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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2D Structure
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Physico-chemical Properties
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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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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
References
1. Anastassiadis T, Deacon SW, Devarajan K, Ma H, Peterson JR. (2011)
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
Nat. Biotechnol., 29 (11): 1039-45. [PMID:22037377]
2. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ. (2013)
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
Biochem. J., 451 (2): 313-28. [PMID:23398362]
3. Machrouhi F, Ouhamou N, Laderoute K, Calaoagan J, Bukhtiyarova M, Ehrlich PJ, Klon AE. (2010)
The rational design of a novel potent analogue of the 5'-AMP-activated protein kinase inhibitor compound C with improved selectivity and cellular activity.
Bioorg. Med. Chem. Lett., 20 (22): 6394-9. [PMID:20932747]
4. Zhou G, Myers R, Li Y, Chen Y, Shen X, Fenyk-Melody J, Wu M, Ventre J, Doebber T, Fujii N et al.. (2001)
Role of AMP-activated protein kinase in mechanism of metformin action.
J. Clin. Invest., 108 (8): 1167-74. [PMID:11602624]