abrocitinib   Click here for help

GtoPdb Ligand ID: 9991

Synonyms: compound 25 [PMID: 29298069] | PF-04965842 | PF04965842
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Abrocitinib (PF-04965842) is an investigational JAK inhibitor [4]. X-ray crystal structures of PF-04965842 bound to both JAK1 and JAK2 have been deposited with the Protein DataBank (accession IDs 6BBU and 6BBV respectively). We used the SMILES string supplied with the article in which the structure was declared [4] to generate our representation of the chemical structure. PubChem CID 78323835 represents the strucutre without specified stereochemistry.
Abrocitinib is an immunokinase inhibitor that is is late stage clinical trials for the potential treatment of immune-mediated diseases.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 99.36
Molecular weight 323.14
XLogP 2.05
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCCS(=O)(=O)NC1CC(C1)N(c1ncnc2c1cc[nH]2)C
Isomeric SMILES CCCS(=O)(=O)N[C@@H]1C[C@@H](C1)N(c1ncnc2c1cc[nH]2)C
InChI InChI=1S/C14H21N5O2S/c1-3-6-22(20,21)18-10-7-11(8-10)19(2)14-12-4-5-15-13(12)16-9-17-14/h4-5,9-11,18H,3,6-8H2,1-2H3,(H,15,16,17)/t10-,11+
InChI Key IUEWXNHSKRWHDY-PHIMTYICSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-{cis-3-[Methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclobutyl}propane-1-sulfonamide
International Nonproprietary Names Click here for help
INN number INN
11012 abrocitinib
Synonyms Click here for help
compound 25 [PMID: 29298069] | PF-04965842 | PF04965842
Database Links Click here for help
BindingDB Ligand 159748
ChEMBL Ligand CHEMBL3655081
GtoPdb PubChem SID 374883878
RCSB PDB Ligand D7D
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SynPHARM 85286 (in complex with Janus kinase 2)