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- ChemComp-MIT: amino{[(4S)-5-[(2R,4R)-2-carboxy-4-methylpiperidin-1-yl]-4-({[(3R... -

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Basic information

EntryDatabase: PDB chemical components / ID: MIT
NameName: amino{[(4S)-5-[(2R,4R)-2-carboxy-4-methylpiperidin-1-yl]-4-({[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonyl}amino)-5-oxopentyl]amino}methaniminium
Synonyms: R-argatroban; MQPA; MD-805; MITSUBISHI INHIBITOR
Commentanticoagulant, inhibitor*YM

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BIRD information

TypePeptide-like / Inhibitor
DownloadsMolecular definition / Chemical definition / Family definition
Synonyms
  • (2R,4R)-1-[(2S)-5-(diaminomethylideneamino)-2-[[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid (DrugBank)
  • (2R,4R)-1-[(2S)-5-[(Aminoiminomethyl)amino]-1-oxo-2-[[(1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl]amino]pentyl]-4-methyl-2-piperidinecarboxylic acid (Merck)
  • (2R,4R)-1-[(S)-5-Ganidino-2-(3-metyl-1,2,3,4-tetrahydro-quinoline-8-sulfonylamino)-pentanoyl]-4-methyl-piperidine-2-carboxylic acid (Beilstein)
  • (2R,4R)-1-{N2-[(3-Methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L-arginyl}-2-piperidinecarboxylic acid (Beilstein)
  • (2R,4R)-4-Methyl-1-((S)-N(sup 2)-(((RS)-1,2,3,4-tetrahydro-3-methyl-8-quinolyl)sulfonyl)arginyl)pipecolic acid (ChemSpider)
  • (2R,4R)-4-Methyl-1[Nalpha-[(3-methyl-1,2,3,4-tetrahydro-8- (eMolecules)
  • (2R,4R)-4-Methyl-1[Nalpha-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L-arginyl)]-2-piperadinecarboxylic acid (KEGG, PubChem)
  • (2R,4R)-4-methyl-1-[(S)-N2-[[(R,S)-1,2,3,4-tetrahydro-3-methyl-8-quinolinyl]sulfonyl]arginyl]pipecolic acid (Merck)
  • (2R,4R)-4-methyl-1-[N2-((RS)-3-methyl,1,2,3,4-tetrahydro-8-quinoline-sulfonyl)-L-arginyl]-2-piperdine-carboxylic acid monohydrate (Beilstein)
  • (2R,4R)-4-methyl-1-[N2-(3-methyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-2-piperidinecarboxylic acid (Merck)
  • (2R,4R_=4=methyl-1-[N2-((RS)-3-metyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-2-piperdinecarboxylic acid hydrate (Beilstein)
  • 2-Piperidinecarboxylic acid, 1-((2S)-5-((aminoiminomethyl)amino)-1-oxo-2-(((1,2,3,4-tetrah ydro-3-methyl-8-quinolinyl)sulfonyl)amino)pentyl)-4-methyl-, (2R,4R)- (ChemSpider)
  • 2-Piperidinecarboxylic acid, 1-(5-((aminoiminomethyl)amino)-1-oxo-2-(((1,2,3,4-tetrahydro- 3-methyl-8-quinolinyl)sulfonyl)amino)pentyl)-4-methyl-thyl-, (2R,4R)- (ChemSpider)
  • 2-Piperidinecarboxylic acid, 1-[5-[(aminoiminomethyl)amino]-1-oxo-2-[[(1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl]amino]pentyl]-4-methyl-, [2R-[1(2S*),2alpha,4beta]]-[partial]- (Scifinder)
  • 2-piperidinecarboxylic acid,1-(5-((aminoiminomethyl)amino)-1-oxo-2-(((1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl)amino)pentyl)-4-methyl-,(2R-(1(S*(R*)),2alpha,4beta))- (ChemBank)
  • 21R-argatroban (ChemBank)
  • 2R,4R)-4-Methyl-1-[N2-(3-methyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-2-piperidinecarboxylic Acid (ChemSpider)
  • 4-methyl-1-{N~2~-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonyl]arginyl}piperidine-2-carboxylic acid (ChemBank)
  • 74863-84-6umcarboxylic acid, 1-(5-((aminoiminomethyl)amino)-1-oxo-2-(((1,2,3,4-tetrahydro- 3-methyl-8-quinolinyl)sulfonyl)amino)pentyl)-4-methyl-thyl-, (2R,4R)- (ChemSpider)
  • ARGATROBANnecarboxylic acid, 1-(5-((aminoiminomethyl)amino)-1-oxo-2-(((1,2,3,4-tetrahydro- 3-methyl-8-quinolinyl)sulfonyl)amino)pentyl)-4-methyl-thyl-, (2R,4R)- (ChemSpider)
  • Acova (Scifinder)
  • Argatra (Scifinder)
  • Argatroban (Scifinder, Merck, KEGG, PubChem, eMolecules)
  • Argatroban-d3 (eMolecules)
  • Argatrobanumcarboxylic acid, 1-(5-((aminoiminomethyl)amino)-1-oxo-2-(((1,2,3,4-tetrahydro- 3-methyl-8-quinolinyl)sulfonyl)amino)pentyl)-4-methyl-thyl-, (2R,4R)- (ChemSpider)
  • Argipidin (Scifinder)
  • Argipidine (Scifinder)
  • Argratroban (DrugBank)
  • DK 7419 (Scifinder)
  • GN 1600 (Scifinder)
  • MCI 9038 (Scifinder)
  • MD 805 (Scifinder)
  • MQPA (PDB, Scifinder, Merck)
  • NCGC00164592-01 (PubChem)
  • Novastan (Scifinder, Beilstein)
  • OM 805 (Scifinder)
  • Slonnon (Scifinder)
  • TL8005144 (PubChem)
  • amino{[(4S)-5-[(2R,4R)-2-carboxy-4-methylpiperidin-1-yl]-4-({[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonyl}amino)-5-oxopentyl]amino}methaniminium (PDB)
  • argatroban (Beilstein)
  • argipidine (Merck)
  • novastan (Beilstein)
Annotation
  • Function: Direct thrombin inhibitor/ anticoagulant / Info source: DrugBank
  • Function: used for prophylaxis or treatment of thrombosis in patients with heparin-indcued thrombocytopenia / Info source: DrugBank
  • Function: approved for use during percutaneous coronary interventions in patients with or at risk for HIT / Info source: DrugBank
  • Function: platelet aggregation inhibitor / Info source: PubChem
  • Function: anticoagulant / Info source: PubChem
  • Function: Inhibitor of EPSILON-THROMBIN, EC: 3.4.21.5EC: Inhibitor of EPSILON-THROMBIN, EC: 3.4.21.5 / Info source: PubMed: 1518046
External info
FamilyArgatroban

