LDN-214117   Click here for help

GtoPdb Ligand ID: 8481

Synonyms: compound 10 [PMID: 25101911] | LDN214117
Compound class: Synthetic organic
Comment: LDN-214117 is an experimental activin A receptor, type I (ACVR1 aka BMP type I receptor kinase ALK2) inhibitor [2]. LDN-214117 may provide a structural template for the preclinical development of novel therapeutics for conditions such as fibrodysplasia ossificans progressiva (FOP), characterised by inappropriate BMP signalling, and reported to be caused by gain-of-function ALK2 mutations [1,3-5].
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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

LDN-214117 is commercially available from our sponsors

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 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 55.85
Molecular weight 419.22
XLogP 4.17
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 COc1cc(cc(c1OC)OC)c1cc(cnc1C)c1ccc(cc1)N1CCNCC1
Isomeric SMILES COc1cc(cc(c1OC)OC)c1cc(cnc1C)c1ccc(cc1)N1CCNCC1
InChI InChI=1S/C25H29N3O3/c1-17-22(19-14-23(29-2)25(31-4)24(15-19)30-3)13-20(16-27-17)18-5-7-21(8-6-18)28-11-9-26-10-12-28/h5-8,13-16,26H,9-12H2,1-4H3
InChI Key BHUXVRVMMYAXKN-UHFFFAOYSA-N
References
1. Kaplan FS, Xu M, Seemann P, Connor JM, Glaser DL, Carroll L, Delai P, Fastnacht-Urban E, Forman SJ, Gillessen-Kaesbach G et al.. (2009)
Classic and atypical fibrodysplasia ossificans progressiva (FOP) phenotypes are caused by mutations in the bone morphogenetic protein (BMP) type I receptor ACVR1.
Hum Mutat, 30 (3): 379-90. [PMID:19085907]
2. Mohedas AH, Wang Y, Sanvitale CE, Canning P, Choi S, Xing X, Bullock AN, Cuny GD, Yu PB. (2014)
Structure-activity relationship of 3,5-diaryl-2-aminopyridine ALK2 inhibitors reveals unaltered binding affinity for fibrodysplasia ossificans progressiva causing mutants.
J Med Chem, 57 (19): 7900-15. [PMID:25101911]
3. Nakahara Y, Katagiri T, Ogata N, Haga N. (2014)
ACVR1 (587T>C) mutation in a variant form of fibrodysplasia ossificans progressiva: second report.
Am J Med Genet A, 164A (1): 220-4. [PMID:24259422]
4. Pignolo RJ, Shore EM, Kaplan FS. (2011)
Fibrodysplasia ossificans progressiva: clinical and genetic aspects.
Orphanet J Rare Dis, 6: 80. [PMID:22133093]
5. Shore EM, Xu M, Feldman GJ, Fenstermacher DA, Cho TJ, Choi IH, Connor JM, Delai P, Glaser DL, LeMerrer M et al.. (2006)
A recurrent mutation in the BMP type I receptor ACVR1 causes inherited and sporadic fibrodysplasia ossificans progressiva.
Nat Genet, 38 (5): 525-7. [PMID:16642017]