ChemComp-2TS: (2S)-N-[[2-(aminomethyl)-5-chloro-phenyl]methyl]-1-[(2R)-5-carbam...

Basic information

• Entry: Database: PDB chemical components / ID: 2TS
• Name: Name: (2S)-N-[[2-(aminomethyl)-5-chloro-phenyl]methyl]-1-[(2R)-5-carbamimidamido-2-(phenylmethylsulfonylamino)pentanoyl]pyrrolidine-2-carboxamide; Synonyms: (S)-1-((R)-5-Guanidino-2-phenylmethanesulfonylamino-pentanoyl)-pyrrolidine-2-carboxylic acid 2aminomethyl-5-chloro-benzylamide

BIRD information

• Type: Peptide-like / Thrombin Inhibitor
• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• (S)-1-((R)-5-Guanidino-2-phenylmethanesulfonylamino-pentanoyl)-pyrrolidine-2-carboxylic acid2-aminomethyl-5-chloro-benzylamide (PDB)

Annotation

• Function: Inhibitor of thrombin,EC: 3.4.21.5 / Info source: DOI:10.2210/pdb3eq0/pdb

External info

• ChEMBL: 1229260
• PubChem: 44144381

Family

Chlorobenzyl-dimethylanamine inhibitors

N~2~-(benzylsulfonyl)-D-arginyl-N-[2-(aminomethyl)-5-chlorobenzyl]-L-prolinamide / N-(BENZYLSULFONYL)-3-CYCLOHEXYL-D-ALANYL-N-[2-(AMINOMETHYL)-5-CHLOROBENZYL]-L-PROLINAMIDE / N-(BENZYLSULFONYL)GLYCYL-N-[2-(AMINOMETHYL)-5-CHLOROBENZYL]-L-PROLINAMIDE / N-(BENZYLSULFONYL)-D-VALYL-N-[2-(AMINOMETHYL)-5-CHLOROBENZYL]-L-PROLINAMIDE / N-(BENZYLSULFONYL)-D-ALANYL-N-[2-(AMINOMETHYL)-5-CHLOROBENZYL]-L-PROLINAMIDE / N-(BENZYLSULFONYL)-D-LEUCYL-N-[2-(AMINOMETHYL)-5-CHLOROBENZYL]-L-PROLINAMIDE / (2S)-N-[[2-(AMINOMETHYL)-5-CHLORANYL-PHENYL]METHYL]-1-[(2S)-2-[(3-CHLORANYL-4-METHOXY-PHENYL)SULFONYLAMINO]-4-[(4-CYANOPHENYL)METHYLAMINO]-4-OXIDANYLIDENE-BUTANOYL]PYRROLIDINE-2-CARBOXAMIDE

Chemical information

Composition

Formula: C₂₆H₃₆ClN₇O₄S / Number of atoms: 75 / Formula weight: 578.127 / Formal charge: 0

Others

3eq0

PMS

DAR

PRO

00T

Type: peptide-like / PDB classification: HETAIN / Three letter code: 2TS / Ideal coordinates details: Corina / Model coordinates PDB-ID: 3EQ0 / Subcomponent: PMS, DAR, PRO, 00T

History

Create component	Oct 1, 2008
Modify subcomponent list	Nov 12, 2010
Modify aromatic flag	Jun 4, 2011
Modify descriptor	Jun 4, 2011
Modify descriptor	Jan 5, 2012
Modify synonyms	Mar 1, 2021

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C(NCc1cc(Cl)ccc1CN)C3N(C(=O)C(NS(=O)(=O)Cc2ccccc2)CCCNC(=[N@H])N)CCC3
• CACTVS 3.385: NCc1ccc(Cl)cc1CNC(=O)[CH]2CCCN2C(=O)[CH](CCCNC(N)=N)N[S](=O)(=O)Cc3ccccc3
• OpenEye OEToolkits 1.7.5: c1ccc(cc1)CS(=O)(=O)NC(CCCNC(=N)N)C(=O)N2CCCC2C(=O)NCc3cc(ccc3CN)Cl

SMILES CANONICAL

• CACTVS 3.385: NCc1ccc(Cl)cc1CNC(=O)[C@@H]2CCCN2C(=O)[C@@H](CCCNC(N)=N)N[S](=O)(=O)Cc3ccccc3
• OpenEye OEToolkits 1.7.5: [H]/N=C(\N)/NCCC[C@H](C(=O)N1CCC[C@H]1C(=O)NCc2cc(ccc2CN)Cl)NS(=O)(=O)Cc3ccccc3

InChI

• InChI 1.03: InChI=1S/C26H36ClN7O4S/c27-21-11-10-19(15-28)20(14-21)16-32-24(35)23-9-5-13-34(23)25(36)22(8-4-12-31-26(29)30)33-39(37,38)17-18-6-2-1-3-7-18/h1-3,6-7,10-11,14,22-23,33H,4-5,8-9,12-13,15-17,28H2,(H,32,35)(H4,29,30,31)/t22-,23+/m1/s1

InChIKey

• InChI 1.03: MWLLGEVAEDIFRC-PKTZIBPZSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N~2~-(benzylsulfonyl)-D-arginyl-N-[2-(aminomethyl)-5-chlorobenzyl]-L-prolinamide
• OpenEye OEToolkits 1.7.0: (2S)-N-[[2-(aminomethyl)-5-chloro-phenyl]methyl]-1-[(2R)-5-carbamimidamido-2-(phenylmethylsulfonylamino)pentanoyl]pyrrolidine-2-carboxamide

PDB entries

Showing all 2 items

PDB-3eq0:
Thrombin Inhibitor

PDB-5jfd:
Thrombin in complex with (S)-N-(2-(aminomethyl)-5-chlorobenzyl)-1-((benzylsulfonyl)-D-arginyl)pyrrolidine-2-carboxamide