bimosiamose   

GtoPdb Ligand ID: 9049

Synonyms: compound 15e [PMID: 9544210] [4] | TBC 1269 | TBC-1269 | TBC1269
Compound class: Synthetic organic
Comment: Bimosiamose is a synthetic pan-selectin antagonist [4] being investigated as a novel anti-inflammatory agent, primarily for controlling allergic respiratory diseases [7,9], but it has also been reported to provide benefit in ischemia/reperfusion injury [1-2,5-6,8]. The primary role of selectin inhibitors appears to be disruption of early events in the migration process (possibly mediated through E-selectin [3]), thereby inhibiting their eventual extravasation from blood to the inflammed tissue.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 14
Hydrogen bond donors 10
Rotatable bonds 19
Topological polar surface area 273.36
Molecular weight 862.34
XLogP 5.95
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
Canonical SMILES OCC1OC(Oc2ccc(cc2c2cccc(c2)CC(=O)O)CCCCCCc2ccc(c(c2)c2cccc(c2)CC(=O)O)OC2OC(CO)C(C(C2O)O)O)C(C(C1O)O)O
Isomeric SMILES OC[C@H]1O[C@H](Oc2ccc(cc2c2cccc(c2)CC(=O)O)CCCCCCc2ccc(c(c2)c2cccc(c2)CC(=O)O)O[C@H]2O[C@H](CO)[C@H]([C@@H]([C@@H]2O)O)O)[C@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C46H54O16/c47-23-35-39(53)41(55)43(57)45(61-35)59-33-15-13-25(19-31(33)29-11-5-9-27(17-29)21-37(49)50)7-3-1-2-4-8-26-14-16-34(60-46-44(58)42(56)40(54)36(24-48)62-46)32(20-26)30-12-6-10-28(18-30)22-38(51)52/h5-6,9-20,35-36,39-48,53-58H,1-4,7-8,21-24H2,(H,49,50)(H,51,52)/t35-,36-,39-,40-,41+,42+,43+,44+,45+,46+/m1/s1
InChI Key RYWCQJDEHXJHRI-XJMXIVSISA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-[3-[5-[6-[3-[3-(carboxymethyl)phenyl]-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]hexyl]-2-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]acetic acid
International Nonproprietary Names
INN number INN
8074 bimosiamose
Synonyms
compound 15e [PMID: 9544210] [4] | TBC 1269 | TBC-1269 | TBC1269
Database Links
BindingDB Ligand 50324667
CAS Registry No. 187269-40-5 (source: PubChem)
ChEMBL Ligand CHEMBL1215923
GtoPdb PubChem SID 315661134
PubChem CID 9811353
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