Np mrd loader

Showing NP-Card for 2,3-Diphosphoglyceric acid (NP0001227)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:58 UTC
NP-MRD IDNP0001227
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,3-Diphosphoglyceric acid
Description2,3-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.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001227 (2,3-Diphosphoglyceric acid)


  Mrv1652309042000212D          

 15 14  0  0  0  0            999 V2000
 9977.9027 9978.9777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9978.6164 9979.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.9027 9978.1521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9977.1870 9979.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.3308 9978.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9977.1870 9977.7385    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9976.4734 9978.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9977.1870 9980.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.0452 9979.3881    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9977.5995 9977.0241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9976.4734 9978.1521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9976.7745 9977.0241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.6338 9980.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.7638 9978.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4588 9980.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
Download

3D MOL for NP0001227 (2,3-Diphosphoglyceric acid)

HMDB0001294
     RDKit          3D
2,3-Diphosphoglyceric acid
 23 22  0  0  0  0  0  0  0  0999 V2000
    1.4418    0.6890   -2.4493 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7468    1.0858   -1.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0561    2.1965   -1.6915 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8200    0.3590   -0.1952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5730   -0.2513    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4964    0.7842    0.1468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274    0.1085    0.3846 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.1734   -0.1256    1.8904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1505   -1.3675   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2395    1.1675   -0.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944   -0.6808   -0.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9443   -0.6707    0.8068 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.6111    0.6725    0.9316 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4266   -1.1287    2.3436 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130   -1.7767    0.2788 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4215    3.0581   -1.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0648    1.0619    0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5610   -0.8775    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254   -0.8266   -0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7650   -1.2543   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0655    1.0495    0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144   -1.9889    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7348   -1.2839   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  7 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  9 20  1  0
 10 21  1  0
 14 22  1  0
 15 23  1  0
M  END
Download

3D SDF for NP0001227 (2,3-Diphosphoglyceric acid)


  Mrv1652309042000212D          

 15 14  0  0  0  0            999 V2000
 9977.9027 9978.9777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9978.6164 9979.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.9027 9978.1521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9977.1870 9979.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.3308 9978.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9977.1870 9977.7385    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9976.4734 9978.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9977.1870 9980.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.0452 9979.3881    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9977.5995 9977.0241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9976.4734 9978.1521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9976.7745 9977.0241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.6338 9980.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.7638 9978.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4588 9980.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001227

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
XOHUEYCVLUUEJJ-UWTATZPHSA-N

> <FORMULA>
C3H8O10P2

> <MOLECULAR_WEIGHT>
266.0371

> <EXACT_MASS>
265.9592695

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.962596431968947

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2,3-bis(phosphonooxy)propanoic acid

> <ALOGPS_LOGP>
-1.55

> <JCHEM_LOGP>
-1.765871547333333

> <ALOGPS_LOGS>
-1.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.2497332376712151

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.4809321990127331

> <JCHEM_POLAR_SURFACE_AREA>
170.82

> <JCHEM_REFRACTIVITY>
42.1293

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diphosphoglycerate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001227 (2,3-Diphosphoglyceric acid)

HMDB0001294
     RDKit          3D
2,3-Diphosphoglyceric acid
 23 22  0  0  0  0  0  0  0  0999 V2000
    1.4418    0.6890   -2.4493 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7468    1.0858   -1.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0561    2.1965   -1.6915 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8200    0.3590   -0.1952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5730   -0.2513    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4964    0.7842    0.1468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274    0.1085    0.3846 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.1734   -0.1256    1.8904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1505   -1.3675   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2395    1.1675   -0.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944   -0.6808   -0.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9443   -0.6707    0.8068 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.6111    0.6725    0.9316 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4266   -1.1287    2.3436 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130   -1.7767    0.2788 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4215    3.0581   -1.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0648    1.0619    0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5610   -0.8775    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254   -0.8266   -0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7650   -1.2543   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0655    1.0495    0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144   -1.9889    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7348   -1.2839   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  7 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  9 20  1  0
 10 21  1  0
 14 22  1  0
 15 23  1  0
M  END
Download

PDB for NP0001227 (2,3-Diphosphoglyceric acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8625.4188627.425   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8626.7518628.191   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8625.4188625.884   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8624.0828628.191   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8628.0848627.425   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0    8624.0828625.112   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0    8622.7508627.425   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8624.0828629.731   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0    8629.4188628.191   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0    8624.8528623.778   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8622.7508625.884   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8623.3128623.778   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8628.6508629.531   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8630.7598627.421   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8630.1908629.531   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9                                                       
CONECT    6    3   10   11   12                                             
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5   13   14   15                                             
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15    9                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END
Download

3D PDB for NP0001227 (2,3-Diphosphoglyceric acid)

COMPND    HMDB0001294
HETATM    1  O1  UNL     1       1.442   0.689  -2.449  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.747   1.086  -1.484  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.056   2.196  -1.691  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.820   0.359  -0.195  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.573  -0.251   0.021  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.496   0.784   0.147  1.00  0.00           O  
HETATM    7  P1  UNL     1      -3.027   0.109   0.385  1.00  0.00           P  
HETATM    8  O4  UNL     1      -3.173  -0.126   1.890  1.00  0.00           O  
HETATM    9  O5  UNL     1      -3.151  -1.367  -0.416  1.00  0.00           O  
HETATM   10  O6  UNL     1      -4.240   1.168  -0.129  1.00  0.00           O  
HETATM   11  O7  UNL     1       1.694  -0.681  -0.313  1.00  0.00           O  
HETATM   12  P2  UNL     1       2.944  -0.671   0.807  1.00  0.00           P  
HETATM   13  O8  UNL     1       3.611   0.672   0.932  1.00  0.00           O  
HETATM   14  O9  UNL     1       2.427  -1.129   2.344  1.00  0.00           O  
HETATM   15  O10 UNL     1       4.113  -1.777   0.279  1.00  0.00           O  
HETATM   16  H1  UNL     1       0.421   3.058  -1.984  1.00  0.00           H  
HETATM   17  H2  UNL     1       1.065   1.062   0.628  1.00  0.00           H  
HETATM   18  H3  UNL     1      -0.561  -0.878   0.917  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.825  -0.827  -0.897  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.765  -1.254  -1.192  1.00  0.00           H  
HETATM   21  H6  UNL     1      -5.066   1.050   0.424  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.914  -1.989   2.286  1.00  0.00           H  
HETATM   23  H8  UNL     1       4.735  -1.284  -0.307  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7
CONECT    7    8    8    9   10
CONECT    9   20
CONECT   10   21
CONECT   11   12
CONECT   12   13   13   14   15
CONECT   14   22
CONECT   15   23
END
Download

SMILES for NP0001227 (2,3-Diphosphoglyceric acid)

OC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O
Download

INCHI for NP0001227 (2,3-Diphosphoglyceric acid)

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
Download
View in JSmol
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-Diphospho-D-glycerateKegg
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-Diphospho-D-glyceric 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-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-Diphosphonooxypropanoic acidHMDB
2,3-Diphosphonooxypropionic acidHMDB
2,3-Diphosphoglyceric acidHMDB
Chemical FormulaC3H8O10P2
Average Mass266.0371 Da
Monoisotopic Mass265.95927 Da
IUPAC Name(2R)-2,3-bis(phosphonooxy)propanoic acid
Traditional Namediphosphoglycerate
CAS Registry Number138-81-8
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-08-18View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.69 g/LALOGPS
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
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
Good Scents IDNot Available
References
General References
  1. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
  2. Mairbaurl H, Schobersberger W, Oelz O, Bartsch P, Eckardt KU, Bauer C: Unchanged in vivo P50 at high altitude despite decreased erythrocyte age and elevated 2,3-diphosphoglycerate. J Appl Physiol (1985). 1990 Mar;68(3):1186-94. [PubMed:2111310 ]
  3. Luganova IS, Blinov MN, Abdulkadyrova AS: [Age composition of the erythrocyte population, ATP and 2,3-diphosphoglycerate composition in erythrocytes in different forms of hemolytic anemia]. Vopr Med Khim. 1978 Jul-Aug;24(4):499-505. [PubMed:685194 ]
  4. Miwa S, Fujii H, Matsumoto N, Nakatsuji T, Oda S, Asano H, Asano S: A case of red-cell adenosine deaminase overproduction associated with hereditary hemolytic anemia found in Japan. Am J Hematol. 1978;5(2):107-15. [PubMed:736030 ]
  5. Sezdi M, Bayik M, Ulgen Y: Storage effects on the Cole-Cole parameters of erythrocyte suspensions. Physiol Meas. 2006 Jul;27(7):623-35. Epub 2006 Apr 28. [PubMed:16705260 ]
  6. Linko K, Hekali R: Influence of the Taurus radiowave blood warmer on human red cells. Hemolysis and erythrocyte ATP and 2,3 DPG concentrations following warming by radiowaves, microwaves and water bath. Acta Anaesthesiol Scand. 1980;24(1):46-52. [PubMed:7376803 ]
  7. Shanoian SA, Gel'shtein GG, Sharova IuA, Metina RA, Lifliandskii DB: [Study of 2,3-diphosphoglyceric acid levels in artificial blood circulation with the use of a perfusate composed of defrosted erythrocytes and donor blood]. Probl Gematol Pereliv Krovi. 1976 Feb;21(2):41-3. [PubMed:1257232 ]
  8. Spodaryk K, Zoladz JA: The 2,3-DPG levels of human red blood cells during an incremental exercise test: relationship to the blood acid-base balance. Physiol Res. 1998;47(1):17-22. [PubMed:9708696 ]
  9. Springer RR, Clark DK, Lea AS, Solis RT: Effects of changes in arterial carbon dioxide tension on oxygen consumption during cardiopulmonary bypass. Chest. 1979 May;75(5):549-54. [PubMed:35315 ]
  10. Coppola L, Giunta R, Verrazzo G, Luongo C, Sammartino A, Vicario C, Giugliano D: Influence of ozone on haemoglobin oxygen affinity in type-2 diabetic patients with peripheral vascular disease: in vitro studies. Diabete Metab. 1995 Oct;21(4):252-5. [PubMed:8529759 ]
  11. Nakano T, Fujioka H, Tamura S, Amuro Y, Nabeshima K, Hada T, Higashino K: Erythrocyte 2,3-diphosphoglycerate in liver diseases. Am J Gastroenterol. 1987 Dec;82(12):1283-6. [PubMed:2825516 ]
  12. diBella G, Scandariato G, Suriano O, Rizzo A: Oxygen affinity and Bohr effect responses to 2,3-diphosphoglycerate in equine and human blood. Res Vet Sci. 1996 May;60(3):272-5. [PubMed:8735521 ]
  13. Pas'ko SA, Volosheniuk TG: [Causes, sequelae and possible ways of preventing hypophosphatemia in patients with cerebral ischemia]. Zh Nevropatol Psikhiatr Im S S Korsakova. 1990;90(10):25-7. [PubMed:1962992 ]
  14. Rosenmund A, Binswanger U, Straub PW: Oxidative injury to erythrocytes, cell rigidity, and splenic hemolysis in hemodialyzed uremic patients. Ann Intern Med. 1975 Apr;82(4):460-5. [PubMed:1119763 ]
  15. Antonowicz J, Andrzejak R, Smolik R: Influence of heavy metal mixtures on erythrocyte metabolism. Int Arch Occup Environ Health. 1990;62(3):195-8. [PubMed:2347640 ]
  16. Krasomski G, Zachara B: [2,3-diphosphoglycerate level in the red blood cells, inorganic phosphorus in the blood serum and the acid-base equilibrium indicators in different periods of normal pregnancy]. Ginekol Pol. 1981 Aug;52(8):687-92. [PubMed:7308813 ]
  17. Wallas CH: Elevated red blood cell 2,3-diphosphoglycerate levels in black blood donors. Transfusion. 1978 Jan-Feb;18(1):108-12. [PubMed:625775 ]
  18. Hirszel P, Maher JF, Tempel GE, Mengel CE: Effect of hemodialysis on factors influencing oxygen transport. J Lab Clin Med. 1975 Jun;85(6):978-86. [PubMed:237054 ]
  19. Lijnen P, Hespel P, Van Oppens S, Fiocchi R, Goossens W, Vanden Eynde E, Amery A: Erythrocyte 2,3-diphosphoglycerate and serum enzyme concentrations in trained and sedentary men. Med Sci Sports Exerc. 1986 Apr;18(2):174-9. [PubMed:3702645 ]
  20. Yoneda S, Kako T, Kohketsu M, Fujinami T: Changes in blood viscosity following nifedipine administration and its relation to the contents of adenosine triphosphate and 2,3-diphosphoglyceric acid in red blood cells in patients with angina pectoris. Arzneimittelforschung. 1989 Apr;39(4):504-6. [PubMed:2751737 ]