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- ChemComp-0P1: N-[(benzyloxy)carbonyl]-L-alanyl-N-{(1S)-1-[(R)-[(1R)-1-benzyl-2-... -

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Basic information

EntryDatabase: PDB chemical components / ID: 0P1
NameName: N-[(benzyloxy)carbonyl]-L-alanyl-N-{(1S)-1-[(R)-[(1R)-1-benzyl-2-methoxy-2-oxoethoxy](hydroxy)phosphoryl]-3-methylbutyl
Synonyms: Cbz-Ala-Ala-Leu(P)-(O)-Phe-OMe

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BIRD information

TypePeptide-like / Inhibitor
DownloadsMolecular definition / Chemical definition / Family definition
Synonyms
  • Benzyloxycarbonylalanyl-alanyl-leucyl phosphinate-3-phenyllactic acid methyl ester (ChemSpider)
  • Cbz-Ala-Ala-Leup-(O)Phe-OMe (Beilstein)
  • Cbz-ala-ala-leu(P)-(O)-phe-ome (PubChem, ChemSpider)
  • Cbzaal(P)(O)fome (PubChem, ChemSpider)
  • L-Alaninamide, N-((phenylmethoxy)carbonyl)-L-alanyl-N-(1-(hydroxy(2-methoxy-2-oxo-1-(phenylmethyl)ethoxy)phosphinyl)-3-methylbutyl)-, (R-(R*,S*))- (PubChem)
  • L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-alanyl-N-[(1R)-1-[hydroxy[(1S)-2-methoxy-2-oxo-1-(phenylmethyl)ethoxy]phosphinyl]-3-methylbutyl]-(9CI) (Scifinder)
  • L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-alanyl-N-[1-[hydroxy[2-methoxy-2-oxo-1-(phenylmethyl)ethoxy]phosphinyl]-3-methylbutyl]-, [R-(R*,S*)]- (Scifinder)
Annotation
  • Function: Inhibitor of aspartyl proteinases / Info source: PubChem
  • Structure: Structural mimic of the tetrahedral transition-state intermediate during proteinase catalysis / Info source: PubChem
External info
FamilyAmino acid phosphonate (Leu(P)-(O)-Phe) containing protease inhibitors

Cbz-Ala-Ala-Leu(P)-(O)-Phe-OMe

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Chemical information

Composition
Formula: C29H40N3O9P / Number of atoms: 82 / Formula weight: 605.616 / Formal charge: 0
Others

1ppm

PHQ

ALA

ALA

ZPH

Type: peptide-like / PDB classification: HETAIN / Three letter code: 0P1 / Ideal coordinates details: Corina / Model coordinates PDB-ID: 1PPM / Model coordinates details: not provided / Subcomponent: PHQ, ALA, ALA, ZPH
History
Other modificationOct 27, 2008
Other modificationOct 26, 2010
Modify aromatic flagJun 4, 2011
Modify descriptorJun 4, 2011
Other modificationNov 15, 2011
Modify synonymsJun 5, 2020
External linksUniChem / ChemSpider / 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(OC)C(OP(=O)(O)C(NC(=O)C(NC(=O)C(NC(=O)OCc1ccccc1)C)C)CC(C)C)Cc2ccccc2
CACTVS 3.370COC(=O)[CH](Cc1ccccc1)O[P](O)(=O)[CH](CC(C)C)NC(=O)[CH](C)NC(=O)[CH](C)NC(=O)OCc2ccccc2
OpenEye OEToolkits 1.7.0CC(C)CC(NC(=O)C(C)NC(=O)C(C)NC(=O)OCc1ccccc1)P(=O)(O)OC(Cc2ccccc2)C(=O)OC

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SMILES CANONICAL

CACTVS 3.370COC(=O)[C@H](Cc1ccccc1)O[P](O)(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OCc2ccccc2
OpenEye OEToolkits 1.7.0C[C@@H](C(=O)N[C@@H](CC(C)C)[P@@](=O)(O)O[C@@H](Cc1ccccc1)C(=O)OC)NC(=O)[C@H](C)NC(=O)OCc2ccccc2

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InChI

InChI 1.03InChI=1S/C29H40N3O9P/c1-19(2)16-25(42(37,38)41-24(28(35)39-5)17-22-12-8-6-9-13-22)32-27(34)20(3)30-26(33)21(4)31-29(36)40-18-23-14-10-7-11-15-23/h6-15,19-21,24-25H,16-18H2,1-5H3,(H,30,33)(H,31,36)(H,32,34)(H,37,38)/t20-,21-,24-,25+/m0/s1

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InChIKey

InChI 1.03VWCUANLUSQBJLX-WIHVIGOGSA-N

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SYSTEMATIC NAME

ACDLabs 12.01N-[(benzyloxy)carbonyl]-L-alanyl-N-{(1R)-1-[(R)-hydroxy{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]oxy}phosphoryl]-3-methylbutyl}-L-alaninamide
OpenEye OEToolkits 1.7.0[(2S)-1-methoxy-1-oxo-3-phenyl-propan-2-yl]oxy-[(1R)-3-methyl-1-[[(2S)-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoyl]amino]butyl]phosphinic acid

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PDB entries

Showing all 1 items

PDB-1ppm:
CRYSTALLOGRAPHIC ANALYSIS OF TRANSITION-STATE MIMICS BOUND TO PENICILLOPEPSIN: PHOSPHORUS-CONTAINING PEPTIDE ANALOGUES

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