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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 00:52:50 UTC
Update Date2021-09-14 15:44:39 UTC
HMDB IDHMDB0006330
Secondary Accession Numbers
  • HMDB0001436
  • HMDB01436
  • HMDB06330
Metabolite Identification
Common NameD-Mannose 1-phosphate
DescriptionD-Mannose 1-phosphate (CAS: 27251-84-9) is a normal metabolite intermediate in fructose and mannose metabolism. It is a substrate of phosphomannomutase 1 (PMM, EC 5.4.2.8), an enzyme necessary for the synthesis of GDP-mannose (a substrate for dolichol-linked oligosaccharide synthesis). PMM converts mannose 6-phosphate into mannose-1-phosphate. A deficiency of phosphomannomutase in carbohydrate-deficient glycoprotein syndrome (CDGS) type I is associated with a decreased synthesis of mannose 1-phosphate. CDGS is a group of autosomal recessively transmitted disorders in which abnormally glycosylated proteins are formed (PMID: 9451026 , 8549746 , 12729595 ).
Structure
Thumb
Synonyms
ValueSource
1-O-Phosphono-alpha-D-mannopyranoseChEBI
alpha-D-Mannose 1-phosphateKegg
1-O-Phosphono-a-D-mannopyranoseGenerator
1-O-Phosphono-α-D-mannopyranoseGenerator
a-D-Mannose 1-phosphateGenerator
a-D-Mannose 1-phosphoric acidGenerator
alpha-D-Mannose 1-phosphoric acidGenerator
Α-D-mannose 1-phosphateGenerator
Α-D-mannose 1-phosphoric acidGenerator
D-Mannose 1-phosphoric acidGenerator
Mannose phosphateHMDB
Mannosyl phosphateHMDB
alpha-D-Mannopyranosyl phosphateHMDB
Α-D-mannopyranosyl phosphateHMDB
D-Mannose 1-phosphateHMDB
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional Nameα-D-mannose 1-phosphate
CAS Registry Number15978-07-1
SMILES
OC[C@H]1O[C@H](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 KeyHXXFSFRBOHSIMQ-RWOPYEJCSA-N
Chemical Taxonomy
Description 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 ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Alkyl phosphate
  • Phosphoric acid ester
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg143.98730932474
[M-H]-Not Available143.987http://allccs.zhulab.cn/database/detail?ID=AllCCS00000402
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
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
FooDB IDFDB031268
KNApSAcK IDC00007389
Chemspider ID388412
KEGG Compound IDC00636
BioCyc IDMANNOSE-1P
BiGG IDNot Available
Wikipedia LinkMannose_1-phosphate
METLIN IDNot Available
PubChem Compound439279
PDB IDNot Available
ChEBI ID18205
Food Biomarker OntologyNot Available
VMH IDMAN1P
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed:12729595 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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