Phosphoethanolamine KDO(2)-lipid (A) (PAMDB001750)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001750
Identification
Name: Phosphoethanolamine KDO(2)-lipid (A)
Description:Phosphoethanolamine kdo(2)-lipid (a) belongs to the class of Polysaccharide Phosphates. These are polysaccharides in which a phosphate group is bound to at least one carbohydrate unit. (inferred from compound structure)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2R,4R,5R,6S)-6-(1R)-1-2-azaniumylethoxy(oxido)phosphoryloxy-2-hydroxyethyl-2-(2R,4R,5R,6R)-2-carboxylato-6-(1R)-1,2-dihydroxyethyl-2-(2R,3S,4R,5R,6R)-5-(3R)-3-dodecanoyloxytetradecanoylamino-6-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonatooxyoxan-2-ylmethoxy-3-phosphonatooxy-4-(3R)-3-tetradecanoyloxytetradecanoyloxyoxan-2-ylmethoxy-5-hydroxyoxan-4-yloxy-4,5-dihydroxyoxane-2-carboxylate
  • (2R,4R,5R,6S)-6-(1R)-1-2-Azaniumylethoxy(oxido)phosphoryloxy-2-hydroxyethyl-2-(2R,4R,5R,6R)-2-carboxylato-6-(1R)-1,2-dihydroxyethyl-2-(2R,3S,4R,5R,6R)-5-(3R)-3-dodecanoyloxytetradecanoylamino-6-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonatooxyoxan-2-ylmethoxy-3-phosphonatooxy-4-(3R)-3-tetradecanoyloxytetradecanoyloxyoxan-2-ylmethoxy-5-hydroxyoxan-4-yloxy-4,5-dihydroxyoxane-2-carboxylic acid
  • (6S)-6-(1R)-1-{(2-ammonioethoxy)phosphinatooxy}-2-hydroxyethyl-3-deoxy-b-L-erythro-hex-2-ulopyranonosyl-(2->4)-(6R)-3-deoxy-6-(1R)-1,2-dihydroxyethyl-b-L-erythro-hex-2-ulopyranonosyl-(2->6)-2-deoxy-2-{(3R)-3-(dodecanoyloxy)tetradecanoylamino}-4-O-phosphonato-3-O-(3R)-3-(tetradecanoyloxy)tetradecanoyl-b-D-glucopyranosyl-(1->6)-2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphonato-a-D-glucopyranose
  • (6S)-6-(1R)-1-{(2-Ammonioethoxy)phosphinatooxy}-2-hydroxyethyl-3-deoxy-beta-L-erythro-hex-2-ulopyranonosyl-(2->4)-(6R)-3-deoxy-6-(1R)-1,2-dihydroxyethyl-beta-L-erythro-hex-2-ulopyranonosyl-(2->6)-2-deoxy-2-{(3R)-3-(dodecanoyloxy)tetradecanoylamino}-4-O-phosphonato-3-O-(3R)-3-(tetradecanoyloxy)tetradecanoyl-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphonato-alpha-D-glucopyranose
  • (6S)-6-(1R)-1-{(2-ammonioethoxy)phosphinatooxy}-2-hydroxyethyl-3-deoxy-β-L-erythro-hex-2-ulopyranonosyl-(2->4)-(6R)-3-deoxy-6-(1R)-1,2-dihydroxyethyl-β-L-erythro-hex-2-ulopyranonosyl-(2->6)-2-deoxy-2-{(3R)-3-(dodecanoyloxy)tetradecanoylamino}-4-O-phosphonato-3-O-(3R)-3-(tetradecanoyloxy)tetradecanoyl-β-D-glucopyranosyl-(1->6)-2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphonato-α-D-glucopyranose
  • Phosphoethanolamine-Kdo2-lipid A
  • Phosphoethanolamine-Kdo2-lipid A hexaanion
Chemical Formula: C112H199N3O42P3
Average Molecular Weight: 2352.728
Monoisotopic Molecular Weight: 2351.277394933
InChI Key: FBBLZLDSYGPWQW-UHFFFAOYSA-G
InChI:InChI=1S/C112H206N3O42P3/c1-7-13-19-25-31-37-38-44-50-56-62-68-94(125)147-84(66-60-54-48-42-35-29-23-17-11-5)74-96(127)151-106-98(115-92(123)73-83(65-59-53-47-41-34-28-22-16-10-4)146-93(124)67-61-55-49-43-36-30-24-18-12-6)107(143-79-89-101(130)105(150-95(126)72-82(119)64-58-52-46-40-33-27-21-15-9-3)97(108(148-89)157-159(138,139)140)114-91(122)71-81(118)63-57-51-45-39-32-26-20-14-8-2)149-90(104(106)156-158(135,136)137)80-144-111(109(131)132)76-87(100(129)102(153-111)86(121)77-116)152-112(110(133)134)75-85(120)99(128)103(154-112)88(78-117)155-160(141,142)145-70-69-113/h81-90,97-108,116-121,128-130H,7-80H2,1-6H3,(H,114,122)(H,115,123)(H,131,132)(H,133,134)(H,141,142)(H2,135,136,137)(H2,138,139,140)/q+1/p-7
CAS number: Not Available
IUPAC Name:(2-{[1-(6-carboxylato-6-{[2-carboxylato-6-(1,2-dihydroxyethyl)-2-({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl}methoxy)-5-hydroxyoxan-4-yl]oxy}-3,4-dihydroxyoxan-2-yl)-2-hydroxyethyl phosphonato]oxy}ethyl)azaniumyl
Traditional IUPAC Name: (2-{[1-(6-carboxylato-6-{[2-carboxylato-6-(1,2-dihydroxyethyl)-2-({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl}methoxy)-5-hydroxyoxan-4-yl]oxy}-3,4-dihydroxyoxan-2-yl)-2-hydroxyethyl phosphonato]oxy}ethyl)ammonio
SMILES:CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)C(OCC2OC(OP([O-])([O-])=O)C(NC(=O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)OC(COC2(CC(OC3(CC(O)C(O)C(O3)C(CO)OP([O-])(=O)OCC[N+])C([O-])=O)C(O)C(O2)C(O)CO)C([O-])=O)C1OP([O-])([O-])=O
Chemical Taxonomy
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-6
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0407 mg/mLALOGPS
logP3.54ALOGPS
logP19.57ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)0.57ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count34ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area716.83 Å2ChemAxon
Rotatable Bond Count103ChemAxon
Refractivity601.44 m3·mol-1ChemAxon
Polarizability260.28 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Adenosine triphosphate + Water + Phosphoethanolamine KDO(2)-lipid (A) > ADP + Hydrogen ion + Phosphate + Phosphoethanolamine KDO(2)-lipid (A)
Adenosine triphosphate + Water + Phosphoethanolamine KDO(2)-lipid (A) > ADP + Hydrogen ion + Phosphate + Phosphoethanolamine KDO(2)-lipid (A)
KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphoethanolamine KDO(2)-lipid (A)
KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Phosphoethanolamine KDO(2)-lipid (A)
a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + PE(12:0/10:0) + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + phosphoethanolamine-Kdo2-lipid A + Phosphoethanolamine KDO(2)-lipid (A)
PE(16:0/16:0) + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > phosphoethanolamine-Kdo2-lipid A + 1,2-dihexadecanoyl-rac-glycerol + Phosphoethanolamine KDO(2)-lipid (A)
Pathways:
Spectra
Spectra:
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID60085
HMDB IDNot Available
Pubchem Compound ID46173153
Kegg IDNot Available
ChemSpider ID26331809
Wikipedia IDNot Available
BioCyc IDCPD-11653
EcoCyc IDCPD-11653

Enzymes

Protein Details
• Lipopolysaccharide export system permease protein lptG
General function:
Involved in lipopolysaccharide transport
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptG
Locus Tag:
PA3827
Molecular weight:
39.2 kDa
Protein Details
• Lipopolysaccharide export system permease protein lptF
General function:
Involved in lipopolysaccharide-transporting ATPase acti
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptF
Locus Tag:
PA3828
Molecular weight:
41.3 kDa
Protein Details
• Lipopolysaccharide export system ATP-binding protein lptB
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. Probably responsible for energy coupling to the transport system
Gene Name:
lptB
Locus Tag:
PA4461
Molecular weight:
26.5 kDa
Protein Details
• Lipopolysaccharide export system protein lptC
General function:
Involved in lipopolysaccharide transmembrane transporter activity
Specific function:
Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptC
Locus Tag:
PA4459
Molecular weight:
21.4 kDa
Protein Details
• Lipopolysaccharide export system protein lptA
General function:
Involved in lipopolysaccharide binding
Specific function:
Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. May act as a chaperone that facilitates LPS transfer across the aquaeous environment of the periplasm. Interacts specifically with the lipid A domain of LPS
Gene Name:
lptA
Locus Tag:
PA0005
Molecular weight:
28.7 kDa

Transporters

Protein Details
• Lipopolysaccharide export system permease protein lptG
General function:
Involved in lipopolysaccharide transport
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptG
Locus Tag:
PA3827
Molecular weight:
39.2 kDa
Protein Details
• Lipopolysaccharide export system permease protein lptF
General function:
Involved in lipopolysaccharide-transporting ATPase acti
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptF
Locus Tag:
PA3828
Molecular weight:
41.3 kDa