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N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol (M2MDB006374)

Record Information
Version2.0
Creation Date2015-09-08 17:50:28 -0600
Update Date2015-09-14 16:46:46 -0600
Secondary Accession Numbers
  • ECMDB24257
Identification
Name:N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol
DescriptionN-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol is an intermediate in several pathways in E. coli, beta-D-galactosaminyl-(1→3)-N-acetyl-alpha-D-galactosamine biosynthesis, enterobacterial common antigen biosynthesis, and teichoic acid (poly-glycerol) biosynthesis, where it is a substrate of N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol 4-epimerase, UDP-N-acetyl-D-mannosaminuronic acid transferase and UDP-N-acetylmannosamine transferase. It is also a product of undecaprenyl-phosphate alpha-N-acetylglucosaminyl transferase in these pathways (BioCyc compound: ACETYL-D-GLUCOSAMINYLDIPHOSPHO-UNDECAPRE).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
N-Acetyl-D-glucosaminyl undecaprenyl diphosphateChEBI
N-Acetyl-D-glucosaminyldiphosphoundecaprenolChEBI
N-Acetyl-D-glucosaminyl undecaprenyl diphosphoric acidGenerator
Chemical Formula:C63H105NO12P2
Weight:Average: 1130.476
Monoisotopic: 1129.711201821
InChI Key:NEVJGTXBHJNFAZ-PSDVTIBRSA-N
InChI:InChI=1S/C63H105NO12P2/c1-47(2)24-14-25-48(3)26-15-27-49(4)28-16-29-50(5)30-17-31-51(6)32-18-33-52(7)34-19-35-53(8)36-20-37-54(9)38-21-39-55(10)40-22-41-56(11)42-23-43-57(12)44-45-73-77(69,70)76-78(71,72)75-63-60(64-58(13)66)62(68)61(67)59(46-65)74-63/h24,26,28,30,32,34,36,38,40,42,44,59-63,65,67-68H,14-23,25,27,29,31,33,35,37,39,41,43,45-46H2,1-13H3,(H,64,66)(H,69,70)(H,71,72)/b48-26+,49-28+,50-30-,51-32-,52-34-,53-36-,54-38-,55-40-,56-42-,57-44-/t59-,60-,61-,62-,63?/m1/s1
CAS number:Not Available
IUPAC Name:N-[(3R,4R,5S,6R)-4,5-dihydroxy-2-{[hydroxy({[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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}-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
Traditional IUPAC Name:N-[(3R,4R,5S,6R)-4,5-dihydroxy-2-{[hydroxy({hydroxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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}-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
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)OC1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])N=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
  • Polyprenyl phospho carbohydrate
  • Bactoprenol diphosphate
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Isoprenoid phosphate
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00039 g/LALOGPS
logP8.48ALOGPS
logP14.83ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)1.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area204.8 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity330.92 m³·mol⁻¹ChemAxon
Polarizability125.54 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
di-trans,octa-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine > Uridine 5'-monophosphate + N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol
N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol + UDP-ManNAcA > Uridine 5'-diphosphate + Hydrogen ion + Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate + Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate
SMPDB Pathways:
Secondary Metabolites: enterobacterial common antigen biosynthesisPW000959 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: enterobacterial common antigen biosynthesis 2PW002045 ThumbThumb?image type=greyscaleThumb?image type=simple
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, Positivesplash10-01ot-3621000901-6ff614f5acc94b6280c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0121000910-05f0454830cf4b971ea3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0121110900-1aecb86a3bd5b807a31cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0570-9400000004-da196e6eda269ca42ac9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-7925000203-a87f9fb6aa9386a53c00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-e4caa11e9b995ebfdc61View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16511
HMDB IDNot Available
Pubchem Compound ID46873827
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Undecaprenyl-phosphate alpha-N-acetylglucosaminyl 1-phosphate transferase
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the transfer of the GlcNAc-1-phosphate moiety from UDP-GlcNAc onto the carrier lipid undecaprenyl phosphate (C55-P), yielding GlcNAc-pyrophosphoryl-undecaprenyl (GlcNAc-PP- C55). It is the first lipid-linked intermediate involved in enterobacterial common antigen (ECA) synthesis and an acceptor for the addition of subsequent sugars to complete the biosynthesis of O-antigen. The apparent affinity of WecA for the polyisoprenyl phosphate substrates increases with the polyisoprenyl chain length. WecA is unable to utilize dolichyl phosphate (Dol-P)
Gene Name:
wecA
Uniprot ID:
P0AC78
Molecular weight:
40957
Reactions
UDP-N-acetyl-D-glucosamine + di-trans,octa-cis-undecaprenyl phosphate = UMP + N-acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol.
Protein Details
2. Probable UDP-N-acetyl-D-mannosaminuronic acid transferase
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the synthesis of Und-PP-GlcNAc-ManNAcA (Lipid II), the second lipid-linked intermediate involved in ECA synthesis
Gene Name:
wecG
Uniprot ID:
P27836
Molecular weight:
27928
Reactions
UDP-ManNAcA + Und-PP-GlcNAc = UDP + Und-PP-GlcNAc-ManNAcA.