MiMeDB: Showing metabocard for (2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid (MMDBc0054820)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:35:38 UTC

Update Date

2025-10-07 16:08:42 UTC

Metabolite ID

MMDBc0054820

Metabolite Identification

Common Name

(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid

Description

(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid is a glycosylated phosphoric acid derivative. There is limited literature available on this metabolite, indicating that further research may be necessary to fully understand its biochemical roles and implications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221352D          

 28 28  0  0  1  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.5230    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.5559   -1.9520    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  1  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  6  0  0  0
  7 13  1  6  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 19  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20  9  1  0  0  0  0
  4 21  1  6  0  0  0
  9 21  1  6  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
 22 18  2  0  0  0  0
 22 19  1  0  0  0  0
  3 23  1  6  0  0  0
  4 24  1  6  0  0  0
  5 25  1  1  0  0  0
  6 26  1  6  0  0  0
  7 27  1  1  0  0  0
  9 28  1  1  0  0  0
M  CHG  3  15  -1  16  -1  17  -1
M  END


  Mrv1652306172221352D          

 28 28  0  0  1  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.5230    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.5559   -1.9520    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  1  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  6  0  0  0
  7 13  1  6  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 19  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20  9  1  0  0  0  0
  4 21  1  6  0  0  0
  9 21  1  6  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
 22 18  2  0  0  0  0
 22 19  1  0  0  0  0
  3 23  1  6  0  0  0
  4 24  1  6  0  0  0
  5 25  1  1  0  0  0
  6 26  1  6  0  0  0
  7 27  1  1  0  0  0
  9 28  1  1  0  0  0
M  CHG  3  15  -1  16  -1  17  -1
M  END
> <DATABASE_ID>
MMDBc0054820

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](COP([O-])([O-])=O)(O[C@@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H17O12P/c10-1-3-5(11)6(12)7(13)9(20-3)21-4(8(14)15)2-19-22(16,17)18/h3-7,9-13H,1-2H2,(H,14,15)(H2,16,17,18)/p-3/t3-,4-,5-,6+,7-,9-/m1/s1

> <INCHI_KEY>
RJDBNSZFZDWPFL-CECBSOHTSA-K

> <FORMULA>
C9H14O12P

> <MOLECULAR_WEIGHT>
345.174

> <EXACT_MASS>
345.023933629

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.329589529214537

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-3-(phosphonooxy)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate

> <JCHEM_LOGP>
-3.4131411616666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.395202433394847

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0350101364508113

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810837202019744

> <JCHEM_POLAR_SURFACE_AREA>
211.92999999999998

> <JCHEM_REFRACTIVITY>
72.2634

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(phosphonooxy)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      -3.231  -0.976   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0      -4.771  -3.644   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      -4.001  -2.310   0.000  0.00  0.00           P+0
HETATM   23  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
CONECT    1    3   10                                                       
CONECT    2    4   19                                                       
CONECT    3    1    5   20   23                                             
CONECT    4    2    8   21   24                                             
CONECT    5    3    6   11   25                                             
CONECT    6    5    7   12   26                                             
CONECT    7    6    9   13   27                                             
CONECT    8    4   14   15                                                  
CONECT    9    7   20   21   28                                             
CONECT   10    1                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    8                                                            
CONECT   16   22                                                            
CONECT   17   22                                                            
CONECT   18   22                                                            
CONECT   19    2   22                                                       
CONECT   20    3    9                                                       
CONECT   21    4    9                                                       
CONECT   22   16   17   18   19                                             
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    9                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

