Structure of PDB 3fl8 Chain A Binding Site BS02

Receptor Information
>3fl8 Chain A (length=166) Species: 1392 (Bacillus anthracis) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]
MIVSFMVAMDENRVIGKDNNLPWRLPSELQYVKKTTMGHPLIMGRKNYEA
IGRPLPGRRNIIVTRNEGYHVEGCEVAHSVEEVFELCKNEEEIFIFGGAQ
IYDLFLPYVDKLYITKIHHAFEGDTFFPEMDMTNWKEVFVEKGLTDEKNP
YTYYYHVYEKQQLVPR
Ligand information
Ligand IDRAR
InChIInChI=1S/C27H30N6O3/c1-4-7-22-21-9-6-5-8-19(21)16-31-33(22)24(34)11-10-18-12-17(14-23(35-2)25(18)36-3)13-20-15-30-27(29)32-26(20)28/h5-6,8-12,14-16,22H,4,7,13H2,1-3H3,(H4,28,29,30,32)/b11-10+/t22-/m0/s1
InChIKeyYGDVMSPWZQHNMB-NEQMZLFVSA-N
SMILES
SoftwareSMILES
CACTVS 3.341CCC[CH]1N(N=Cc2ccccc12)C(=O)C=Cc3cc(Cc4cnc(N)nc4N)cc(OC)c3OC
OpenEye OEToolkits 1.5.0CCCC1c2ccccc2C=NN1C(=O)C=Cc3cc(cc(c3OC)OC)Cc4cnc(nc4N)N
OpenEye OEToolkits 1.5.0CCC[C@H]1c2ccccc2C=NN1C(=O)\C=C\c3cc(cc(c3OC)OC)Cc4cnc(nc4N)N
CACTVS 3.341CCC[C@@H]1N(N=Cc2ccccc12)C(=O)\C=C\c3cc(Cc4cnc(N)nc4N)cc(OC)c3OC
ACDLabs 10.04O=C(N2N=Cc1c(cccc1)C2CCC)\C=C\c3cc(cc(OC)c3OC)Cc4cnc(nc4N)N
FormulaC27 H30 N6 O3
Name5-(3,4-dimethoxy-5-{(1E)-3-oxo-3-[(1S)-1-propylphthalazin-2(1H)-yl]prop-1-en-1-yl}benzyl)pyrimidine-2,4-diamine;
(S)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
ChEMBLCHEMBL1235617
DrugBank
ZINCZINC000043100694
PDB chain3fl8 Chain A Residue 200 [Download ligand structure] [Download structure with residue number starting from 1] [View ligand structure]
Receptor-Ligand Complex Structure
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PDB3fl8 Crystal structure of Bacillus anthracis dihydrofolate reductase with the dihydrophthalazine-based trimethoprim derivative RAB1 provides a structural explanation of potency and selectivity.
Resolution2.2881 Å
Binding residue
(original residue number in PDB)		M6 V7 A8 L21 E28 L29 V32 I51 L55 R58 F96
Binding residue
(residue number reindexed from 1)		M6 V7 A8 L21 E28 L29 V32 I51 L55 R58 F96
Annotation score1
Binding affinityMOAD: ic50=54nM
PDBbind-CN: -logKd/Ki=7.27,IC50=54nM
BindingDB: IC50=54nM
Enzymatic activity
Catalytic site (original residue number in PDB) M6 L21 W23 E28 L29 V32 L55 I93 T115
Catalytic site (residue number reindexed from 1) M6 L21 W23 E28 L29 V32 L55 I93 T115
Enzyme Commision number 1.5.1.3: dihydrofolate reductase.
Gene Ontology
Molecular Function
GO:0000166 nucleotide binding
GO:0004146 dihydrofolate reductase activity
GO:0016491 oxidoreductase activity
GO:0046872 metal ion binding
GO:0050661 NADP binding
Biological Process
GO:0006730 one-carbon metabolic process
GO:0046452 dihydrofolate metabolic process
GO:0046654 tetrahydrofolate biosynthetic process
GO:0046655 folic acid metabolic process
Cellular Component
GO:0005829 cytosol

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Molecular Function
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Biological Process
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Cellular Component
External links
PDB RCSB:3fl8, PDBe:3fl8, PDBj:3fl8
PDBsum3fl8
PubMed19364848
UniProtQ81R22

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