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Receptor Information

>2pr3 Chain A (length=234) Species: 9606 (Homo sapiens) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]

IVGGQECKDGECPWQALLINEENEGFCGGTILSEFYILTAAHCLYQAKRF
KVRVGDRNTEQEEGGEAVHEVEVVIKHNRFTKETYDFDIAVLRLKTPITF
RMNVAPACLPERDWAESTLMTQKTGIVSGFGRTHEKGRQSTRLKMLEVPY
VDRNSCKLSSSFIITQNMFCAGYDTKQEDACQGDSGGPHVTRFKDTYFVT
GIVSWGEGCARKGKYGIYTKVTAFLKWIDRSMKT

Ligand ID

237

InChI

InChI=1S/C26H25ClFN3O5S/c1-36-19-14-23(31(15-19)26(33)29-18-10-8-17(27)9-11-18)25(32)30-22-12-7-16(13-21(22)28)20-5-3-4-6-24(20)37(2,34)35/h3-13,19,23H,14-15H2,1-2H3,(H,29,33)(H,30,32)/t19-,23-/m1/s1

InChIKey

QBTQRXKLWHEJQY-AUSIDOKSSA-N

SMILES

Software	SMILES
OpenEye OEToolkits 1.5.0	COC1CC(N(C1)C(=O)Nc2ccc(cc2)Cl)C(=O)Nc3ccc(cc3F)c4ccccc4S(=O)(=O)C
OpenEye OEToolkits 1.5.0	CO[C@@H]1C[C@@H](N(C1)C(=O)Nc2ccc(cc2)Cl)C(=O)Nc3ccc(cc3F)c4ccccc4S(=O)(=O)C
ACDLabs 10.04	O=C(Nc1ccc(Cl)cc1)N4C(C(=O)Nc3ccc(c2ccccc2S(=O)(=O)C)cc3F)CC(OC)C4
CACTVS 3.341	CO[CH]1C[CH](N(C1)C(=O)Nc2ccc(Cl)cc2)C(=O)Nc3ccc(cc3F)c4ccccc4[S](C)(=O)=O
CACTVS 3.341	CO[C@@H]1C[C@@H](N(C1)C(=O)Nc2ccc(Cl)cc2)C(=O)Nc3ccc(cc3F)c4ccccc4[S](C)(=O)=O

Formula

C26 H25 Cl F N3 O5 S

Name

(2R,4R)-N~1~-(4-CHLOROPHENYL)-N~2~-[3-FLUORO-2'-(METHYLSULFONYL)BIPHENYL-4-YL]-4-METHOXYPYRROLIDINE-1,2-DICARBOXAMIDE

PDB chain

2pr3 Chain A Residue 1001 [Download ligand structure] [Download structure with residue number starting from 1] [View ligand structure]

Receptor-Ligand Complex Structure

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Structure summary

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PDB	2pr3 Structure-based drug design of pyrrolidine-1, 2-dicarboxamides as a novel series of orally bioavailable factor Xa inhibitors
Resolution	1.5 Å
Binding residue (original residue number in PDB)	E97 T98 Y99 F174 A190 C191 V213 W215 G216 G219 C220 G226 I227 Y228
Binding residue (residue number reindexed from 1)	E83 T84 Y85 F162 A180 C181 V203 W205 G206 G208 C209 G216 I217 Y218
Annotation score	1
Binding affinity	MOAD: ic50=0.16nM BindingDB: IC50=0.16nM

Catalytic site (original residue number in PDB)	H57 D102 Q192 G193 D194 S195 G196
Catalytic site (residue number reindexed from 1)	H42 D88 Q182 G183 D184 S185 G186
Enzyme Commision number	3.4.21.6: coagulation factor Xa.

	Molecular Function
GO:0004252	serine-type endopeptidase activity

	Biological Process
GO:0006508	proteolysis

PDB	RCSB:2pr3, PDBe:2pr3, PDBj:2pr3
PDBsum	2pr3
PubMed	17581239
UniProt	P00742\|FA10_HUMAN Coagulation factor X (Gene Name=F10)

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Structure of PDB 2pr3 Chain A Binding Site BS03