Structure of PDB 5hg1 Chain A Binding Site BS02

Receptor Information
>5hg1 Chain A (length=867) Species: 9606 (Homo sapiens) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]
DQVQKVDQYLYHMRLSDETLLEISKRFRKEMEKGLGATTHPTAAVKMLPT
FVRSTPDGTEHGEFLALDLGGTNFRVLWVKVTDNGLQKVEMENQIYGTQL
FDHIAECLANFMDKLQIKDKKLPLGFTFSFPCHQTKLDESFLVSGRDVVA
LIRKAIQIDIVAVVNDTVGTMMTCGYDDHNCEIGLIVGTGSNACYMEEMR
HIDMVEGDEGRMCINMEWGAFGDDGSLNDIRTEFDQEIDMGSLNPGKQLF
EKMISGMYMGELVRLILVKMAKEELLFGGKLSPELLNTGRFETKDISDIE
GEKDGIRKAREVLMRLGLDPTQEDCVATHRICQIVSTRSASLCAATLAAV
LQRIKENKGEERLRSTIGVDGSVYKKHPHFAKRLHKTVRRLVPGCDVRFL
RSEDGSGKGAAMVTAVAYRLADQHRARQKTLEHLQLSHDQLLEVKRRMKV
EMERGLSKETHASAPVKMLPTYVCATPDGTEKGDFLALDLGGTNFRVLLV
RVRNGGVEMHNKIYAIPQEVMHGTGDELFDHIVQCIADFLEYMGMKGVSL
PLGFTFSFPCQQNSLDESILLKWTKGFKASGCEGEDVVTLLKEAIHRREE
FDLDVVAVVNDTVGTMMTCGFEDPHCEVGLIVGTGSNACYMEEMRNVELV
EGEEGRMCVNMEWGAFGDNGCLDDFRTEFDVAVDELSLNPGKQRFEKMIS
GMYLGEIVRNILIDFTKRGLLFRGRISERLKTRGIFETKFLSQIESDCLA
LLQVRAILQHLGLESTCDDSIIVKEVCTVVARRAAQLCGAGMAAVVDRIR
ENRGLDALKVTVGVDGTLYKLHPHFAKVMHETVKDLAPKCDVSFLQSEDG
SGKGAALITAVACRIRE
Ligand information
Ligand ID62C
InChIInChI=1S/C15H17Cl2NO6/c16-8-3-1-7(5-9(8)17)2-4-11(20)18-12-14(22)13(21)10(6-19)24-15(12)23/h1-5,10,12-15,19,21-23H,6H2,(H,18,20)/b4-2+/t10-,12-,13-,14-,15+/m1/s1
InChIKeyZBHWRKZTEDNOAJ-GJAUZLMESA-N
SMILES
SoftwareSMILES
OpenEye OEToolkits 2.0.4c1cc(c(cc1/C=C/C(=O)N[C@@H]2[C@H]([C@@H]([C@H](O[C@@H]2O)CO)O)O)Cl)Cl
CACTVS 3.385OC[CH]1O[CH](O)[CH](NC(=O)C=Cc2ccc(Cl)c(Cl)c2)[CH](O)[CH]1O
OpenEye OEToolkits 2.0.4c1cc(c(cc1C=CC(=O)NC2C(C(C(OC2O)CO)O)O)Cl)Cl
ACDLabs 12.01C2(C(CO)OC(C(NC(=O)\C=C\c1ccc(c(c1)Cl)Cl)C2O)O)O
CACTVS 3.385OC[C@H]1O[C@H](O)[C@H](NC(=O)\C=C\c2ccc(Cl)c(Cl)c2)[C@@H](O)[C@@H]1O
FormulaC15 H17 Cl2 N O6
Name2-deoxy-2-{[(2E)-3-(3,4-dichlorophenyl)prop-2-enoyl]amino}-alpha-D-glucopyranose
ChEMBL
DrugBank
ZINCZINC000205324579
PDB chain5hg1 Chain A Residue 1002 [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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PDB5hg1 Discovery of a Novel 2,6-Disubstituted Glucosamine Series of Potent and Selective Hexokinase 2 Inhibitors.
Resolution2.76 Å
Binding residue
(original residue number in PDB)		D209 N235 E260 K290 E294
Binding residue
(residue number reindexed from 1)		D166 N192 E217 K247 E251
Annotation score1
Binding affinityPDBbind-CN: -logKd/Ki=5.20,IC50=6.3uM
Enzymatic activity
Catalytic site (original residue number in PDB) R539 S603 K618 D657
Catalytic site (residue number reindexed from 1) R496 S557 K572 D611
Enzyme Commision number 2.7.1.1: hexokinase.
Gene Ontology
Molecular Function
GO:0004340 glucokinase activity
GO:0004396 hexokinase activity
GO:0005515 protein binding
GO:0005524 ATP binding
GO:0005536 D-glucose binding
GO:0008865 fructokinase activity
GO:0016301 kinase activity
GO:0016773 phosphotransferase activity, alcohol group as acceptor
Biological Process
GO:0001666 response to hypoxia
GO:0001678 intracellular glucose homeostasis
GO:0002931 response to ischemia
GO:0005975 carbohydrate metabolic process
GO:0006002 fructose 6-phosphate metabolic process
GO:0006006 glucose metabolic process
GO:0006096 glycolytic process
GO:0007595 lactation
GO:0008637 apoptotic mitochondrial changes
GO:0016310 phosphorylation
GO:0019318 hexose metabolic process
GO:0035795 negative regulation of mitochondrial membrane permeability
GO:0045766 positive regulation of angiogenesis
GO:0046324 regulation of D-glucose import
GO:0046835 carbohydrate phosphorylation
GO:0051156 glucose 6-phosphate metabolic process
GO:0061621 canonical glycolysis
GO:0072655 establishment of protein localization to mitochondrion
GO:0072656 maintenance of protein location in mitochondrion
GO:1901135 carbohydrate derivative metabolic process
GO:1990830 cellular response to leukemia inhibitory factor
GO:2000378 negative regulation of reactive oxygen species metabolic process
Cellular Component
GO:0005737 cytoplasm
GO:0005739 mitochondrion
GO:0005741 mitochondrial outer membrane
GO:0005813 centrosome
GO:0005829 cytosol
GO:0016020 membrane
GO:0016529 sarcoplasmic reticulum
GO:0043231 intracellular membrane-bounded organelle

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Molecular Function
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Biological Process
View graph for
Cellular Component
External links
PDB RCSB:5hg1, PDBe:5hg1, PDBj:5hg1
PDBsum5hg1
PubMed26985301
UniProtP52789|HXK2_HUMAN Hexokinase-2 (Gene Name=HK2)

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