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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:05 UTC
Update Date2017-12-07 02:35:59 UTC
HMDB IDHMDB0012152
Secondary Accession Numbers
  • HMDB12152
Metabolite Identification
Common Name2-O-(6-Phospho-alpha-mannosyl)-D-glycerate
Description2-O-(6-Phospho-alpha-mannosyl)-D-glycerate is an alpha-D-mannosylglycerate (MG) that is an intermediate in 2-O-alpha-mannosyl-D-glycerate degradation. It can be generated from 2-O-alpha-mannosyl-D-glycerate via the enzyme 2-O-alpha-mannosyl-D-glycerate transporting phosphotransferase system (mngA). 2-O-Alpha-mannosyl-D-glycerate is a natural extremolyte identified in microorganisms growing under extremely high temperatures up to 100 oC, and had been shown to protect proteins against various stress conditions such as heat, freezing, thawing, and drying. MG that is naturally occurring hyperthermophilic osmolytes, could be potential drug candidates or lead compounds against alpha,beta aggregation associated with Alzheimer's disease(PMID: 18304694 ). In most organisms MG is produced from guanosine pyrophosphate mannose (GDP-alpha-D-mannose) via mannosyl-3-phosphoglycerate in two steps, catalyzed by the enzymes mannosyl-3-phosphoglycerate synthase and mannosyl-3-phosphoglycerate phosphatase.
Structure
Thumb
Synonyms
ValueSource
2-O-(6-phospho-alpha-D-Mannosyl)-D-glycerateKegg
2-O-(6-phospho-a-D-Mannosyl)-D-glycerateGenerator
2-O-(6-phospho-a-D-Mannosyl)-D-glyceric acidGenerator
2-O-(6-phospho-alpha-D-Mannosyl)-D-glyceric acidGenerator
2-O-(6-phospho-α-D-mannosyl)-D-glycerateGenerator
2-O-(6-phospho-α-D-mannosyl)-D-glyceric acidGenerator
2-O-(6-phospho-a-Mannosyl)-D-glycerateGenerator
2-O-(6-phospho-a-Mannosyl)-D-glyceric acidGenerator
2-O-(6-phospho-alpha-Mannosyl)-D-glyceric acidGenerator
2-O-(6-phospho-α-mannosyl)-D-glycerateGenerator
2-O-(6-phospho-α-mannosyl)-D-glyceric acidGenerator
2-O-(6-phospho-alpha-Mannosyl)-delta-glycerateHMDB
2-O-(6-phospho-alpha-Mannosyl)-delta-glyceric acidHMDB
Chemical FormulaC9H17O12P
Average Molecular Weight348.1978
Monoisotopic Molecular Weight348.04576252
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 Name(2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}propanoic acid
CAS Registry NumberNot Available
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
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)/t3-,4-,5-,6+,7+,9+/m1/s1
InChI KeyBOLXAGHGKNGVBE-MTXRGOKVSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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 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
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028809
KNApSAcK IDNot Available
Chemspider ID26332075
KEGG Compound IDC16699
BioCyc IDCPD0-1063
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24892815
PDB IDNot Available
ChEBI ID61001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. doi: 10.1016/j.peptides.2007.12.014. Epub 2008 Jan 9. [PubMed:18304694 ]