Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate (M2MDB003401)

Record Information
Version2.0
Creation Date2012-10-10 12:12:11 -0600
Update Date2015-06-03 17:25:43 -0600
Secondary Accession Numbers
  • ECMDB23011
Identification
Name:2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate
Description2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate is a substrate for 2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate acylhydrolase. The enzyme participates in the mannosylglycerate degradation pathway of some bacteria. Mannosylglycerate is phosphorylated during transport into the cell, and the phosphorylated form is hydrolysed by this enzyme. It is involved in 2-O-alpha-mannosyl-D-glycerate degradation.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2R)-3-Hydroxy-2-(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(phosphonooxymethyl)oxan-2-yloxypropanoate
  • (2R)-3-hydroxy-2-(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(phosphonooxymethyl)oxan-2-yloxypropanoic acid
  • (2R)-3-Hydroxy-2-(6-O-phosphono-a-D-mannopyranosyl)oxypropanoate
  • (2R)-3-Hydroxy-2-(6-O-phosphono-a-D-mannopyranosyl)oxypropanoic acid
  • (2R)-3-Hydroxy-2-(6-O-phosphono-alpha-D-mannopyranosyl)oxypropanoate
  • (2R)-3-Hydroxy-2-(6-O-phosphono-alpha-D-mannopyranosyl)oxypropanoic acid
  • (2R)-3-Hydroxy-2-(6-O-phosphono-α-D-mannopyranosyl)oxypropanoate
  • (2R)-3-Hydroxy-2-(6-O-phosphono-α-D-mannopyranosyl)oxypropanoic acid
  • 2(α-D-mannosyl-6-phosphate)-D-glycerate
  • 2(α-D-mannosyl-6-phosphoric acid)-D-glyceric acid
  • 2-O-(6-phospho-a-D-Mannosyl)-D-glycerate
  • 2-O-(6-phospho-a-D-Mannosyl)-D-glyceric acid
  • 2-O-(6-Phospho-a-mannosyl)-D-glycerate
  • 2-O-(6-Phospho-a-mannosyl)-D-glyceric acid
  • 2-O-(6-phospho-a-Mannosyl)-delta-glycerate
  • 2-O-(6-phospho-a-Mannosyl)-delta-glyceric acid
  • 2-O-(6-phospho-a-Mannosyl)-δ-glycerate
  • 2-O-(6-phospho-a-Mannosyl)-δ-glyceric acid
  • 2-O-(6-phospho-alpha-D-Mannosyl)-D-glyceric acid
  • 2-O-(6-Phospho-alpha-mannosyl)-D-glycerate
  • 2-O-(6-Phospho-alpha-mannosyl)-D-glyceric acid
  • 2-O-(6-Phospho-alpha-mannosyl)-delta-glycerate
  • 2-O-(6-Phospho-alpha-mannosyl)-delta-glyceric acid
  • 2-O-(6-phospho-α-D-Mannosyl)-D-glycerate
  • 2-O-(6-phospho-α-D-Mannosyl)-D-glyceric acid
  • 2-O-(6-phospho-α-Mannosyl)-D-glycerate
  • 2-O-(6-phospho-α-Mannosyl)-D-glyceric acid
  • 2-O-(6-phospho-α-Mannosyl)-δ-glycerate
  • 2-O-(6-phospho-α-Mannosyl)-δ-glyceric acid
Chemical Formula:C9H17O12P
Weight:Average: 348.1978
Monoisotopic: 348.04576252
InChI Key:BOLXAGHGKNGVBE-MTXRGOKVSA-N
InChI: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)/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-[(phosphonooxy)methyl]oxan-2-yl]oxy}propanoic acid
Traditional IUPAC Name:(2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}propanoic acid
SMILES:OC[C@@H](O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O)C(O)=O
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose 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
  • Monoalkyl phosphate
  • 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
  • Acetal
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility28.4 g/LALOGPS
logP-2.4ALOGPS
logP-3.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity63.67 m³·mol⁻¹ChemAxon
Polarizability28.12 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid
2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid
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 degradationPW002096 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-9624000000-b2eb9ad809dfb1614adcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00di-3530239000-c31601470a21a35a479dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("2-O-(6-Phospho-alpha-mannosyl)-D-glycerate,3TBDMS,#8" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053j-9437000000-c5fa5dddffe828fd1b0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9310000000-ada2af57904347782db9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9600000000-d6cbf6642be6233baf9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054t-9324000000-66e5bfc65619e1fbc660View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-fff4af92a3b80c0f63c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4927cd7fdf9692a12431View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1391000000-9b1fea4aa36b2edf8641View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pa-9620000000-e994296d32e32ffdaeb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fs-9300000000-c68a692330ed21620ab7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9011000000-4784bc2eb78346de6c49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9010000000-ea3e1896d17fa5092d85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-849c1c60f1e41f399334View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Ryu J, Kanapathipillai M, Lentzen G, Park CB: Inhibition of beta-amyloid peptide aggregation and neurotoxicity by alpha-d-mannosylglycerate, a natural extremolyte. Peptides. 2008 Apr;29(4):578-84. Epub 2008 Jan 9. Pubmed: 18304694
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID61001
HMDB IDHMDB12152
Pubchem Compound ID24892815
Kegg IDC16699
ChemSpider ID26332075
Wikipedia IDNot Available
BioCyc IDCPD0-1063
EcoCyc IDCPD0-1063

Enzymes

Protein Details
1. Alpha-mannosidase mngB
General function:
Involved in catalytic activity
Specific function:
May hydrolyze mannosyl-D-glycerate to mannose-6- phosphate and glycerate
Gene Name:
mngB
Uniprot ID:
P54746
Molecular weight:
100014
Reactions
2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate + H(2)O = D-mannose 6-phosphate + D-glycerate.

Transporters

Protein Details
1. 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