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Record Information
Version	2.0
Creation Date	2015-07-03 14:11:42 -0600
Update Date	2015-07-23 12:07:37 -0600
Secondary Accession Numbers	ECMDB23937
Identification
Name:	alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A
Description
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa1307590> Close
Synonyms:	a-kdo-(2->4)-a-kdo-(2->6)-[4-P-L-ara4n]-lipid a α-kdo-(2->4)-α-kdo-(2->6)-[4-P-L-ara4n]-lipid a
Chemical Formula:	C115H211N3O42P2
Weight:	Average: 2369.88 Monoisotopic: 2368.394241842
InChI Key:	LXMYMRJTVHRJDS-QKIYZXJESA-N
InChI:	InChI=1S/C115H211N3O42P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-94(129)150-83(66-60-54-48-42-35-29-23-17-11-5)72-96(131)154-108-98(118-92(127)71-82(65-59-53-47-41-34-28-22-16-10-4)149-93(128)67-61-55-49-43-36-30-24-18-12-6)109(147-78-89-102(135)107(153-95(130)70-81(122)64-58-52-46-40-33-27-21-15-9-3)97(110(151-89)159-161(141,142)143)117-91(126)69-80(121)63-57-51-45-39-32-26-20-14-8-2)152-90(106(108)158-162(144,145)160-111-103(136)99(132)84(116)77-146-111)79-148-114(112(137)138)74-88(101(134)105(156-114)87(125)76-120)155-115(113(139)140)73-85(123)100(133)104(157-115)86(124)75-119/h80-90,97-111,119-125,132-136H,7-79,116H2,1-6H3,(H,117,126)(H,118,127)(H,137,138)(H,139,140)(H,144,145)(H2,141,142,143)/t80-,81-,82-,83-,84+,85-,86-,87-,88-,89-,90-,97-,98-,99+,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,114-,115-/m1/s1
CAS number:	Not Available
IUPAC Name:	(2R,4R,5R,6R)-2-{[(2R,3S,4R,5R,6R)-3-[({[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-{[(2R,4R,5R,6R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-5-hydroxyoxane-2-carboxylic acid
Traditional IUPAC Name:	(2R,4R,5R,6R)-2-{[(2R,3S,4R,5R,6R)-3-({[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy(hydroxy)phosphoryl}oxy)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-{[(2R,4R,5R,6R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-5-hydroxyoxane-2-carboxylic acid
SMILES:	CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@H](OC[C@H]2O[C@H](OP(O)(O)=O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO[C@@]2(C[C@@H](O[C@@]3(C[C@@H](O)[C@@H](O)[C@H](O3)[C@H](O)CO)C(O)=O)[C@@H](O)[C@H](O2)[C@H](O)CO)C(O)=O)[C@H]1OP(O)(=O)O[C@H]1OC[C@H](N)[C@H](O)[C@H]1O
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Acylaminosugars
Alternative Parents	Oligosaccharide phosphates Hexacarboxylic acids and derivatives Saccharolipids Hexose phosphates N-acyl-alpha-hexosamines C-glucuronides C-glycosyl compounds O-glycosyl compounds Dialkyl phosphates Fatty acid esters Ketals Monoalkyl phosphates Beta hydroxy acids and derivatives Pyrans N-acyl amines Oxanes Secondary alcohols Secondary carboxylic acid amides 1,2-aminoalcohols Amino acids Carboxylic acid esters Oxacyclic compounds Carboxylic acids Carbonyl compounds Monoalkylamines Organic oxides Organopnictogen compounds Hydrocarbon derivatives Primary alcohols
Substituents	Oligosaccharide phosphate Oligosaccharide Hexacarboxylic acid or derivatives Acylaminosugar Saccharolipid Hexose phosphate N-acyl-alpha-hexosamine C-glucuronide C-glycosyl compound Glycosyl compound O-glycosyl compound Beta-hydroxy acid Ketal Fatty acid ester Dialkyl phosphate Monoalkyl phosphate Fatty amide Fatty acyl Hydroxy acid N-acyl-amine Alkyl phosphate Pyran Organic phosphoric acid derivative Oxane Phosphoric acid ester Amino acid or derivatives Secondary alcohol Secondary carboxylic acid amide Amino acid Carboxamide group Carboxylic acid ester 1,2-aminoalcohol Organoheterocyclic compound Carboxylic acid derivative Acetal Carboxylic acid Oxacycle Primary amine Carbonyl group Organic nitrogen compound Primary aliphatic amine Alcohol Amine Primary alcohol Organic oxide Organopnictogen compound Hydrocarbon derivative Organonitrogen compound Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.039 g/L ALOGPS logP 1.28 ALOGPS logP 18.11 ChemAxon logS -4.8 ALOGPS pKa (Strongest Acidic) 0.98 ChemAxon pKa (Strongest Basic) 8.79 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 36 ChemAxon Hydrogen Donor Count 20 ChemAxon Polar Surface Area 703.14 Ų ChemAxon Rotatable Bond Count 100 ChemAxon Refractivity 591.43 m³·mol⁻¹ ChemAxon Polarizability 263.02 ų ChemAxon Number of Rings 5 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:	undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + Di-trans,poly-cis-undecaprenyl phosphate + Lipid IIA undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + Di-trans,poly-cis-undecaprenyl phosphate + Lipid IIA
SMPDB Pathways:	Not Available
KEGG Pathways:	Cationic antimicrobial peptide (CAMP) resistance eco01503
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID Not Available Kegg ID C19890 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available