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Human Metabolome Database Version 3.5

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Showing metabocard for Lipid A (HMDB13244)

Record Information
Version 3.5
Creation Date 2009-11-30 08:51:36 -0700
Update Date 2013-02-08 17:29:59 -0700
HMDB ID HMDB13244
Secondary Accession Numbers None
Metabolite Identification
Common Name Lipid A
Description Lipid A is a lipid component of an endotoxin held responsible for toxicity of Gram-negative bacteria. It is the innermost of the three regions of the lipopolysaccharide (LPS, also called endotoxin) molecule, and its hydrophobic nature allows it to anchor the LPS to the outer membrane. While its toxic effects can be damaging, the sensing of lipid A by the human immune system may also be critical for the onset of immune responses to Gram-negative infection, and for the subsequent successful fight against the infection. Many of the immune activating abilities of LPS can be attributed to the lipid A unit. It is a very potent stimulant of the immune system, activating cells (for example, monocytes or macrophages) at picogram per milliliter quantities.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Diphosphoryl hexaacyl lipid A
  2. Synthetic E. coli lipid A
Chemical Formula C94H178N2O25P2
Average Molecular Weight 1798.365
Monoisotopic Molecular Weight 1797.21939228
IUPAC Name {[(2R,3S,4R,5R,6R)-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}-2-(hydroxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4R,5R,6R)-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}-2-(hydroxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecano
CAS Registry Number Not Available
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@H]1OP(O)(O)=O
InChI Identifier InChI=1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)/t75-,76-,77-,78-,79-,80-,87-,88-,89-,90-,91-,92-,93-,94-/m1/s1
InChI Key GZQKNULLWNGMCW-PWQABINMSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Disaccharides
Sub Class Dihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • lipid As(ChEBI)
Substituents
  • Acetal
  • Acylaminosugar
  • Beta Hydroxy Acid
  • Carboxamide Group
  • Carboxylic Acid Ester
  • Disaccharide Phosphate
  • Fatty Acid Ester
  • Glucosamine
  • Glycosyl Compound
  • Mannosamine
  • N Acetyl Alpha Hexosamine 1 Phosphate
  • N Acyl Amine
  • O Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent Dihexoses
Ontology
Status Expected and Not Quantified
Origin
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0012 g/L ALOGPS
LogP 6.80 ALOGPS
LogP 23.97 ChemAxon
LogS -6.17 ALOGPS
pKa (strongest acidic) 0.61 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 19 ChemAxon
Hydrogen Donor Count 10 ChemAxon
Polar Surface Area 405.53 A2 ChemAxon
Rotatable Bond Count 88 ChemAxon
Refractivity 477.18 ChemAxon
Polarizability 213.02 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029354
KNApSAcK ID Not Available
Chemspider ID 8052983 Link_out
KEGG Compound ID C13908 Link_out
BioCyc ID CPD0-1283 Link_out
BiGG ID Not Available
Wikipedia Link Lipid A Link_out
NuGOwiki Link HMDB13244 Link_out
Metagene Link HMDB13244 Link_out
METLIN ID Not Available
PubChem Compound 9877306 Link_out
PDB ID Not Available
ChEBI ID 47040 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available