Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate (CHEM040770)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:32:02 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040770
Identification
Common NameUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate 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 pyrophosphoric acidGenerator
C55-PP-GlcNAc-mannacaHMDB
Lipid IIHMDB
ManNAcA-glcnac-PP-lipidHMDB
ManNAcA-glcnac-pyrophosphorylundecaprenolHMDB
Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronateHMDB
Muramyl-nac-(pentapeptide)pyrophosphoryl-undecaprenolMeSH, HMDB
MPPPUPMeSH, HMDB
Lipid II, peptidoglycan precursorMeSH, HMDB
Chemical FormulaC71H116N2O18P2
Average Molecular Mass1347.631 g/mol
Monoisotopic Mass1346.770 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3S,4R,5S,6R)-5-acetamido-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}-3,4-dihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4R,5S,6R)-5-acetamido-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}-3,4-dihydroxyoxane-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](O)[C@@H]1NC(=O)C
InChI IdentifierInChI=1S/C71H116N2O18P2/c1-48(2)25-15-26-49(3)27-16-28-50(4)29-17-30-51(5)31-18-32-52(6)33-19-34-53(7)35-20-36-54(8)37-21-38-55(9)39-22-40-56(10)41-23-42-57(11)43-24-44-58(12)45-46-86-92(82,83)91-93(84,85)90-71-63(73-60(14)76)65(78)67(61(47-74)87-71)88-70-62(72-59(13)75)64(77)66(79)68(89-70)69(80)81/h25,27,29,31,33,35,37,39,41,43,45,61-68,70-71,74,77-79H,15-24,26,28,30,32,34,36,38,40,42,44,46-47H2,1-14H3,(H,72,75)(H,73,76)(H,80,81)(H,82,83)(H,84,85)/b49-27+,50-29+,51-31+,52-33+,53-35+,54-37+,55-39+,56-41+,57-43+,58-45+/t61-,62+,63-,64-,65-,66+,67-,68+,70-,71-/m1/s1
InChI KeyIGGGNUSEBUZFTR-CDDUTUKUSA-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
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • Disaccharide phosphate
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Isoprenoid phosphate
  • Organic pyrophosphate
  • Beta-hydroxy acid
  • Monoalkyl phosphate
  • Pyran
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • 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 Solubility0.00099 g/LALOGPS
logP7.45ALOGPS
logP12.83ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area306.4 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity373.78 m³·mol⁻¹ChemAxon
Polarizability154.12 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0139110801-e4f0aa2df75c1ef904cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0122010900-9b106c0e2d8580c82c7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0132000900-8ff3a9c22fc0c458e87dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-2679000003-4f7ddc73372e689f62d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvr-7936360205-bef2936e8f8a21368dc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4910200002-1420d6705e92b84ee95cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1129000000-67a4f2e718e63150b4a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-2954000000-07a238965cd4850365b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900010001-e1deeb3583eebc955997Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007k-3094411300-d22f9382f61c839dc6d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-3032978200-3c6ebccc60db8ff4963bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-8134933800-18701968901478a16b14Spectrum
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 IDHMDB0012306
FooDB IDFDB028929
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDC55-PP-GLCNAC-MANNACA
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35032432
ChEBI IDNot Available
PubChem Compound ID25245571
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. The lipid handbook with CD-ROM