bombesin

Bombesin is a 14-amino acid peptide originally isolated from the skin of the European fire-bellied toad (Bombina bombina)

Chemical data

Formula: C71H110N24O18S
Molecular weight: 1619.9 g/mol
IUPAC name: N-[1-[[1-[[2-[[4-amino-1-[[5-amino-1-[[1-[[1-[[1-[[2-[[1-[[1-[(1-amino-4-methylsulfanyl-1-oxobutan-2-yl)amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]-2-[(5-oxopyrrolidine-2-carbonyl)amino]pentanediamide
SMILES: CC(C)CC(C(=O)NCC(=O)NC(CC(=O)N)C(=O)NC(CCC(=O)N)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(C)C(=O)NC(C(C)C)C(=O)NCC(=O)NC(CC3=CNC=N3)C(=O)NC(CC(C)C)C(=O)NC(CCSC)C(=O)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)N)NC(=O)C4CCC(=O)N4
InChIKey: QXZBMSIDSOZZHK-UHFFFAOYSA-N
XLogP: -4.4
Polar surface area: 711 Å²
H-bond donors: 23
H-bond acceptors: 21
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 1
Molecule type: Protein

via ChEMBL · EBI

Research

5,610 papers

Bombesin-like peptides and their receptors: recent findings in pharmacology and physiology.Current opinion in endocrinology, diabetes, and obesity · 2015
Bombesin receptor antagonists.Critical reviews in oncology/hematology · 1996
Bombesin and its family of peptides: prospects for the treatment of obesity.European journal of pharmacology · 2002
Bombesin-like peptides and cancer.Critical reviews in oncology/hematology · 1996
Bombesin and the brain-gut axis.Peptides · 2000

via PubMed

Wikidata facts

Mass: 1618.8150636799987

Show 4 more facts

isomeric SMILES: C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N)NC(=O)[C@H](Cc2cc3ccccc3[nH]2)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]4CCC(=O)N4
chemical formula: C₇₁H₁₁₀N₂₄O₁₈S
subject has role: neurotransmitter
canonical SMILES: CSCCC(NC(=O)C(CC(C)C)NC(=O)C(Cc1cnc[nH]1)NC(=O)CNC(=O)C(NC(=O)C(C)NC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(N)=O)NC(=O)C1CCC(=O)N1)C(C)C)C(N)=O

Sources (2)

via Wikidata · CC0

~1 min read

Encyclopedic overview

4 sections

Contents

Receptors
Effects
See also
References

Bombesin is a 14-amino acid peptide originally isolated from the skin of the European fire-bellied toad (Bombina bombina) by Vittorio Erspamer et al. and named after its source. It has two known homologs in mammals called neuromedin B and gastrin-releasing peptide. It stimulates gastrin release from G cells. It activates three different G-protein-coupled receptors known as BBR1, -2, and -3. It also activates these receptors in the brain. Together with cholecystokinin, it is the second major source of negative feedback signals that stop eating behaviour.

Bombesin is also a tumor marker for small cell carcinoma of lung, gastric cancer, pancreatic cancer, and neuroblastoma.

Excerpted from Wikipedia’s “bombesin” article, available under the CC BY-SA 4.0 licence.

Available in 16 languages

via Wikidata sitelinks · CC0