bromocriptine   Click here for help

GtoPdb Ligand ID: 35

Synonyms: 2-bromoergocryptine | bromocryptine | CB-154 | Parlodel®
Approved drug PDB Ligand
bromocriptine is an approved drug (FDA (1978))
Compound class: Synthetic organic
Comment: Bromocriptine exhibits potent dopaminergic activity.
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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 CDK toolkit. 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 9
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 118.21
Molecular weight 653.22
XLogP 3.79
No. Lipinski's rules broken 0
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 CC(CC1C(=O)N2CCCC2C2(N1C(=O)C(O2)(NC(=O)C1CN(C)C2C(=C1)c1cccc3c1c(C2)c([nH]3)Br)C(C)C)O)C
Isomeric SMILES CC(C[C@H]1C(=O)N2CCC[C@H]2[C@]2(N1C(=O)[C@@](O2)(NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c([nH]3)Br)C(C)C)O)C
InChI InChI=1S/C32H40BrN5O5/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39)/t18-,23-,24+,25+,31-,32+/m1/s1
InChI Key OZVBMTJYIDMWIL-AYFBDAFISA-N
References
1. Boess FG, Monsma Jr FJ, Sleight AJ. (1998)
Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor.
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2. Freedman SB, Patel S, Marwood R, Emms F, Seabrook GR, Knowles MR, McAllister G. (1994)
Expression and pharmacological characterization of the human D3 dopamine receptor.
J Pharmacol Exp Ther, 268 (1): 417-26. [PMID:8301582]
3. Kohen R, Metcalf MA, Khan N, Druck T, Huebner K, Lachowicz JE, Meltzer HY, Sibley DR, Roth BL, Hamblin MW. (1996)
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.
J Neurochem, 66 (1): 47-56. [PMID:8522988]
4. Millan MJ, Maiofiss L, Cussac D, Audinot V, Boutin JA, Newman-Tancredi A. (2002)
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes.
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5. Sautel F, Griffon N, Lévesque D, Pilon C, Schwartz JC, Sokoloff P. (1995)
A functional test identifies dopamine agonists selective for D3versus D2receptors.
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6. Shen Y, Monsma Jr FJ, Metcalf MA, Jose PA, Hamblin MW, Sibley DR. (1993)
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.
J Biol Chem, 268 (24): 18200-4. [PMID:8394362]
7. Sokoloff P, Giros B, Martres MP, Bouthenet ML, Schwartz JC. (1990)
Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics.
Nature, 347 (6289): 146-51. [PMID:1975644]
8. Sunahara RK, Guan HC, O'Dowd BF, Seeman P, Laurier LG, Ng G, George SR, Torchia J, Van Tol HH, Niznik HB. (1991)
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
Nature, 350 (6319): 614-9. [PMID:1826762]