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Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose (M2MDB001761)

Record Information
Version2.0
Creation Date2012-07-30 14:55:30 -0600
Update Date2015-06-03 17:21:14 -0600
Secondary Accession Numbers
  • ECMDB21365
Identification
Name:Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose
DescriptionUndecaprenyl phosphate-4-amino-4-formyl-L-arabinose is an intermediate in LPS (lipopolysaccharide) biosynthesis. It is a substrate for the enzyme Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase (arnC). This enzyme 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. The reaction is: 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose
  • Undecaprenyl phosphoric acid-4-amino-4-formyl-L-arabinose
Chemical Formula:C61H99NO8P
Weight:Average: 1005.4144
Monoisotopic: 1004.710830661
InChI Key:YYVYMEXYAGAGTM-MOVGJWTDSA-M
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)70-60-58(64)59(65)61(62,45-63)46-68-60/h23,25,27,29,31,33,35,37,39,41,43,45,58-60,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44,46,62H2,1-12H3,(H,66,67)/p-1/b48-25+,49-27+,50-29+,51-31+,52-33+,53-35+,54-37+,55-39+,56-41+,57-43+/t58-,59-,60+,61?/m1/s1
CAS number:Not Available
IUPAC Name:(2S,3R,4S)-5-amino-5-formyl-3,4-dihydroxyoxan-2-yl (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 phosphate
Traditional IUPAC Name:(2S,3R,4S)-5-amino-5-formyl-3,4-dihydroxyoxan-2-yl (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 phosphate
SMILES:O=CC1(N)CO[C@@]([H])(OP([O-])(=O)OC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@@](O)([H])[C@]1(O)[H]
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 nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aldehyde
  • 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 Solubility0.00063 g/LALOGPS
logP8.65ALOGPS
logP14.34ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.58ChemAxon
pKa (Strongest Basic)6.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area151.37 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity308.2 m³·mol⁻¹ChemAxon
Polarizability123.65 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Undecaprenyl phosphate + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose > Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose + Uridine 5'-diphosphate
Water + Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose > Formic acid + undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose
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, Positivesplash10-0a4i-9000000000-2982ba298bdf3bdfb6cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-044j-9100000203-bf1f89269752c4019fe9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac0-9500000310-4df2aec407b352d310b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-8900000000-e31265a3712da0fb15edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fri-9420000000-e1cad192df39889413f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-9500000000-50933f6d5bcb42e090c4View 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 ID45479642
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2153
EcoCyc IDCPD0-2153

Enzymes

Protein Details
1. Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase
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.
Protein Details
2. Probable 4-deoxy-4-formamido-L-arabinose-phosphoundecaprenol deformylase ArnD
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:
Catalyzes the deformylation of 4-deoxy-4-formamido-L- arabinose-phosphoundecaprenol to 4-amino-4-deoxy-L-arabinose- phosphoundecaprenol. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides (Probable)
Gene Name:
arnD
Uniprot ID:
P76472
Molecular weight:
33112
Reactions
4-deoxy-4-formamido-beta-L-arabinose di-trans,poly-cis-undecaprenyl phosphate + H(2)O = 4-amino-4-deoxy-alpha-L-arabinose di-trans,poly-cis-undecaprenyl phosphate + formate.