Structure of PDB 4k9g Chain A Binding Site BS01

Receptor Information
>4k9g Chain A (length=114) Species: 9606 (Homo sapiens) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]
PMFIVNTNVPRASVPDGFLSELTQQLAQATGKPPQYIAVHVVPDQLMAFG
GSSEPCALCSLHSIGKIGGAQNRSYSKLLCGLLAERLRISPDRVYINYYD
MNAANVGWNNSTFA
Ligand information
Ligand ID1Q2
InChIInChI=1S/C12H14FNO3/c1-7(15)4-9(16)6-11(14)8-2-3-12(17)10(13)5-8/h2-3,5,9,14,16-17H,4,6H2,1H3/b14-11-/t9-/m0/s1
InChIKeyDBWKEXPZAPNKOY-ZQQXWWNKSA-N
SMILES
SoftwareSMILES
OpenEye OEToolkits 1.7.6[H]/N=C(/C[C@H](CC(=O)C)O)\c1ccc(c(c1)F)O
CACTVS 3.370CC(=O)C[CH](O)CC(=N)c1ccc(O)c(F)c1
CACTVS 3.370CC(=O)C[C@H](O)CC(=N)c1ccc(O)c(F)c1
OpenEye OEToolkits 1.7.6CC(=O)CC(CC(=N)c1ccc(c(c1)F)O)O
ACDLabs 12.01Fc1cc(C(=[N@H])CC(O)CC(=O)C)ccc1O
FormulaC12 H14 F N O3
Name(4R,6Z)-6-(3-fluoro-4-hydroxyphenyl)-4-hydroxy-6-iminohexan-2-one
ChEMBL
DrugBank
ZINC
PDB chain4k9g Chain A Residue 201 [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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PDB4k9g ISO-66, a novel inhibitor of macrophage migration, shows efficacy in melanoma and colon cancer models.
Resolution1.55 Å
Binding residue
(original residue number in PDB)		P1 M2 K32 Y36 H62 S63 I64 M101 V106 F113
Binding residue
(residue number reindexed from 1)		P1 M2 K32 Y36 H62 S63 I64 M101 V106 F113
Annotation score1
Enzymatic activity
Enzyme Commision number 5.3.2.1: phenylpyruvate tautomerase.
5.3.3.12: L-dopachrome isomerase.
Gene Ontology
Molecular Function
GO:0002020 protease binding
GO:0004167 dopachrome isomerase activity
GO:0005125 cytokine activity
GO:0005126 cytokine receptor binding
GO:0005515 protein binding
GO:0016853 isomerase activity
GO:0042056 chemoattractant activity
GO:0042802 identical protein binding
GO:0050178 phenylpyruvate tautomerase activity
Biological Process
GO:0001516 prostaglandin biosynthetic process
GO:0001819 positive regulation of cytokine production
GO:0001934 positive regulation of protein phosphorylation
GO:0002906 negative regulation of mature B cell apoptotic process
GO:0006954 inflammatory response
GO:0007166 cell surface receptor signaling pathway
GO:0008284 positive regulation of cell population proliferation
GO:0010629 negative regulation of gene expression
GO:0010760 negative regulation of macrophage chemotaxis
GO:0019752 carboxylic acid metabolic process
GO:0030330 DNA damage response, signal transduction by p53 class mediator
GO:0030336 negative regulation of cell migration
GO:0030890 positive regulation of B cell proliferation
GO:0031666 positive regulation of lipopolysaccharide-mediated signaling pathway
GO:0032760 positive regulation of tumor necrosis factor production
GO:0033033 negative regulation of myeloid cell apoptotic process
GO:0042127 regulation of cell population proliferation
GO:0042327 positive regulation of phosphorylation
GO:0043030 regulation of macrophage activation
GO:0043066 negative regulation of apoptotic process
GO:0043406 positive regulation of MAP kinase activity
GO:0043518 negative regulation of DNA damage response, signal transduction by p53 class mediator
GO:0045087 innate immune response
GO:0048146 positive regulation of fibroblast proliferation
GO:0050918 positive chemotaxis
GO:0051248 negative regulation of protein metabolic process
GO:0061078 positive regulation of prostaglandin secretion involved in immune response
GO:0061081 positive regulation of myeloid leukocyte cytokine production involved in immune response
GO:0070207 protein homotrimerization
GO:0070374 positive regulation of ERK1 and ERK2 cascade
GO:0090238 positive regulation of arachidonate secretion
GO:0090398 cellular senescence
GO:0141163 positive regulation of cAMP/PKA signal transduction
GO:1902166 negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator
GO:2000343 positive regulation of chemokine (C-X-C motif) ligand 2 production
GO:2000773 negative regulation of cellular senescence
Cellular Component
GO:0005576 extracellular region
GO:0005615 extracellular space
GO:0005654 nucleoplasm
GO:0005737 cytoplasm
GO:0005829 cytosol
GO:0005886 plasma membrane
GO:0009986 cell surface
GO:0031982 vesicle
GO:0034774 secretory granule lumen
GO:0070062 extracellular exosome
GO:1904813 ficolin-1-rich granule lumen

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Molecular Function
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Biological Process
View graph for
Cellular Component
External links
PDB RCSB:4k9g, PDBe:4k9g, PDBj:4k9g
PDBsum4k9g
PubMed25050663
UniProtP14174|MIF_HUMAN Macrophage migration inhibitory factor (Gene Name=MIF)

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