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Record Information
Version	2.0
Creation Date	2015-07-03 14:12:38 -0600
Update Date	2015-09-14 16:46:26 -0600
Secondary Accession Numbers	ECMDB23940
Identification
Name:	(9Z)-Hexadec-9-enoyl-KDO2-lipid IV(A)
Description	(9Z)-hexadec-9-enoyl-[acyl-carrier protein]:KDO2-lipid IV(A) O-palmitoleoyltransferase (EC: 2.3.1.242) is an enzyme that catalyzes the chemical reaction Hexadecenoyl-[acyl-carrier protein] + Di[3-deoxy-D-manno-octulosonyl]-lipid IV(A) <=> (9Z)-Hexadec-9-enoyl-KDO2-lipid IV(A) + Acyl-carrier protein in E. coli (KEGG).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa5e2651c> Close
Synonyms:	Palmitoleoyl-kdo2-lipid iv(a)
Chemical Formula:	C100H182N2O38P2
Weight:	Average: 2082.48 Monoisotopic: 2081.184583424
InChI Key:	GUGOELZTMNFFOJ-MHGVWHNGSA-N
InChI:	InChI=1S/C100H182N2O38P2/c1-6-11-16-21-26-31-32-33-34-39-44-49-54-59-82(113)131-73(58-53-48-43-38-30-25-20-15-10-5)63-81(112)102-86-94(135-84(115)62-72(107)57-52-47-42-37-29-24-19-14-9-4)92(139-141(123,124)125)79(69-130-99(97(119)120)65-77(88(117)91(137-99)76(110)67-104)136-100(98(121)122)64-74(108)87(116)90(138-100)75(109)66-103)133-95(86)129-68-78-89(118)93(134-83(114)61-71(106)56-51-46-41-36-28-23-18-13-8-3)85(96(132-78)140-142(126,127)128)101-80(111)60-70(105)55-50-45-40-35-27-22-17-12-7-2/h31-32,70-79,85-96,103-110,116-118H,6-30,33-69H2,1-5H3,(H,101,111)(H,102,112)(H,119,120)(H,121,122)(H2,123,124,125)(H2,126,127,128)/b32-31-/t70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,99-,100-/m1/s1
CAS number:	Not Available
IUPAC Name:	(2R,4R,5R,6R)-4-{[(2R,4R,5R,6R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-[(3R)-3-[(9Z)-hexadec-9-enoyloxy]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-hydroxytetradecanoyl]oxy}-3-(phosphonooxy)oxan-2-yl]methoxy}-5-hydroxyoxane-2-carboxylic acid
Traditional IUPAC Name:	(2R,4R,5R,6R)-4-{[(2R,4R,5R,6R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-[(3R)-3-[(9Z)-hexadec-9-enoyloxy]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-hydroxytetradecanoyl]oxy}-3-(phosphonooxy)oxan-2-yl]methoxy}-5-hydroxyoxane-2-carboxylic acid
SMILES:	CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(O)(O)=O)O[C@H](CO[C@@H]2O[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@H]2NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC)[C@@H](O)[C@@H]1OC(=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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Acylaminosugars
Alternative Parents	Oligosaccharide phosphates Saccharolipids Hexose phosphates Pentacarboxylic acids and derivatives N-acyl-alpha-hexosamines C-glucuronides C-glycosyl compounds O-glycosyl compounds Beta hydroxy acids and derivatives Fatty acid esters Ketals Monoalkyl phosphates Oxanes N-acyl amines Pyrans Secondary alcohols Secondary carboxylic acid amides Carboxylic acid esters Carboxylic acids Oxacyclic compounds Primary alcohols Carbonyl compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds
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 Framework	Aliphatic heteromonocyclic compounds
External Descriptors	lipid As (CHEBI:61558 )
Physical Properties
State:	Not Available
Charge:	-6
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.034 g/L ALOGPS logP 3.87 ALOGPS logP 16.39 ChemAxon logS -4.8 ALOGPS pKa (Strongest Acidic) 0.6 ChemAxon Physiological Charge -6 ChemAxon Hydrogen Acceptor Count 33 ChemAxon Hydrogen Donor Count 19 ChemAxon Polar Surface Area 632.36 Ų ChemAxon Rotatable Bond Count 87 ChemAxon Refractivity 518.72 m³·mol⁻¹ ChemAxon Polarizability 228.38 ų ChemAxon Number of Rings 4 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:	Hexadecenoyl-[acyl-carrier protein] + KDO(2)-lipid IV(A) <> (9Z)-Hexadec-9-enoyl-KDO2-lipid IV(A) + Acyl-carrier protein
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
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 61558 HMDB ID Not Available Pubchem Compound ID 25246184 Kegg ID C20933 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available