Compound: BQ-123
SMILES: O=C1N2[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(N[C@@H](C(N[C@@H]1CC(=O)O)=O)Cc3c4c(cccc4)[nH]c3)=O)CC(C)C)C(C)C)CCC2
InChIKey: VYCMAAOURFJIHD-PJNXIOHISA-N
Synonyms: BQ-123, 136553-81-6, BQ123, Cyclo(D-trp-D-asp-pro-D-val-leu), BQ 123, cyclo(Trp-Asp-Pro-Val-Leu), S2A8YZM151, DTXSID70929476, cyclo[D-Trp-D-Asp-Pro-D-Val-Leu], 2-((3R,6R,9S,12R,15S)-6-(1H-indol-3-ylmethyl)-9-isobutyl-12-isopropyl-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentazabicyclo(13.3.0)octadecan-3-yl)acetic acid, 2-[(3R,6R,9S,12R,15S)-6-(1H-indol-3-ylmethyl)-9-isobutyl-12-isopropyl-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentazabicyclo[13.3.0]octadecan-3-yl]acetic acid, RefChem:121190, DTXCID401358224, 2-((3S,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, 2-((3R,6S,9R,12R,17aS)-9-((1H-indol-3-yl)methyl)-6-isobutyl-3-isopropyl-1,4,7,10,13-pentaoxohexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13]pentaazacyclopentadecin-12-yl)acetic acid, C31H42N6O7, Cyclo(D-alpha-aspartyl-L-prolyl-D-valyl-L-leucyl-D-tryptophyl), CHEBI:2965, CHEMBL314691, 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, cyclo(D-Asp-Pro-D-Val-Leu-D-Trp), MFCD00133204, cyclo(-D-Trp-D-Asp-Pro-D-Val-Leu), cyclo-(D-Asp-Pro-D-Val-Leu-D-Trp), cyclo-[D-Asp-Pro-d-Val-Leu-d-Trp], cyclo(D-Asp-L-Pro-D-Val-L-Leu-D-Trp), cyclo[(D)Trp-(D)Asp-Pro-(D)Val-Leu], cyclo[D-Asp-L-Pro-D-Val-L-Leu-D-Trp], UNII-S2A8YZM151, Cyclo[D-trp-D-asp-L-pro-D-val-L-leu], 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, GTPL997, orb1300461, SCHEMBL1290617, SCHEMBL29388467, EX-A4062, BDBM50197954, HB3213, s7883, AKOS030526454, cyclo-(D-Trp-D-Asp-Pro-D-Val-Leu), BQ-123?, CCG-270231, CS-5694, DB12054, BQ-123, >=99%, lyophilized powder, cyclo(-D-Trp-D-Asp-Pro-D-Val-Leu-), cyclo-(-D-Trp-D-Asp-Pro-D-Val-Leu), cyclo[-D-Asp-Pro-D-Val-Leu-D-Trp-], AC-36502, BS-15415, cyclo(L-Leu-D-Trp-D-Asp-L-Pro-D-Val), cyclo(L-Pro-D-Val-L-Leu-D-Trp-D-Asp), DA-51362, FB108394, HY-12378, cyclo(-D-Trp-D-Asp-L-Pro-D-Val-L-Leu), cyclo-(D-Trp-D-Asp-L-Pro-D-Val-L-Leu), cyclo-[D-Asp-L-Pro-D-Val-L-Leu-D-Trp-], NS00069585, BQ-123 Cyclo(-D-Trp-D-Asp-Pro-D-Val-Leu), C72461, Q4836304, Cyclo(D-a-aspartyl-L-prolyl-D-valyl-L-leucyl-D-tryptophyl), Cyclo(D-|_-aspartyl-L-prolyl-D-valyl-L-leucyl-D-tryptophyl), WDPVL (modifications: Trp-1 = D-Trp, Val-4 = D-Val, Cyclized), CYCLO(D-.ALPHA.-ASPARTYL-L-PROLYL-D-VALYL-L-LEUCYL-D-TRYPTOPHYL)
Theoretical properties:
molecular_formula: C31H42N6O7
molecular_weight: 610.7 g/mol
exact_mass: 610.31149770 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 7
heavy_atom_count: 44
topological_polar_surface_area: 190 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: BQ 123 is a cyclic peptide.
chembl: BQ-123 is a protein listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: 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).