Record Information
Version1.0
Creation date2011-09-21 01:38:36 UTC
Update date2015-07-21 06:59:23 UTC
Primary IDFDB028362
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-1,4-D-Mannosylchitobiosyldiphosphodolichol
DescriptionBeta-1,4-D-Mannosylchitobiosyldiphosphodolichol is a lipid-linked oligosaccharide. It is part of the N-glycan biosynthesis pathway. Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol is formed by chitobiosyldiphosphodolichol beta-mannosyltransferase (EC 2.4.1.142) via the reaction: GDP-mannose + chitobiosyldiphosphodolichol = GDP + beta-(1->4)-D-mannosylchitobiosyldiphosphodolichol. It is also a reactant or product of glycolipid 3-alpha-mannosyltransferase or mannosyltransferase II. This enzyme transfers an alpha-D-mannosyl residue from GDP-mannose to a lipid-linked (dolichol) oligosaccharide, forming an alpha-(1->3)-D-mannosyl-D-mannose linkage. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
b-1,4-D-MannosylchitobiosyldiphosphodolicholGenerator
Β-1,4-D-mannosylchitobiosyldiphosphodolicholGenerator
b-(1->4)-D-mannosylchitobiosyldiphosphodolicholHMDB
beta-(1->4)-D-mannosylchitobiosyldiphosphodolicholHMDB
beta-(1->4)-delta-mannosylchitobiosyldiphosphodolicholHMDB
beta-1,4-delta-MannosylchitobiosyldiphosphodolicholHMDB
beta-D-MannosyldiacetylchitobiosyldiphosphodolicholHMDB
beta-delta-MannosyldiacetylchitobiosyldiphosphodolicholHMDB
Man-beta1->4glcnac-beta1->4glcnac-PP-dolHMDB
N-[(2S,3R,4R,5S,6R)-4-Hydroxy-2-{[(2R,3S,4R,5R,6R)-4-hydroxy-6-{[hydroxy({[hydroxy({[(6E,10E,14E)-3,7,11,15,19-pentamethylicosa-6,10,14,18-tetraen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidateGenerator
b-(1->4)-D-mannosylchitobiosyldiodolicholHMDB
b-(1->4)-D-Mannosylchitobiosyldiphosphodolicholhmdb
b-1,4-D-MannosylchitobiosyldiodolicholHMDB
beta-(1->4)-D-mannosylchitobiosyldiodolicholHMDB
beta-(1->4)-D-Mannosylchitobiosyldiphosphodolicholhmdb
beta-(1->4)-delta-mannosylchitobiosyldiodolicholHMDB
beta-(1->4)-delta-Mannosylchitobiosyldiphosphodolicholhmdb
beta-1,4-delta-MannosylchitobiosyldiodolicholHMDB
beta-D-MannosyldiacetylchitobiosyldiodolicholHMDB
beta-delta-MannosyldiacetylchitobiosyldiodolicholHMDB
Man-beta1->4GlcNAc-beta1->4GlcNAc-PP-Dolhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP1.84ALOGPS
logP1.03ChemAxon
logS-3.9ALOGPS
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 Count29ChemAxon
Refractivity262.81 m³·mol⁻¹ChemAxon
Polarizability112.14 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC47H82N2O22P2
IUPAC name{[(2R,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}({[hydroxy({[(6E,10E,14E)-3,7,11,15,19-pentamethylicosa-6,10,14,18-tetraen-1-yl]oxy})phosphoryl]oxy})phosphinic acid
InChI IdentifierInChI=1S/C47H82N2O22P2/c1-26(2)13-9-14-27(3)15-10-16-28(4)17-11-18-29(5)19-12-20-30(6)21-22-64-72(60,61)71-73(62,63)70-46-37(49-32(8)54)40(57)43(35(25-52)67-46)68-45-36(48-31(7)53)39(56)44(34(24-51)66-45)69-47-42(59)41(58)38(55)33(23-50)65-47/h13,15,17,19,30,33-47,50-52,55-59H,9-12,14,16,18,20-25H2,1-8H3,(H,48,53)(H,49,54)(H,60,61)(H,62,63)/b27-15+,28-17+,29-19+/t30?,33-,34-,35-,36-,37-,38-,39-,40-,41+,42+,43-,44-,45+,46-,47+/m1/s1
InChI KeyCMBCFQGXXHOGEH-LSMBNOQWSA-N
Isomeric SMILESOC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(=O)C)[C@@H](O[C@@H]2CO)O[C@H]2[C@H](O)[C@@H](NC(=O)C)[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)CCC=C(C)C)[C@@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight1089.1017
Monoisotopic Molecular Weight1088.483445342
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
  • Polyprenyl phospho carbohydrate
  • Dolichyl diphosphate
  • Oligosaccharide phosphate
  • Polyprenyl monophosphate
  • Oligosaccharide
  • Polyprenyl phosphate skeleton
  • Sesterterpenoid
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Acetal
  • Oxacycle
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • 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
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0597-9004010114-de697cc038745af3f74cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-2119330204-60687570e93ae5acb5f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-2329310014-fe696fe548cc70e9db62JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3482950000-9ac2d17f15601ded1f63JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fvi-9512160512-3dc048458007d2f79fbcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdl-3901330000-bbec6d21c700735a20f6JSpectraViewer
ChemSpider ID26333131
ChEMBL IDNot Available
KEGG Compound IDC05860
Pubchem Compound ID45259170
Pubchem Substance IDNot Available
ChEBI ID18396
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11673
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