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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
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ChemBase ID:
132912
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Molecular Formular:
C94H178N2O25P2
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Molecular Mass:
1798.365042
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Monoisotopic Mass:
1797.21939247
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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
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Cite this record
CBID:132912 http://www.chembase.cn/molecule-132912.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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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
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IUPAC Traditional name
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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}oxyphosphonic acid
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Synonyms
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Lipid A, diphosphoryl from Salmonella enterica serotype minnesota Re 595 (Re mutant)
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Lipid A, diphosphoryl from Escherichia coli F583 (Rd mutant)
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CAS Number
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MDL Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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0.6083911
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H Acceptors
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19
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H Donor
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10
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LogD (pH = 5.5)
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18.968218
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LogD (pH = 7.4)
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16.488445
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Log P
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23.97029
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Molar Refractivity
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477.1785 cm3
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Polarizability
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192.28253 Å3
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Polar Surface Area
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405.53 Å2
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Rotatable Bonds
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88
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Lipinski's Rule of Five
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false
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DETAILS
DETAILS
Sigma Aldrich
Sigma Aldrich -
L5399
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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. |
PATENTS
PATENTS
PubChem Patent
Google Patent