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95991-05-2 molecular structure
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({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl}oxy)phosphonic acid

ChemBase ID: 132912
Molecular Formular: C94H178N2O25P2
Molecular Mass: 1798.365042
Monoisotopic Mass: 1797.21939247
SMILES and InChIs

SMILES:
CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(C(OC(C1OP(=O)(O)O)CO)OCC1C(C(C(C(O1)OP(=O)(O)O)NC(=O)CC(CCCCCCCCCCC)O)OC(=O)CC(CCCCCCCCCCC)O)O)NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
Canonical SMILES:
CCCCCCCCCCCCCC(=O)OC(CC(=O)OC1C(NC(=O)CC(OC(=O)CCCCCCCCCCC)CCCCCCCCCCC)C(OCC2OC(OP(=O)(O)O)C(C(C2O)OC(=O)CC(CCCCCCCCCCC)O)NC(=O)CC(CCCCCCCCCCC)O)OC(C1OP(=O)(O)O)CO)CCCCCCCCCCC
InChI:
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)
InChIKey:
GZQKNULLWNGMCW-UHFFFAOYSA-N

Cite this record

CBID:132912 http://www.chembase.cn/molecule-132912.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl}oxy)phosphonic acid
IUPAC Traditional name
{5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl}oxyphosphonic acid
Synonyms
Lipid A, diphosphoryl from Salmonella enterica serotype minnesota Re 595 (Re mutant)
Lipid A, diphosphoryl from Escherichia coli F583 (Rd mutant)
CAS Number
95991-05-2
MDL Number
MFCD00131510
PubChem SID
24896402
162227189
24896265
PubChem CID
5043498

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5043498 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 0.6083911  H Acceptors 19 
H Donor 10  LogD (pH = 5.5) 18.968218 
LogD (pH = 7.4) 16.488445  Log P 23.97029 
Molar Refractivity 477.1785 cm3 Polarizability 192.28253 Å3
Polar Surface Area 405.53 Å2 Rotatable Bonds 88 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Bioassay(PubChem)
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - L5399 external link
Biochem/physiol Actions
Lipid A molecules compose the lipid membrane anchoring core components of endotoxins produced by Gram-negative bacteria. Lipid A molecules induce immune responses. Structually, lipid A molecules are composed of two glucosamine unites with varied, species dependent, fatty acyl chain number and identity and degree of phosphorylation. Lipid A, diphosphoryl from Escherichia coli F583 may be used in comparative assessment of the antigenicity of specific structures within different LPA molecules and analogues.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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