BIBP3226   Click here for help

GtoPdb Ligand ID: 1485

Synonyms: BIBP 3226
Compound class: Synthetic organic
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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
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 5
Rotatable bonds 13
Topological polar surface area 142.83
Molecular weight 473.24
XLogP 3.15
No. Lipinski's rules broken 1

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/)
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 O=C(C(NC(=O)C(c1ccccc1)c1ccccc1)CCCN=C(N)N)NCc1ccc(cc1)O
Isomeric SMILES O=C([C@H](NC(=O)C(c1ccccc1)c1ccccc1)CCCN=C(N)N)NCc1ccc(cc1)O
InChI InChI=1S/C27H31N5O3/c28-27(29)30-17-7-12-23(25(34)31-18-19-13-15-22(33)16-14-19)32-26(35)24(20-8-3-1-4-9-20)21-10-5-2-6-11-21/h1-6,8-11,13-16,23-24,33H,7,12,17-18H2,(H,31,34)(H,32,35)(H4,28,29,30)/t23-/m1/s1
InChI Key KUWBXRGRMQZCSS-HSZRJFAPSA-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. Bonini JA, Jones KA, Adham N, Forray C, Artymyshyn R, Durkin MM, Smith KE, Tamm JA, Boteju LW, Lakhlani PP et al.. (2000)
Identification and characterization of two G protein-coupled receptors for neuropeptide FF.
J Biol Chem, 275 (50): 39324-31. [PMID:11024015]
2. Doods HN, Wienen W, Entzeroth M, Rudolf K, Eberlein W, Engel W, Wieland HA. (1995)
Pharmacological characterization of the selective nonpeptide neuropeptide Y Y1 receptor antagonist BIBP 3226.
J Pharmacol Exp Ther, 275 (1): 136-42. [PMID:7562541]
3. Gehlert DR, Schober DA, Gackenheimer SL, Beavers L, Gadski R, Lundell I, Larhammar D. (1997)
[125I]Leu31, Pro34-PYY is a high affinity radioligand for rat PP1/Y4 and Y1 receptors: evidence for heterogeneity in pancreatic polypeptide receptors.
Peptides, 18 (3): 397-401. [PMID:9145427]
4. Gouardères C, Quelven I, Mollereau C, Mazarguil H, Rice SQ, Zajac JM. (2002)
Quantitative autoradiographic distribution of NPFF1 neuropeptide FF receptor in the rat brain and comparison with NPFF2 receptor by using [125I]YVP and [(125I]EYF as selective radioligands.
Neuroscience, 115 (2): 349-61. [PMID:12421602]
5. Holliday ND, Cox HM. (1996)
The functional investigation of a human adenocarcinoma cell line, stably transfected with the neuropeptide Y Y1 receptor.
Br J Pharmacol, 119 (2): 321-9. [PMID:8886416]
6. Mollereau C, Gouardères C, Dumont Y, Kotani M, Detheux M, Doods H, Parmentier M, Quirion R, Zajac JM. (2001)
Agonist and antagonist activities on human NPFF(2) receptors of the NPY ligands GR231118 and BIBP3226.
Br J Pharmacol, 133 (1): 1-4. [PMID:11325787]
7. Mollereau C, Mazarguil H, Marcus D, Quelven I, Kotani M, Lannoy V, Dumont Y, Quirion R, Detheux M, Parmentier M et al.. (2002)
Pharmacological characterization of human NPFF(1) and NPFF(2) receptors expressed in CHO cells by using NPY Y(1) receptor antagonists.
Eur J Pharmacol, 451 (3): 245-56. [PMID:12242085]
8. Wieland HA, Willim KD, Entzeroth M, Wienen W, Rudolf K, Eberlein W, Engel W, Doods HN. (1995)
Subtype selectivity and antagonistic profile of the nonpeptide Y1 receptor antagonist BIBP 3226.
J Pharmacol Exp Ther, 275 (1): 143-9. [PMID:7562543]