E55

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

Created: 2007-08-01
Last modified:  2020-05-27

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Chemical Details

Formal Charge0
Atom Count215
Chiral Atom Count11
Bond Count216
Aromatic Bond Count0
2D diagram of E55
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Chemical Component Summary

Name3-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
SynonymsE5564; ERITORAN
Systematic Name (OpenEye OEToolkits)[(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-phosphonooxy-oxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] dihydrogen phosphate
FormulaC66 H126 N2 O19 P2
Molecular Weight1,313.656
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=P(OC1OC(C(O)C(OCCCCCCCCCC)C1NC(=O)CC(=O)CCCCCCCCCCC)COC2OC(COC)C(OP(=O)(O)O)C(OCCC(OC)CCCCCCC)C2NC(=O)CCCCCCCCC\C=C/CCCCCC)(O)O
SMILESCACTVS3.341CCCCCCCCCCCC(=O)CC(=O)N[CH]1[CH](O[CH](CO[CH]2O[CH](COC)[CH](O[P](O)(O)=O)[CH](OCC[CH](CCCCCCC)OC)[CH]2NC(=O)CCCCCCCCCC=CCCCCCC)[CH](O)[CH]1OCCCCCCCCCC)O[P](O)(O)=O
SMILESOpenEye OEToolkits1.5.0CCCCCCCCCCCC(=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
Canonical SMILESCACTVS3.341 CCCCCCCCCCCC(=O)CC(=O)N[C@H]1[C@H](O[C@H](CO[C@@H]2O[C@H](COC)[C@@H](O[P](O)(O)=O)[C@H](OCC[C@@H](CCCCCCC)OC)[C@H]2NC(=O)CCCCCCCCC\C=C/CCCCCC)[C@@H](O)[C@@H]1OCCCCCCCCCC)O[P](O)(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 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
InChIInChI1.03 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
InChIKeyInChI1.03 BPSMYQFMCXXNPC-MFCPCZTFSA-N

Drug Info: DrugBank

DrugBank IDDB04933 
NameEritoran
Groups investigational
DescriptionEritoran is a structural analogue of the lipid A portion of lipopolysaccharide (LPS). It is being developed by Eisai Research Institute of Boston for the treatment of severe sepsis.
Synonyms
  • Eritorán
  • Eritoranum
  • Éritoran
  • Eritoran
  • Eritoran tetrasodium
IndicationInvestigated for use/treatment in sepsis and septicemia.
Categories
  • Antigens
  • Antigens, Bacterial
  • Bacterial Toxins
  • Biological Factors
  • Carbohydrates
CAS number185955-34-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Toll-like receptor 4MMSASRLAGTLIPAMAFLSCVRPESWEPCVEVVPNITYQCMELNFYKIPD...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL501259
PubChem 6912404
ChEMBL CHEMBL501259
ChEBI CHEBI:68609