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Record Information
Version	2.0
Creation Date	2012-05-31 14:43:00 -0600
Update Date	2015-06-03 17:19:56 -0600
Secondary Accession Numbers	ECMDB20401
Identification
Name:	Lipid IVb
Description	Lipid IVb is an intermediate in the syntheis of lipopolysaccharide (LPS).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaa6c14fc> Close
Synonyms:	Lipid IVB
Chemical Formula:	C82H152N2O24P2
Weight:	Average: 1612.0308 Monoisotopic: 1611.021026826
InChI Key:	XWVMRMCVAPUFAU-KZOCSRIOSA-J
InChI:	InChI=1S/C82H156N2O24P2/c1-6-11-16-21-26-31-32-37-42-47-52-57-72(91)102-67(56-51-46-41-36-30-25-20-15-10-5)61-71(90)84-75-79(105-73(92)59-65(87)54-49-44-39-34-28-23-18-13-8-3)77(94)69(104-82(75)108-110(98,99)100)63-101-81-76(83-70(89)58-64(86)53-48-43-38-33-27-22-17-12-7-2)80(78(68(62-85)103-81)107-109(95,96)97)106-74(93)60-66(88)55-50-45-40-35-29-24-19-14-9-4/h64-69,75-82,85-88,94H,6-63H2,1-5H3,(H,83,89)(H,84,90)(H2,95,96,97)(H2,98,99,100)/p-4/t64-,65-,66-,67-,68-,69-,75-,76-,77-,78-,79-,80-,81-,82-/m1/s1
CAS number:	Not Available
IUPAC Name:	(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-{[(3R)-1-oxido-3-(tetradecanoyloxy)tetradecylidene]amino}-6-(phosphonooxy)oxan-2-yl]methoxy}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-(phosphonatooxy)oxan-3-yl]tetradecanecarboximidate
Traditional IUPAC Name:	(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-{[(3R)-1-oxido-3-(tetradecanoyloxy)tetradecylidene]amino}-6-(phosphonooxy)oxan-2-yl]methoxy}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-(phosphonatooxy)oxan-3-yl]tetradecanecarboximidate
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@@]([H])(OP([O-])([O-])=O)[C@]([H])(OC(=O)C[C@]([H])(O)CCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C([O-])C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC
Chemical Taxonomy
Description	belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Saccharolipids
Sub Class	Not Available
Direct Parent	Saccharolipids
Alternative Parents	Hexose phosphates N-acyl-alpha-hexosamines Disaccharide phosphates O-glycosyl compounds Tricarboxylic acids and derivatives Monoalkyl phosphates Fatty acid esters Beta hydroxy acids and derivatives Oxanes Secondary alcohols Carboxylic acid esters Oxacyclic compounds Carboximidic acids Acetals Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic anions
Substituents	Saccharolipid Hexose phosphate N-acyl-alpha-hexosamine Disaccharide phosphate O-glycosyl compound Glycosyl compound Disaccharide Tricarboxylic acid or derivatives Monoalkyl phosphate Fatty acid ester Beta-hydroxy acid Fatty acyl Alkyl phosphate Phosphoric acid ester Oxane Organic phosphoric acid derivative Hydroxy acid Secondary alcohol Carboxylic acid ester Oxacycle Organoheterocyclic compound Carboxylic acid derivative Carboximidic acid derivative Carboximidic acid Acetal Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Primary alcohol Organooxygen compound Organonitrogen compound Carbonyl group Alcohol Organic anion 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 0.0044 g/L ALOGPS logP 6.35 ALOGPS logP 20.47 ChemAxon logS -5.6 ALOGPS pKa (Strongest Acidic) 0.55 ChemAxon pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 21 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 417.76 Ų ChemAxon Rotatable Bond Count 76 ChemAxon Refractivity 441.89 m³·mol⁻¹ ChemAxon Polarizability 187.71 ų ChemAxon Number of Rings 2 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:
SMPDB Pathways:	Lipopolysaccharide biosynthesis PW000831
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:	superpathway of lipopolysaccharide biosynthesis LPSSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-0200009000-a808728357430486b4fc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01ox-2530097000-defc032dc666d152a6d5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-029x-4911111000-8654c825d94dba6f33ba View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-2210009000-ac323a627fd4155421ae View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01u0-5970306000-25d43b63ece631861a8b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-002f-9340000000-cc438782833c1714e08b View in MoNA
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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 25203200 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID CPD0-1281 EcoCyc ID CPD0-1281