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- ChemComp-MID: 1-[N-(naphthalen-2-ylsulfonyl)glycyl-4-carbamimidoyl-D-phenylalan... -

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Basic information

EntryDatabase: PDB chemical components / ID: MID
NameName: 1-[N-(naphthalen-2-ylsulfonyl)glycyl-4-carbamimidoyl-D-phenylalanyl]piperidine
Synonyms: NAPAP
Commentmedication*YM

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BIRD information

TypePeptide-like / Inhibitor
DownloadsMolecular definition / Chemical definition / Family definition
Synonyms
  • Acetamide, N-[1-[[4-(aminoiminomethyl)phenyl]methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[(2-naphthalenylsulfonyl)amino]-, (+/-)- (Scifinder)
  • MID (ChemSpider)
  • N alpha -(2-napthylsulfonylglycyl)-p-amidinophenyl-alanyl-piperidine (Beilstein)
  • N alpha-(2-Naphtylsulfonylglycyl)-4-amidinophneylalaninpiperidid (Beilstein)
  • N alpha-(2-naphthylsulfonylglycl)-4-amidinophenyl-alanyl-piperidine (Beilstein)
  • N(alpha)-(2-naphthylsulfonylglycyl)-4-amidinophenylalanine piperidide (PubChem)
  • N-[1-(4-Carbamimidoyl-benzyl)-2-oxo-2-piperidin-1-yl-ethyl]-2-(naphthalene-2-sulfonylamino)-acetamide (Beilstein)
  • N-alpha-(2-Naphthylsulfonyl-gly)-4-amindino-phe piperidide hydroiodide (PubChem)
  • N-alpha-(2-Naphthylsulfonylglycyl)-4-amidinophenylalanine piperidide (PubChem)
  • NAPAP (PDB, Scifinder, Beilstein, PubChem, eMolecules)
  • NAS-GLY-APH-PIPphthyl-sulfonyl-glycyl)-para-amidinophenyl-alanyl-piperidine (ChemSpider)
  • NAS-GLY-PAP-PIPphthyl-sulfonyl-glycyl)-para-amidinophenyl-alanyl-piperidine (ChemSpider)
  • Na-(2-Naphthalenesulfonylglycyl)-4-amidino-D,L-phenylalaninepiperidide (eMolecules)
  • Napappha==(2-naphthyl-sulfonyl-glycyl)-para-amidinophenyl-alanyl-piperidine (ChemSpider)
  • Nas-gly-pam-phe-P (PubChem)
  • Nas-gly-phe-4-Am-pip (PubChem)
  • SR 25477 (Scifinder)
  • Thrombstop (Scifinder)
  • Thromstop (Scifinder, PubChem)
  • a-NAPAP (eMolecules)
  • alpha-NAPAP (Scifinder)
  • n==alpha==(2-naphthyl-sulfonyl-glycyl)-para-amidinophenyl-alanyl-piperidine (ChemSpider, eMolecules)
Annotation
  • Function: thrombin inhibitor / Info source: PubChem
  • Function: anticoagulant / Info source: PubChem
  • Function: Inhibitor of TRYPSIN, EC: 3.4.21.4EC: Inhibitor of TRYPSIN, EC: 3.4.21.4 / Info source: PubMed: 2226434
External info
Familybenzamidine-based piperidine containing inhibitors

N(alpha)-(2-naphthylsulfonylglycyl)-4-amidinophenylalanine piperidide / [N-[N-(4-METHOXY-2,3,6-TRIMETHYLPHENYLSULFONYL)-L-ASPARTYL]-D-(4-AMIDINO-PHENYLALANYL)]-PIPERIDINE

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Chemical information

Composition
Formula: C27H31N5O4S / Number of atoms: 68 / Formula weight: 521.631 / Formal charge: 0
Others

1ppc

NAS

GLY

APH

PIP

Type: peptide-like / PDB classification: HETAIN / Three letter code: MID / Ideal coordinates details: Corina / Model coordinates PDB-ID: 1PPC / Model coordinates details: not provided / Subcomponent: NAS, GLY, APH, PIP
History
Create componentJul 8, 1999
Modify aromatic flagJun 4, 2011
Modify descriptorJun 4, 2011
Modify synonymsMar 1, 2021
External linksUniChem / ChemSpider / BindingDB / ChEMBL / Nikkaji / PubChem / PubChem_TPharma / SureChEMBL / ZINC / 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 10.04O=C(N1CCCCC1)C(NC(=O)CNS(=O)(=O)c3cc2ccccc2cc3)Cc4ccc(C(=[N@H])N)cc4
CACTVS 3.341NC(=N)c1ccc(C[CH](NC(=O)CN[S](=O)(=O)c2ccc3ccccc3c2)C(=O)N4CCCCC4)cc1
OpenEye OEToolkits 1.5.0[H]N=C(c1ccc(cc1)CC(C(=O)N2CCCCC2)NC(=O)CNS(=O)(=O)c3ccc4ccccc4c3)N

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SMILES CANONICAL

CACTVS 3.341NC(=N)c1ccc(C[C@@H](NC(=O)CN[S](=O)(=O)c2ccc3ccccc3c2)C(=O)N4CCCCC4)cc1
OpenEye OEToolkits 1.5.0[H]/N=C(/c1ccc(cc1)C[C@H](C(=O)N2CCCCC2)NC(=O)CNS(=O)(=O)c3ccc4ccccc4c3)\N

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InChI

InChI 1.03InChI=1S/C27H31N5O4S/c28-26(29)21-10-8-19(9-11-21)16-24(27(34)32-14-4-1-5-15-32)31-25(33)18-30-37(35,36)23-13-12-20-6-2-3-7-22(20)17-23/h2-3,6-13,17,24,30H,1,4-5,14-16,18H2,(H3,28,29)(H,31,33)/t24-/m1/s1

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InChIKey

InChI 1.03XXTWZTPVNIYSJZ-XMMPIXPASA-N

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SYSTEMATIC NAME

ACDLabs 10.041-[N-(naphthalen-2-ylsulfonyl)glycyl-4-carbamimidoyl-D-phenylalanyl]piperidine
OpenEye OEToolkits 1.5.0N-[(2R)-3-(4-carbamimidoylphenyl)-1-oxo-1-piperidin-1-yl-propan-2-yl]-2-(naphthalen-2-ylsulfonylamino)ethanamide

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PDB entries

Showing all 3 items

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

PDB-1ets:
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

PDB-1ppc:
GEOMETRY OF BINDING OF THE BENZAMIDINE-AND ARGININE-BASED INHIBITORS N-ALPHA-(2-NAPHTHYL-SULPHONYL-GLYCYL)-DL-P-AMIDINOPHENYLALANYL-PIPERIDINE (NAPAP) AND (2R,4R)-4-METHYL-1-[N-ALPHA-(3-METHYL-1,2,3,4-TETRAHYDRO-8-QUINOLINESULPHONYL)-L-ARGINYL]-2-PIPERIDINE CARBOXYLIC ACID (MQPA) TO HUMAN ALPHA-THROMBIN: X-RAY CRYSTALLOGRAPHIC DETERMINATION OF THE NAPAP-TRYPSIN COMPLEX AND MODELING OF NAPAP-THROMBIN AND MQPA-THROMBIN

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