dorsomorphin   Click here for help

GtoPdb Ligand ID: 4907

Synonyms: AMPK Inhibitor, Compound C
PDB Ligand
Compound class: Synthetic organic
Comment: Dorsomorphin is a potent, reversible, selective AMP-activated protein kinase (AMPK) inhibitor [4]. It is an ATP-competitive inhibitor of the catalytic α subunit of the heterotrimeric enzyme.
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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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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 0
Rotatable bonds 6
Topological polar surface area 55.55
Molecular weight 399.21
XLogP 3.72
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 C1CCN(CC1)CCOc1ccc(cc1)c1cnc2n(c1)ncc2c1ccncc1
Isomeric SMILES C1CCN(CC1)CCOc1ccc(cc1)c1cnc2n(c1)ncc2c1ccncc1
InChI InChI=1S/C24H25N5O/c1-2-12-28(13-3-1)14-15-30-22-6-4-19(5-7-22)21-16-26-24-23(17-27-29(24)18-21)20-8-10-25-11-9-20/h4-11,16-18H,1-3,12-15H2
InChI Key XHBVYDAKJHETMP-UHFFFAOYSA-N
Bioactivity Comments
Dorsomorphin also has inhibitory activity at other kinases as detailed in the Bioactivity table below. Note that some bioactivity data may be associated with dorsomorphin dihydrochloride (PubChem CID 49761481).
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
SRC proto-oncogene, non-receptor tyrosine kinase Hs Inhibitor Inhibition 8.7 pIC50 - 3
⤷ pIC50 8.7 (IC50 2x10-9 M) [3]
Description: Assayed using AMPK heterotrimeric complex containing α2, β1, γ1 subunits
MAPK interacting serine/threonine kinase 1 Hs Inhibitor Inhibition 8.0 pIC50 - 3
⤷ pIC50 8.0 (IC50 1.1x10-8 M) [3]
Description: Assayed using AMPK heterotrimeric complex containing α2, β1, γ1 subunits
LCK proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 7.8 pIC50 - 3
⤷ pIC50 7.8 (IC50 1.6x10-8 M) [3]
Description: Assayed using AMPK heterotrimeric complex containing α2, β1, γ1 subunits
AMP kinase Primary target of this compound Hs Inhibitor Inhibition 7.4 pIC50 - 3
⤷ pIC50 7.4 (IC50 4.1x10-8 M) [3]
Description: Assayed using AMPK heterotrimeric complex containing α2, β1, γ1 subunits
ribosomal protein S6 kinase A1 Hs Inhibitor Inhibition 6.7 pIC50 - 3
⤷ pIC50 6.7 (IC50 2.1x10-7 M) [3]
Description: Assayed using AMPK heterotrimeric complex containing α2, β1, γ1 subunits
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
fms related receptor tyrosine kinase 3 Hs Inhibitor Inhibition >9.0 pIC50 - 3
⤷ pIC50 >9.0 (IC50 <1x10-9 M) [3]
Description: Assayed using AMPK heterotrimeric complex containing α2, β1, γ1 subunits
kinase insert domain receptor Hs Inhibitor Inhibition 8.4 pIC50 - 3
⤷ pIC50 8.4 (IC50 4x10-9 M) [3]
Description: Assayed using AMPK heterotrimeric complex containing α2, β1, γ1 subunits
fms related receptor tyrosine kinase 1 Hs Inhibitor Inhibition 8.0 pIC50 - 3
⤷ pIC50 8.0 (IC50 1.1x10-8 M) [3]
Description: Assayed using AMPK heterotrimeric complex containing α2, β1, γ1 subunits
EPH receptor A2 Hs Inhibitor Inhibition 8.0 pIC50 - 3
⤷ pIC50 8.0 (IC50 1.1x10-8 M) [3]
Description: Assayed using AMPK heterotrimeric complex containing α2, β1, γ1 subunits
Ligand mentioned in the following text fields
Receptor serine/threonine kinase (RSTK) family comments