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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:42 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012307
Secondary Accession Numbers
  • HMDB12307
Metabolite Identification
Common NameUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate
DescriptionUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate is synthesized on the cytoplasmic side of the membrane. It is then translocated to the periplasmic side of the membrane by the flippase, where assembly of the polysaccharide chains occurs by a block-polymerization mechanism. The polysaccharide chains are then transferred to an as yet unidentified glyceride acceptor to yield ECAPG. Completed ECAPG polymers are then incorporated into the exterior leaflet of the outer membrane (PMID: 12621029 ). Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate + dTDP-4-acetamido-4,6-dideoxy-D-galactose = undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate + dTDP.
Structure
Data?1582753039
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 Weight1534.824
Monoisotopic Molecular Weight1533.854295851
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
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]2O[C@H](C)C(NC(C)=O)[C@H](O)[C@H]2O)[C@H](O)[C@@H]1NC(=O)C
InChI Identifier
InChI=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
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 Solubility0.003 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

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-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 10V, Positive-QTOFsplash10-0002-0107651901-5d2fb76a53e28c193c832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 20V, Positive-QTOFsplash10-0002-0101120900-d5a528f78dbfbd08a4e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 40V, Positive-QTOFsplash10-0002-0103220900-6240dba6699d3dfac8eb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 10V, Negative-QTOFsplash10-004l-0642910002-2e026fe8d49f2e0d81622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 20V, Negative-QTOFsplash10-0bt9-6855550709-3673ba5ef837620eac652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 40V, Negative-QTOFsplash10-0a4i-4910200003-281a64f8616d394629be2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 10V, Negative-QTOFsplash10-001i-0001090000-16fd8ce670774d49e8202021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 20V, Negative-QTOFsplash10-001i-1193340000-9dbd03d5d4fc6fcffd742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 40V, Negative-QTOFsplash10-0a4i-4912050002-b947a659c9bd694b4e0b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 10V, Positive-QTOFsplash10-053r-4000966103-ea9764d80655086db1a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 20V, Positive-QTOFsplash10-001i-3011964025-62a8e1cdbf10f9e886262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate 40V, Positive-QTOFsplash10-0032-9212745800-09948d172da1ec184f3d2021-09-24Wishart 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 IDFDB028930
KNApSAcK IDNot Available
Chemspider ID35032433
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481400
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. 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. [PubMed:12621029 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.