UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine (ECMDB24216) (M2MDB006333)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (3)
Record Information
Version2.0
Creation Date2015-09-08 17:50:07 -0600
Update Date2015-09-14 16:46:36 -0600
Secondary Accession Numbers
  • ECMDB24216
Identification
Name:UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine
DescriptionUDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine is an intermediate in lipid IVA biosynthesis pathway in E.coli. It is a substrate for the enzyme UDP-2,3-diacylglucosamine hydrolase which catalyzes the reaction UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + H2O -> 2,3-bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosaminyl 1-phosphate + UMP + 2 H+. It is also a product for enzyme UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase which catalyzes reaction a (3R)-3-hydroxymyristoyl-[acp] + UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine -> UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + a holo-[acyl-carrier protein] + H+ (BioCyc compound: OH-MYRISTOYL).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamineChEBI
UDP-2,3-Bis(beta-hydroxymyristoyl)-D-glucosamineChEBI
UDP-2,3-Bis(b-hydroxymyristoyl)-D-glucosamineGenerator
UDP-2,3-Bis(β-hydroxymyristoyl)-D-glucosamineGenerator
Chemical Formula:C43H77N3O20P2
Weight:Average: 1018.038
Monoisotopic: 1017.457565887
InChI Key:KOJCFMYSTWNMQW-LNGUGUEYSA-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:N-[(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-[(3-hydroxytetradecanoyl)oxy]oxan-3-yl]-3-hydroxytetradecanimidic acid
Traditional IUPAC Name:N-[(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-[(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)OC([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)CC([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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP2.93ALOGPS
logP5.06ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area353.92 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity241.06 m³·mol⁻¹ChemAxon
Polarizability103.7 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
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
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine + Water > Uridine 5'-monophosphate + Hydrogen ion + 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate
2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate + UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine > Uridine 5'-diphosphate + Hydrogen ion + (2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate)
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2910000101-46860ca31ec971b6dd89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2910001100-53f313794898ec8fecedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3910000100-1158711cf21b4e95e971View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9822230205-2ea21d2ff53d2b4aa05bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vp-8912030614-d3d1eb5aea19bc3f5320View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5912100000-acba712642beaf0be36eView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17787
HMDB IDNot Available
Pubchem Compound ID16048612
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Lipid-A-disaccharide synthase
General function:
Involved in lipid-A-disaccharide synthase activity
Specific function:
Condensation of UDP-2,3-diacylglucosamine and 2,3- diacylglucosamine-1-phosphate to form lipid A disaccharide, a precursor of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell
Gene Name:
lpxB
Uniprot ID:
P10441
Molecular weight:
42382
Reactions
UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate = UDP + 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate.
Protein Details
2. UDP-3-O-[3-hydroxymyristoyl] glucosamine N-acyltransferase
General function:
Involved in transferase activity
Specific function:
UDP-3-O-(3-hydroxytetradecanoyl)glucosamine + (R)-3-hydroxytetradecanoyl-[acyl-carrier-protein] = UDP-2,3-bis(3- hydroxytetradecanoyl)glucosamine + [acyl-carrier-protein]
Gene Name:
lpxD
Uniprot ID:
P21645
Molecular weight:
36038
Reactions
(3R)-3-hydroxymyristoyl-[acyl-carrier-protein] + UDP-3-O-((3R)-hydroxymyristoyl)-alpha-D-glucosamine = UDP-2,3-bis(O-(3R)-3-hydroxymyristoyl)-alpha-D-glucosamine + a holo-[acyl-carrier-protein].
Protein Details
3. UDP-2,3-diacylglucosamine hydrolase
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of the pyrophosphate bond of UDP-2,3-diacylglucosamine to yield 2,3-diacylglucosamine 1- phosphate (lipid X) and UMP
Gene Name:
lpxH
Uniprot ID:
P43341
Molecular weight:
26894
Reactions
UDP-2,3-bis((3R)-3-hydroxymyristoyl)-alpha-D-glucosamine + H(2)O = 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate + UMP.