Structure of PDB 4qhp Chain A Binding Site BS01

Receptor Information
>4qhp Chain A (length=866) Species: 487 (Neisseria meningitidis) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]
SKTVHYLKDYQTPAYHILKTDLHFDINEPQTVVKSRLTVEPQRVGEPLVL
DGSAKLLSVKINGAAADYVLEGETLTIAGVPSERFTVEVETEILPAENKS
LMGLYASGGNLFTQCEPEGFRKITFYIDRPDVMSKFTTTIVADKKRYPVL
LSNGNKIDGGEFSDGRHWVKWEDPFSKPSYLFALVAGDLAVTEDYFTTMS
GRNVKIEFYTTEADKPKVGFAVESLKNAMKWDETRFGLEYDLDIFMVVAV
GDFNMGAMENKGLNIFNTKFVLADSRTATDTDFEGIESVVGHEYFHNWTG
NRVTCRDWFQLSLKEGLTVFRDQEFSGDRASRAVRRIENIRLLRQHQFPE
DAGPTAHPVRPASYEEMNNFYTMTVYEKGAEVVRMYHTLLGEEGFQKGMK
LYFQRHDGQAVTCDDFRAAMADANGINLDQFALWYSQAGTPVLEAEGRLK
NNIFELTVKQTVPPTPDMTDKQPMMIPVKVGLLNRNGEAVAFDYQGKRAT
EAVLLLTEAEQTFLLEGVTEAVVPSLLRGFSAPVHLNYPYSDDDLLLLLA
HDSDAFTRWEAAQTLYRRAVAANLATLSDGVELPKHEKLLAAVEKVISDD
LLDNAFKALLLGVPSEAELWDGAENIDPLRYHQAREALLDTLAVHFLPKW
HELNRQAAKQENQSYEYSPEAAGWRTLRNVCRAFVLRADPAHIETVAEKY
GEMAQNMTHEWGILSAVNGNESDTRNRLLAQFADKFSDDALVMDKYFALV
GSSRRSDTLQQVRTALQHPKFSLENPNKARSLIGSFSRNVPHFHAEDGSG
YRFIADKVIEIDRFNPQVAARLVQAFNLCNKLEPHRKNLVKQALQRIRAQ
EGLSKDVGEIVGKILD
Ligand information
Ligand ID32Q
InChIInChI=1S/C20H27N2O4P/c21-13-17-8-6-16(7-9-17)12-18(20(23)24)14-27(25,26)19(22)11-10-15-4-2-1-3-5-15/h1-9,18-19H,10-14,21-22H2,(H,23,24)(H,25,26)/t18-,19-/m1/s1
InChIKeyXZFPYKBNMOQQLL-RTBURBONSA-N
SMILES
SoftwareSMILES
ACDLabs 12.01O=C(O)C(Cc1ccc(cc1)CN)CP(=O)(O)C(N)CCc2ccccc2
CACTVS 3.385NCc1ccc(C[CH](C[P](O)(=O)[CH](N)CCc2ccccc2)C(O)=O)cc1
OpenEye OEToolkits 1.7.6c1ccc(cc1)CCC(N)P(=O)(CC(Cc2ccc(cc2)CN)C(=O)O)O
OpenEye OEToolkits 1.7.6c1ccc(cc1)CC[C@H](N)P(=O)(C[C@@H](Cc2ccc(cc2)CN)C(=O)O)O
CACTVS 3.385NCc1ccc(C[C@H](C[P](O)(=O)[C@@H](N)CCc2ccccc2)C(O)=O)cc1
FormulaC20 H27 N2 O4 P
Name(2S)-2-[4-(aminomethyl)benzyl]-3-[(R)-[(1R)-1-amino-3-phenylpropyl](hydroxy)phosphoryl]propanoic acid
ChEMBL
DrugBank
ZINCZINC000098208387
PDB chain4qhp Chain A Residue 901 [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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PDB4qhp Structure-guided, single-point modifications in the phosphinic dipeptide structure yield highly potent and selective inhibitors of neutral aminopeptidases.
Resolution1.6 Å
Binding residue
(original residue number in PDB)		Q115 E117 M256 G257 A258 M259 E260 H293 E294 H297 E316 D323 Y377
Binding residue
(residue number reindexed from 1)		Q114 E116 M255 G256 A257 M258 E259 H292 E293 H296 E315 D322 Y376
Annotation score1
Binding affinityMOAD: Ki=9nM
PDBbind-CN: -logKd/Ki=8.05,Ki=9.0nM
Enzymatic activity
Catalytic site (original residue number in PDB) E260 H293 E294 H297 E316 N369 Y377
Catalytic site (residue number reindexed from 1) E259 H292 E293 H296 E315 N368 Y376
Enzyme Commision number 3.4.11.2: membrane alanyl aminopeptidase.
Gene Ontology
Molecular Function
GO:0004177 aminopeptidase activity
GO:0008237 metallopeptidase activity
GO:0008270 zinc ion binding
GO:0046872 metal ion binding
Biological Process
GO:0006508 proteolysis

View graph for
Molecular Function
View graph for
Biological Process
External links
PDB RCSB:4qhp, PDBe:4qhp, PDBj:4qhp
PDBsum4qhp
PubMed25192493
UniProtQ9JYV4

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