bombesin   Click here for help

GtoPdb Ligand ID: 616

Comment: Originally isolated from the skin of Bombina orientalis (oriental fire-bellied toad). As with many natural peptide ligands, there is some ambiguity in the literature and on other resources as to the exact stereochemistry of bombesin. The structure shown here matches those in the PubChem and ChEMBL entries that can be accessed via the Database Links table.
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2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES CSCCC(C(=O)N)NC(=O)C(NC(=O)C(Cc1nc[nH]c1)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C1CCC(=O)N1)CCC(=O)N)CCCNC(=N)N)CC(C)C)CC(=O)N)CCC(=O)N)C)CC(C)C
Isomeric SMILES CSCC[C@@H](C(=O)N)NC(=O)[C@@H](NC(=O)[C@H](Cc1nc[nH]c1)NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCC(=O)N1)CCC(=O)N)CCCNC(=N)N)CC(C)C)CC(=O)N)CCC(=O)N)C)CC(C)C
InChI InChI=1S/C71H110N24O18S/c1-34(2)24-47(92-62(105)43(14-11-22-79-71(76)77)89-64(107)45(15-18-52(72)96)90-63(106)44-17-20-55(99)85-44)61(104)81-31-56(100)87-51(28-54(74)98)69(112)91-46(16-19-53(73)97)65(108)94-49(26-38-29-80-41-13-10-9-12-40(38)41)66(109)84-37(7)60(103)95-58(36(5)6)70(113)82-32-57(101)86-50(27-39-30-78-33-83-39)68(111)93-48(25-35(3)4)67(110)88-42(59(75)102)21-23-114-8/h9-10,12-13,29-30,33-37,42-51,58,80H,11,14-28,31-32H2,1-8H3,(H2,72,96)(H2,73,97)(H2,74,98)(H2,75,102)(H,78,83)(H,81,104)(H,82,113)(H,84,109)(H,85,99)(H,86,101)(H,87,100)(H,88,110)(H,89,107)(H,90,106)(H,91,112)(H,92,105)(H,93,111)(H,94,108)(H,95,103)(H4,76,77,79)/t37-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,58-/m0/s1
InChI Key QXZBMSIDSOZZHK-DOPDSADYSA-N
References
1. Benya RV, Kusui T, Pradhan TK, Battey JF, Jensen RT. (1995)
Expression and characterization of cloned human bombesin receptors.
Mol Pharmacol, 47 (1): 10-20. [PMID:7838118]
2. Ryan RR, Katsuno T, Mantey SA, Pradhan TK, Weber HC, Coy DH, Battey JF, Jensen RT. (1999)
Comparative pharmacology of the nonpeptide neuromedin B receptor antagonist PD 168368.
J Pharmacol Exp Ther, 290 (3): 1202-11. [PMID:10454496]
3. Uehara H, Gonz├ílez N, Sancho V, Mantey SA, Nuche-Berenguer B, Pradhan T, Coy DH, Jensen RT. (2011)
Pharmacology and selectivity of various natural and synthetic bombesin related peptide agonists for human and rat bombesin receptors differs.
Peptides, 32 (8): 1685-99. [PMID:21729729]