Phosphoethanolamine KDO(2)-lipid (A) (ECMDB21352) (M2MDB001750)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (6)Transporters (2)XML
Proteins (6)
Record Information
Version2.0
Creation Date2012-07-30 14:55:24 -0600
Update Date2015-09-18 09:17:49 -0600
Secondary Accession Numbers
  • ECMDB21352
Identification
Name:Phosphoethanolamine KDO(2)-lipid (A)
DescriptionPhosphoethanolamine 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
MOLSDFPDBSMILESInChI
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
Weight:Average: 2352.728
Monoisotopic: 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
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Oligosaccharide phosphate
  • Oligosaccharide
  • Hexacarboxylic acid or derivatives
  • Saccharolipid
  • Acylaminosugar
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • O-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Ketal
  • Dialkyl phosphate
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Alkyl phosphate
  • Pyran
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Hydroxy acid
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-6
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count103ChemAxon
Refractivity601.44 m³·mol⁻¹ChemAxon
Polarizability260.28 ųChemAxon
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)
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
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
1. Phosphoethanolamine transferase eptB
General function:
Involved in catalytic activity
Specific function:
Catalyzes the addition of a phosphoethanolamine (pEtN) moiety to the outer 3-deoxy-D-manno-octulosonic acid (KDO) residue of a KDO(2)-lipid A. Phosphatidylethanolamines with one unsaturated acyl group functions as pEtN donors and the reaction releases diacylglycerol
Gene Name:
eptB
Uniprot ID:
P37661
Molecular weight:
63804
Protein Details
2. 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
Uniprot ID:
P0ADC6
Molecular weight:
39618
Protein Details
3. 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
Uniprot ID:
P0AF98
Molecular weight:
40357
Protein Details
4. 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
Uniprot ID:
P0A9V1
Molecular weight:
26800
Protein Details
5. 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
Uniprot ID:
P0ADV9
Molecular weight:
21703
Protein Details
6. 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
Uniprot ID:
P0ADV1
Molecular weight:
20127

Transporters

Protein Details
1. 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
Uniprot ID:
P0ADC6
Molecular weight:
39618
Protein Details
2. 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
Uniprot ID:
P0AF98
Molecular weight:
40357