MiMeDB: Showing metabocard for (2R)-2-O-(6-phospho-alpha-D-mannosyl)-glyceric acid (MMDBc0054819)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:35:37 UTC

Update Date

2022-08-12 20:09:05 UTC

Metabolite ID

MMDBc0054819

Metabolite Identification

Common Name

(2R)-2-O-(6-phospho-alpha-D-mannosyl)-glyceric acid

Description

2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate, also known as (2R)-2-O-(6-phospho-a-D-mannosyl)-glyceric acid or 2-(alpha-D-mannosyl-6-phosphate)-D-glycerate, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Based on a literature review very few articles have been published on 2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221352D          

 28 28  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  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
   -0.0000   -1.6500    0.0000 C   0  0  2  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
    0.7145    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  1  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  1  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
    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
    4.2868    1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.9849    0.5230    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.1599    1.9520    0.0000 O   0  0  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
    0.7145   -1.2375    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
    3.5724    1.2375    0.0000 P   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
    1.4289    1.6500    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  0  0  0  0
  4  2  1  1  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  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  1  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 19  2  1  0  0  0  0
  3 20  1  6  0  0  0
  9 20  1  6  0  0  0
 21  4  1  0  0  0  0
 21  9  1  0  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  6  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
   -0.7145   -1.2375    0.0000 C   0  0  0  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
   -0.0000   -1.6500    0.0000 C   0  0  2  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
    0.7145    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  1  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  1  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
    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
    4.2868    1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.9849    0.5230    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.1599    1.9520    0.0000 O   0  0  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
    0.7145   -1.2375    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
    3.5724    1.2375    0.0000 P   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
    1.4289    1.6500    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  0  0  0  0
  4  2  1  1  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  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  1  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 19  2  1  0  0  0  0
  3 20  1  6  0  0  0
  9 20  1  6  0  0  0
 21  4  1  0  0  0  0
 21  9  1  0  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  6  0  0  0
  9 28  1  1  0  0  0
M  CHG  3  15  -1  16  -1  17  -1
M  END
> <DATABASE_ID>
MMDBc0054819

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H17O12P/c10-1-3(8(14)15)20-9-7(13)6(12)5(11)4(21-9)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>
BOLXAGHGKNGVBE-MTXRGOKVSA-K

> <FORMULA>
C9H14O12P

> <MOLECULAR_WEIGHT>
345.174

> <EXACT_MASS>
345.023933629

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.09433989968423

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]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>
3.3481191831666854

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.218638917806274

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0496705103610067

> <JCHEM_POLAR_SURFACE_AREA>
211.92999999999998

> <JCHEM_REFRACTIVITY>
72.26339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   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      -2.667  -3.080   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       8.002   3.080   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0       7.438   0.976   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0       5.898   3.644   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0       6.668   2.310   0.000  0.00  0.00           P+0
HETATM   23  H   UNK     0      -1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.667   3.080   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    8   20   23                                             
CONECT    4    2    5   21   24                                             
CONECT    5    4    6   11   25                                             
CONECT    6    5    7   12   26                                             
CONECT    7    6    9   13   27                                             
CONECT    8    3   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-(6-Phospho-alpha-D-mannosyl)-glycerate	ChEBI
2-(alpha-D-Mannosyl-6-phosphate)-D-glycerate	ChEBI
(2R)-2-O-(6-Phospho-a-D-mannosyl)-glycerate	Generator
(2R)-2-O-(6-Phospho-a-D-mannosyl)-glyceric acid	Generator
(2R)-2-O-(6-Phospho-alpha-D-mannosyl)-glyceric acid	Generator
(2R)-2-O-(6-Phospho-α-D-mannosyl)-glycerate	Generator
(2R)-2-O-(6-Phospho-α-D-mannosyl)-glyceric acid	Generator
2-(a-D-Mannosyl-6-phosphate)-D-glycerate	Generator
2-(a-D-Mannosyl-6-phosphoric acid)-D-glyceric acid	Generator
2-(alpha-D-Mannosyl-6-phosphoric acid)-D-glyceric acid	Generator
2-(Α-D-mannosyl-6-phosphate)-D-glycerate	Generator
2-(Α-D-mannosyl-6-phosphoric acid)-D-glyceric acid	Generator
2-O-(6-Phospho-a-D-mannosyl)-D-glycerate	Generator
2-O-(6-Phospho-a-D-mannosyl)-D-glyceric acid	Generator
2-O-(6-Phospho-alpha-D-mannosyl)-D-glyceric acid	Generator
2-O-(6-Phospho-α-D-mannosyl)-D-glycerate	Generator
2-O-(6-Phospho-α-D-mannosyl)-D-glyceric acid	Generator

Molecular Formula

C₉H₁₄O₁₂P

Average Mass

345.174

Monoisotopic Mass

345.023933629

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H17O12P/c10-1-3(8(14)15)20-9-7(13)6(12)5(11)4(21-9)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

BOLXAGHGKNGVBE-MTXRGOKVSA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

carbohydrate acid derivative anion (CHEBI:60331 )
monocarboxylic acid anion (CHEBI:60331 )
organophosphate oxoanion (CHEBI:60331 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-3.4	ChemAxon
pKa (Strongest Acidic)	1.22	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	27.09 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

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014744	(2R)-2-O-(6-phospho-alpha-D-mannosyl)-glyceric acid	Glyceric acid	Putative mannosylglycerate hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0024906	(2R)-2-O-(alpha-D-mannosyl)-glyceric acid	L-Histidine	PTS system 2-O-alpha-mannosyl-D-glycerate-specific EIIABC component		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	Microbial Links
Bacteria	Firmicutes	1	Human feces
Bacteria	Proteobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	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

26331883

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1063

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46906104

PDB ID

Not Available

ChEBI ID

60331

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-(6-phospho-alpha-D-mannosyl)-glyceric acid (MMDBc0054819)

MOL for #<Metabolite:0x0000564af311e678>

3D MOL for #<Metabolite:0x0000564af311e678>

3D SDF for #<Metabolite:0x0000564af311e678>

3D-SDF for #<Metabolite:0x0000564af311e678>

PDB for #<Metabolite:0x0000564af311e678>

3D PDB for #<Metabolite:0x0000564af311e678>

SMILES for #<Metabolite:0x0000564af311e678>

INCHI for #<Metabolite:0x0000564af311e678>

Structure for #<Metabolite:0x0000564af311e678>

3D Structure for #<Metabolite:0x0000564af311e678>