BQ-123

BQ-123^[1]

Names
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
Other names Cyclo(D-trp-D-asp-L-pro-D-val-L-leu)
Identifiers
CAS Number	136553-81-6
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL1269102
ChemSpider	25069753
IUPHAR/BPS	997 1003
PubChem	443289
UNII	S2A8YZM151
InChI InChI=1S/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)/t21-,22+,23-,24-,26+/m0/s1 Key: VYCMAAOURFJIHD-AOYLRGCGSA-N InChI=1/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)/t21-,22+,23-,24-,26+/m0/s1 Key: VYCMAAOURFJIHD-AOYLRGCGBG
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
Properties
Chemical formula	C31H42N6O7
Molar mass	610.71 g·mol^−1
Hazards
S-phrases	S22 S24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

BQ-123 is a cyclic peptide consisting of five amino acids. The amino acid sequence is D-tryptamine-D-aspartic acid-L-proline-D-valine-L-leucine.

BQ-123 is a selective ET_A endothelin receptor antagonist.^[1][2] As such, it is used as a biochemical tool in the study of endothelin receptor function.

References

1. BQ-123 at Sigma-Aldrich
2. Ishikawa, Kiyofumi; Fukami, Takehiro; Nagase, Toshio; Fujita, Kagari; Hayama, Takashi; Niiyama, Kenji; Mase, Toshiaki; Ihara, Masaki; Yano, Mitsuo (1992). "Cyclic pentapeptide endothelin antagonists with high ETA selectivity. Potency- and solubility-enhancing modifications.". Journal of Medicinal Chemistry. 35 (11): 1239–42. doi:10.1021/jm00089a028.