Record Information
Version1.0
Creation date2011-09-21 01:54:30 UTC
Update date2017-04-03 05:02:20 UTC
Primary IDFDB029354
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLipid A
DescriptionLipid 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. [HMDB]
CAS Number302-72-7
Structure
Thumb
Synonyms
SynonymSource
E. coli lipid aChEBI
Diphosphoryl hexaacyl lipid aHMDB
Synthetic e. coli lipid aHMDB
a, LipidMeSH, HMDB
Lipid aMeSH
Dioryl hexaacyl lipid aHMDB
Diphosphoryl hexaacyl lipid Ahmdb
synthetic E. coli lipid Ahmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP6.8ALOGPS
logP23.97ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)0.61ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area405.53 ŲChemAxon
Rotatable Bond Count88ChemAxon
Refractivity477.18 m³·mol⁻¹ChemAxon
Polarizability213.02 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC94H178N2O25P2
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
InChI IdentifierInChI=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 KeyGZQKNULLWNGMCW-PWQABINMSA-N
Isomeric SMILESCCCCCCCCCCCCCC(=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
Average Molecular Weight1798.365
Monoisotopic Molecular Weight1797.21939228
Classification
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
  • Acylaminosugar
  • Saccharolipid
  • Hexose phosphate
  • Disaccharide phosphate
  • N-acyl-alpha-hexosamine
  • Tetracarboxylic acid or derivatives
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Monoalkyl phosphate
  • Beta-hydroxy acid
  • Fatty acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Hydroxy acid
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0089-0123161900-a0b29cb2a5620669c282Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff1-1223093400-c7c1cee9a9256bd28b6eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00e9-0242489600-77966b68d48be8286cb4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9510133200-a35ef4a869747eee82f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010121101-806a5bc007a2af4acfaeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0c15069faff9658a6001Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-1290020200-6ff62fce7a1fc5f77865Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-4390030000-fc40ff09fa4e7b1694bfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056v-9640124000-40187fa65042441659caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ul1-0001090300-7844b0b3a9cc31e69e69Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kor-3740180900-796c703855f3e6dcf409Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-4910012000-0ea888969ae27836334eSpectrum
NMRNot Available
ChemSpider ID8052983
ChEMBL IDNot Available
KEGG Compound IDC13908
Pubchem Compound ID9877306
Pubchem Substance IDNot Available
ChEBI ID47040
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13244
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLipid A
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference