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Record Information
Version	2.0
Creation Date	2012-10-10 12:21:46 -0600
Update Date	2015-06-03 17:26:08 -0600
Secondary Accession Numbers	ECMDB23199
Identification
Name:	UDP-4-Deoxy-4-formamido-beta-L-arabinose
Description	UDP-4-Deoxy-4-formamido-beta-L-arabinose is an intermediate in the polymixin resistance pathway. It is a substrate for the enzyme Bifunctional polymyxin resistance protein ArnA that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto-arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4-amino-4-deoxy-L-arabinose (UDP-L-Ara4N) to form UDP-L-4-formamido-arabinose (UDP-L-Ara4FN). The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides. Some Gram-negative bacteria, specifically Salmonella typhimurium and Escherichia coli, can become resistant to polymyxin by the modification of their lipid A structure via the attachment of 4-amino-4-deoxy-L-arabinopyranose (L-Ara4N) groups to one or more phosphate groups. This addition causes an absolute increase in lipid A charge, thus lowering the affinity of positively charged polymyxins.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaf37afa0> Close
Synonyms:	(2R,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-3,4-dihydroxytetrahydro-2-furanylmethyl (2R,3R,4S,5S)-5-formamido-3,4-dihydroxytetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferre d name) (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-1(2H)-Pyrimidinyl)-3,4-dihydroxytetrahydro-2-furanylmethyl (2R,3R,4S,5S)-5-formamido-3,4-dihydroxytetrahydro-2H-pyran-2-yl dihydrogen diphosphoric acid (non-preferre D name) (2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (2R,3R,4S,5S)-5-formamido-3,4-dihydroxyoxan-2-yl hydrogen phosphate (2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (2R,3R,4S,5S)-5-formamido-3,4-dihydroxyoxan-2-yl hydrogen phosphoric acid UDP-4-Deoxy-4-formamido-b-L-arabinose UDP-4-Deoxy-4-formamido-β-L-arabinose UDP-b-L-Ara4fn UDP-beta-L-Ara4FN UDP-L-Ara4FN UDP-β-L-Ara4fn Uridine 5'-diphospho-b-(4-deoxy-4-formamido-L-arabinose) Uridine 5'-diphospho-beta-(4-deoxy-4-formamido-L-arabinose) Uridine 5'-diphospho-β-(4-deoxy-4-formamido-L-arabinose)
Chemical Formula:	C15H23N3O16P2
Weight:	Average: 563.3011 Monoisotopic: 563.055354727
InChI Key:	QGYFHZBDXXNYAX-RTXATJJPSA-N
InChI:	InChI=1S/C15H23N3O16P2/c19-5-16-6-3-30-14(12(24)9(6)21)33-36(28,29)34-35(26,27)31-4-7-10(22)11(23)13(32-7)18-2-1-8(20)17-15(18)25/h1-2,5-7,9-14,21-24H,3-4H2,(H,16,19)(H,26,27)(H,28,29)(H,17,20,25)/t6-,7+,9-,10+,11+,12+,13+,14+/m0/s1
CAS number:	Not Available
IUPAC Name:	N-[(3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxyoxan-3-yl]carboximidic acid
Traditional IUPAC Name:	udp-L-ara4FN
SMILES:	[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OC[C@]([H])(N=CO)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleotides
Sub Class	Pyrimidine ribonucleotides
Direct Parent	Pyrimidine ribonucleoside diphosphates
Alternative Parents	Pentose phosphates Glycosylamines Monosaccharide phosphates Organic pyrophosphates Monoalkyl phosphates Pyrimidones Hydropyrimidines Oxanes Tetrahydrofurans Heteroaromatic compounds Vinylogous amides Secondary carboxylic acid amides Ureas Lactams Secondary alcohols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Pyrimidine ribonucleoside diphosphate Pentose phosphate Pentose-5-phosphate Glycosyl compound N-glycosyl compound Monosaccharide phosphate Organic pyrophosphate Pyrimidone Monoalkyl phosphate Hydropyrimidine Monosaccharide Organic phosphoric acid derivative Oxane Phosphoric acid ester Pyrimidine Alkyl phosphate Vinylogous amide Tetrahydrofuran Heteroaromatic compound Urea Carboxamide group Secondary carboxylic acid amide Secondary alcohol Lactam Azacycle Organoheterocyclic compound Carboxylic acid derivative Oxacycle Organic nitrogen compound Alcohol Carbonyl group Organonitrogen compound Organooxygen compound Organopnictogen compound Organic oxide Organic oxygen compound Hydrocarbon derivative Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	UDP-amino sugar (CHEBI:47027 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 10.4 g/L ALOGPS logP -1.5 ALOGPS logP -4.6 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) 1.61 ChemAxon pKa (Strongest Basic) 2.53 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 15 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 287.16 Ų ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 107.95 m³·mol⁻¹ ChemAxon Polarizability 46.42 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	N10-Formyl-THF + 4-Amino-4-deoxy-L-arabinose > Tetrahydrofolic acid + UDP-4-Deoxy-4-formamido-beta-L-arabinose UDP-4-Deoxy-4-formamido-beta-L-arabinose + di-trans,octa-cis-undecaprenyl phosphate > Uridine 5'-diphosphate + 4-deoxy-4-formamido-alpha-L-arabinose di-trans,octa-cis-undecaprenyl phosphate Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + an N10-formyl-tetrahydrofolate + N10-Formyl-THF > UDP-4-Deoxy-4-formamido-beta-L-arabinose + Hydrogen ion + a tetrahydrofolate + Tetrahydrofolic acid UDP-4-Deoxy-4-formamido-beta-L-arabinose + di-trans,octa-cis-undecaprenyl phosphate > Uridine 5'-diphosphate + 4-deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate
SMPDB Pathways:	Amino sugar and nucleotide sugar metabolism III PW000895 One Carbon Pool by Folate I PW001735 polymyxin resistance PW002052
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_21) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-0901120000-8c46a03f73f7f398767f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-3911000000-b4cab5f793e5beaf70ef View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-4900000000-6d1bce8d76549b349101 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0ik9-6901140000-33d8688917904f4103f1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-06r6-7906010000-dffdf6a6c3314c45f1ab View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06r6-5901000000-6169fa44322865858538 View in MoNA
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 47027 HMDB ID Not Available Pubchem Compound ID 17756768 Kegg ID C16154 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

Enzymes