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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:50 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012255
Secondary Accession Numbers
  • HMDB12255
Metabolite Identification
Common NameMannosyl-(N-acetylglucosaminyl)2-diphosphodolichol
DescriptionMannosyl-(N-acetylglucosaminyl)2-diphosphodolichol is involved in dolichyl-diphosphooligosaccharide biosynthesis. (N-acetylglucosaminyl)2-diphosphodolichol reacts with GDP-α-D-mannose to produce mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol and GDP. The reaction is catalyzed by chitobiosyldiphosphodolichol α-mannosyltransferase. Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol reacts with GDP-α-D-mannose to produce (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol and GDP.
Structure
Data?1582753034
Synonyms
ValueSource
a-D-MannosylchitobiosyldiphosphodolicholHMDB
alpha-delta-MannosylchitobiosyldiphosphodolicholHMDB
b-1,4-D-MannosylchitobiosyldiphosphodolicholHMDB
beta-1,4-delta-MannosylchitobiosyldiphosphodolicholHMDB
{b-D-mannosyl-(1->4)-N-acetyl- b-D-glucosaminyl-(1->4)-N-acetyl-D-glucosaminyl}diphosphodolicholHMDB
{b-delta-mannosyl-(1->4)-N-acetyl- b-delta-glucosaminyl-(1->4)-N-acetyl-delta-glucosaminyl}diphosphodolicholHMDB
Chemical FormulaC102H170N2O22P2
Average Molecular Weight1838.3889
Monoisotopic Molecular Weight1837.172048158
IUPAC Name{[(2S,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}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-hydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}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
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]2CO)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](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C102H170N2O22P2/c1-70(2)35-20-36-71(3)37-21-38-72(4)39-22-40-73(5)41-23-42-74(6)43-24-44-75(7)45-25-46-76(8)47-26-48-77(9)49-27-50-78(10)51-28-52-79(11)53-29-54-80(12)55-30-56-81(13)57-31-58-82(14)59-32-60-83(15)61-33-62-84(16)63-34-64-85(17)65-66-119-127(115,116)126-128(117,118)125-101-92(104-87(19)109)95(112)98(90(69-107)122-101)123-100-91(103-86(18)108)94(111)99(89(68-106)121-100)124-102-97(114)96(113)93(110)88(67-105)120-102/h35,37,39,41,43,45,47,49,51,53,55,57,59,61,63,85,88-102,105-107,110-114H,20-34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,64-69H2,1-19H3,(H,103,108)(H,104,109)(H,115,116)(H,117,118)/b71-37+,72-39+,73-41+,74-43+,75-45+,76-47+,77-49+,78-51+,79-53+,80-55+,81-57+,82-59+,83-61+,84-63+/t85?,88-,89-,90-,91-,92-,93-,94-,95-,96+,97+,98-,99-,100+,101+,102+/m1/s1
InChI KeyWFPHPSFEEKVIHM-OXIGOQSHSA-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
Disposition

Biological location

Source

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 Solubility0.00088 g/LALOGPS
logP7.82ALOGPS
logP19.29ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area368.48 ŲChemAxon
Rotatable Bond Count62ChemAxon
Refractivity524.64 m³·mol⁻¹ChemAxon
Polarizability218.02 ųChemAxon
Number of Rings3ChemAxon
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-(N-acetylglucosaminyl)2-diphosphodolichol 10V, Positive-QTOFsplash10-05bf-7110219580-c97ff39933902d8cae8e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 20V, Positive-QTOFsplash10-0006-9220414110-e3160be4b901b9a7639e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 40V, Positive-QTOFsplash10-052f-9210216120-2ab90bd9ec5939c0ef102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 10V, Negative-QTOFsplash10-0udi-0292610010-89d5377c3fbb7700c3c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 20V, Negative-QTOFsplash10-00os-9772334450-351a86f577e850b2d83e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 40V, Negative-QTOFsplash10-0a6v-3930210000-cac678ff7d0e8fd18a4a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 10V, Positive-QTOFsplash10-001i-1000002920-8bc2fe26fb9ac57ae7dd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 20V, Positive-QTOFsplash10-001i-3000537889-87e2b08602ce63c31f002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 40V, Positive-QTOFsplash10-0hj2-7201938385-1fa59a1e89ce44729c1b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 10V, Negative-QTOFsplash10-000i-0000000190-a7db7dc30141f972ee852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 20V, Negative-QTOFsplash10-07bu-0302204970-6c050bac96d4fcb20dde2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol 40V, Negative-QTOFsplash10-0pb9-2981376000-9758f5f5432224b8617f2021-09-24Wishart 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 IDFDB028894
KNApSAcK IDNot Available
Chemspider ID35032423
KEGG Compound IDNot Available
BioCyc IDALPHA-D-MANNOSYLCHITOBIO
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481395
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.