ISA-2011B   Click here for help

GtoPdb Ligand ID: 8444

Compound class: Synthetic organic
Comment: Patent search with this structure reveals SCHEMBL10020974 ID matching a structure (Analogue 1) in patent WO2010149944 [3]. ISA-2011B is being evaluated pre-clinically as a potential anti-prostate cancer therapeutic [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 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 1
Rotatable bonds 1
Topological polar surface area 74.87
Molecular weight 423.1
XLogP 2.08
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 Clc1ccc2c(c1)c(c[nH]2)C1N2C(=O)CN(C(=O)C2Cc2c1cc1OCOc1c2)C
Isomeric SMILES Clc1ccc2c(c1)c(c[nH]2)[C@H]1N2C(=O)CN(C(=O)[C@@H]2Cc2c1cc1OCOc1c2)C
InChI InChI=1S/C22H18ClN3O4/c1-25-9-20(27)26-17(22(25)28)4-11-5-18-19(30-10-29-18)7-13(11)21(26)15-8-24-16-3-2-12(23)6-14(15)16/h2-3,5-8,17,21,24H,4,9-10H2,1H3/t17-,21-/m0/s1
InChI Key FSEZESVJDPKRDS-UWJYYQICSA-N
References
1. Hennessy BT, Smith DL, Ram PT, Lu Y, Mills GB. (2005)
Exploiting the PI3K/AKT pathway for cancer drug discovery.
Nat Rev Drug Discov, 4 (12): 988-1004. [PMID:16341064]
2. Loijens JC, Anderson RA. (1996)
Type I phosphatidylinositol-4-phosphate 5-kinases are distinct members of this novel lipid kinase family.
J Biol Chem, 271 (51): 32937-43. [PMID:8955136]
3. Persson J, Larsson R, Sterner O, Johansson M. (2011)
Indolyl-substituted pyrazino-quinolines and their use for the treatment of cancer.
Patent number: WO2010149944. Assignee: Oncorel Ab.. Priority date: 25/06/2009. Publication date: 24/02/2011.
4. Saito K, Tolias KF, Saci A, Koon HB, Humphries LA, Scharenberg A, Rawlings DJ, Kinet JP, Carpenter CL. (2003)
BTK regulates PtdIns-4,5-P2 synthesis: importance for calcium signaling and PI3K activity.
Immunity, 19 (5): 669-78. [PMID:14614854]
5. Semenas J, Hedblom A, Miftakhova RR, Sarwar M, Larsson R, Shcherbina L, Johansson ME, Härkönen P, Sterner O, Persson JL. (2014)
The role of PI3K/AKT-related PIP5K1α and the discovery of its selective inhibitor for treatment of advanced prostate cancer.
Proc Natl Acad Sci USA, 111 (35): E3689-98. [PMID:25071204]