Structure of PDB 3dds Chain A Binding Site BS04

Receptor Information
>3dds Chain A (length=811) Species: 9606 (Homo sapiens) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]
QISIRGIVGVENVAELKKSFNRHLHFTLVKDRNVATTRDYYFALAHTVRD
HLVGRWIRTQQHYYDKCPKRVYYLSLEFYMGRTLQNTMINLGLQNACDEA
IYQLGLDIEELEEIEEDAGLGNGGLGRLAACFLDSMATLGLAAYGYGIRY
EYGIFNQKIRDGWQVEEADDWLRYGNPWEKSRPEFMLPVHFYGKVEHTNT
GTKWIDTQVVLALPYDTPVPGYMNNTVNTMRLWSARAPNDGDYIQAVLDR
NLAENISRVLYPNDNFFEGKELRLKQEYFVVAATLQDIIRRFKASKFGST
RGAGTVFDAFPDQVAIQLNDTHPALAIPELMRIFVDIEKLPWSKAWELTQ
KTFAYTNHTVLPEALERWPVDLVEKLLPRHLEIIYEINQKHLDRIVALFP
KDVDRLRRMSLIEEEGSKRINMAHLCIVGSHAVNGVAKIHSDIVKTKVFK
DFSELEPDKFQNKTNGITPRRWLLLCNPGLAELIAEKIGEDYVKDLSQLT
KLHSFLGDDVFLRELAKVKQENKLKFSQFLETEYKVKINPSSMFDVQVKR
IHEYKRQLLNCLHVITMYNRIKKDPKKLFVPRTVIIGGKAAPGYHMAKMI
IKLITSVADVVNNDPMVGSKLKVIFLENYRVSLAEKVIPATDLSEQISTA
GTEASGTGNMKFMLNGALTIGTMDGANVEMAEEAGEENLFIFGMRIDDVA
ALDKKGYEAKEYYEALPELKLVIDQIDNGFFSPKQPDLFKDIINMLFYHD
RFKVFADYEAYVKCQDKVSQLYMNPKAWNTMVLKNIAASGKFSSDRTIKE
YAQNIWNVEPS
Ligand information
Ligand ID26B
InChIInChI=1S/C29H35N3O5/c1-16-12-17(2)24(18(3)13-16)32-28(36)30-23-15-21-11-9-8-10-20(21)14-22(23)26(33)31-25(27(34)35)19(4)37-29(5,6)7/h8-15,19,25H,1-7H3,(H,31,33)(H,34,35)(H2,30,32,36)/t19-,25+/m1/s1
InChIKeySIVVDUDKHBTSKI-CLOONOSVSA-N
SMILES
SoftwareSMILES
OpenEye OEToolkits 1.5.0Cc1cc(c(c(c1)C)NC(=O)Nc2cc3ccccc3cc2C(=O)NC(C(C)OC(C)(C)C)C(=O)O)C
CACTVS 3.341C[CH](OC(C)(C)C)[CH](NC(=O)c1cc2ccccc2cc1NC(=O)Nc3c(C)cc(C)cc3C)C(O)=O
CACTVS 3.341C[C@@H](OC(C)(C)C)[C@H](NC(=O)c1cc2ccccc2cc1NC(=O)Nc3c(C)cc(C)cc3C)C(O)=O
ACDLabs 10.04O=C(Nc1c(cc(cc1C)C)C)Nc3cc2ccccc2cc3C(=O)NC(C(=O)O)C(OC(C)(C)C)C
OpenEye OEToolkits 1.5.0Cc1cc(c(c(c1)C)NC(=O)Nc2cc3ccccc3cc2C(=O)N[C@@H]([C@@H](C)OC(C)(C)C)C(=O)O)C
FormulaC29 H35 N3 O5
NameO-tert-butyl-N-[(3-{[(2,4,6-trimethylphenyl)carbamoyl]amino}naphthalen-2-yl)carbonyl]-L-threonine
ChEMBLCHEMBL473851
DrugBank
ZINCZINC000040405605
PDB chain3dds Chain A Residue 905 [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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PDB3dds Anthranilimide based glycogen phosphorylase inhibitors for the treatment of type 2 diabetes. Part 3: X-ray crystallographic characterization, core and urea optimization and in vivo efficacy.
Resolution1.8 Å
Binding residue
(original residue number in PDB)		W67 Q71 Q72 R193 F196 D227 T240 R310
Binding residue
(residue number reindexed from 1)		W56 Q60 Q61 R182 F185 D216 T229 R291
Annotation score1
Binding affinityMOAD: ic50=506nM
BindingDB: IC50=7nM
Enzymatic activity
Catalytic site (original residue number in PDB) H377 K568 R569 K574 T676 K680
Catalytic site (residue number reindexed from 1) H358 K549 R550 K555 T657 K661
Enzyme Commision number 2.4.1.1: glycogen phosphorylase.
Gene Ontology
Molecular Function
GO:0000166 nucleotide binding
GO:0002060 purine nucleobase binding
GO:0004645 1,4-alpha-oligoglucan phosphorylase activity
GO:0005515 protein binding
GO:0005524 ATP binding
GO:0005536 D-glucose binding
GO:0008184 glycogen phosphorylase activity
GO:0016208 AMP binding
GO:0016757 glycosyltransferase activity
GO:0019842 vitamin binding
GO:0030170 pyridoxal phosphate binding
GO:0030246 carbohydrate binding
GO:0032052 bile acid binding
GO:0042802 identical protein binding
Biological Process
GO:0005975 carbohydrate metabolic process
GO:0005977 glycogen metabolic process
GO:0005980 glycogen catabolic process
GO:0006015 5-phosphoribose 1-diphosphate biosynthetic process
GO:0009617 response to bacterium
GO:0042593 glucose homeostasis
GO:0070266 necroptotic process
Cellular Component
GO:0005576 extracellular region
GO:0005737 cytoplasm
GO:0005829 cytosol
GO:0034774 secretory granule lumen
GO:0070062 extracellular exosome
GO:1904813 ficolin-1-rich granule lumen

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Molecular Function
View graph for
Biological Process
View graph for
Cellular Component
External links
PDB RCSB:3dds, PDBe:3dds, PDBj:3dds
PDBsum3dds
PubMed19138846
UniProtP06737|PYGL_HUMAN Glycogen phosphorylase, liver form (Gene Name=PYGL)

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