Record Information
Version1.0
Creation Date2016-09-30 22:40:48 UTC
Update Date2020-05-21 16:26:57 UTC
BMDB IDBMDB0001078
Secondary Accession Numbers
  • BMDB01078
Metabolite Identification
Common NameMannose 6-phosphate
DescriptionMannose 6-phosphate, also known as alpha-D-mannose-6-p or mannose 6-phosphate, 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. Mannose 6-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Mannose 6-phosphate exists in all eukaryotes, ranging from yeast to humans. Mannose 6-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Mannose 6-phosphate can be converted into fructose 6-phosphate; which is catalyzed by the enzyme mannose 6-phosphate isomerase. In addition, Mannose 6-phosphate can be biosynthesized from D-mannose through the action of the enzyme hexokinase-1. In cattle, mannose 6-phosphate is involved in the metabolic pathway called the fructose and mannose degradation pathway.
Structure
Thumb
Synonyms
ValueSource
Mannose 6-phosphoric acidGenerator
alpha-D-Mannose-6-pHMDB
alpha-D-Mannose-6-phosphateHMDB
alpha-delta-Mannose-6-pHMDB
alpha-delta-Mannose-6-phosphateHMDB
D-Mannose 6-phosphateHMDB
delta-Mannose 6-phosphateHMDB
Man-6-pHMDB
Mannose-6-phosphateHMDB
Mannose-6-phosphate dilithium saltHMDB
Mannose-6-phosphate disodium saltHMDB
Mannose-6-phosphate sodium salt, (D)-isomerHMDB
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Namemannose 6 phosphate
CAS Registry Number3672-15-9
SMILES
O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1
InChI KeyNBSCHQHZLSJFNQ-RWOPYEJCSA-N
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
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • Hemiacetal
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m³·mol⁻¹ChemAxon
Polarizability20.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Fibroblasts
  • Intestine
  • Liver
  • Prostate Tissue
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001078
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022411
KNApSAcK IDNot Available
Chemspider ID388338
KEGG Compound IDC00275
BioCyc IDNot Available
BiGG ID34471
Wikipedia LinkMannose 6-phosphate
METLIN ID5987
PubChem Compound439198
PDB IDNot Available
ChEBI ID49728
References
Synthesis ReferencePascual, C.; Herrera, L. Use of permeabilized yeast cells as a system of enzyme immobilization. Its use for the preparation of mannose 6-phosphate. Folia Microbiologica (Prague, Czech Republic) (1981), 26(2), 103-6.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
Gene Name:
HK1
Uniprot ID:
P27595
Molecular weight:
103064.0
Reactions
D-Mannose + Adenosine triphosphate → Mannose 6-phosphate + ADPdetails
General function:
Carbohydrate transport and metabolism
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions.
Gene Name:
MPI
Uniprot ID:
Q3SZI0
Molecular weight:
46369.0
Reactions
Mannose 6-phosphate → Fructose 6-phosphatedetails
General function:
Involved in phosphomannomutase activity
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions.
Gene Name:
PMM2
Uniprot ID:
Q3SZJ9
Molecular weight:
27997.0
Reactions
D-Mannose 1-phosphate → Mannose 6-phosphatedetails
General function:
Involved in mannose binding
Specific function:
Transport of phosphorylated lysosomal enzymes from the Golgi complex and the cell surface to lysosomes. Lysosomal enzymes bearing phosphomannosyl residues bind specifically to mannose-6-phosphate receptors in the Golgi apparatus and the resulting receptor-ligand complex is transported to an acidic prelyosomal compartment where the low pH mediates the dissociation of the complex.
Gene Name:
M6PR
Uniprot ID:
P11456
Molecular weight:
31201.0
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
PLIN3
Uniprot ID:
Q3SX32
Molecular weight:
47603.0
General function:
Involved in receptor activity
Specific function:
Acts as a positive regulator of T-cell coactivation, by binding DPP4 (By similarity). Transport of phosphorylated lysosomal enzymes from the Golgi complex and the cell surface to lysosomes. Lysosomal enzymes bearing phosphomannosyl residues bind specifically to mannose-6-phosphate receptors in the Golgi apparatus and the resulting receptor-ligand complex is transported to an acidic prelyosomal compartment where the low pH mediates the dissociation of the complex. This receptor also binds IGF2.
Gene Name:
IGF2R
Uniprot ID:
P08169
Molecular weight:
274529.0