SRT2104   Click here for help

GtoPdb Ligand ID: 9515

Synonyms: compound 4 [Ng et al., 2013] [5] | GSK2245840 | SRT-2104
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: SRT2104 (GSK2245840) is an investigational, selective and orally available SIRT1 activator [4-5].
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 7
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 141.13
Molecular weight 516.14
XLogP 2.65
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C(c1sc(nc1C)c1cccnc1)Nc1ccccc1c1cn2c(n1)scc2CN1CCOCC1
Isomeric SMILES O=C(c1sc(nc1C)c1cccnc1)Nc1ccccc1c1cn2c(n1)scc2CN1CCOCC1
InChI InChI=1S/C26H24N6O2S2/c1-17-23(36-25(28-17)18-5-4-8-27-13-18)24(33)29-21-7-3-2-6-20(21)22-15-32-19(16-35-26(32)30-22)14-31-9-11-34-12-10-31/h2-8,13,15-16H,9-12,14H2,1H3,(H,29,33)
InChI Key LAMQVIQMVKWXOC-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Baksi A, Kraydashenko O, Zalevkaya A, Stets R, Elliott P, Haddad J, Hoffmann E, Vlasuk GP, Jacobson EW. (2014)
A phase II, randomized, placebo-controlled, double-blind, multi-dose study of SRT2104, a SIRT1 activator, in subjects with type 2 diabetes.
Br J Clin Pharmacol, 78 (1): 69-77. [PMID:24446723]
2. Jiang M, Zheng J, Peng Q, Hou Z, Zhang J, Mori S, Ellis JL, Vlasuk GP, Fries H, Suri V et al.. (2014)
Sirtuin 1 activator SRT2104 protects Huntington's disease mice.
Ann Clin Transl Neurol, 1 (12): 1047-52. [PMID:25574479]
3. Krueger JG, Suárez-Fariñas M, Cueto I, Khacherian A, Matheson R, Parish LC, Leonardi C, Shortino D, Gupta A, Haddad J et al.. (2015)
A Randomized, Placebo-Controlled Study of SRT2104, a SIRT1 Activator, in Patients with Moderate to Severe Psoriasis.
PLoS ONE, 10 (11): e0142081. [PMID:26556603]
4. Mercken EM, Mitchell SJ, Martin-Montalvo A, Minor RK, Almeida M, Gomes AP, Scheibye-Knudsen M, Palacios HH, Licata JJ, Zhang Y et al.. (2014)
SRT2104 extends survival of male mice on a standard diet and preserves bone and muscle mass.
Aging Cell, 13 (5): 787-96. [PMID:24931715]
5. Ng PY, Bemis JE, Disch JS, Vu CB, Oalmann CJ, Lynch AV, Carney DP, Riera TV, Song J, Smith JJ et al.. (2013)
The Identification of the SIRT1 Activator SRT2104 as a Clinical Candidate.
Lett Drug Des Discov, 10: 793-797.
6. Sands BE, Joshi S, Haddad J, Freudenberg JM, Oommen DE, Hoffmann E, McCallum SW, Jacobson E. (2016)
Assessing Colonic Exposure, Safety, and Clinical Activity of SRT2104, a Novel Oral SIRT1 Activator, in Patients with Mild to Moderate Ulcerative Colitis.
Inflamm Bowel Dis, 22 (3): 607-14. [PMID:26595549]