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Showing metabocard for N-Acetylglucosaminyl-diphosphodolichol (HMDB12264)

Record Information
Version 3.5
Creation Date 2009-04-06 10:21:59 -0600
Update Date 2013-02-08 17:28:38 -0700
HMDB ID HMDB12264
Secondary Accession Numbers None
Metabolite Identification
Common Name N-Acetylglucosaminyl-diphosphodolichol
Description N-Acetylglucosaminyl-diphosphodolichol is found in the dolichyl-diphosphooligosaccharide biosynthesis pathway. Dolichyl-phosphate reacts with UDP-N-acetyl-D-glucosamine to produce N-acetylglucosaminyl-diphosphodolichol and UMP. UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase catalyzes this reaction. N-acetylglucosaminyl-diphosphodolichol reacts with UDP-N-acetyl-D-glucosamine to produce (N-acetylglucosaminyl)2-diphosphodolichol and UDP. N-acetylglucosaminyldiphosphodolichol N-acetylglucosaminyltransferase catalyzes this reaction.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. N-Acetyl-D-glucosaminyldiphosphodolichol
Chemical Formula C88H147NO12P2
Average Molecular Weight 1473.0558
Monoisotopic Molecular Weight 1472.039852197
IUPAC Name {[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}[({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional IUPAC Name [(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pe
CAS Registry Number Not Available
SMILES OC[C@H]1O[C@@H](OP(=O)(O)OP(=O)(O)OCCC(C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(C)=O)[C@@H](O)[C@@H]1O
InChI Identifier InChI=1S/C88H147NO12P2/c1-67(2)34-19-35-68(3)36-20-37-69(4)38-21-39-70(5)40-22-41-71(6)42-23-43-72(7)44-24-45-73(8)46-25-47-74(9)48-26-49-75(10)50-27-51-76(11)52-28-53-77(12)54-29-55-78(13)56-30-57-79(14)58-31-59-80(15)60-32-61-81(16)62-33-63-82(17)64-65-98-102(94,95)101-103(96,97)100-88-85(89-83(18)91)87(93)86(92)84(66-90)99-88/h34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,82,84-88,90,92-93H,19-33,35,37,39,41,43,45,47,49,51,53,55,57,59,61,63-66H2,1-18H3,(H,89,91)(H,94,95)(H,96,97)/b68-36+,69-38+,70-40+,71-42+,72-44+,73-46+,74-48+,75-50+,76-52+,77-54+,78-56+,79-58+,80-60+,81-62+/t82?,84-,85-,86-,87-,88+/m1/s1
InChI Key PJOHRMFBCONSHW-HWUFQLITSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Polyterpenes
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
Substituents
  • 1,2 Diol
  • Carboxamide Group
  • Farnesane Phosphate
  • Glucosamine
  • Hexose Monosaccharide
  • Isoprene
  • Mannosamine
  • Monosaccharide Phosphate
  • N Acetyl Alpha Hexosamine 1 Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxane
  • Phosphoric Acid Ester
  • Polyprenyl Phosphate Skeleton
  • Polyprenyl Phospho Carbohydrate
  • Primary Alcohol
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Tetraterpene Backbone
Direct Parent Polyterpenes
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
  • Extracellular
  • Membrane
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 5.830E-04 g/L ALOGPS
LogP 9.11 ALOGPS
LogP 23.12 ChemAxon
LogS -6.40 ALOGPS
pKa (strongest acidic) 1.75 ChemAxon
pKa (strongest basic) -0.78 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 201.31 A2 ChemAxon
Rotatable Bond Count 55 ChemAxon
Refractivity 448.71 ChemAxon
Polarizability 182.96 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12264 Link_out
Metagene Link HMDB12264 Link_out
METLIN ID Not Available
PubChem Compound Not Available
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available