SRIF-14   Click here for help

GtoPdb Ligand ID: 2019

Synonyms: somatostatin-14 | SS14 | SST-14
Compound class: Endogenous peptide in human, mouse or rat
Species: Human, Mouse, Rat
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: srif-14

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.

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Canonical SMILES NCCCCC1NC(=O)C(CSSCC(NC(=O)C(CO)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CC(=O)N)Cc1ccccc1)Cc1ccccc1)Cc1c[nH]c2c1cccc2)CCCCN)C(O)C)C(=O)O)NC(=O)CNC(=O)C(N)C
Isomeric SMILES NCCCC[C@H]1NC(=O)[C@@H](CSSC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CC(=O)N)Cc1ccccc1)Cc1ccccc1)Cc1c[nH]c2c1cccc2)CCCCN)[C@H](O)C)C(=O)O)NC(=O)CNC(=O)[C@@H](N)C
InChI InChI=1S/C63H88N16O16S2/c1-34(66)53(84)69-30-51(83)70-48-32-96-97-33-49(63(94)95)78-60(91)47(31-80)77-62(93)52(35(2)81)79-55(86)42(22-12-14-24-65)71-58(89)45(27-38-29-68-40-20-10-9-19-39(38)40)75-57(88)44(26-37-17-7-4-8-18-37)73-56(87)43(25-36-15-5-3-6-16-36)74-59(90)46(28-50(67)82)76-54(85)41(72-61(48)92)21-11-13-23-64/h3-10,15-20,29,34-35,41-49,52,68,80-81H,11-14,21-28,30-33,64-66H2,1-2H3,(H2,67,82)(H,69,84)(H,70,83)(H,71,89)(H,72,92)(H,73,87)(H,74,90)(H,75,88)(H,76,85)(H,77,93)(H,78,91)(H,79,86)(H,94,95)/t34-,35+,41+,42-,43+,44-,45+,46-,47-,48+,49-,52+/m0/s1
InChI Key VVEJUSYNERNRME-XGFVQVCISA-N
References
1. Bruns C, Raulf F, Hoyer D, Schloos J, Lübbert H, Weckbecker G. (1996)
Binding properties of somatostatin receptor subtypes.
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2. Corness JD, Demchyshyn LL, Seeman P, Van Tol HH, Srikant CB, Kent G, Patel YC, Niznik HB. (1993)
A human somatostatin receptor (SSTR3), located on chromosome 22, displays preferential affinity for somatostatin-14 like peptides.
FEBS Lett, 321 (2-3): 279-84. [PMID:8097479]
3. Engström M, Tomperi J, El-Darwish K, Ahman M, Savola JM, Wurster S. (2005)
Superagonism at the human somatostatin receptor subtype 4.
J Pharmacol Exp Ther, 312 (1): 332-8. [PMID:15333679]
4. Feuerbach D, Fehlmann D, Nunn C, Siehler S, Langenegger D, Bouhelal R, Seuwen K, Hoyer D. (2000)
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5. Liu Q, Cescato R, Dewi DA, Rivier J, Reubi JC, Schonbrunn A. (2005)
Receptor signaling and endocytosis are differentially regulated by somatostatin analogs.
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6. Meyerhof W. (1998)
The elucidation of somatostatin receptor functions: a current view.
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7. Patel YC, Srikant CB. (1994)
Subtype selectivity of peptide analogs for all five cloned human somatostatin receptors (hsstr 1-5).
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8. Poitout L, Roubert P, Contour-Galcéra MO, Moinet C, Lannoy J, Pommier J, Plas P, Bigg D, Thurieau C. (2001)
Identification of potent non-peptide somatostatin antagonists with sst(3) selectivity.
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9. Raynor K, Murphy WA, Coy DH, Taylor JE, Moreau JP, Yasuda K, Bell GI, Reisine T. (1993)
Cloned somatostatin receptors: identification of subtype-selective peptides and demonstration of high affinity binding of linear peptides.
Mol Pharmacol, 43 (6): 838-44. [PMID:8100350]
10. Rohrer SP, Birzin ET, Mosley RT, Berk SC, Hutchins SM, Shen DM, Xiong Y, Hayes EC, Parmar RM, Foor F et al.. (1998)
Rapid identification of subtype-selective agonists of the somatostatin receptor through combinatorial chemistry.
Science, 282 (5389): 737-40. [PMID:9784130]
11. Siehler S, Seuwen K, Hoyer D. (1998)
[125I]Tyr10-cortistatin14 labels all five somatostatin receptors.
Naunyn Schmiedebergs Arch Pharmacol, 357 (5): 483-9. [PMID:9650799]
12. Siehler S, Seuwen K, Hoyer D. (1998)
[125I][Tyr3]octreotide labels human somatostatin sst2 and sst5 receptors.
Eur J Pharmacol, 348 (2-3): 311-20. [PMID:9652348]
13. Siehler S, Seuwen K, Hoyer D. (1999)
Characterisation of human recombinant somatostatin receptors. 1. Radioligand binding studies.
Naunyn Schmiedebergs Arch Pharmacol, 360 (5): 488-99. [PMID:10598788]
14. Viollet C, Bodenant C, Prunotto C, Roosterman D, Schaefer J, Meyerhof W, Epelbaum J, Vaudry H, Leroux P. (1997)
Differential expression of multiple somatostatin receptors in the rat cerebellum during development.
J Neurochem, 68 (6): 2263-72. [PMID:9166718]
15. Yang L, Berk SC, Rohrer SP, Mosley RT, Guo L, Underwood DJ, Arison BH, Birzin ET, Hayes EC, Mitra SW et al.. (1998)
Synthesis and biological activities of potent peptidomimetics selective for somatostatin receptor subtype 2.
Proc Natl Acad Sci USA, 95 (18): 10836-41. [PMID:9724791]