P. aeruginosa Metabolome Database: UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine (PAMDB001696)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB001696

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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

790.6641

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Saccharolipid
Glucosamine
Amino sugar
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
Monoalkyl phosphate
Amino saccharide
Pyrimidone
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Organic phosphate
Monosaccharide
Hydroxy acid
Hydropyrimidine
Saccharide
Heteroaromatic compound
Oxolane
Secondary alcohol
Carboxylic acid ester
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
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 mg/mL	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 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	184.89 m³·mol^-1	ChemAxon
Polarizability	75.94 Å³	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-[(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

Pathways:

Lipopolysaccharide biosynthesis pae00540
Metabolic pathways pae01100

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

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	Not Available
Pubchem Compound ID	25244806
Kegg ID	C06022
ChemSpider ID	28533665
Wikipedia ID	Not Available
BioCyc ID	UDP-OHMYR-GLUCOSAMINE
EcoCyc ID	UDP-OHMYR-GLUCOSAMINE

UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine (PAMDB001696)

Structure for UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine (PAMDB001696)