mifamurtide   

GtoPdb Ligand ID: 8274

Synonyms: CGP 19835 | CGP-19835 | L-MTP-PE | liposomal muramyl tripeptide phosphatidyl ethanolamine | Mepact® | MLV 19835A
mifamurtide is an approved drug (EMA (2009))
Compound class: Synthetic organic
Comment: Mifamurtide is a synthetic analogue of the bacterial cell wall component, muramyl dipeptide (MDP). MDP stimulates the immune system via activation of microbial pattern recognition receptors such as TLR4 and NOD2 [3,9].
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 25
Hydrogen bond donors 10
Rotatable bonds 59
Topological polar surface area 385.91
Molecular weight 1236.75
XLogP 9.69
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCCCCCCCCCCC(=O)OC(COP(=O)(OCCNC(=O)C(NC(=O)CCC(C(=O)N)NC(=O)C(NC(=O)C(OC1C(NC(=O)C)C(O)OC(C1O)CO)C)C)C)O)COC(=O)CCCCCCCCCCCCCCC
Isomeric SMILES CCCCCCCCCCCCCCCC(=O)OC(COP(=O)(OCCNC(=O)[C@@H](NC(=O)CC[C@H](C(=O)N)NC(=O)[C@@H](NC(=O)[C@H](O[C@@H]1[C@@H](NC(=O)C)[C@H](O)O[C@@H](C1O)CO)C)C)C)O)COC(=O)CCCCCCCCCCCCCCC
InChI InChI=1S/C59H109N6O19P/c1-7-9-11-13-15-17-19-21-23-25-27-29-31-33-50(69)79-40-46(83-51(70)34-32-30-28-26-24-22-20-18-16-14-12-10-8-2)41-81-85(77,78)80-38-37-61-56(73)42(3)62-49(68)36-35-47(55(60)72)65-57(74)43(4)63-58(75)44(5)82-54-52(64-45(6)67)59(76)84-48(39-66)53(54)71/h42-44,46-48,52-54,59,66,71,76H,7-41H2,1-6H3,(H2,60,72)(H,61,73)(H,62,68)(H,63,75)(H,64,67)(H,65,74)(H,77,78)/t42-,43-,44+,46?,47+,48+,52+,53?,54+,59+/m0/s1
InChI Key JMUHBNWAORSSBD-ZXSMYVEWSA-N
Bioactivity Comments
We have been unable to find publicly available affinity data for this drug at its proposed molecular target.
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Peptide transporter 1 8