livoletide   Click here for help

GtoPdb Ligand ID: 10884

Synonyms: AZP-531 | AZP531 | Cyclo(des-acyl ghrelin(6-13)) | Des-acyl ghrelin
Compound class: Peptide
Comment: Livoletide (AZP-531) is a first-in-class analogue of unacylated ghrelin (UAG) [2]. The exact mechanism of action is still unclear. When UAG is co-administered with ghrelin it is reported to act either as a functional antagonist or is acting via another receptor [2,4]. Other studies suggest that UAG is a full agonist [3].

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC[C@@H]1NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C1=O)CCC2)CCC(=O)O)Cc1cnc[nH]1)CCC(=O)N)C(C)C
Isomeric SMILES OC[C@@H]1NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C1=O)CCC2)CCC(=O)O)Cc1cnc[nH]1)CCC(=O)N)C(C)C
InChI InChI=1S/C40H63N15O13/c1-19(2)31-38(67)51-23(8-11-29(42)58)34(63)53-26(17-56)39(68)55-14-4-6-27(55)37(66)50-24(9-12-30(59)60)33(62)52-25(15-20-16-45-18-47-20)36(65)49-22(7-10-28(41)57)32(61)48-21(35(64)54-31)5-3-13-46-40(43)44/h16,18-19,21-27,31,56H,3-15,17H2,1-2H3,(H2,41,57)(H2,42,58)(H,45,47)(H,48,61)(H,49,65)(H,50,66)(H,51,67)(H,52,62)(H,53,63)(H,54,64)(H,59,60)(H4,43,44,46)/t21-,22-,23-,24-,25-,26-,27-,31-/m0/s1
InChI Key JXPWLIYXIWGWSA-CLBRJLNISA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Allas S, Caixàs A, Poitou C, Coupaye M, Thuilleaux D, Lorenzini F, Diene G, Crinò A, Illouz F, Grugni G et al.. (2018)
AZP-531, an unacylated ghrelin analog, improves food-related behavior in patients with Prader-Willi syndrome: A randomized placebo-controlled trial.
PLoS ONE, 13 (1): e0190849. [PMID:29320575]
2. Delhanty PJ, Neggers SJ, van der Lely AJ. (2013)
Des-acyl ghrelin: a metabolically active peptide.
Endocr Dev, 25: 112-21. [PMID:23652397]
3. Gauna C, van de Zande B, van Kerkwijk A, Themmen AP, van der Lely AJ, Delhanty PJ. (2007)
Unacylated ghrelin is not a functional antagonist but a full agonist of the type 1a growth hormone secretagogue receptor (GHS-R).
Mol Cell Endocrinol, 274 (1-2): 30-4. [PMID:17601657]
4. Granata R, Settanni F, Julien M, Nano R, Togliatto G, Trombetta A, Gallo D, Piemonti L, Brizzi MF, Abribat T et al.. (2012)
Des-acyl ghrelin fragments and analogues promote survival of pancreatic β-cells and human pancreatic islets and prevent diabetes in streptozotocin-treated rats.
J Med Chem, 55 (6): 2585-96. [PMID:22352743]