Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate (CHEM040771)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:32:05 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040771
Identification
Common NameUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid-4-acetamido-4,6-dideoxy-D-galactose pyrophosphoric acidGenerator
C55-PP-GlcNAc-mannaca-fuc4nacHMDB
Lipid IIIHMDB
ManNAcA-glcnac-fuc4nac-PP-lipidHMDB
ManNAcA-glcnac-fuc4nac-pyrophosphorylundecaprenolHMDB
Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactoseHMDB
Ceramide nonasaccharideMeSH, HMDB
Chemical FormulaC79H129N3O22P2
Average Molecular Mass1534.824 g/mol
Monoisotopic Mass1533.854 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3S,4R,5S,6R)-5-acetamido-3-{[(2R,3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-{[hydroxy({[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4R,5S,6R)-5-acetamido-3-{[(2R,3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-{[hydroxy({hydroxy[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxyphosphoryl}oxy)phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxyoxane-2-carboxylic acid
SMILESOC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC\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[C@@H]1O[C@H](C(=O)O)[C@@H](O[C@H]2O[C@H](C)C(NC(C)=O)[C@H](O)[C@H]2O)[C@H](O)[C@@H]1NC(=O)C
InChI IdentifierInChI=1S/C79H129N3O22P2/c1-50(2)27-17-28-51(3)29-18-30-52(4)31-19-32-53(5)33-20-34-54(6)35-21-36-55(7)37-22-38-56(8)39-23-40-57(9)41-24-42-58(10)43-25-44-59(11)45-26-46-60(12)47-48-97-105(93,94)104-106(95,96)103-78-68(82-64(16)86)70(88)73(65(49-83)99-78)100-77-67(81-63(15)85)71(89)74(75(102-77)76(91)92)101-79-72(90)69(87)66(61(13)98-79)80-62(14)84/h27,29,31,33,35,37,39,41,43,45,47,61,65-75,77-79,83,87-90H,17-26,28,30,32,34,36,38,40,42,44,46,48-49H2,1-16H3,(H,80,84)(H,81,85)(H,82,86)(H,91,92)(H,93,94)(H,95,96)/b51-29+,52-31+,53-33+,54-35+,55-37+,56-39+,57-41+,58-43+,59-45+,60-47+/t61-,65-,66?,67+,68-,69+,70-,71-,72-,73-,74+,75+,77-,78-,79-/m1/s1
InChI KeyPSONHUYFSWYIME-JNYPHZTQSA-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
  • Polyterpenoid
  • Bactoprenol diphosphate
  • Polyprenyl phospho carbohydrate
  • Oligosaccharide phosphate
  • Polyprenyl monophosphate
  • Oligosaccharide
  • Polyprenyl phosphate skeleton
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Isoprenoid phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyran
  • Acetamide
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Acetal
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • 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 Solubility0.003 g/LALOGPS
logP6.83ALOGPS
logP11.82ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area374.19 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity415.75 m³·mol⁻¹ChemAxon
Polarizability172.9 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0107651901-5d2fb76a53e28c193c83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0101120900-d5a528f78dbfbd08a4e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0103220900-6240dba6699d3dfac8ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-0642910002-2e026fe8d49f2e0d8162Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-6855550709-3673ba5ef837620eac65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4910200003-281a64f8616d394629beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001090000-16fd8ce670774d49e820Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1193340000-9dbd03d5d4fc6fcffd74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4912050002-b947a659c9bd694b4e0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053r-4000966103-ea9764d80655086db1a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3011964025-62a8e1cdbf10f9e88626Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0032-9212745800-09948d172da1ec184f3dSpectrum
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 IDHMDB0012307
FooDB IDFDB028930
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35032433
ChEBI IDNot Available
PubChem Compound ID53481400
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Rick PD, Barr K, Sankaran K, Kajimura J, Rush JS, Waechter CJ: Evidence that the wzxE gene of Escherichia coli K-12 encodes a protein involved in the transbilayer movement of a trisaccharide-lipid intermediate in the assembly of enterobacterial common antigen. J Biol Chem. 2003 May 9;278(19):16534-42. Epub 2003 Mar 5.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. 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.
4. 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.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. The lipid handbook with CD-ROM