Human Metabolome Database Version 3.5

Showing metabocard for Dolichol phosphate (HMDB06353)

Record Information
Version 3.5
Creation Date 2007-05-22 19:44:46 -0600
Update Date 2013-05-29 13:43:37 -0600
HMDB ID HMDB06353
Secondary Accession Numbers None
Metabolite Identification
Common Name Dolichol phosphate
Description Dolichol phosphate is the most prevalent polyisoprenyl-glycosyl carrier found in mammals. It is involved in reactions such as the C-4 and O-mannosylation of proteins, the formation of glycosylphosphatidylinositol (GPI) anchors and the N-glycosylation of proteins. The chain length of eukaryotic dolichol molecules differs from 14 to 17 isoprene units in unicellular organisms like yeast whereas mammalian cells produce dolichol with 18-21 isoprene units. During the de novo synthesis of dolichol in eukaryotes, farnesyl pyrophosphate, a metabolite of cholesterol biosynthesis, is elongated by successive condensations to isopentenyl pyrophosphate molecules. These reactions are catalyzed by cis-isopentenyltransferases. After the polyisoprene pyrophosphate chain has reached its final length, both phosphate residues are released by mono- or pyrophosphatases. The isoprene unit of the polyprenol is then reduced by a nicotinamide adenine dinucleotide phosphate (NADPH)-dependent microsomal reductase. The final step in dolichol phosphate synthesis is catalyzed by dolichol kinase (DK1), an enzyme that transfers a phosphate from choline-phosphate cytidine triphosphate (CTP) to dolichol. Once synthesized, dolichol phosphate can react with cytosolic GDP-mannose in the endoplasmic reticulum membrane to form dolichyl phosphate D-mannose. A new inherited metabolic disorder, Dolichol kinase (DK1) deficiency has recently been discovered. Affected patients present with a very severe clinical phenotype, with death in early infancy. Symptoms include secondary microencephaly, dry, thin, parchmentlike skin, hyperkeratosis, minimal hair growth and muscular hypotonia. (PMID: 17273964 Link_out).
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  1. Dolichol monophosphate
  2. Dolichol-P
  3. Dolichol-phosphate
  4. Dolichol-PO4
  5. Dolichyl-phosphate
  6. Dolychol phosphate
Chemical Formula Not Available
Average Molecular Weight Not Available
Monoisotopic Molecular Weight Not Available
IUPAC Name Not Available
Traditional IUPAC Name Not Available
CAS Registry Number 34457-14-2
SMILES Not Available
InChI Identifier InChI=1S/C15H29O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,15H,5-6,8,10-12H2,1-4H3,(H2,16,17,18)/b14-9+
InChI Key DZHSRPJGCZHWOM-NTEUORMPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Sesquiterpenes
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Isoprene
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
Direct Parent Sesquiterpenes
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
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
Formal Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
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 FDB023901
KNApSAcK ID Not Available
Chemspider ID 4444045 Link_out
KEGG Compound ID C00110 Link_out
BioCyc ID CPD-171 Link_out
BiGG ID 1809214 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06353 Link_out
Metagene Link HMDB06353 Link_out
METLIN ID Not Available
PubChem Compound 5280322 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Kranz C, Jungeblut C, Denecke J, Erlekotte A, Sohlbach C, Debus V, Kehl HG, Harms E, Reith A, Reichel S, Grobe H, Hammersen G, Schwarzer U, Marquardt T: A defect in dolichol phosphate biosynthesis causes a new inherited disorder with death in early infancy. Am J Hum Genet. 2007 Mar;80(3):433-40. Epub 2007 Jan 31. Pubmed: 17273964 Link_out

Enzymes
Name: Dolichol-phosphate mannosyltransferase
Reactions: Not Available
Gene Name: DPM1
Uniprot ID: O60762 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein O-mannosyl-transferase 1
Reactions: Not Available
Gene Name: POMT1
Uniprot ID: Q9Y6A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein O-mannosyl-transferase 2
Reactions: Not Available
Gene Name: POMT2
Uniprot ID: Q9UKY4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dolichyl-phosphate beta-glucosyltransferase
Reactions: Not Available
Gene Name: ALG5
Uniprot ID: Q9Y673 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase
Reactions: Not Available
Gene Name: DPAGT1
Uniprot ID: Q9H3H5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dolichyldiphosphatase 1
Reactions: Not Available
Gene Name: DOLPP1
Uniprot ID: Q86YN1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA