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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:41 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012306
Secondary Accession Numbers
  • HMDB12306
Metabolite Identification
Common NameUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate
DescriptionUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it. Based on a literature review a small amount of articles have been published on Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate.
Structure
Data?1582753039
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 Weight1347.6309
Monoisotopic Molecular Weight1346.769837942
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
CAS Registry NumberNot Available
SMILES
OC[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 Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
Role
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 Solubility0.00099 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+378.73230932474
DeepCCS[M-H]-377.06230932474
DeepCCS[M-2H]-411.09430932474
DeepCCS[M+Na]+384.88930932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 10V, Positive-QTOFsplash10-0002-0139110801-e4f0aa2df75c1ef904cf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 20V, Positive-QTOFsplash10-0002-0122010900-9b106c0e2d8580c82c7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 40V, Positive-QTOFsplash10-0002-0132000900-8ff3a9c22fc0c458e87d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 10V, Negative-QTOFsplash10-0a6r-2679000003-4f7ddc73372e689f62d02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 20V, Negative-QTOFsplash10-0bvr-7936360205-bef2936e8f8a21368dc92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 40V, Negative-QTOFsplash10-0a4i-4910200002-1420d6705e92b84ee95c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 10V, Negative-QTOFsplash10-0002-1129000000-67a4f2e718e63150b4a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 20V, Negative-QTOFsplash10-002f-2954000000-07a238965cd4850365b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 40V, Negative-QTOFsplash10-0a4i-3900010001-e1deeb3583eebc9559972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 10V, Positive-QTOFsplash10-007k-3094411300-d22f9382f61c839dc6d62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 20V, Positive-QTOFsplash10-052f-3032978200-3c6ebccc60db8ff4963b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate 40V, Positive-QTOFsplash10-0002-8134933800-18701968901478a16b142021-09-22Wishart 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 IDFDB028929
KNApSAcK IDNot Available
Chemspider ID35032432
KEGG Compound IDNot Available
BioCyc IDC55-PP-GLCNAC-MANNACA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25245571
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.