2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate (PAMDB003630)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003630
Identification
Name: 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate
Description:2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate is an intermediate in Lipid IVA synthesis which is essesntial for the production of LPS. Lipopolysaccharide (LPS), a major outer membrane component, is composed of three domains: Lipid A, the core, which is an oligosaccharide consisting of an inner and outer region; and a distal repeating unit known as the O-antigen. Lipid A is linked to a beta-1,6-linked glucosamine disaccharide. Attached to this is the inner core containing at least two 3-deoxy-D-manno-octulosonate (KDO) units followed by two units of heptose. The outer core region and the O-antigen are attached to one of the heptose units. For some time it was thought that the minimum structure for cell viability in Pseudomonas aeruginosa had the di-Kdo moiety, but viable mutants lacking Kdo and with the basic tetra-acyl form of lipid A, i.e. lacking the two secondary acyl groups (and termed 'lipid IVA'), have recently been produced. Indeed, lipid IVA may be the minimum structure required for the viability of Pseudomonas aeruginosa.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2R,3S,4R,5R,6R)-3-hydroxy-2-(hydroxymethyl)-5-(3R)-3-hydroxytetradecanoylamino-6-phosphonooxyoxan-4-yl (3R)-3-hydroxytetradecanoate
  • (2R,3S,4R,5R,6R)-3-Hydroxy-2-(hydroxymethyl)-5-(3R)-3-hydroxytetradecanoylamino-6-phosphonooxyoxan-4-yl (3R)-3-hydroxytetradecanoic acid
  • 2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphate
  • 2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate
  • 2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3R)-3-hydroxymyristoyl-a-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3R)-3-hydroxymyristoyl-a-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3R)-3-hydroxymyristoyl-alpha-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3R)-3-hydroxymyristoyl-alpha-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(3R)-3-hydroxymyristoyl-α-D-glucosaminyl 1-phosphate
  • 2,3-Bis(3R)-3-hydroxymyristoyl-α-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(b-hydoroxymyristoyl)-b-D-glucosaminyl 1-phosphate
  • 2,3-Bis(b-hydoroxymyristoyl)-b-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(beta-hydoroxymyristoyl)-beta-D-glucosaminyl 1-phosphate
  • 2,3-Bis(beta-hydoroxymyristoyl)-beta-D-glucosaminyl 1-phosphoric acid
  • 2,3-Bis(β-hydoroxymyristoyl)-β-D-glucosaminyl 1-phosphate
  • 2,3-Bis(β-hydoroxymyristoyl)-β-D-glucosaminyl 1-phosphoric acid
  • 2,3-Diacylglucosamine 1-phosphate
  • 2,3-Diacylglucosamine 1-phosphoric acid
  • 2-Deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphono-a-D-glucopyranose
  • 2-Deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphono-alpha-D-glucopyranose
  • 2-Deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphono-α-D-glucopyranose
  • Lipid X
Chemical Formula: C34H66NO12P
Average Molecular Weight: 711.8611
Monoisotopic Molecular Weight: 711.432263093
InChI Key: HEHQDWUWJVPREQ-XQJZMFRCSA-N
InChI:InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26-,27-,28-,31-,32-,33-,34-/m1/s1
CAS number: Not Available
IUPAC Name:{[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name: lipid X
SMILES:CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(O)(O)=O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct Parent Acylaminosugars
Alternative Parents
Substituents
  • Saccharolipid
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-acyl-amine
  • Monosaccharide
  • Hydroxy acid
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00633 mg/mLALOGPS
logP4.38ALOGPS
logP5.82ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area212.31 Å2ChemAxon
Rotatable Bond Count30ChemAxon
Refractivity180.56 m3·mol-1ChemAxon
Polarizability80.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
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
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01r6-0010409200-dc9e868ae4b7c3f9d21cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016v-5251928000-f7e47fd0819ffd3e4060View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0693-2491325000-ce7b99b0dafa1b81f642View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9011121100-e8bdff78108540e8031eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010111000-c7f37736fa4eb93cbeaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-32488362320385f7b7a3View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16942
HMDB IDNot Available
Pubchem Compound ID123907
Kegg IDC04824
ChemSpider ID110438
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoLP5