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Record Information
Version3.6
Creation Date2007-05-23 00:52:50 UTC
Update Date2016-02-11 01:07:28 UTC
HMDB IDHMDB06330
Secondary Accession Numbers
  • HMDB01436
Metabolite Identification
Common NameD-Mannose 1-phosphate
DescriptionD-Mannose 1-phosphate is a normal metabolite intermediate in the Fructose and mannose metabolism, and substrate of phosphomannomutase 1(PMM, EC: 5.4.2.8), an enzyme necessary for the synthesis of GDP-mannose. PMM converts mannose 6-phosphate to mannose-1-phosphate, which is required for the synthesis of GDP-mannose, a substrate for dolichol-linked oligosaccharide synthesis. Deficiency of phosphomannomutase in Carbohydrate-deficient glycoprotein syndrome (CDGS, a group of autosomal recessively transmitted disorders in which abnormally glycosylated proteins are formed) type 1 is associated with decreased synthesis of mannose 1-phosphate. (PMID: 9451026 , 8549746 , 12729595 ).
Structure
Thumb
Synonyms
ValueSource
1-(Dihydrogen phosphate)-D-mannopyranoseHMDB
1-(Dihydrogen phosphate)-delta-mannopyranoseHMDB
alpha-D-Mannose 1-phosphateHMDB
alpha-delta-Mannose 1-phosphateHMDB
D-Mannose 1-phosphatesHMDB
D-Mannose-1-phosphateHMDB
delta-Mannose 1-phosphatesHMDB
delta-Mannose-1-phosphateHMDB
Mannose 1-phosphateHMDB
Mannose 1-phosphate-mannopyranoseHMDB
Mannose-1-PHMDB
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional NameD-mannose 1-phosphate
CAS Registry Number27251-84-9
SMILES
OC[C@H]1OC(OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6?/m1/s1
InChI KeyInChIKey=HXXFSFRBOHSIMQ-QTVWNMPRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • 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
Water Solubility32.3 mg/mLALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m3·mol-1ChemAxon
Polarizability20.68 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1893000000-0ec9e139257029be0d07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-4057005941a73b47e92bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-2b520b8d7520453613e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-adafd3ed58bf5371e4a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-9480000000-6d21f499da6e13bbe38dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-68aeffe1ebca2d4d4362View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581aeView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064map00051
Fructose intolerance, hereditarySMP00725Not Available
FructosuriaSMP00561Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023892
KNApSAcK IDNot Available
Chemspider ID559210
KEGG Compound IDC00636
BioCyc IDMANNOSE-1P
BiGG ID42578
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06330
Metagene LinkHMDB06330
METLIN ID6245
PubChem Compound644175
PDB IDNot Available
ChEBI ID35374
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Korner C, Lehle L, von Figura K: Abnormal synthesis of mannose 1-phosphate derived carbohydrates in carbohydrate-deficient glycoprotein syndrome type I fibroblasts with phosphomannomutase deficiency. Glycobiology. 1998 Feb;8(2):165-71. [9451026 ]
  2. Van Schaftingen E, Jaeken J: Phosphomannomutase deficiency is a cause of carbohydrate-deficient glycoprotein syndrome type I. FEBS Lett. 1995 Dec 27;377(3):318-20. [8549746 ]
  3. Orvisky E, Stubblefield B, Long RT, Martin BM, Sidransky E, Krasnewich D: Phosphomannomutase activity in congenital disorders of glycosylation type Ia determined by direct analysis of the interconversion of mannose-1-phosphate to mannose-6-phosphate by high-pH anion-exchange chromatography with pulsed amperometric detection. Anal Biochem. 2003 Jun 1;317(1):12-8. [12729595 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions (By similarity).
Gene Name:
PMM2
Uniprot ID:
O15305
Molecular weight:
28081.925
Reactions
D-Mannose 1-phosphate → Mannose 6-phosphatedetails
Mannose 6-phosphate → D-Mannose 1-phosphatedetails
General function:
Involved in metal ion binding
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions. In addition, may be responsible for the degradation of glucose-1,6-bisphosphate in ischemic brain.
Gene Name:
PMM1
Uniprot ID:
Q92871
Molecular weight:
29746.545
Reactions
D-Mannose 1-phosphate → Mannose 6-phosphatedetails
Mannose 6-phosphate → D-Mannose 1-phosphatedetails
General function:
Involved in transferase activity
Specific function:
Not Available
Gene Name:
GMPPB
Uniprot ID:
Q9Y5P6
Molecular weight:
42649.34
Reactions
Guanosine triphosphate + D-Mannose 1-phosphate → Pyrophosphate + Guanosine diphosphate mannosedetails
General function:
Involved in transferase activity
Specific function:
Not Available
Gene Name:
GMPPA
Uniprot ID:
Q96IJ6
Molecular weight:
46290.785
Reactions
Guanosine triphosphate + D-Mannose 1-phosphate → Pyrophosphate + Guanosine diphosphate mannosedetails
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Catalyzes the conversion of the nucleoside breakdown products ribose-1-phosphate and deoxyribose-1-phosphate to the corresponding 5-phosphopentoses. May also catalyze the interconversion of glucose-1-phosphate and glucose-6-phosphate. Has low glucose 1,6-bisphosphate synthase activity.
Gene Name:
PGM2
Uniprot ID:
Q96G03
Molecular weight:
68282.765