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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:30 UTC
Update Date2022-03-07 02:51:21 UTC
HMDB IDHMDB0012118
Secondary Accession Numbers
  • HMDB12118
Metabolite Identification
Common Name(Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol
Description(Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol (Man2GlcNAc2-Dol) is an isoprene-based lipid where an oligosaccharide moiety Man2GlcNAc2 is linked to dolichol lipid via a pyrophosphate linkage. Man2GlcNAc2-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, (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol is formed from Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol via reaction with Dolichyl β-D-mannosyl phosphate. In the next step, one more mannose residue is added to Man2GlcNAc2-Dol via reaction with Dolichyl β-D-mannosyl phosphate. (Adapted from Human Cyc).
Structure
Data?1582753015
SynonymsNot Available
Chemical FormulaC108H180N2O27P2
Average Molecular Weight2000.5295
Monoisotopic Molecular Weight1999.224871588
IUPAC Name{[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-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
Traditional Name[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-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
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)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]2O)[C@@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C108H180N2O27P2/c1-71(2)35-20-36-72(3)37-21-38-73(4)39-22-40-74(5)41-23-42-75(6)43-24-44-76(7)45-25-46-77(8)47-26-48-78(9)49-27-50-79(10)51-28-52-80(11)53-29-54-81(12)55-30-56-82(13)57-31-58-83(14)59-32-60-84(15)61-33-62-85(16)63-34-64-86(17)65-66-128-138(124,125)137-139(126,127)136-106-94(110-88(19)116)98(120)102(92(70-114)132-106)133-105-93(109-87(18)115)97(119)103(91(69-113)131-105)134-108-101(123)104(96(118)90(68-112)130-108)135-107-100(122)99(121)95(117)89(67-111)129-107/h35,37,39,41,43,45,47,49,51,53,55,57,59,61,63,86,89-108,111-114,117-123H,20-34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,64-70H2,1-19H3,(H,109,115)(H,110,116)(H,124,125)(H,126,127)/b72-37+,73-39+,74-41+,75-43+,76-45+,77-47+,78-49+,79-51+,80-53+,81-55+,82-57+,83-59+,84-61+,85-63+/t86?,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99+,100+,101+,102-,103-,104+,105+,106+,107-,108+/m1/s1
InChI KeyZTJFEYPCTFISRM-FSEKKYFOSA-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
  • Oligosaccharide phosphate
  • Polyprenyl monophosphate
  • Oligosaccharide
  • 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
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0031 g/LALOGPS
logP7.24ALOGPS
logP17.52ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area447.63 ŲChemAxon
Rotatable Bond Count65ChemAxon
Refractivity557.06 m³·mol⁻¹ChemAxon
Polarizability233.5 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 10V, Positive-QTOFsplash10-053u-5110106259-679c7d27f005f1919a7c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 20V, Positive-QTOFsplash10-0006-9210305033-30b83c8f89881f50db9f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 40V, Positive-QTOFsplash10-0536-9300308145-e1408fffc084141e06992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 10V, Negative-QTOFsplash10-014i-1272956002-18b593b41eeeb73675ba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 20V, Negative-QTOFsplash10-06u2-6592412137-ca43660c9b7f5df833812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 40V, Negative-QTOFsplash10-054k-3941200000-69ce64069326e0ad49512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 10V, Negative-QTOFsplash10-0002-0000000009-ee036398ba037b92adef2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 20V, Negative-QTOFsplash10-05pk-0000110049-cff151460210597a8bac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 40V, Negative-QTOFsplash10-0pb9-2790537121-7459d188cbe6de364d2e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 10V, Positive-QTOFsplash10-00dl-4000001479-19ba43f942ecfc7cbb9a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 20V, Positive-QTOFsplash10-0f8d-4000213239-6d02d0fcff3fbde3c0ff2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol 40V, Positive-QTOFsplash10-0udj-9201638374-91b533e6a04d2e7ee94f2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028782
KNApSAcK IDNot Available
Chemspider ID35032402
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481370
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.