Synonyms

Value	Source
(2R)-2-O-(alpha-D-Glucopyranosyl)-3-phospho-glycerate	ChEBI
2-O-(alpha-D-Glucopyranosyl)-3-O-phosphonato-D-glycerate	ChEBI
2-O-(alpha-D-Glucopyranosyl)-3-phospho-D-glycerate(3-)	ChEBI
2-O-(alpha-D-Glucopyranosyl)-3-phosphonato-D-glycerate	ChEBI
2-O-(alpha-D-Glucopyranosyl)-3-phosphonato-D-glycerate(3-)	ChEBI
2-O-(alpha-D-Glucosyl)-3-O-phosphonato-D-glycerate	ChEBI
2-O-(alpha-D-Glucosyl)-3-phospho-D-glycerate	ChEBI
2-O-(alpha-D-Glucosyl)-3-phosphonato-D-glycerate	ChEBI
(2R)-2-O-(a-D-Glucopyranosyl)-3-phospho-glycerate	Generator
(2R)-2-O-(a-D-Glucopyranosyl)-3-phospho-glyceric acid	Generator
(2R)-2-O-(alpha-D-Glucopyranosyl)-3-phospho-glyceric acid	Generator
(2R)-2-O-(Α-D-glucopyranosyl)-3-phospho-glycerate	Generator
(2R)-2-O-(Α-D-glucopyranosyl)-3-phospho-glyceric acid	Generator
2-O-(a-D-Glucopyranosyl)-3-O-phosphonato-D-glycerate	Generator
2-O-(a-D-Glucopyranosyl)-3-O-phosphonato-D-glyceric acid	Generator
2-O-(alpha-D-Glucopyranosyl)-3-O-phosphonato-D-glyceric acid	Generator
2-O-(Α-D-glucopyranosyl)-3-O-phosphonato-D-glycerate	Generator
2-O-(Α-D-glucopyranosyl)-3-O-phosphonato-D-glyceric acid	Generator
2-O-(a-D-Glucopyranosyl)-3-phospho-D-glycerate(3-)	Generator
2-O-(a-D-Glucopyranosyl)-3-phospho-D-glyceric acid(3-)	Generator
2-O-(alpha-D-Glucopyranosyl)-3-phospho-D-glyceric acid(3-)	Generator
2-O-(Α-D-glucopyranosyl)-3-phospho-D-glycerate(3-)	Generator
2-O-(Α-D-glucopyranosyl)-3-phospho-D-glyceric acid(3-)	Generator
2-O-(a-D-Glucopyranosyl)-3-phosphonato-D-glycerate	Generator
2-O-(a-D-Glucopyranosyl)-3-phosphonato-D-glyceric acid	Generator
2-O-(alpha-D-Glucopyranosyl)-3-phosphonato-D-glyceric acid	Generator
2-O-(Α-D-glucopyranosyl)-3-phosphonato-D-glycerate	Generator
2-O-(Α-D-glucopyranosyl)-3-phosphonato-D-glyceric acid	Generator
2-O-(a-D-Glucopyranosyl)-3-phosphonato-D-glycerate(3-)	Generator
2-O-(a-D-Glucopyranosyl)-3-phosphonato-D-glyceric acid(3-)	Generator
2-O-(alpha-D-Glucopyranosyl)-3-phosphonato-D-glyceric acid(3-)	Generator
2-O-(Α-D-glucopyranosyl)-3-phosphonato-D-glycerate(3-)	Generator
2-O-(Α-D-glucopyranosyl)-3-phosphonato-D-glyceric acid(3-)	Generator
2-O-(a-D-Glucosyl)-3-O-phosphonato-D-glycerate	Generator
2-O-(a-D-Glucosyl)-3-O-phosphonato-D-glyceric acid	Generator
2-O-(alpha-D-Glucosyl)-3-O-phosphonato-D-glyceric acid	Generator
2-O-(Α-D-glucosyl)-3-O-phosphonato-D-glycerate	Generator
2-O-(Α-D-glucosyl)-3-O-phosphonato-D-glyceric acid	Generator
2-O-(a-D-Glucosyl)-3-phospho-D-glycerate	Generator
2-O-(a-D-Glucosyl)-3-phospho-D-glyceric acid	Generator
2-O-(alpha-D-Glucosyl)-3-phospho-D-glyceric acid	Generator
2-O-(Α-D-glucosyl)-3-phospho-D-glycerate	Generator
2-O-(Α-D-glucosyl)-3-phospho-D-glyceric acid	Generator
2-O-(a-D-Glucosyl)-3-phosphonato-D-glycerate	Generator
2-O-(a-D-Glucosyl)-3-phosphonato-D-glyceric acid	Generator
2-O-(alpha-D-Glucosyl)-3-phosphonato-D-glyceric acid	Generator
2-O-(Α-D-glucosyl)-3-phosphonato-D-glycerate	Generator
2-O-(Α-D-glucosyl)-3-phosphonato-D-glyceric acid	Generator
2-O-(a-D-Glucopyranosyl)-3-phospho-D-glycerate	Generator
2-O-(a-D-Glucopyranosyl)-3-phospho-D-glyceric acid	Generator
2-O-(alpha-D-Glucopyranosyl)-3-phospho-D-glyceric acid	Generator
2-O-(Α-D-glucopyranosyl)-3-phospho-D-glycerate	Generator
2-O-(Α-D-glucopyranosyl)-3-phospho-D-glyceric acid	Generator

