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(N-Acetylglucosaminyl)2-diphosphodolichol (FDB028790)

Record Information
Version1.0
Creation date2011-09-21 01:44:59 UTC
Update date2015-07-21 06:59:32 UTC
Primary IDFDB028790
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(N-Acetylglucosaminyl)2-diphosphodolichol
Description(N-Acetylglucosaminyl)2-diphosphodolichol is a lipid-linked disaccharide that is an intermediate in dolichyl-diphosphooligosaccharide biosynthesis. The dolichyl-diphosphooligosaccharide biosynthesis pathway is of particular interest in humans, because defects in the glycosyltransferases involved lead to congenital disorders of glycosylation. The genetic analysis of this pathway in a model organism, the budding yeast Saccharomyces cerevisiae, has helped to elucidate the molecular basis of these disorders. Humanization of the N-glycosylation pathway in yeast may allow production of therapeutically useful glycoproteins. Humanization is necessary because N-glycosylation in yeast is of the high-mannose type, which would create a shorter glycoprotein half-life in humans. In this biosynthetic pathway, N-Acetylglucosaminyl)2-diphosphodolichol is a substrate for Chitobiosyldiphosphodolichol α-mannosyltransferase and formed from the enzymatic glycosylation of N-Acetylglucosaminyl-diphosphodolichol. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
logP8.4ALOGPS
logP21.06ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area289.33 ŲChemAxon
Rotatable Bond Count59ChemAxon
Refractivity492.23 m³·mol⁻¹ChemAxon
Polarizability203.07 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC96H160N2O17P2
IUPAC name{[(2S,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-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
InChI IdentifierInChI=1S/C96H160N2O17P2/c1-69(2)35-20-36-70(3)37-21-38-71(4)39-22-40-72(5)41-23-42-73(6)43-24-44-74(7)45-25-46-75(8)47-26-48-76(9)49-27-50-77(10)51-28-52-78(11)53-29-54-79(12)55-30-56-80(13)57-31-58-81(14)59-32-60-82(15)61-33-62-83(16)63-34-64-84(17)65-66-110-116(106,107)115-117(108,109)114-96-90(98-86(19)102)93(105)94(88(68-100)112-96)113-95-89(97-85(18)101)92(104)91(103)87(67-99)111-95/h35,37,39,41,43,45,47,49,51,53,55,57,59,61,63,84,87-96,99-100,103-105H,20-34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,64-68H2,1-19H3,(H,97,101)(H,98,102)(H,106,107)(H,108,109)/b70-37+,71-39+,72-41+,73-43+,74-45+,75-47+,76-49+,77-51+,78-53+,79-55+,80-57+,81-59+,82-61+,83-63+/t84?,87-,88-,89-,90-,91-,92-,93-,94-,95+,96+/m1/s1
InChI KeyAGKFOAYTTMSUFA-AYIKJQCISA-N
Isomeric SMILESOC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]2CO)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
Average Molecular Weight1676.2483
Monoisotopic Molecular Weight1675.119224728
Classification
Description Belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenyl phospho carbohydrates
Alternative Parents
Substituents
  • Polyprenyl phospho oligosaccharide
  • Polyterpenoid
  • Polyprenyl phospho carbohydrate
  • Dolichyl diphosphate
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • Disaccharide phosphate
  • N-acyl-alpha-hexosamine
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Alcohol
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)Not Available2022-08-06View Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-6010319000-bba7db1d675717edd6f72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9221212000-99015c6ad993213c09742017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9111002000-0f6ee3c46488576617a32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00r6-2191000000-38d90409c07f91c975152017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08i1-9472452000-1d689f2ac72a31c86e322017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6v-4940200000-5b29fd9d452ed8b13ef22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0000109000-fe8e77c1b992c933b0672021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi0-3130937000-c154a59ced911edb5c992021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3921111000-50e3e07dd6baa06862772021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-069r-2020029000-b60e082e0d239128cc892021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00pj-2000239136-10f29554ab93013b491e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0mlb-8101947354-e178345eb9b568944acf2021-09-23View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC04537
Pubchem Compound ID53481378
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12126
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Chitobiosyldiphosphodolichol beta-mannosyltransferaseALG1Q9BT22
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference