(N-Acetylglucosaminyl)2-diphosphodolichol (CHEM040654)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:18:56 UTC
Update Date2016-11-09 01:22:18 UTC
Accession NumberCHEM040654
Identification
Common Name(N-Acetylglucosaminyl)2-diphosphodolichol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ChitobiosyldiphosphodolicholHMDB
N,N'-diacetylchitobiosyldiphosphodolicholHMDB
[N-Acetyl-b-D-glucosaminyl-(1->4)- N-acetyl-D-glucosaminyl]diphosphodolicholHMDB
[N-Acetyl-beta-D-glucosaminyl-(1->4)- N-acetyl-D-glucosaminyl]diphosphodolicholHMDB
[N-Acetyl-beta-delta-glucosaminyl-(1->4)- N-acetyl-delta-glucosaminyl]diphosphodolicholHMDB
Chemical FormulaC96H160N2O17P2
Average Molecular Mass1676.248 g/mol
Monoisotopic Mass1675.119 g/mol
CAS Registry NumberNot Available
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
Traditional 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
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
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-6010319000-bba7db1d675717edd6f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9221212000-99015c6ad993213c0974Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9111002000-0f6ee3c46488576617a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00r6-2191000000-38d90409c07f91c97515Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08i1-9472452000-1d689f2ac72a31c86e32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6v-4940200000-5b29fd9d452ed8b13ef2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0000109000-fe8e77c1b992c933b067Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi0-3130937000-c154a59ced911edb5c99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3921111000-50e3e07dd6baa0686277Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-069r-2020029000-b60e082e0d239128cc89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00pj-2000239136-10f29554ab93013b491eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0mlb-8101947354-e178345eb9b568944acfSpectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012126
FooDB IDFDB028790
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNN-DIACETYLCHITOBIOSYLDIPHOSPHODOLICHO
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35032410
ChEBI IDNot Available
PubChem Compound ID53481378
Kegg Compound IDC04537
YMDB IDYMDB16232
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM