bilorphin   Click here for help

GtoPdb Ligand ID: 10518

Synonyms: peptide 3c [PMID: 31611414]
Compound class: Synthetic organic
Comment: Bilorphin is a derivative of a naturally ocurring tetrapeptide that was isolated from an Australian estuarine isolate of Penicillium species MST-MF667 [1]. It acts as a G protein signalling biased agonist of the μ-opioid receptor in vitro. Bilorphin promotes minimal β-arrestin recruitment and receptor internalization. Systemic and oral activity was achieved by glycosylating the C-terminal residue of bilorphin to create bilactorphin. The in vivo analgesic potency of bilactorphin is similar to that of morphine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 16
Topological polar surface area 176.64
Molecular weight 553.33
XLogP 2.38
No. Lipinski's rules broken 2
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Canonical SMILES Oc1cc(C)c(c(c1)C)CC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)Cc1ccccc1)C(C)C)C(C)C)N
Isomeric SMILES Oc1cc(C)c(c(c1)C)C[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N)Cc1ccccc1)C(C)C)C(C)C)N
InChI InChI=1S/C30H43N5O5/c1-16(2)25(29(39)33-24(27(32)37)14-20-10-8-7-9-11-20)35-30(40)26(17(3)4)34-28(38)23(31)15-22-18(5)12-21(36)13-19(22)6/h7-13,16-17,23-26,36H,14-15,31H2,1-6H3,(H2,32,37)(H,33,39)(H,34,38)(H,35,40)/t23-,24-,25-,26+/m1/s1
1. Dekan Z, Sianati S, Yousuf A, Sutcliffe KJ, Gillis A, Mallet C, Singh P, Jin AH, Wang AM, Mohammadi SA et al.. (2019)
A tetrapeptide class of biased analgesics from an Australian fungus targets the µ-opioid receptor.
Proc Natl Acad Sci USA, 116 (44): 22353-22358. [PMID:31611414]