Record Information
Version2.0
Creation Date2015-09-08 17:50:22 -0600
Update Date2015-09-14 16:46:43 -0600
Secondary Accession Numbers
  • ECMDB24241
Identification
Name:4-deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate
Description4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate is an intermediate in polymyxin resistance pathway in E.coli. It is a substrate in the reaction 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + H2O -> 4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + formate. It is also a product for enzyme undecaprenyl phosphate-L-Ara4FN transferase which catalyzes reaction UDP-4-deoxy-4-formamido-beta-L-arabinopyranose + di-trans,octa-cis-undecaprenyl phosphate → 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + UDP (BioCyc compound: CPD0-888).
Structure
Thumb
Synonyms:
  • 4-Deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphoric acid
Chemical Formula:C61H100NO8P
Weight:Average: 1006.444
Monoisotopic: 1005.718656182
InChI Key:KDTATMYQJZYGGT-QTBHONTMSA-N
InChI:InChI=1S/C61H100NO8P/c1-47(2)23-13-24-48(3)25-14-26-49(4)27-15-28-50(5)29-16-30-51(6)31-17-32-52(7)33-18-34-53(8)35-19-36-54(9)37-20-38-55(10)39-21-40-56(11)41-22-42-57(12)43-44-69-71(66,67)70-61-60(65)59(64)58(45-68-61)62-46-63/h23,25,27,29,31,33,35,37,39,41,43,46,58-61,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44-45H2,1-12H3,(H,62,63)(H,66,67)/b48-25+,49-27+,50-29-,51-31-,52-33-,53-35-,54-37-,55-39-,56-41-,57-43-
CAS number:Not Available
IUPAC Name:[(5-formamido-3,4-dihydroxyoxan-2-yl)oxy]({[(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})phosphinic acid
Traditional IUPAC Name:(5-formamido-3,4-dihydroxyoxan-2-yl)oxy[(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]oxyphosphinic acid
SMILES:CC(C)=CCC\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/COP(O)(=O)OC1OCC(NC=O)C(O)C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as bactoprenol monophosphates. These are polyprenyl compounds consisting of a monophosphate group substituted by a bactoprenyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentBactoprenol monophosphates
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol monophosphate
  • Polyprenyl monophosphate
  • Isoprenoid phosphate
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • 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 Solubility0.00064 g/LALOGPS
logP9.01ALOGPS
logP15.57ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.58ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.55 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity309.07 m³·mol⁻¹ChemAxon
Polarizability122.12 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IIIPW000895 ThumbThumb?image type=greyscaleThumb?image type=simple
polymyxin resistancePW002052 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, Positivesplash10-0002-2100000892-af073e8afb21b069b7e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000900-6c213e1729b19c20b0f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1100000920-67ca603d3c743baa7a80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-6920000032-ad310555c6c0236db241View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9120000110-7dea105b922fb269fbb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f73e656c65f3c33fc8cfView 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 IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the transfer of 4-deoxy-4-formamido-L- arabinose from UDP to undecaprenyl phosphate. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Gene Name:
arnC
Uniprot ID:
P77757
Molecular weight:
36339
Reactions
UDP-4-deoxy-4-formamido-beta-L-arabinose + di-trans,octa-cis-undecaprenyl phosphate = UDP + 4-deoxy-4-formamido-alpha-L-arabinose di-trans,octa-cis-undecaprenyl phosphate.