P. aeruginosa Metabolome Database: UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine (PAMDB003524)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB003524

Identification

Name:

UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine

Description:

UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine is an intermediate in Lipid IVA synthesis. It is a substrate for the enzyme UDP-2,3-diacylglucosamine diphosphatase which catalyzes the reaction UDP-2,3-bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + H2O = 2,3-bis[(3R)-3-hydroxymyristoyl]-beta-D-glucosaminyl 1-phosphate + UMP.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

OH-MYRISTOYL
UDP-2,3-bis(3-hydroxymyristoyl)glucosamine
UDP-2,3-bis(3-hydroxytetradecanoyl)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-Bis(O-(3R)-3-hydroxymyristoyl)-a-D-glucosamine
UDP-2,3-Bis(O-(3R)-3-hydroxymyristoyl)-α-D-glucosamine
UDP-2,3-biso-(3R)-3-Hydroxymyristoyl-a-D-glucosamine
UDP-2,3-bisO-(3R)-3-hydroxymyristoyl-alpha-D-glucosamine
UDP-2,3-biso-(3R)-3-Hydroxymyristoyl-α-D-glucosamine
UDP-2,3-diacyl-glucosamine

Chemical Formula:

C₄₃H₇₅N₃O₂₀P₂

Average Molecular Weight:

1016.0112

Monoisotopic Molecular Weight:

1015.441914879

InChI Key:

KOJCFMYSTWNMQW-RUAJDYCTSA-L

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)/p-2/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-oxido-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-hydroxytetradecanecarboximidate

Traditional IUPAC Name:

(3R)-N-[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-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-hydroxytetradecanecarboximidate

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

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
N-acyl-alpha-hexosamine
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
Carboximidic acid derivative
Carboximidic acid
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organic molecular entity (CHEBI:78847 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.646 mg/mL	ALOGPS
logP	3.32	ALOGPS
logP	5.06	ChemAxon
logS	-3.2	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	8	ChemAxon
Polar Surface Area	359.58 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	262.16 m³·mol^-1	ChemAxon
Polarizability	105.07 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:

Membrane

Reactions:

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03xr-9100000000-ff037811dffd71bb2f75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-6420000009-b8b6523908978fb04445	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-5910001002-3e3c925ae584f1e111e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dl-9000000001-1a49ddada35d93c31506	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9430010000-507653e03e5b6557f747	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0037-9441000000-773a819aef4b199daa61	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	78847
HMDB ID	Not Available
Pubchem Compound ID	25246209
Kegg ID	Not Available
ChemSpider ID	34448517
Wikipedia ID	Not Available
BioCyc ID	Not Available

UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine (PAMDB003524)

Structure for UDP-2,3-bis(O-(3R)-3-Hydroxymyristoyl)-alpha-D-glucosamine (PAMDB003524)