rosiptor   Click here for help

GtoPdb Ligand ID: 9249

Synonyms: AQX-1125 | AQX1125
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Rosiptor (AQX-1125) is an investigational allosteric activator of the SH2 domain-containing inositol 5'-phosphatase 1, SHIP1 (HGNC gene symbol INPP5D) [3]. SHIP1 is a negative regulatory phosphatase in the PI3K pathway, a signalling pathway that plays a central role in cellular activation, proliferation, and survival, and which is strongly implicated in inflammatory disorders and cancer. Agonists that activate SHIP1 are being actively developed (as alternatives to direct PI3K inhibitors) for their potential anti-inflammatory action. AQX-1125 is claimed in patent WO2014158654, where it appears to be referred to as compound 9 (without the acetate) [1].
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 3
Rotatable bonds 3
Topological polar surface area 66.48
Molecular weight 321.27
XLogP 3.55
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 NCC1C(CCC2(C1CCC2=C)C)C1(C)CCC(CC1CO)O
Isomeric SMILES NC[C@@H]1[C@H](CC[C@]2([C@H]1CCC2=C)C)[C@@]1(C)CC[C@@H](C[C@@H]1CO)O
InChI InChI=1S/C20H35NO2/c1-13-4-5-17-16(11-21)18(7-9-19(13,17)2)20(3)8-6-15(23)10-14(20)12-22/h14-18,22-23H,1,4-12,21H2,2-3H3/t14-,15+,16+,17+,18+,19-,20+/m1/s1
InChI Key MDEJTPWQNNMAQF-BVMLLJBZSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(1S,3S,4R)-4-[(3aS,4R,5S,7aS)-4-(aminomethyl)-7a-methyl-1-methylidene-3,3a,4,5,6,7-hexahydro-2H-inden-5-yl]-3-(hydroxymethyl)-4-methylcyclohexan-1-ol
International Nonproprietary Names Click here for help
INN number INN
10126 rosiptor
Synonyms Click here for help
AQX-1125 | AQX1125
Database Links Click here for help
CAS Registry No. 782487-28-9 (source: WHO INN record)
GtoPdb PubChem SID 315661324
PubChem CID 76965484
Search Google for chemical match using the InChIKey MDEJTPWQNNMAQF-BVMLLJBZSA-N
Search Google for chemicals with the same backbone MDEJTPWQNNMAQF
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UniChem Compound Search for chemical match using the InChIKey MDEJTPWQNNMAQF-BVMLLJBZSA-N
UniChem Connectivity Search for chemical match using the InChIKey MDEJTPWQNNMAQF-BVMLLJBZSA-N