octreotide   Click here for help

GtoPdb Ligand ID: 2055

Synonyms: DRG-0115 | Mycapssa® | Sandostatin® | SMS 201,995
Approved drug
octreotide is an approved drug (FDA (1988), EMA (2022))
Compound class: Peptide
Comment: Octreotide is a somatostatin mimetic.
As with many peptide molecules there is ambiguity around representations of the stereochemistry of octreotide. The chemical structure shown here does not specifiy stereochemistry and so may differ from representations on other chemical information resources in the Database Links table.
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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
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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Click here for structure editor
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 NCCCCC1NC(=O)C(NC(=O)C(Cc2ccccc2)NC(=O)C(CSSCC(NC(=O)C(NC1=O)C(O)C)C(=O)NC(C(O)C)CO)NC(=O)C(Cc1ccccc1)N)Cc1c[nH]c2c1cccc2
Isomeric SMILES NCCCCC1NC(=O)C(NC(=O)C(Cc2ccccc2)NC(=O)C(CSSCC(NC(=O)C(NC1=O)C(O)C)C(=O)NC(C(O)C)CO)NC(=O)C(Cc1ccccc1)N)Cc1c[nH]c2c1cccc2
InChI InChI=1S/C49H66N10O10S2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64)
InChI Key DEQANNDTNATYII-UHFFFAOYSA-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. Bruns C, Raulf F, Hoyer D, Schloos J, Lübbert H, Weckbecker G. (1996)
Binding properties of somatostatin receptor subtypes.
Metab Clin Exp, 45 (8 Suppl 1): 17-20. [PMID:8769372]
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. Feuerbach D, Fehlmann D, Nunn C, Siehler S, Langenegger D, Bouhelal R, Seuwen K, Hoyer D. (2000)
Cloning, expression and pharmacological characterisation of the mouse somatostatin sst(5) receptor.
Neuropharmacology, 39 (8): 1451-62. [PMID:10818261]
4. Meyerhof W. (1998)
The elucidation of somatostatin receptor functions: a current view.
Rev Physiol Biochem Pharmacol, 133: 55-108. [PMID:9600011]
5. Patel YC, Srikant CB. (1994)
Subtype selectivity of peptide analogs for all five cloned human somatostatin receptors (hsstr 1-5).
Endocrinology, 135 (6): 2814-7. [PMID:7988476]
6. 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]
7. 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]
8. 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]
9. 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]
10. 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]