[Sar,D-Phe8,des-Arg9]bradykinin   Click here for help

GtoPdb Ligand ID: 643

Synonyms: [N-methylglycine,D-Phe8,des-Arg9]bradykinin | [sarcosine,D-Phe8,des-Arg9]bradykinin | Sar[DPhe8][des-Arg9]BK
Comment: This is a metabolocally stabilised analogue of bradykinin (BK) [2]. It ellicits a hypotensive effect in LPS-treated rabbits [1].
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2D Structure
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Canonical SMILES CNCC(=O)NC(C(=O)N1CCCC1C(=O)N1CCCC1C(=O)NCC(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)O)Cc1ccccc1)CO)Cc1ccccc1)CCCN=C(N)N
Isomeric SMILES CNCC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(=O)O)Cc1ccccc1)CO)Cc1ccccc1)CCCN=C(N)N
InChI InChI=1S/C47H66N12O11/c1-50-26-38(61)53-31(16-8-20-51-47(48)49)43(66)59-23-11-19-37(59)45(68)58-22-9-17-35(58)41(64)52-27-39(62)54-32(24-29-12-4-2-5-13-29)40(63)56-34(28-60)44(67)57-21-10-18-36(57)42(65)55-33(46(69)70)25-30-14-6-3-7-15-30/h2-7,12-15,31-37,50,60H,8-11,16-28H2,1H3,(H,52,64)(H,53,61)(H,54,62)(H,55,65)(H,56,63)(H,69,70)(H4,48,49,51)/t31-,32-,33+,34-,35-,36-,37-/m0/s1
1. Audet R, Rioux F, Drapeau G, Marceau F. (1997)
Cardiovascular effects of Sar-[D-Phe8]des-Arg9-bradykinin, a metabolically protected agonist of B1 receptor for kinins, in the anesthetized rabbit pretreated with a sublethal dose of bacterial lipopolysaccharide.
J Pharmacol Exp Ther, 280 (1): 6-15. [PMID:8996175]
2. Drapeau G, deBlois D, Marceau F. (1991)
Hypotensive effects of Lys-des-Arg9-bradykinin and metabolically protected agonists of B1 receptors for kinins.
J Pharmacol Exp Ther, 259 (3): 997-1003. [PMID:1662280]
3. Jones C, Phillips E, Davis C, Arbuckle J, Yaqoob M, Burgess GM, Docherty RJ, Webb M, Bevan SJ, McIntyre P. (1999)
Molecular characterisation of cloned bradykinin B1 receptors from rat and human.
Eur J Pharmacol, 374: 423-433. [PMID:10422787]