MiMeDB: Showing metabocard for (2R)-2-O-(alpha-D-glucopyranosyl)-glyceric acid (MMDBc0054821)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:35:39 UTC

Update Date

2022-08-12 20:09:05 UTC

Metabolite ID

MMDBc0054821

Metabolite Identification

Common Name

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

Description

2-O-(alpha-D-glucopyranosyl)-D-glycerate, also known as (2R)-2-O-(a-D-glucopyranosyl)-glyceric acid or O-α-D-glucopyranosyl-(1->2)-D-glycerate, 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. Based on a literature review very few articles have been published on 2-O-(alpha-D-glucopyranosyl)-D-glycerate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221352D          

 24 24  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
    1.4289   -2.4750    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
    1.4289   -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
    2.1434   -1.2375    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
    2.1434   -2.8875    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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  5  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
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -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
 11  2  1  0  0  0  0
  5 12  1  6  0  0  0
  6 13  1  6  0  0  0
  7 14  1  6  0  0  0
 15  8  2  0  0  0  0
 16  8  1  0  0  0  0
 17  3  1  0  0  0  0
 17  9  1  0  0  0  0
  4 18  1  6  0  0  0
  9 18  1  6  0  0  0
  3 19  1  6  0  0  0
  4 20  1  6  0  0  0
  5 21  1  1  0  0  0
  6 22  1  6  0  0  0
  7 23  1  1  0  0  0
  9 24  1  1  0  0  0
M  CHG  1  16  -1
M  END
> <DATABASE_ID>
MMDBc0054821

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](CO)(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/C9H16O9/c10-1-3-5(12)6(13)7(14)9(17-3)18-4(2-11)8(15)16/h3-7,9-14H,1-2H2,(H,15,16)/p-1/t3-,4-,5-,6+,7-,9-/m1/s1

> <INCHI_KEY>
DDXCFDOPXBPUJC-CECBSOHTSA-M

> <FORMULA>
C9H15O9

> <MOLECULAR_WEIGHT>
267.211

> <EXACT_MASS>
267.072155643

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.266245074623484

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.289575130333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.209615689822073

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3488944419839086

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810837201868274

> <JCHEM_POLAR_SURFACE_AREA>
159.73999999999998

> <JCHEM_REFRACTIVITY>
63.6339

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-hydroxy-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       2.667  -4.620   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       2.667  -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       4.001  -2.310   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       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
CONECT    1    3   10                                                       
CONECT    2    4   11                                                       
CONECT    3    1    5   17   19                                             
CONECT    4    2    8   18   20                                             
CONECT    5    3    6   12   21                                             
CONECT    6    5    7   13   22                                             
CONECT    7    6    9   14   23                                             
CONECT    8    4   15   16                                                  
CONECT    9    7   17   18   24                                             
CONECT   10    1                                                            
CONECT   11    2                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    8                                                            
CONECT   17    3    9                                                       
CONECT   18    4    9                                                       
CONECT   19    3                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24    9                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

Synonyms

Value	Source
(2R)-2-O-(alpha-D-Glucopyranosyl)-glycerate	ChEBI
(R)-2-O-alpha-D-Glucopyranosyl glycerate	ChEBI
O-alpha-D-Glucopyranosyl-(1->2)-D-glycerate	ChEBI
(2R)-2-O-(a-D-Glucopyranosyl)-glycerate	Generator
(2R)-2-O-(a-D-Glucopyranosyl)-glyceric acid	Generator
(2R)-2-O-(alpha-D-Glucopyranosyl)-glyceric acid	Generator
(2R)-2-O-(Α-D-glucopyranosyl)-glycerate	Generator
(2R)-2-O-(Α-D-glucopyranosyl)-glyceric acid	Generator
(R)-2-O-a-D-Glucopyranosyl glycerate	Generator
(R)-2-O-a-D-Glucopyranosyl glyceric acid	Generator
(R)-2-O-alpha-D-Glucopyranosyl glyceric acid	Generator
(R)-2-O-Α-D-glucopyranosyl glycerate	Generator
(R)-2-O-Α-D-glucopyranosyl glyceric acid	Generator
O-a-D-Glucopyranosyl-(1->2)-D-glycerate	Generator
O-a-D-Glucopyranosyl-(1->2)-D-glyceric acid	Generator
O-alpha-D-Glucopyranosyl-(1->2)-D-glyceric acid	Generator
O-Α-D-glucopyranosyl-(1->2)-D-glycerate	Generator
O-Α-D-glucopyranosyl-(1->2)-D-glyceric acid	Generator
2-O-(a-D-Glucopyranosyl)-D-glycerate	Generator
2-O-(a-D-Glucopyranosyl)-D-glyceric acid	Generator
2-O-(alpha-D-Glucopyranosyl)-D-glyceric acid	Generator
2-O-(Α-D-glucopyranosyl)-D-glycerate	Generator
2-O-(Α-D-glucopyranosyl)-D-glyceric acid	Generator

Molecular Formula

C₉H₁₅O₉

Average Mass

267.211

Monoisotopic Mass

267.072155643

IUPAC Name

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

Traditional Name

(2R)-3-hydroxy-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@](CO)(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/C9H16O9/c10-1-3-5(12)6(13)7(14)9(17-3)18-4(2-11)8(15)16/h3-7,9-14H,1-2H2,(H,15,16)/p-1/t3-,4-,5-,6+,7-,9-/m1/s1

InChI Key

DDXCFDOPXBPUJC-CECBSOHTSA-M

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
Beta-hydroxy acid
Glyceric_acid
Sugar acid
Hydroxy acid
Monosaccharide
Oxane
Secondary alcohol
Polyol
Acetal
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid
Alcohol
Primary alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

hydroxy monocarboxylic acid anion (CHEBI:62510 )
alpha-D-glucoside (CHEBI:62510 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-3.3	ChemAxon
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	159.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	63.63 m³·mol⁻¹	ChemAxon
Polarizability	23.27 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Thermotogae	2
Bacteria	Actinobacteria	4	Human
Archaea/Archaea	Euryarchaeota	1
Bacteria	Aquificae	1
Bacteria	Proteobacteria	1
Bacteria	Deinococcus-thermus	1
Bacteria	Spirochaetes	1

Exposure Sources

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

26332739

KEGG Compound ID

Not Available

BioCyc ID

CPD-9190

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53262367

PDB ID

Not Available

ChEBI ID

62510

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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)-glyceric acid (MMDBc0054821)

MOL for #<Metabolite:0x00007fdb59633d00>

3D MOL for #<Metabolite:0x00007fdb59633d00>

3D SDF for #<Metabolite:0x00007fdb59633d00>

3D-SDF for #<Metabolite:0x00007fdb59633d00>

PDB for #<Metabolite:0x00007fdb59633d00>

3D PDB for #<Metabolite:0x00007fdb59633d00>

SMILES for #<Metabolite:0x00007fdb59633d00>

INCHI for #<Metabolite:0x00007fdb59633d00>

Structure for #<Metabolite:0x00007fdb59633d00>

3D Structure for #<Metabolite:0x00007fdb59633d00>