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Record Information
Version	2.0
Creation Date	2012-05-31 14:32:51 -0600
Update Date	2015-06-03 17:19:31 -0600
Secondary Accession Numbers	ECMDB20201
Identification
Name:	UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine
Description	UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine is a member of the chemical class known as Sulfanylbenzoic Acid Derivatives. These are benzoic acid derivatives which bear a sulfanyl group (R-SH) attached to the benzene ring.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xad2657e8> Close
Synonyms:	UDP-2,3-Bis(3-hydroxymyristoyl)glucosamine UDP-2,3-Bis(3-hydroxytetradecanoyl)-D-glucosamine UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine UDP-2,3-Bis(b-hydroxymyristoyl)-D-glucosamine UDP-2,3-Bis(beta-hydroxymyristoyl)-D-glucosamine UDP-2,3-Bis(β-hydroxymyristoyl)-D-glucosamine UDP-2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosamine UDP-2,3-Bis[(3r)-3-hydroxymyristoyl]-α-D-glucosamine UDP-2,3-Bis[(3R)-3-hydroxymyristoyl]-a-D-glucosamine UDP-2,3-Bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine UDP-2,3-Bis[(3R)-3-hydroxymyristoyl]-α-D-glucosamine UDP-2,3-Diacyl-glucosamine UDP-BHMyrGlc
Chemical Formula:	C43H77N3O20P2
Weight:	Average: 1018.0271 Monoisotopic: 1017.457564943
InChI Key:	KOJCFMYSTWNMQW-RUAJDYCTSA-N
InChI:	InChI=1S/C43H77N3O20P2/c1-3-5-7-9-11-13-15-17-19-21-29(48)25-34(51)44-36-40(64-35(52)26-30(49)22-20-18-16-14-12-10-8-6-4-2)38(54)31(27-47)63-42(36)65-68(59,60)66-67(57,58)61-28-32-37(53)39(55)41(62-32)46-24-23-33(50)45-43(46)56/h23-24,29-32,36-42,47-49,53-55H,3-22,25-28H2,1-2H3,(H,44,51)(H,57,58)(H,59,60)(H,45,50,56)/t29-,30-,31-,32-,36-,37-,38-,39-,40-,41-,42-/m1/s1
CAS number:	Not Available
IUPAC Name:	(3R)-N-[(2R,3R,4R,5S,6R)-2-({[({[(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)-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]-3-hydroxytetradecanimidic acid
Traditional IUPAC Name:	(3R)-N-[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]-3-hydroxytetradecanimidic acid
SMILES:	[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[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)[C@]1([H])N=C(O)C[C@]([H])(O)CCCCCCCCCCC
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 Acylaminosugars Pentose phosphates N-acyl-alpha-hexosamines Glycosylamines Monosaccharide phosphates Organic pyrophosphates Monoalkyl phosphates Fatty acid esters Beta hydroxy acids and derivatives Pyrimidones Hydropyrimidines N-acyl amines Oxanes Heteroaromatic compounds Tetrahydrofurans Vinylogous amides Carboxylic acid esters Ureas Secondary carboxylic acid amides Secondary alcohols Lactams Monocarboxylic acids and derivatives Azacyclic compounds Oxacyclic compounds Hydrocarbon derivatives Organic oxides Carbonyl compounds Organonitrogen compounds Organopnictogen compounds Primary alcohols
Substituents	Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Acylaminosugar Saccharolipid Pentose phosphate Pentose-5-phosphate N-acyl-alpha-hexosamine Glycosyl compound N-glycosyl compound Monosaccharide phosphate Organic pyrophosphate Beta-hydroxy acid Fatty acid ester Monoalkyl phosphate Pyrimidone Fatty amide Hydropyrimidine Hydroxy acid Monosaccharide N-acyl-amine Organic phosphoric acid derivative Oxane Fatty acyl Phosphoric acid ester Alkyl phosphate Pyrimidine Tetrahydrofuran Heteroaromatic compound Vinylogous amide Secondary carboxylic acid amide Carboxamide group Secondary alcohol Urea Lactam Carboxylic acid ester Carboxylic acid derivative Azacycle Oxacycle Monocarboxylic acid or derivatives Organoheterocyclic compound Organooxygen compound Hydrocarbon derivative Alcohol Organopnictogen compound Primary alcohol Organic nitrogen compound Organic oxide Organic oxygen compound Carbonyl group Organonitrogen compound Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	UDP-amino sugar (CHEBI:82845 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.43 g/L ALOGPS logP 2.66 ALOGPS logP 5.06 ChemAxon logS -3.4 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 18 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 353.92 Ų ChemAxon Rotatable Bond Count 36 ChemAxon Refractivity 241.06 m³·mol⁻¹ ChemAxon Polarizability 105.54 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:	Membrane
Reactions:	(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 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate Water + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <>2 Hydrogen ion + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + Uridine 5'-monophosphate UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + Water <> Uridine 5'-monophosphate + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate 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-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate <> Uridine 5'-diphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine > Hydrogen ion + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate Water + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine > Hydrogen ion + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + Uridine 5'-monophosphate UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate > Uridine 5'-diphosphate + 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate 2 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion +2 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate 2 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion +2 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
SMPDB Pathways:	Lipopolysaccharide biosynthesis PW000831
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540
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 splash10-03di-2910000101-46860ca31ec971b6dd89 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-2910001100-53f313794898ec8feced View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-3910000100-1158711cf21b4e95e971 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-9822230205-2ea21d2ff53d2b4aa05b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01vp-8912030614-d3d1eb5aea19bc3f5320 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06tf-5912100000-acba712642beaf0be36e 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 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 17787 HMDB ID Not Available Pubchem Compound ID 2372447 Kegg ID C04652 ChemSpider ID 1772247 Wikipedia ID Not Available BioCyc ID OH-MYRISTOYL EcoCyc ID OH-MYRISTOYL Ligand Expo UDG

Enzymes