Record Information
Version2.0
Creation Date2012-05-31 14:25:31 -0600
Update Date2015-06-03 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
Thumb
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
DescriptionThis compound belongs to the class of chemical entities known as fatty acyl glycosides of mono- and disaccharides. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentFatty 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility305.0 mg/mLALOGPS
logP-2.9ALOGPS
logP-3.3ChemAxon
logS0.06ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity52.8 m3·mol-1ChemAxon
Polarizability23.81 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
2-O-alpha-mannosyl-D-glycerate degradationPW002096 Pw002096Pw002096 greyscalePw002096 simple
Collection of Reactions without pathwaysPW001891 Pw001891Pw001891 greyscalePw001891 simple
inner membrane transportPW000786 Pw000786Pw000786 greyscalePw000786 simple
KEGG Pathways:
  • Fructose and mannose metabolism ec00051
  • Phosphotransferase system (PTS) ec02060
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ktr-9680000000-56a0078d75bec56fd925View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9410000000-e059382cb6870a61db4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9300000000-a6321edff5c3c46d128cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05n0-8980000000-73f78c0f546e332b3594View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9730000000-99b599bd8caa3df36308View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-3565fbd97cdac31702dbView in MoNA
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
External Links:
ResourceLink
CHEBI ID15847
HMDB IDNot Available
Pubchem Compound ID443262
Kegg IDC11544
ChemSpider ID4573823
Wikipedia IDNot Available
BioCyc ID2-O-ALPHA-MANNOSYL-D-GLYCERATE
EcoCyc ID2-O-ALPHA-MANNOSYL-D-GLYCERATE

Enzymes

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.
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.
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.
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

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
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
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
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
General function:
transcription, DNA-templated
Specific function:
Represses mngA and mngB. Regulates its own expression.
Gene Name:
mngR
Uniprot ID:
P13669
Molecular weight:
28273