-phospho-L-histidines + G3P | |
| BioCyc:RXN-15510 | Protein-pi-phospho-L-histidines + 2-PG<=>Protein-Histidines + 23-DIPHOSPHOGLYCERATE | |
| BioCyc:RXN-15509 | Protein-Histidines + 23-DIPHOSPHOGLYCERATE<=>Protein-pi-phospho-L-histidines + CPD-16758 | |
| BioCyc:RXN-20986 | 6.5.1.9 | 23-DIPHOSPHOGLYCERATE + ATP + PROTON --> CPD-22623 + ADP + Pi |
| BioCyc:RXN-17276 | Protein-pi-phospho-L-histidines + G3P --> Protein-Histidines + 23-DIPHOSPHOGLYCERATE | |
| BioCyc:RXN-20987 | 2.7.2.16 | ATP + 2-PG --> ADP + 23-DIPHOSPHOGLYCERATE + PROTON |
| BioCyc:BISPHOSPHOGLYCERATE-MUTASE-RXN | 5.4.2.4 | DPG --> PROTON + 23-DIPHOSPHOGLYCERATE |
| BioCyc:RXN-11102 | 3.1.3.80 | 23-DIPHOSPHOGLYCERATE + WATER --> 2-PG + Pi |
| BioCyc:RXN-20988 | 3.1.4.61 | CPD-22623 + WATER --> 23-DIPHOSPHOGLYCERATE + 2 PROTON |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| PathBank:SMP0120846 | Triosephosphate Isomerase Deficiency |
| PathBank:SMP0120488 | Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease |
| PathBank:SMP0120637 | Glycogenosis, Type IB |
| PathBank:SMP0120645 | Glycogenosis, Type IA. Von Gierke Disease |
| PathBank:SMP0000374 | Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease |
| PathBank:SMP0000560 | Phosphoenolpyruvate Carboxykinase Deficiency 1 (PEPCK1) |
| PathBank:SMP0000572 | Fanconi-Bickel Syndrome |
| PathBank:SMP0087318 | Gluconeogenesis |
| PathBank:SMP0087446 | Glycolysis |
| PathBank:SMP0120845 | Fructose-1,6-diphosphatase Deficiency |
| PathBank:SMP0120857 | Glycogenosis, Type IC |
| PathBank:SMP0120596 | Glycogenosis, Type VII. Tarui Disease |
| PathBank:SMP0120624 | Phosphoenolpyruvate Carboxykinase Deficiency 1 (PEPCK1) |
| PathBank:SMP0120636 | Fanconi-Bickel Syndrome |
| PathBank:SMP0000040 | Glycolysis |
| PathBank:SMP0000531 | Glycogenosis, Type VII. Tarui Disease |
| PathBank:SMP0000563 | Triosephosphate Isomerase Deficiency |
| PathBank:SMP0002312 | Glycolysis I |
| PathBank:SMP0002356 | Ethanol Fermentation |
| PathBank:SMP0087317 | Glycolysis |