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Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate (M2MDB001739)

Record Information
Version2.0
Creation Date2012-07-30 14:55:22 -0600
Update Date2015-06-03 17:21:11 -0600
Secondary Accession Numbers
  • ECMDB21339
Identification
Name:Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate
DescriptionGlucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate belongs to the class of Polyterpenes. These are terpenes consisting of more than eight isoprene units.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate
  • Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphoric acid
Chemical Formula:C77H125NO22P2
Weight:Average: 1478.7574
Monoisotopic: 1477.816847713
InChI Key:QZKSQRMITRSRFM-QUNHHUOXSA-L
InChI:InChI=1S/C77H127NO22P2/c1-50(2)26-16-27-51(3)28-17-29-52(4)30-18-31-53(5)32-19-33-54(6)34-20-35-55(7)36-21-37-56(8)38-22-39-57(9)40-23-41-58(10)42-24-43-59(11)44-25-45-60(12)46-47-92-101(88,89)100-102(90,91)99-75-66(78-62(14)81)72(69(85)65(49-80)95-75)97-77-74(94-63(15)82)73(67(83)61(13)93-77)98-76-71(87)70(86)68(84)64(48-79)96-76/h26,28,30,32,34,36,38,40,42,44,46,61,64-77,79-80,83-87H,16-25,27,29,31,33,35,37,39,41,43,45,47-49H2,1-15H3,(H,78,81)(H,88,89)(H,90,91)/p-2/b51-28+,52-30+,53-32+,54-34+,55-36+,56-38+,57-40+,58-42+,59-44+,60-46+
CAS number:Not Available
IUPAC Name:N-(4-{[3-(acetyloxy)-5-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-{[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 phosphonato]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanecarboximidate
Traditional IUPAC Name:N-(4-{[3-(acetyloxy)-5-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-({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 phosphonato]oxyphosphoryl}oxy)-6-(hydroxymethyl)oxan-3-yl)ethanecarboximidate
SMILES:[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])COP([O-])(=O)OP(O)(=O)OC1OC(CO)C(O)C(OC2OC(C)C(O)C(OC3OC(CO)C(O)C(O)C3O)C2OC(C)=O)C1N=C(C)[O-])=C(\C)CCC=C(C)C
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
  • O-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0027 g/LALOGPS
logP7.04ALOGPS
logP13.34ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area354.6 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity412.78 m³·mol⁻¹ChemAxon
Polarizability166.07 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + UDP-Glucose > Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + Hydrogen ion + Uridine 5'-diphosphate
Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + UDP-D-Galacto-1,4-furanose > Galactofuranosyl-glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + Hydrogen ion + Uridine 5'-diphosphate
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-2100900000-446b7d0bf47397888080View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-1100900100-4c551904c97b1ee4de99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9702300200-12cbfd17bd7c60190dedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-9101600000-ad85c5a32c2f7a3f135aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200100000-3d54b18caa6f583f3d6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-adbbbfa95abfcd3e9fd5View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID46173427
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2215
EcoCyc IDCPD0-2215

Enzymes

Protein Details
1. Uncharacterized protein yefI
General function:
Involved in biosynthetic process
Specific function:
May be a glycosyltransferase involved in the transfer of UDP-GalF and UDP-glucose
Gene Name:
yefI
Uniprot ID:
P37751
Molecular weight:
43188
Protein Details
2. Uncharacterized protein yefG
General function:
Involved in lipopolysaccharide-1,6-galactosyltransferas
Specific function:
May be a glycosyltransferase involved in the transfer of UDP-GalF to the lipopolysaccharide
Gene Name:
yefG
Uniprot ID:
P37749
Molecular weight:
37757