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Structure via PubChem · Public domain (PubChem)
BQ-123
Sign in to saveAlso known as BQ 123, Cyclo[D-trp-D-asp-L-pro-D-val-L-leu], BQ123
BQ-123, also known as cyclo(-D-Trp-D-Asp-Pro-D-Val-Leu-), is a cyclic pentapeptide that was first isolated from a fermentation broth of Streptomyces misakiensis in 1991. NMR studies indicate that the polypeptide backbone consists of a type II beta turn and an inverse gamma turn. The side-chains adopt different orientations depending on the solvent used. The proline carbonyl oxygen atom located at the onset of a beta turn is a sodium ion binding site. It has a high affinity for sodium ions and can coordinate up to three of them. Studies have shown that BQ123 is effective in reversing Ischemia-i
Chemical data
- Formula
- C31H42N6O7
- Molecular weight
- 610.7 g/mol
- IUPAC name
- 2-[(3R,6R,9S,12R,15S)-6-(1H-indol-3-ylmethyl)-9-(2-methylpropyl)-2,5,8,11,14-pentaoxo-12-propan-2-yl-1,4,7,10,13-pentazabicyclo[13.3.0]octadecan-3-yl]acetic acid
- SMILES
- CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(=O)N1)C(C)C)CC(=O)O)CC3=CNC4=CC=CC=C43
- InChIKey
- VYCMAAOURFJIHD-PJNXIOHISA-N
- XLogP
- 2.2
- Polar surface area
- 190 Ų
- H-bond donors
- 6
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Protein
- Indications
- cardiovascular disease, heart failure, ST Elevation Myocardial Infarction, pulmonary hypertension
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 610.311498
Show 4 more facts
- chemical formula
- C₃₁H₄₂N₆O₇
- canonical SMILES
- CC(C)CC1C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)N1)C(C)C)CC(=O)O)CC3=CNC4=CC=CC=C43
- isomeric SMILES
- CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(=O)N1)C(C)C)CC(=O)O)CC3=CNC4=CC=CC=C43
- subject has role
- Endothelin receptor antagonist
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
BQ-123, also known as cyclo(-D-Trp-D-Asp-Pro-D-Val-Leu-), is a cyclic pentapeptide that was first isolated from a fermentation broth of Streptomyces misakiensis in 1991. NMR studies indicate that the polypeptide backbone consists of a type II beta turn and an inverse gamma turn. The side-chains adopt different orientations depending on the solvent used. The proline carbonyl oxygen atom located at the onset of a beta turn is a sodium ion binding site. It has a high affinity for sodium ions and can coordinate up to three of them. Studies have shown that BQ123 is effective in reversing Ischemia-induced acute renal failure, and it has been suggested that this might be because BQ123 increases reabsorption of sodium ions in the proximal tubule cells.
BQ-123 is a selective ETA endothelin receptor antagonist. As such, it is used as a biochemical tool in the study of endothelin receptor function. BQ-123 works as an ET-1 antagonist by reversing already established contractions to ET-1. This indicates that BQ-123 can work as an antagonist to remove ET-1 from its receptor (ETA).
Excerpted from Wikipedia’s “BQ-123” article, available under the CC BY-SA 4.0 licence.