Human Metabolome Database Version 3.5

Showing metabocard for Dolichyl phosphate D-mannose (HMDB00994)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:01 -0600
HMDB ID HMDB00994
Secondary Accession Numbers None
Metabolite Identification
Common Name Dolichyl phosphate D-mannose
Description Dolichyl phosphate D-mannose (DPM) is an intermediate in the biosynthesis of N-glycans. It is a substrate for dolichol-phosphate mannosyltransferase (PMID: 10835346 Link_out). Dolichol-phosphate mannosyltransferase is a heterotrimeric protein embedded in the endoplasmic reticulum membrane. The first subunit of the heterotrimer appears to be the actual catalyst, and the other two subunits appear to stabilize it. More specifically, dolichol-phosphate-mannose is the donor of mannose groups in the synthesis of the dolichol pyrophosphate-linked precursor oligosaccharide in asparagine-linked glycosylation, in the synthesis of glycosyl phosphatidylinositol (GPI) anchor precursors, in protein O-mannosylation and in protein C-mannosylation. Its synthesis proceeds in two steps. First, cytosolic GDP-mannose reacts with dolichol phosphate exposed on the cytosolic face of the endoplasmic reticulum membrane to form DPM with its mannose moiety oriented toward the cytosol. The DPM molecule then flips in the endoplasmic reticulum membrane, so that its mannose moiety is in the endoplasmic reticulum lumen, accessible to the enzymes that catalyze its transfer to growing glycolipids and glycoproteins. (PMID: 11102867 Link_out). Dolichyl phosphate D-mannose is also a substrate for protein O-mannosyl-transferase 2 and protein O-mannosyl-transferase 1.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Dolichol phosphate mannose
  2. Dolichyl D-mannosyl phosphate
  3. Dolichyl phosphate D-mannose
  4. DPM
Chemical Formula C6H13O9P
Average Molecular Weight 260.1358
Monoisotopic Molecular Weight 260.029718526
IUPAC Name {[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name [(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid
CAS Registry Number 908211-94-9
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 Key HXXFSFRBOHSIMQ-PQMKYFCFSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
Substituents
  • 1,2 Diol
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Hexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of N-Glycan biosynthesis
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 32.3 g/L ALOGPS
LogP -2.00 ALOGPS
LogP -3.1 ChemAxon
LogS -0.91 ALOGPS
pKa (strongest acidic) 1.16 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 156.91 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 46.8 ChemAxon
Polarizability 20.33 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022356
KNApSAcK ID Not Available
Chemspider ID 2496902 Link_out
KEGG Compound ID C03862 Link_out
BioCyc ID CPD-171 Link_out
BiGG ID 1809321 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB00994 Link_out
Metagene Link HMDB00994 Link_out
METLIN ID 5925 Link_out
PubChem Compound 3246168 Link_out
PDB ID Not Available
ChEBI ID 1220424 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Maeda Y, Tanaka S, Hino J, Kangawa K, Kinoshita T: Human dolichol-phosphate-mannose synthase consists of three subunits, DPM1, DPM2 and DPM3. EMBO J. 2000 Jun 1;19(11):2475-82. Pubmed: 10835346 Link_out
  2. Kinoshita T, Inoue N: Dissecting and manipulating the pathway for glycosylphos-phatidylinositol-anchor biosynthesis. Curr Opin Chem Biol. 2000 Dec;4(6):632-8. Pubmed: 11102867 Link_out

Enzymes
Name: Dolichol-phosphate mannosyltransferase
Reactions:
Guanosine diphosphate mannose + Dolichol-20 unknown Guanosine diphosphate + Dolichyl phosphate D-mannose details
Gene Name: DPM1
Uniprot ID: O60762 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein O-mannosyl-transferase 1
Reactions:
Dolichyl phosphate D-mannose + protein unknown Dolichol-20 + O-D-mannosylprotein details
Gene Name: POMT1
Uniprot ID: Q9Y6A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein O-mannosyl-transferase 2
Reactions:
Dolichyl phosphate D-mannose + protein unknown Dolichol-20 + O-D-mannosylprotein details
Gene Name: POMT2
Uniprot ID: Q9UKY4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dol-P-Man:Man(5)GlcNAc(2)-PP-Dol alpha-1,3-mannosyltransferase
Reactions:
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol unknown D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20 details
Gene Name: ALG3
Uniprot ID: Q92685 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dol-P-Man:Man(7)GlcNAc(2)-PP-Dol alpha-1,6-mannosyltransferase
Reactions:
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol unknown D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20 details
Gene Name: ALG12
Uniprot ID: Q9BV10 Link_out
Protein Sequence: FASTA
Name: Alpha-1,2-mannosyltransferase ALG9
Reactions:
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol unknown D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20 details
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol unknown D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-[D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->6))-D-Man-alpha-(1->6)]-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20 details
Gene Name: ALG9
Uniprot ID: Q9H6U8 Link_out
Protein Sequence: FASTA
Name: Dolichol phosphate-mannose biosynthesis regulatory protein
Reactions:
Guanosine diphosphate mannose + Dolichol-20 unknown Guanosine diphosphate + Dolichyl phosphate D-mannose details
Gene Name: DPM2
Uniprot ID: O94777 Link_out
Name: Dolichol-phosphate mannosyltransferase subunit 3
Reactions:
Guanosine diphosphate mannose + Dolichol-20 unknown Guanosine diphosphate + Dolichyl phosphate D-mannose details
Gene Name: DPM3
Uniprot ID: Q9P2X0 Link_out