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(Glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol (FDB028781)

Record Information
Version1.0
Creation date2011-09-21 01:44:52 UTC
Update date2015-07-21 06:59:32 UTC
Primary IDFDB028781
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(Glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol
Description(Glucosyl)2-(Mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol (Glc2Man9GlcNAc2-Dol) is an isoprene-based lipid where an oligosaccharide moiety Glc2Man9GlcNAc2 is linked to dolichol lipid via a pyrophosphate linkage. Glc2Man9GlcNAc2-Dol is an intermediate in dolichyl-diphosphooligosaccaride biosynthesis pathway and synthesis of N-glycans. The biosynthetic pathway for this lipid-linked precursor begins with the phosphorylation of dolichol, followed by stepwise addition of sugar residues to form the product dolichyl-diphosphooligosaccharide. This pathway is of particular interest in humans, because defects in the glycosyltransferases involved lead to congenital disorders of N-glycosylation of proteins. In this pathway, (Glucosyl)2-(Mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol is formed from Glucosyl-(Mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol via reaction with Dolichyl β-D-glucosyl phosphate. In the next step, one more glucose residue is added to Glc2Man9GlcNAc2-Dol via reaction with Dolichyl β-D-glucosyl phosphate. (Adapted from Human Cyc) [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP3.04ALOGPS
logP1.58ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count69ChemAxon
Hydrogen Donor Count42ChemAxon
Polar Surface Area1159.98 ŲChemAxon
Rotatable Bond Count92ChemAxon
Refractivity848.77 m³·mol⁻¹ChemAxon
Polarizability368.95 ųChemAxon
Number of Rings13ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC162H270N2O72P2
IUPAC name{[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-6-({[(2S,3S,4S,5R,6R)-4-{[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-({[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxyoxan-2-yl]oxy}methyl)-4-{[(2R,3S,4S,5S,6R)-3-{[(2R,3S,4S,5S,6R)-3-{[(2R,3S,4S,5R,6R)-4-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-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/C162H270N2O72P2/c1-80(2)35-20-36-81(3)37-21-38-82(4)39-22-40-83(5)41-23-42-84(6)43-24-44-85(7)45-25-46-86(8)47-26-48-87(9)49-27-50-88(10)51-28-52-89(11)53-29-54-90(12)55-30-56-91(13)57-31-58-92(14)59-32-60-93(15)61-33-62-94(16)63-34-64-95(17)65-66-211-237(205,206)236-238(207,208)235-151-112(164-97(19)177)125(190)140(108(77-175)222-151)225-150-111(163-96(18)176)124(189)141(107(76-174)221-150)226-158-139(204)145(230-161-149(132(197)119(184)103(72-170)219-161)234-162-148(131(196)118(183)104(73-171)220-162)233-157-138(203)143(121(186)106(75-173)216-157)228-156-137(202)142(120(185)105(74-172)215-156)227-153-133(198)126(191)113(178)98(67-165)212-153)123(188)110(224-158)78-209-152-136(201)144(229-160-147(130(195)117(182)102(71-169)218-160)232-155-135(200)128(193)115(180)100(69-167)214-155)122(187)109(223-152)79-210-159-146(129(194)116(181)101(70-168)217-159)231-154-134(199)127(192)114(179)99(68-166)213-154/h35,37,39,41,43,45,47,49,51,53,55,57,59,61,63,95,98-162,165-175,178-204H,20-34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,64-79H2,1-19H3,(H,163,176)(H,164,177)(H,205,206)(H,207,208)/b81-37+,82-39+,83-41+,84-43+,85-45+,86-47+,87-49+,88-51+,89-53+,90-55+,91-57+,92-59+,93-61+,94-63+/t95?,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126+,127+,128+,129+,130+,131+,132+,133-,134+,135+,136+,137-,138+,139+,140-,141-,142+,143+,144+,145+,146+,147+,148+,149+,150+,151+,152+,153-,154-,155-,156-,157-,158+,159+,160-,161-,162-/m1/s1
InChI KeyAALOZWVGCDVETJ-XSNQQLSJSA-N
Isomeric SMILESOC[C@H]1O[C@H](OC[C@H]2O[C@H](OC[C@H]3O[C@@H](O[C@H]4[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]4CO)O[C@H]4[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]4CO)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](O)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@H]5O)[C@@H]4O)[C@@H]3O)[C@@H](O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H]2O)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O
Average Molecular Weight3459.7949
Monoisotopic Molecular Weight3457.700282458
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
  • Polysaccharide
  • Polyterpenoid
  • Polyprenyl phospho carbohydrate
  • Dolichyl diphosphate
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • 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
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-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1330905023-5f9d3a87bcded0595cb92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059x-5720809144-7e8e340bf8ba778e33e72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059x-3721809156-0f28f3843bd48c79a0632017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-022j-4461931284-18262f1d37b0f383913c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-1493511020-950075041fed245c68762017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1591100000-7270ebf6cf6b08d3e9632017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052g-1115901001-1340f99219660d1d3b0b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5d-1350902123-494917eecec28b022b172021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2113913121-b0c0d00b6a1bcb28fa512021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0102900000-3668a7a955b9a522ab8c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-1209701000-c77cde02ffd90ac710fb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5767945000-8505e09fab409f3f72362021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481369
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12117
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference