Eritoran

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Also known as: 185955-34-4, Eritoran [inn], E5564, Chembl501259, Chebi:68609, 551541vi0y

Molecular Formula

C₆₆H₁₂₆N₂O₁₉P₂

Molecular Weight

1313.7 g/mol

InChI Key

BPSMYQFMCXXNPC-MFCPCZTFSA-N

FDA UNII

551541VI0Y

Eritoran is a synthetic analogue of the lipid A portion of the endotoxin lipopolysaccharide (LPS) with potential immunomodulating activity. Eritoran binds to a receptor complex composed of toll-like receptor 4 (TLR4), CD14 and MD2 (MD-2, LY96) that is present on most cells of the immune system, inhibiting the activation of the receptor complex by LPS, which may result in the inhibition of pro-inflammatory cytokine secretion and a potentially fatal systemic inflammatory response syndrome (SIRS). LPS is found in the outer membrane of Gram-negative bacteria and binds to the TLR4/CD14/MD2 receptor complex of immune cells, including macrophages, resulting in the release of pro-inflammatory cytokines.

1 2D Structure

Eritoran

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3R,4R,5S,6R)-4-decoxy-5-hydroxy-6-[[(2R,3R,4R,5S,6R)-4-[(3R)-3-methoxydecoxy]-6-(methoxymethyl)-3-[[(Z)-octadec-11-enoyl]amino]-5-phosphonooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] dihydrogen phosphate

2.1.2 InChI

InChI=1S/C66H126N2O19P2/c1-7-11-15-19-22-25-26-27-28-29-30-32-34-38-42-46-57(70)67-60-64(82-49-47-54(80-6)45-41-36-18-14-10-4)62(86-88(73,74)75)56(51-79-5)85-65(60)83-52-55-61(72)63(81-48-43-39-35-24-21-17-13-9-3)59(66(84-55)87-89(76,77)78)68-58(71)50-53(69)44-40-37-33-31-23-20-16-12-8-2/h25-26,54-56,59-66,72H,7-24,27-52H2,1-6H3,(H,67,70)(H,68,71)(H2,73,74,75)(H2,76,77,78)/b26-25-/t54-,55-,56-,59-,60-,61-,62-,63-,64-,65-,66-/m1/s1

2.1.3 InChI Key

BPSMYQFMCXXNPC-MFCPCZTFSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCC(=O)CC(=O)NC1C(C(C(OC1OP(=O)(O)O)COC2C(C(C(C(O2)COC)OP(=O)(O)O)OCCC(CCCCCCC)OC)NC(=O)CCCCCCCCCC=CCCCCCC)O)OCCCCCCCCCC

2.1.5 Isomeric SMILES

CCCCCCCCCCCC(=O)CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)O)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC)OP(=O)(O)O)OCC[C@@H](CCCCCCC)OC)NC(=O)CCCCCCCCC/C=C\CCCCCC)O)OCCCCCCCCCC

2.2 Other Identifiers

2.2.1 UNII

551541VI0Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-(3-methoxydecyl)-6-o-methyl-2-((1-oxo-11-octadecenyl)amino)-4-o-phosphonoglucopyranosyl)-2-((1,3-dioxotetradecyl)amino)-1-(dihydroxy Phosphate)glucopyranose

2.3.2 Depositor-Supplied Synonyms

1. 185955-34-4

2. Eritoran [inn]

3. E5564

4. Chembl501259

5. Chebi:68609

6. 551541vi0y

7. [(2r,3r,4r,5s,6r)-4-decoxy-5-hydroxy-6-[[(2r,3r,4r,5s,6r)-4-[(3r)-3-methoxydecoxy]-6-(methoxymethyl)-3-[[(z)-octadec-11-enoyl]amino]-5-phosphonooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] Dihydrogen Phosphate

8. 3-o-decyl-2-deoxy-6-o-[2-deoxy-3-o-[(3r)-3-methoxydecyl]-6-o-methyl-2-[[(11z)-1-oxo-11-octadecenyl]amino]-4-o-phosphono-beta-d-glucopyranosyl]-2-[(1,3-dioxotetradecyl)amino]-alpha-d-glucopyranose1-(dihydrogenphosphat

9. 3-o-decyl-2-deoxy-6-o-{2-deoxy-3-o-[(3r)-3-methoxydecyl]-6-o-methyl-2-[(11e)-octadec-11-enoylamino]-4-o-phosphonato-beta-d-glucopyranosyl}-2-[(3-oxotetradecanoyl)amino]-1-o-phosphono-alpha-d-glucopyranose

10. 3-o-decyl-2-deoxy-6-o-{2-deoxy-3-o-[(3r)-3-methoxydecyl]-6-o-methyl-2-[(11z)-octadec-11-enoylamino]-4-o-phosphono-beta-d-glucopyranosyl}-2-[(3-oxotetradecanoyl)amino]-1-o-phosphono-alpha-d-glucopyranose

11. B1287

12. Unii-551541vi0y

13. Eritoran [mi]

14. Eritoran [who-dd]

15. E5564; Eritoran

16. Gtpl4919

17. Schembl10042156

18. Dtxsid60873217

19. Ex-a5458

20. Bdbm50274760

21. Db04933

22. 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-(3-methoxydecyl)-6-o-methyl-2-((1-oxo-11-octadecenyl)amino)-4-o-phosphonoglucopyranosyl)-2-((1,3-dioxotetradecyl)amino)-1-(dihydroxy Phosphate)glucopyranose

23. Q5389586

24. .alpha.-d-glucopyranose, 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-((3r)-3-methoxydecyl)-6-o-methyl-2-(((11z)-1-oxo-11-octadecenyl)amino)-4-o-phosphono-.beta.-d-glucopyranosyl)-2-((1,3-dioxotetradecyl)amino)-, 1-(dihydrogen Phosphate)

25. [(2r,3s,4r,5r,6r)-6-[[(2r,3s,4r,5r,6r)-4-decoxy-3-hydroxy-5-(3-oxotetradecanoylamino)-6-phosphonooxyoxan-2-yl]methoxy]-4-[(3r)-3-methoxydecoxy]-2-(methoxymethyl)-5-[[(z)-octadec-11-enoyl]amino]oxan-3-yl] Dihydrogen Phosphate

26. 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-((3r)-3-methoxydecyl)-6-o-methyl-2-((11z)-octadec-11-enoylamino)-4-o-phosphono-.beta.-d-glucopyranosyl)-2-((3-oxotetradecanoyl)amino)-1-o-phosphono-.alpha.-d-glucopyranose

2.4 Create Date

2006-07-04

3 Chemical and Physical Properties

Molecular Formula	C₆₆H₁₂₆N₂O₁₉P₂
Molecular Weight	1313.7 g/mol
XLogP3	15.4
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	59
Exact Mass	1312.84300379 g/mol
Monoisotopic Mass	1312.84300379 g/mol
Topological Polar Surface Area	294 Å²
Heavy Atom Count	89
Formal Charge	0
Complexity	1900
Isotope Atom Count	0
Defined Atom Stereocenter Count	11
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1