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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-02-04 09:52:18 UTC
Update Date2022-03-07 02:51:13 UTC
HMDB IDHMDB0011673
Secondary Accession Numbers
  • HMDB11673
Metabolite Identification
Common 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.
Structure
Data?1582752937
Synonyms
ValueSource
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]ethanimidateHMDB
Chemical FormulaC47H82N2O22P2
Average Molecular Weight1089.1017
Monoisotopic Molecular Weight1088.483445342
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
Traditional 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]oxyphosphoryl}oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
OC[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
InChI Identifier
InChI=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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Cysteine or derivatives
  • Alpha-amino acid or derivatives
  • N-acyl-amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Alkylthiol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
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 Solubility0.16 g/LALOGPS
logP1.84ALOGPS
logP1.03ChemAxon
logS-3.8ALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+313.57330932474
DeepCCS[M-H]-311.84930932474
DeepCCS[M-2H]-345.88130932474
DeepCCS[M+Na]+319.90230932474
AllCCS[M+H]+319.632859911
AllCCS[M+H-H2O]+319.832859911
AllCCS[M+NH4]+319.332859911
AllCCS[M+Na]+319.232859911
AllCCS[M-H]-313.632859911
AllCCS[M+Na-2H]-320.632859911
AllCCS[M+HCOO]-328.132859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 10V, Positive-QTOFsplash10-0597-9004010114-de697cc038745af3f74c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 20V, Positive-QTOFsplash10-052f-2119330204-60687570e93ae5acb5f82016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 40V, Positive-QTOFsplash10-052f-2329310014-fe696fe548cc70e9db622016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 10V, Negative-QTOFsplash10-0udi-3482950000-9ac2d17f15601ded1f632016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 20V, Negative-QTOFsplash10-0fvi-9512160512-3dc048458007d2f79fbc2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 40V, Negative-QTOFsplash10-0pdl-3901330000-bbec6d21c700735a20f62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 10V, Negative-QTOFsplash10-000i-9000000000-63fde6f7ba9f34f93cb12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 20V, Negative-QTOFsplash10-02di-9202000302-bac1ce5762d5fa0fd1e72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 40V, Negative-QTOFsplash10-0zfr-8950150412-b1c3bbd81d8735270d872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 10V, Positive-QTOFsplash10-003i-9001000012-38cce817270368bac5052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 20V, Positive-QTOFsplash10-001j-9210000010-44302c6b7e71301324f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol 40V, Positive-QTOFsplash10-000x-9842001001-a8d084685b1f1ffa51b02021-09-22Wishart 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 IDFDB028362
KNApSAcK IDNot Available
Chemspider ID26333131
KEGG Compound IDC05860
BioCyc IDD-GALACTOSYL-14-D-GALACTOSYL-14-D-
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45259170
PDB IDNot Available
ChEBI ID18396
Food Biomarker OntologyNot Available
VMH IDMPDOL_L
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.

Enzymes

General function:
Involved in biosynthetic process
Specific function:
Participates in the formation of the lipid-linked precursor oligosaccharide for N-glycosylation. Involved in assembling the dolichol-pyrophosphate-GlcNAc(2)-Man(5) intermediate on the cytoplasmic surface of the ER.
Gene Name:
ALG1
Uniprot ID:
Q9BT22
Molecular weight:
52517.685