Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


Lauroyl-KDO2-lipid IV(A) (M2MDB004216)

Record Information
Version2.0
Creation Date2015-06-04 15:14:06 -0600
Update Date2015-08-05 16:22:04 -0600
Secondary Accession Numbers
  • ECMDB23769
Identification
Name:Lauroyl-KDO2-lipid IV(A)
DescriptionA lipid A comprising lipid IVA glycosylated with two 3-deoxy-D-manno-octulosonic acid (KDO) residues and carrying an additional dodecanoyl group
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Lauroyl-kdo2-lipid IV(a)
Chemical Formula:C96H176N2O38P2
Weight:Average: 2028.388
Monoisotopic: 2027.137633231
InChI Key:JVUUYJGQIVCMIU-ZODGSCPMSA-N
InChI:InChI=1S/C96H176N2O38P2/c1-6-11-16-21-26-31-36-41-46-51-66(101)56-76(107)97-81-89(130-79(110)57-67(102)52-47-42-37-32-27-22-17-12-7-2)85(114)74(128-92(81)136-138(122,123)124)64-125-91-82(98-77(108)59-69(54-49-44-39-34-29-24-19-14-9-4)127-78(109)55-50-45-40-35-30-25-20-15-10-5)90(131-80(111)58-68(103)53-48-43-38-33-28-23-18-13-8-3)88(135-137(119,120)121)75(129-91)65-126-95(93(115)116)61-73(84(113)87(133-95)72(106)63-100)132-96(94(117)118)60-70(104)83(112)86(134-96)71(105)62-99/h66-75,81-92,99-106,112-114H,6-65H2,1-5H3,(H,97,107)(H,98,108)(H,115,116)(H,117,118)(H2,119,120,121)(H2,122,123,124)/t66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,95-,96-/m1/s1
CAS number:Not Available
IUPAC Name:(2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-5-{[(3R)-1,3-dihydroxytetradecylidene]amino}-3-hydroxy-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-5-{[(3R)-3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-3-(phosphonooxy)oxan-2-yl]methoxy}-5-hydroxyoxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name:(2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-5-{[(3R)-1,3-dihydroxytetradecylidene]amino}-3-hydroxy-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-5-{[(3R)-3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-3-(phosphonooxy)oxan-2-yl]methoxy}-5-hydroxyoxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylic acid
SMILES:[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])O[C@]([H])(CO[C@@]3(C[C@@]([H])(O[C@@]4(C[C@@]([H])(O)[C@@]([H])(O)[C@]([H])(O4)[C@]([H])(O)CO)C(O)=O)[C@@]([H])(O)[C@]([H])(O3)[C@]([H])(O)CO)C(O)=O)[C@@]([H])(OP(O)(O)=O)[C@]([H])(OC(=O)C[C@]([H])(O)CCCCCCCCCCC)[C@@]2([H])N=C(O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C(O)C[C@]([H])(O)CCCCCCCCCCC
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
  • Acylaminosugar
  • Saccharolipid
  • Hexose phosphate
  • Pentacarboxylic acid or derivatives
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Ketal
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty amide
  • Fatty acyl
  • Hydroxy acid
  • N-acyl-amine
  • Alkyl phosphate
  • Pyran
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Primary alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-6
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP3.3ALOGPS
logP16.61ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)0.55ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count35ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area639.34 ŲChemAxon
Rotatable Bond Count84ChemAxon
Refractivity500.25 m³·mol⁻¹ChemAxon
Polarizability225.44 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
KDO2-Lipid A + Acyl-carrier protein + Tetradecanoyl-[acp] + Lauroyl-KDO2-lipid IV(A) <> Tetradecanoyl-[acp] + Lauroyl-KDO2-lipid IV(A) + Acyl-carrier protein
Lauroyl-KDO2-lipid IV(A) + Acyl-carrier protein + Dodecanoyl-[acyl-carrier protein] + KDO(2)-lipid IV(A) <> Dodecanoyl-[acyl-carrier protein] + Di[3-deoxy-D-manno-octulosonyl]-lipid IV(A) + Lauroyl-KDO2-lipid IV(A) + Acyl-carrier protein
a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + dodecanoyl-[acp]  + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > Lauroyl-KDO2-lipid IV(A) + a holo-[acyl-carrier protein]
Lauroyl-KDO2-lipid IV(A) + myristoyl-[acp] > a holo-[acyl-carrier protein] + (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
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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27422
HMDB IDNot Available
Pubchem Compound ID25201427
Kegg IDC06251
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Lipid A biosynthesis lauroyl acyltransferase
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Acylates the intermediate (KDO)2-lipid IVA to form (KDO)2-(lauroyl)-lipid IVA. Has 10 fold selectivity for lauroyl- ACP over myristoyl-ACP
Gene Name:
htrB
Uniprot ID:
P0ACV0
Molecular weight:
35407
Protein Details
2. Lipid A biosynthesis (KDO)2-(lauroyl)-lipid IVA acyltransferase
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Transfers myristate or laurate, activated on ACP, to the lipid IVA moiety of (KDO)2-(lauroyl)-lipid IVA. Decanoyl, palmitoyl, palmitoleoyl, and (R)-3-hydroxymyristoyl-ACP are poor acyl donors. Functions optimally after laurate incorporation by htrB has taken place. Acylates (KDO)2-(lauroyl)-lipid IVA about 100 times faster than (KDO)2-lipid IVA. Displays a preference for myristoyl-ACP over lauroyl-ACP
Gene Name:
msbB
Uniprot ID:
P24205
Molecular weight:
37410