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Record Information
Version	2.0
Creation Date	2012-08-09 09:25:08 -0600
Update Date	2015-06-03 17:21:39 -0600
Secondary Accession Numbers	ECMDB21497
Identification
Name:	4-Amino-4-deoxy-L-arabinose
Description	4-amino-4-deoxy-L-arabinose is invovled in Modification of lipid A. Attachment of the cationic sugar 4-amino-4-deoxy-l-arabinose (l-Ara4N) to lipid A is required for the maintenance of polymyxin resistance in Escherichia coli. The enzyme called AmT synthesizes this molecule and transfers it to lipid A.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa762ca94> Close
Synonyms:	UDP-4-amino-4-Deoxy-b-L-arabinopyranose UDP-4-Amino-4-deoxy-beta-L-arabinopyranose UDP-4-Amino-4-deoxy-L-arabinose UDP-4-amino-4-Deoxy-β-L-arabinopyranose UDP-Ara4N UDP-L-Ara4N
Chemical Formula:	C14H23N3O15P2
Weight:	Average: 535.291 Monoisotopic: 535.060440105
InChI Key:	GWBAKYBSWHQNMQ-IAZOVDBXSA-N
InChI:	InChI=1S/C14H23N3O15P2/c15-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)17-2-1-7(18)16-14(17)23/h1-2,5-6,8-13,19-22H,3-4,15H2,(H,24,25)(H,26,27)(H,16,18,23)/t5-,6+,8-,9+,10+,11+,12+,13+/m0/s1
CAS number:	Not Available
IUPAC Name:	[({[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid
Traditional IUPAC Name:	{[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy(hydroxy)phosphoryl}oxy[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxyphosphinic acid
SMILES:	[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OC[C@]([H])(N)[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 alcohols Ureas Lactams 1,2-aminoalcohols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
Substituents	Pyrimidine ribonucleoside diphosphate Pentose phosphate Pentose-5-phosphate Glycosyl compound N-glycosyl compound Monosaccharide phosphate Organic pyrophosphate Monoalkyl phosphate Pyrimidone Hydropyrimidine Monosaccharide Organic phosphoric acid derivative Oxane Alkyl phosphate Phosphoric acid ester Pyrimidine Heteroaromatic compound Vinylogous amide Tetrahydrofuran Urea Secondary alcohol Lactam 1,2-aminoalcohol Organoheterocyclic compound Azacycle Oxacycle Alcohol Organonitrogen compound Hydrocarbon derivative Organic oxide Primary aliphatic amine Organooxygen compound Organopnictogen compound Organic oxygen compound Organic nitrogen compound Primary amine Amine Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	UDP-amino sugar (CHEBI:47025 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 20.5 g/L ALOGPS logP -1.8 ALOGPS logP -5.3 ChemAxon logS -1.4 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) 8.84 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 14 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 280.59 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 102.47 m³·mol⁻¹ ChemAxon Polarizability 43.73 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 4-Amino-4-deoxy-L-arabinose + Oxoglutaric acid > UDP-beta-L-Threo-pentapyranos-4-ulose + DL-Glutamic acid
SMPDB Pathways:	One Carbon Pool by Folate I PW001735
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_4_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-0901110000-fbeb9b44095b857eb1e1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-3910000000-e8c467c395f811f73ca6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-4900000000-48cb7dd1dcba1e6dc2bb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03kc-9700330000-d9c4002f1991a8940ffa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-06rl-9622000000-6efc782dd2f2da611230 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06tf-4900000000-ef9346105ef1e2f60ab9 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 47025 HMDB ID Not Available Pubchem Compound ID 17756769 Kegg ID C16153 ChemSpider ID 21865443 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes