Structure of PDB 3cwe Chain A Binding Site BS01

Receptor Information
>3cwe Chain A (length=285) Species: 9606 (Homo sapiens) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]
AADKLEFMEMEKEFEQIDKSGSWAAIYQDIRHEASDFPCRVAKLPKNKNR
NRYRDVSPFDHSRIKLHQEDNDYINASLIKMEEAQRSYILTQGPLPNTCG
HFWEMVWEQKSRGVVMLNRVMKCAQYWPQKEEKEMIFEDTNLKLTLISED
IKSYYTVRQLELENLTTQETREILHFHYTTWPDFGVPESPASFLNFLFKV
RESGSLSPEHGPVVVHCSAGIGRSGTFCLADTCLLLMDKRKDPSSVDIKK
VLLEMRKFRMGLIQTADQLRFSYLAVIEGAKFIMG
Ligand information
Ligand ID825
InChIInChI=1S/C22H18BrF2O4P/c23-20-14-15(11-12-19(20)22(24,25)30(27,28)29)13-18(16-7-3-1-4-8-16)21(26)17-9-5-2-6-10-17/h1-12,14,18H,13H2,(H2,27,28,29)/t18-/m1/s1
InChIKeyWDTMVBQZDFMOIK-GOSISDBHSA-N
SMILES
SoftwareSMILES
ACDLabs 10.04Brc1cc(ccc1C(F)(F)P(=O)(O)O)CC(c2ccccc2)C(=O)c3ccccc3
OpenEye OEToolkits 1.5.0c1ccc(cc1)C(Cc2ccc(c(c2)Br)C(F)(F)P(=O)(O)O)C(=O)c3ccccc3
OpenEye OEToolkits 1.5.0c1ccc(cc1)[C@@H](Cc2ccc(c(c2)Br)C(F)(F)P(=O)(O)O)C(=O)c3ccccc3
CACTVS 3.341O[P](O)(=O)C(F)(F)c1ccc(C[CH](C(=O)c2ccccc2)c3ccccc3)cc1Br
CACTVS 3.341O[P](O)(=O)C(F)(F)c1ccc(C[C@@H](C(=O)c2ccccc2)c3ccccc3)cc1Br
FormulaC22 H18 Br F2 O4 P
Name[{2-bromo-4-[(2R)-3-oxo-2,3-diphenylpropyl]phenyl}(difluoro)methyl]phosphonic acid
ChEMBL
DrugBankDB07263
ZINCZINC000024980465
PDB chain3cwe Chain A Residue 784 [Download ligand structure] [Download structure with residue number starting from 1] [View ligand structure]
Receptor-Ligand Complex Structure
Global viewLocal viewStructure summary

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PDB3cwe Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor
Resolution1.6 Å
Binding residue
(original residue number in PDB)		Y546 D548 D681 F682 C715 S716 A717 I719 G720 R721 Q762
Binding residue
(residue number reindexed from 1)		Y53 D55 D183 F184 C217 S218 A219 I221 G222 R223 Q264
Annotation score1
Binding affinityMOAD: ic50=0.12uM
PDBbind-CN: -logKd/Ki=6.92,IC50=0.12uM
BindingDB: IC50=120nM,EC50=1200nM
Enzymatic activity
Catalytic site (original residue number in PDB) D681 C715 R721 S722 Q762
Catalytic site (residue number reindexed from 1) D183 C217 R223 S224 Q264
Enzyme Commision number 3.1.3.48: protein-tyrosine-phosphatase.
Gene Ontology
Molecular Function
GO:0004725 protein tyrosine phosphatase activity
Biological Process
GO:0006470 protein dephosphorylation
GO:0016311 dephosphorylation

View graph for
Molecular Function
View graph for
Biological Process
External links
PDB RCSB:3cwe, PDBe:3cwe, PDBj:3cwe
PDBsum3cwe
PubMed18477508
UniProtP18031|PTN1_HUMAN Tyrosine-protein phosphatase non-receptor type 1 (Gene Name=PTPN1)

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