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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:15 -0600
Update Date	2015-06-03 17:21:05 -0600
Secondary Accession Numbers	ECMDB21292
Identification
Name:	UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine
Description	UDP-3-o-(3-hydroxytetradecanoyl)-D-glucosamine is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9fa59674> Close
Synonyms:	UDP-3-O-(3-hydroxytetradecanoyl)-D-glucosamine UDP-3-O-(3-hydroxytetradecanoyl)glucosamine UDP-3-O-[(3R)-3-hydroxymyristoyl]-D-glucosamine UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine UDP-3-O-(3-Hydroxytetradecanoyl)glucosamine UDP-3-O-(b-Hydroxymyristoyl)-D-glucosamine UDP-3-O-(beta-Hydroxymyristoyl)-D-glucosamine UDP-3-O-(β-Hydroxymyristoyl)-D-glucosamine UDP-3-O-[(3R)-3-Hydroxymyristoyl]-a-D-glucosamine UDP-3-O-[(3R)-3-Hydroxymyristoyl]-alpha-D-glucosamine UDP-3-O-[(3R)-3-Hydroxymyristoyl]-D-glucosamine UDP-3-O-[(3R)-3-Hydroxymyristoyl]-α-D-glucosamine UDP-HMyrGlc Uridine 5'-{3-[2-amino-2-deoxy-3-O-(3-hydroxytetradecanoyl)-D-glucopyranosyl] dihydrogen diphosphate} Uridine 5'-{3-[2-amino-2-deoxy-3-O-(3-hydroxytetradecanoyl)-D-glucopyranosyl] dihydrogen diphosphoric acid}
Chemical Formula:	C29H50N3O18P2
Weight:	Average: 790.6641 Monoisotopic: 790.256459835
InChI Key:	ZFPNNOXCEDQJQS-SSVOXRMNSA-M
InChI:	InChI=1S/C29H51N3O18P2/c1-2-3-4-5-6-7-8-9-10-11-17(34)14-21(36)48-26-22(30)28(47-18(15-33)24(26)38)49-52(43,44)50-51(41,42)45-16-19-23(37)25(39)27(46-19)32-13-12-20(35)31-29(32)40/h12-13,17-19,22-28,33-34,37-39H,2-11,14-16,30H2,1H3,(H,41,42)(H,43,44)(H,31,35,40)/p-1/t17-,18-,19-,22-,23-,24-,25-,26-,27-,28-/m1/s1
CAS number:	Not Available
IUPAC Name:	1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-olate
Traditional IUPAC Name:	1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-oxopyrimidin-4-olate
SMILES:	[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@]1([H])[C@@]([H])(N)[C@@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)O[C@]([H])(CO)[C@@]1([H])O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleotides
Sub Class	Pyrimidine nucleotide sugars
Direct Parent	Pyrimidine nucleotide sugars
Alternative Parents	Pyrimidine ribonucleoside diphosphates Saccharolipids Pentose phosphates Glycosylamines Monosaccharide phosphates Organic pyrophosphates Pyrimidones Aminosaccharides Beta hydroxy acids and derivatives Fatty acid esters Oxanes Hydropyrimidines Alkyl phosphates Tetrahydrofurans Vinylogous amides Heteroaromatic compounds Secondary alcohols Ureas Carboxylic acid esters Amino acids and derivatives Lactams Azacyclic compounds Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Primary alcohols Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic anions
Substituents	Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Saccharolipid Pentose phosphate Pentose-5-phosphate Glycosyl compound N-glycosyl compound Monosaccharide phosphate Organic pyrophosphate Beta-hydroxy acid Fatty acid ester Pyrimidone Amino saccharide Hydropyrimidine Hydroxy acid Monosaccharide Organic phosphoric acid derivative Oxane Phosphoric acid ester Fatty acyl Pyrimidine Alkyl phosphate Tetrahydrofuran Vinylogous amide Heteroaromatic compound Urea Secondary alcohol Carboxylic acid ester Amino acid or derivatives Lactam Azacycle Oxacycle Organoheterocyclic compound Carboxylic acid derivative Monocarboxylic acid or derivatives Organic oxygen compound Primary amine Primary aliphatic amine Hydrocarbon derivative Amine Alcohol Organic oxide Organopnictogen compound Organonitrogen compound Organooxygen compound Organic nitrogen compound Carbonyl group Primary alcohol Organic anion Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	UDP-3-O-[(3R)-3-hydroxytetradecanoyl]-D-glucosamine(1-) (CHEBI:71573 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 8.66 g/L ALOGPS logP 0.5 ALOGPS logP -1.1 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 1.72 ChemAxon pKa (Strongest Basic) 8.47 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 329.95 Ų ChemAxon Rotatable Bond Count 23 ChemAxon Refractivity 184.89 m³·mol⁻¹ ChemAxon Polarizability 75.94 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:	Water + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine <> Acetic acid + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine (R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine > acyl carrier protein + Hydrogen ion + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + Acyl-carrier protein + (3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] <> UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine + (3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + Acyl-carrier protein UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine + Water > UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine + Acetic acid UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-α-D-glucosamine + Water > Acetic acid + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine + (3R)-3-hydroxymyristoyl-[acp] > Hydrogen ion + a holo-[acyl-carrier protein] + UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine Water + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine <> Acetic acid + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine Water + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine <> Acetic acid + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine
SMPDB Pathways:	Lipopolysaccharide biosynthesis PW000831 lipopolysaccharide biosynthesis II PW001905 lipopolysaccharide biosynthesis III PW002059
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540 Metabolic pathways eco01100
EcoCyc Pathways:	superpathway of (KDO)2-lipid A biosynthesis NAGLIPASYN-PWY superpathway of lipopolysaccharide biosynthesis LPSSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000f-0200000900-850443cc67ced397ce01 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014r-1210000900-f0e611c59f3f2c811d38 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9610000100-1134e9367fc69fc66ea0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000l-9111000800-b29ffb0877264b8db7e3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a5c-8679010300-700bdce8df74b7d4ab17 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-002f-9440000000-cd20a6dd7a444538fcd4 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:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 27392 HMDB ID HMDB0304525 Pubchem Compound ID 25244806 Kegg ID C06022 ChemSpider ID 28533665 Wikipedia ID Not Available BioCyc ID UDP-OHMYR-GLUCOSAMINE EcoCyc ID UDP-OHMYR-GLUCOSAMINE

Enzymes