Argatroban / S-argatroban

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Chemical information

Composition
Formula: C23H37N6O5S / Number of atoms: 72 / Formula weight: 509.642 / Formal charge: 1
Others

1etr

34T

ARG

MCP

Type: peptide-like / PDB classification: HETAIN / Three letter code: MIT / Ideal coordinates details: Corina / Model coordinates PDB-ID: 1ETR / Model coordinates details: not provided / Subcomponent: 34T, ARG, MCP
History
Create componentJul 8, 1999
Modify descriptorJun 4, 2011
Modify synonymsOct 16, 2012
Modify synonymsMay 27, 2020
Modify synonymsMar 13, 2021
External linksUniChem / ChemSpider / PubChem / Wikipedia search / Google search

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Structure visualization

Structure viewerMolecule:
MolmilJmol/JSmol

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Details

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SMILES

ACDLabs 12.01O=C(N1C(C(=O)O)CC(C)CC1)C(NS(=O)(=O)c3cccc2c3NCC(C)C2)CCCNC(=[NH2+])\N
CACTVS 3.370C[CH]1CCN([CH](C1)C(O)=O)C(=O)[CH](CCCNC(N)=[NH2+])N[S](=O)(=O)c2cccc3C[CH](C)CNc23
OpenEye OEToolkits 1.7.6CC1CCN(C(C1)C(=O)O)C(=O)C(CCCNC(=[NH2+])N)NS(=O)(=O)c2cccc3c2NCC(C3)C

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SMILES CANONICAL

CACTVS 3.370C[C@@H]1CCN([C@H](C1)C(O)=O)C(=O)[C@H](CCCNC(N)=[NH2+])N[S](=O)(=O)c2cccc3C[C@@H](C)CNc23
OpenEye OEToolkits 1.7.6C[C@@H]1CCN([C@H](C1)C(=O)O)C(=O)[C@H](CCCNC(=[NH2+])N)NS(=O)(=O)c2cccc3c2NC[C@@H](C3)C

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InChI

InChI 1.03InChI=1S/C23H36N6O5S/c1-14-8-10-29(18(12-14)22(31)32)21(30)17(6-4-9-26-23(24)25)28-35(33,34)19-7-3-5-16-11-15(2)13-27-20(16)19/h3,5,7,14-15,17-18,27-28H,4,6,8-13H2,1-2H3,(H,31,32)(H4,24,25,26)/p+1/t14-,15-,17+,18-/m1/s1

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InChIKey

InChI 1.03KXNPVXPOPUZYGB-XYVMCAHJSA-O

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SYSTEMATIC NAME

ACDLabs 12.01amino{[(4S)-5-[(2R,4R)-2-carboxy-4-methylpiperidin-1-yl]-4-({[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonyl}amino)-5-oxopentyl]amino}methaniminium
OpenEye OEToolkits 1.7.6[azanyl-[[(4S)-5-[(2R,4R)-2-carboxy-4-methyl-piperidin-1-yl]-4-[[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonylamino]-5-oxidanylidene-pentyl]amino]methylidene]azanium

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PDB entries

Showing all 2 items

PDB-1dwc:
CRYSTALLOGRAPHIC ANALYSIS AT 3.0-ANGSTROMS RESOLUTION OF THE BINDING TO HUMAN THROMBIN OF FOUR ACTIVE SITE-DIRECTED INHIBITORS

PDB-1etr:
REFINED 2.3 ANGSTROMS X-RAY CRYSTAL STRUCTURE OF BOVINE THROMBIN COMPLEXES FORMED WITH THE BENZAMIDINE AND ARGININE-BASED THROMBIN INHIBITORS NAPAP, 4-TAPAP AND MQPA: A STARTING POINT FOR IMPROVING ANTITHROMBOTICS

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