Molecular Formula

C₉H₁₄O₁₂P

Average Mass

345.174

Monoisotopic Mass

345.023933629

IUPAC Name

(2R)-3-(phosphonooxy)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate

Traditional Name

(2R)-3-(phosphonooxy)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate

CAS Registry Number

Not Available

SMILES

[H][C@](COP([O-])([O-])=O)(O[C@@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C([O-])=O

InChI Identifier

InChI=1S/C9H17O12P/c10-1-3-5(11)6(12)7(13)9(20-3)21-4(8(14)15)2-19-22(16,17)18/h3-7,9-13H,1-2H2,(H,14,15)(H2,16,17,18)/p-3/t3-,4-,5-,6+,7-,9-/m1/s1

InChI Key

RJDBNSZFZDWPFL-CECBSOHTSA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Glyceric_acid
Sugar acid
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Secondary alcohol
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

carbohydrate acid derivative anion (CHEBI:62600 )
monocarboxylic acid anion (CHEBI:62600 )
organophosphate oxoanion (CHEBI:62600 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-3.4	ChemAxon
pKa (Strongest Acidic)	1.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	211.93 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	72.26 m³·mol⁻¹	ChemAxon
Polarizability	27.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	520.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	269.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	72.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	315.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	251.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	272.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	948.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	620.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	939.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	161.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	256.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	170.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	40.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	465.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	582.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	68.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	243.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	970.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	627.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_1	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@@H](O)[C@@H]1O	standard non polar	2025-10-24	2007.5
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_2	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@H]1O	standard non polar	2025-10-24	1346.96
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_3	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@@H]1O	standard non polar	2025-10-24	2304.19
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_4	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H](COP(=O)([O-])[O-])C(=O)[O-]	standard non polar	2025-10-24	2178.47
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_5	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard non polar	2025-10-24	2088.87
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_6	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-24	675.753
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_7	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	2316.61
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_8	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])O[C@@H]1CO	standard non polar	2025-10-24	1794.3
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_9	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1966.04
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_10	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1275.17
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_11	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-24	2481.04
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_12	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	2266.52
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_13	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1643.33
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_14	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1705.66
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_15	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	856.489
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_1	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@@H](O)[C@@H]1O	standard polar	2025-10-24	2254.12
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_2	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@H]1O	standard polar	2025-10-24	1829.88
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_3	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@@H]1O	standard polar	2025-10-24	2395.46
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_4	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H](COP(=O)([O-])[O-])C(=O)[O-]	standard polar	2025-10-24	1644.26
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_5	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard polar	2025-10-24	1623.97
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_6	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-24	1593.02
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_7	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	1784.7
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_8	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])O[C@@H]1CO	standard polar	2025-10-24	1894.69
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_9	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@H]1O[Si](C)(C)C	standard polar	2025-10-24	1832.06
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_10	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	2499.31
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_11	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-24	2292.83
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_12	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	3001.43
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_13	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	2433.18
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_14	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	1163.84
Gas Chromatography	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid_TMS_15	C[Si](C)(C)OC[C@H]1O[C@H](O[C@H](COP(=O)([O-])[O-])C(=O)[O-])[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	3020.19

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0025263	(2R)-3-phosphoglyceric acid	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid	Glucosyl-3-phosphoglycerate synthase	Synthesis	RHEA	34755880
MMDBr0025264	(2R)-3-phosphoglyceric acid	(2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid	Glucosyl-3-phosphoglycerate synthase	Synthesis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria/Eubacteria	Actinobacteria	6	Cattle ; Human
Bacteria/Eubacteria	Thermotogae	1
Archaea/Archaea	Euryarchaeota	1
Bacteria/Eubacteria	Aquificae	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26332783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53262383

PDB ID

Not Available

ChEBI ID

62600

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (2R)-2-O-(alpha-D-glucopyranosyl)-3-phospho-glyceric acid (MMDBc0054820)

MOL for #<Metabolite:0x00007f9ab3304a08>

3D MOL for #<Metabolite:0x00007f9ab3304a08>

3D SDF for #<Metabolite:0x00007f9ab3304a08>

3D-SDF for #<Metabolite:0x00007f9ab3304a08>

PDB for #<Metabolite:0x00007f9ab3304a08>

3D PDB for #<Metabolite:0x00007f9ab3304a08>

SMILES for #<Metabolite:0x00007f9ab3304a08>

INCHI for #<Metabolite:0x00007f9ab3304a08>

Structure for #<Metabolite:0x00007f9ab3304a08>

3D Structure for #<Metabolite:0x00007f9ab3304a08>