Endotoxin
(2R,4R,5S,6R)-2-[(2R,4R,5S,6R)-5-[(3S,4R,5R,6R)-4-[(3S,4S,5R,6R)-4-[(3R,4S,5R,6R)-4-[(2R,3R,4S,5R,6R)-3-[(3R,4S,5R,6R)-4-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2R,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxyoxan-2-yl]oxy-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-[(1S)-2-[(3S,4R,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-5-phosphonooxyoxan-2-yl]oxy-1-hydroxyethyl]-3,5-dihydroxyoxan-2-yl]oxy-5-[[2-aminoethoxy(hydroxy)phosphoryl]oxy-hydroxyphosphoryl]oxy-6-[(1S)-1,2-dihydroxyethyl]-3-hydroxyoxan-2-yl]oxy-2-carboxy-6-[(1S)-1,2-dihydroxyethyl]-2-[[(2R,3S,4R,5R,6R)-5-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-6-[[(2R,3S,4R,5R,6R)-3-hydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxy-6-phosphonooxyoxan-2-yl]methoxy]-3-phosphonooxy-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]methoxy]oxan-4-yl]oxy-4-[(2R,4R,5R,6R)-4-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-carboxy-6-[(1S)-1,2-dihydroxyethyl]-5-hydroxyoxan-2-yl]oxy-6-[(1S)-1,2-dihydroxyethyl]-5-hydroxyoxane-2-carboxylic acid
Molecular Identity
Endotoxin
(2R,4R,5S,6R)-2-[(2R,4R,5S,6R)-5-[(3S,4R,5R,6R)-4-[(3S,4S,5R,6R)-4-[(3R,4S,5R,6R)-4-[(2R,3R,4S,5R,6R)-3-[(3R,4S,5R,6R)-4-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2R,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxyoxan-2-yl]oxy-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-[(1S)-2-[(3S,4R,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-5-phosphonooxyoxan-2-yl]oxy-1-hydroxyethyl]-3,5-dihydroxyoxan-2-yl]oxy-5-[[2-aminoethoxy(hydroxy)phosphoryl]oxy-hydroxyphosphoryl]oxy-6-[(1S)-1,2-dihydroxyethyl]-3-hydroxyoxan-2-yl]oxy-2-carboxy-6-[(1S)-1,2-dihydroxyethyl]-2-[[(2R,3S,4R,5R,6R)-5-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-6-[[(2R,3S,4R,5R,6R)-3-hydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxy-6-phosphonooxyoxan-2-yl]methoxy]-3-phosphonooxy-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]methoxy]oxan-4-yl]oxy-4-[(2R,4R,5R,6R)-4-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-carboxy-6-[(1S)-1,2-dihydroxyethyl]-5-hydroxyoxan-2-yl]oxy-6-[(1S)-1,2-dihydroxyethyl]-5-hydroxyoxane-2-carboxylic acid
PubChem CID: 53481793
LPS with O-antigen is a polysaccharide.
2D Structure
Properties
C211H376N8O126P6
Molecular Formula
5227.00
Molecular Weight
g/mol
5226.1753
Exact Mass
Da
-14.8
XLogP
Drug-like (Lipinski: < 5)
2100
TPSA
May have limited oral absorption
68
H-Bond Donors
128
H-Bond Acceptors
11000
Complexity
SMILES
Canonical SMILES
SMILES: CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(C(OC(C1OP(=O)(O)O)COC2(CC(C(C(O2)C(CO)O)OC3C(C(C(C(O3)C(CO)O)OP(=O)(O)OP(=O)(O)OCCN)OC4C(C(C(C(O4)C(COC5C(C(C(C(O5)C(CO)O)OP(=O)(O)O)O)O)O)O)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)CO)O)OC1C(C(C(C(O1)COC1C(C(C(C(O1)CO)O)O)NC(=O)C)O)OC1C(C(C(C(O1)CO)O)OC1C(C(C(C(O1)COC1C(C(C(C(O1)CO)O)O)O)O)O)O)NC(=O)C)NC(=O)C)OC1C(C(C(C(O1)CO)O)O)NC(=O)C)O)O)O)OC1(CC(C(C(O1)C(CO)O)O)OC1(CC(C(C(O1)C(CO)O)O)OP(=O)(O)OCCN)C(=O)O)C(=O)O)C(=O)O)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)CCCCCCCCCCCIsomeric SMILES
SMILES: CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@H]([C@@H](O[C@@H]([C@H]1OP(=O)(O)O)CO[C@@]2(C[C@H]([C@@H]([C@H](O2)[C@H](CO)O)OC3[C@H]([C@H]([C@@H]([C@H](O3)[C@H](CO)O)OP(=O)(O)OP(=O)(O)OCCN)OC4[C@H]([C@H]([C@@H]([C@H](O4)[C@H](COC5[C@H]([C@H]([C@@H]([C@H](O5)[C@H](CO)O)OP(=O)(O)O)O)O)O)O)OC6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O)O)O[C@@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)OC9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)O)O)O)NC(=O)C)NC(=O)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C)O)O)O)O[C@@]1(C[C@H]([C@@H]([C@H](O1)[C@H](CO)O)O)O[C@@]1(C[C@H]([C@@H]([C@H](O1)[C@H](CO)O)O)OP(=O)(O)OCCN)C(=O)O)C(=O)O)C(=O)O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OP(=O)(O)O)NC(=O)C[C@@H](CCCCCCCCCCC)O)OC(=O)C[C@@H](CCCCCCCCCCC)O)O)NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCSynonyms(16)
EndotoxinEndotoxinsBacterial PyrogenRefChem:590839Salmonella typhi endotoxinEndotoxin, salmonella typhiSalmonella typhosa endotoxin11034-88-1DTXSID0040468Salmonella typhi lipopolysaccharide WLipopolysaccharide W, salmonella typhi881-019-9NOCAS_40468LPS with O-antigenEndotoxin LPS
Data from PubChem (NCBI)
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