yohimbine   Click here for help

GtoPdb Ligand ID: 102

Synonyms: Actibine® | corynine | quebrachin | yohimbin
Approved drug
yohimbine is an approved drug (FDA (no date available))
Compound class: Natural product or derivative
Comment: Yohimbine exerts actions on many receptors of the dopamine, serotonin and adrenergic families, with highest activity as an antagonist of α2-adrenoceptors.
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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 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 65.56
Molecular weight 354.19
XLogP 2.72
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 COC(=O)C1C(O)CCC2C1CC1N(C2)CCc2c1[nH]c1c2cccc1
Isomeric SMILES COC(=O)[C@H]1[C@@H](O)CC[C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1
InChI InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
InChI Key BLGXFZZNTVWLAY-SCYLSFHTSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (no date available))
IUPAC Name Click here for help
methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
Synonyms Click here for help
Actibine® | corynine | quebrachin | yohimbin
Database Links Click here for help
Specialist databases
GPCRdb Ligand yohimbine
Other databases
BitterDB Ligand 70
CAS Registry No. 146-48-5 (source: Scifinder)
ChEBI CHEBI:10093
ChEMBL Ligand CHEMBL15245
DrugBank Ligand DB01392
DrugCentral Ligand 3659
GtoPdb PubChem SID 135652727
PubChem CID 8969
Search Google for chemical match using the InChIKey BLGXFZZNTVWLAY-SCYLSFHTSA-N
Search Google for chemicals with the same backbone BLGXFZZNTVWLAY
UniChem Compound Search for chemical match using the InChIKey BLGXFZZNTVWLAY-SCYLSFHTSA-N
UniChem Connectivity Search for chemical match using the InChIKey BLGXFZZNTVWLAY-SCYLSFHTSA-N
Wikipedia Yohimbine