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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:42 UTC
HMDB IDHMDB01445
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetyl-D-glucosaminyldiphosphodolichol
DescriptionThis compound is an intermediate in N-glycan biosynthesis, and the byproduct of N-acetylglucosaminyldiphosphodolichol (EC 2.4.1.141) and UDP-N-acetylglucosamine-dolichyl-phosphate (EC 2.7.8.15). (KEGG) This compound and its corresponding enzymes are implicated in the developmental programmes of a variety of eukaryotes. (PMID: 10024536 ).
Structure
Thumb
Synonyms
ValueSource
N-Acetyl-D-glucosaminyl-diphosphodolicholHMDB
Chemical FormulaC23H43NO12P2
Average Molecular Weight587.5345
Monoisotopic Molecular Weight587.226048869
IUPAC Name{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[hydroxy({[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional Name[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({hydroxy[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxyphosphoryl}oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OP(O)(=O)OP(O)(=O)OCCC(C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(=O)C)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C23H43NO12P2/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-33-37(29,30)36-38(31,32)35-23-20(24-18(5)26)22(28)21(27)19(14-25)34-23/h8,10,17,19-23,25,27-28H,6-7,9,11-14H2,1-5H3,(H,24,26)(H,29,30)(H,31,32)/b16-10+/t17?,19-,20-,21-,22-,23+/m1/s1
InChI KeyInChIKey=OZGJPDIBINDRGZ-GKXPKBPWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • N-acyl-alpha-hexosamine
  • Glucosamine
  • Amino sugar
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of N-Glycan biosynthesis
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility1.0 mg/mLALOGPS
logP1.3ALOGPS
logP1.54ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)1.75ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.31 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity139.28 m3·mol-1ChemAxon
Polarizability58.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot 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 IDFDB022628
KNApSAcK IDNot Available
Chemspider ID10128137
KEGG Compound IDC04500
BioCyc IDNot Available
BiGG ID1809448
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01445
Metagene LinkHMDB01445
METLIN ID6251
PubChem Compound11953837
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Meissner JD, Naumann A, Mueller WH, Scheibe RJ: Regulation of UDP-N-acetylglucosamine:dolichyl-phosphate N-acetylglucosamine-1-phosphate transferase by retinoic acid in P19 cells. Biochem J. 1999 Mar 1;338 ( Pt 2):561-8. [10024536 ]

Enzymes

General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
Catalyzes the initial step in the synthesis of dolichol-P-P-oligosaccharides.
Gene Name:
DPAGT1
Uniprot ID:
Q9H3H5
Molecular weight:
46089.485
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Isoform 2 may be involved in protein N-glycosylation, second step of the dolichol-linked oligosaccharide pathway.
Gene Name:
ALG13
Uniprot ID:
Q9NP73
Molecular weight:
15149.285