ECMDB: 2(alpha-D-Mannosyl)-D-glycerate (ECMDB20063) (M2MDB000912)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)Transporters (5)XML

Proteins (39)

Record Information

Version

2.0

Creation Date

2012-05-31 14:25:31 -0600

Update Date

2015-06-03 17:19:14 -0600

Secondary Accession Numbers

ECMDB20063

Identification

Name:

2(alpha-D-Mannosyl)-D-glycerate

Description

2(alpha-D-mannosyl)-D-glycerate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Mannosylglycerate (MG) is a common compatible solute found in thermophilic and hyperthermophilic prokaryotes. (PMID 15205409) Rubrobacter xylanophilus is the only Gram-positive bacterium known to synthesize the compatible solute mannosylglycerate (MG), which is commonly found in hyperthermophilic archaea and some thermophilic bacteria. (PMID 18678952) Rubrobacter xylanophilus is the only actinobacterium known to accumulate the organic solute mannosylglycerate (MG); moreover, the accumulation of MG is constitutive. (PMID 21166895)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2(α-D-mannosyl)-D-glycerate
2(α-D-mannosyl)-D-glyceric acid
2(a-D-Mannosyl)-D-glycerate
2(a-D-Mannosyl)-D-glyceric acid
2(alpha-D-Mannosyl)-D-glycerate
2(alpha-D-Mannosyl)-D-glyceric acid
2(α-D-Mannosyl)-D-glycerate
2(α-D-Mannosyl)-D-glyceric acid
2-(α-D-mannopyranosyl)-D-glycerate
2-(α-D-mannopyranosyl)-D-glyceric acid
2-(a-D-Mannopyranosyl)-D-glycerate
2-(a-D-Mannopyranosyl)-D-glyceric acid
2-(alpha-D-Mannopyranosyl)-D-glycerate
2-(alpha-D-Mannopyranosyl)-D-glyceric acid
2-(α-D-Mannopyranosyl)-D-glycerate
2-(α-D-Mannopyranosyl)-D-glyceric acid
2-O-a-Mannosyl-D-glycerate
2-O-a-Mannosyl-D-glyceric acid
2-O-alpha-Mannosyl-D-glycerate
2-O-alpha-Mannosyl-D-glyceric acid
2-O-α-Mannosyl-D-glycerate
2-O-α-Mannosyl-D-glyceric acid
a-Mannosylglycerate
a-Mannosylglyceric acid
Alpha-Mannosylglycerate
Alpha-Mannosylglyceric acid
Mannosylglycerate
Mannosylglyceric acid
α-Mannosylglycerate
α-Mannosylglyceric acid

Chemical Formula:

C₉H₁₆O₉

Weight:

Average: 268.2179
Monoisotopic: 268.07943211

InChI Key:

DDXCFDOPXBPUJC-SAYMMRJXSA-N

InChI:

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)/t3-,4-,5-,6+,7+,9-/m1/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

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

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

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-mannosyl-D-glyceric acid (CHEBI:15847 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	305 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.3	ChemAxon
logS	0.06	ALOGPS
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	52.8 m³·mol⁻¹	ChemAxon
Polarizability	23.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acid
2-(alpha-D-Mannosyl)-3-phosphoglycerate + Water + 2(alpha-D-mannosyl)-3-phosphoglycerate <> 2(alpha-D-Mannosyl)-D-glycerate + Phosphate
Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acid
2(alpha-D-mannosyl)-3-phosphoglycerate + Water > 2(alpha-D-Mannosyl)-D-glycerate + Inorganic phosphate
2(alpha-D-Mannosyl)-D-glycerate + HPr - phosphorylated > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + HPr
2-(alpha-D-Mannosyl)-3-phosphoglycerate + Water > 2(alpha-D-Mannosyl)-D-glycerate + Phosphate
2(alpha-D-Mannosyl)-D-glycerate + HPr - phosphorylated > 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + HPr

SMPDB Pathways:

2-O-alpha-mannosyl-D-glycerate degradation	PW002096
Collection of Reactions without pathways	PW001891
inner membrane transport	PW000786

KEGG Pathways:

Fructose and mannose metabolism ec00051
Phosphotransferase system (PTS) ec02060

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ktr-9680000000-56a0078d75bec56fd925	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-9410000000-e059382cb6870a61db4d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-9300000000-a6321edff5c3c46d128c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05n0-8980000000-73f78c0f546e332b3594	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9730000000-99b599bd8caa3df36308	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9400000000-3565fbd97cdac31702db	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Empadinhas, N., Albuquerque, L., Costa, J., Zinder, S. H., Santos, M. A., Santos, H., da Costa, M. S. (2004). "A gene from the mesophilic bacterium Dehalococcoides ethenogenes encodes a novel mannosylglycerate synthase." J Bacteriol 186:4075-4084. Pubmed: 15205409
Empadinhas, N., Pereira, P. J., Albuquerque, L., Costa, J., Sa-Moura, B., Marques, A. T., Macedo-Ribeiro, S., da Costa, M. S. (2011). "Functional and structural characterization of a novel mannosyl-3-phosphoglycerate synthase from Rubrobacter xylanophilus reveals its dual substrate specificity." Mol Microbiol 79:76-93. Pubmed: 21166895
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Sa-Moura, B., Albuquerque, L., Empadinhas, N., da Costa, M. S., Pereira, P. J., Macedo-Ribeiro, S. (2008). "Crystallization and preliminary crystallographic analysis of mannosyl-3-phosphoglycerate synthase from Rubrobacter xylanophilus." Acta Crystallogr Sect F Struct Biol Cryst Commun 64:760-763. Pubmed: 18678952

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15847
HMDB ID	Not Available
Pubchem Compound ID	443262
Kegg ID	C11544
ChemSpider ID	4573823
Wikipedia ID	Not Available
BioCyc ID	2-O-ALPHA-MANNOSYL-D-GLYCERATE
EcoCyc ID	2-O-ALPHA-MANNOSYL-D-GLYCERATE

Enzymes

Protein Details

1. Phosphoenolpyruvate-protein phosphotransferase

General function:: Involved in transferase activity, transferring phosphorus-containing groups
Specific function:: General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:: ptsI
Uniprot ID:: P08839
Molecular weight:: 63561

Reactions

Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.

Protein Details

2. Heat-responsive suppressor hrsA

General function:: Involved in transporter activity
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane
Gene Name:: hrsA
Uniprot ID:: P54745
Molecular weight:: 69667

Reactions

Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.

Protein Details

3. Putative mannosyl-3-phosphoglycerate phosphatase

General function:: Involved in catalytic activity
Specific function:: 2(alpha-D-mannosyl)-3-phosphoglycerate + H(2)O = 2(alpha-D-mannosyl)-D-glycerate + phosphate
Gene Name:: yedP
Uniprot ID:: P76329
Molecular weight:: 30439

Reactions

2(alpha-D-mannosyl)-3-phosphoglycerate + H(2)O = 2(alpha-D-mannosyl)-D-glycerate + phosphate.

Protein Details

4. Phosphocarrier protein HPr

General function:: Involved in sugar:hydrogen symporter activity
Specific function:: General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:: ptsH
Uniprot ID:: P0AA04
Molecular weight:: 9119

Reactions

Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.

Transporters

Protein Details

1. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

2. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

3. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

4. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

Protein Details

5. Mannosyl-D-glycerate transport/metabolism system repressor MngR

General function:: transcription, DNA-templated
Specific function:: Represses mngA and mngB. Regulates its own expression.
Gene Name:: mngR
Uniprot ID:: P13669
Molecular weight:: 28273

2(alpha-D-Mannosyl)-D-glycerate (ECMDB20063) (M2MDB000912)

Structure for #<Compound:0x904f2a00>

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters