ChemComp-YPP: Hydrolyzed piperacillin

Basic information

• Entry: Database: PDB chemical components / ID: YPP
• Name: Name: Hydrolyzed piperacillin; Synonyms: (2R,4S)-2-[(R)-carboxy{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

Chemical information

Composition

Formula: C₂₃H₂₉N₅O₈S / Number of atoms: 66 / Formula weight: 535.57 / Formal charge: 0

Others

3q07

Type: NON-POLYMER / PDB classification: HETAIN / Three letter code: YPP / Ideal coordinates details: Corina / Model coordinates PDB-ID: 3Q07

History

Create component	Jan 6, 2011
Modify aromatic flag	Jun 4, 2011
Modify descriptor	Jun 4, 2011
Modify synonyms	Mar 13, 2021

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Details

SMILES

• ACDLabs 12.01: O=C(NC(C(=O)O)C1SC(C(N1)C(=O)O)(C)C)C(c2ccccc2)NC(=O)N3C(=O)C(=O)N(CC)CC3
• CACTVS 3.370: CCN1CCN(C(=O)N[CH](C(=O)N[CH]([CH]2N[CH](C(O)=O)C(C)(C)S2)C(O)=O)c3ccccc3)C(=O)C1=O
• OpenEye OEToolkits 1.7.0: CCN1CCN(C(=O)C1=O)C(=O)NC(c2ccccc2)C(=O)NC(C3NC(C(S3)(C)C)C(=O)O)C(=O)O

SMILES CANONICAL

• CACTVS 3.370: CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]([C@@H]2N[C@@H](C(O)=O)C(C)(C)S2)C(O)=O)c3ccccc3)C(=O)C1=O
• OpenEye OEToolkits 1.7.0: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c2ccccc2)C(=O)N[C@@H]([C@@H]3N[C@H](C(S3)(C)C)C(=O)O)C(=O)O

InChI

• InChI 1.03: InChI=1S/C23H29N5O8S/c1-4-27-10-11-28(19(31)18(27)30)22(36)25-13(12-8-6-5-7-9-12)16(29)24-14(20(32)33)17-26-15(21(34)35)23(2,3)37-17/h5-9,13-15,17,26H,4,10-11H2,1-3H3,(H,24,29)(H,25,36)(H,32,33)(H,34,35)/t13-,14+,15+,17-/m1/s1

InChIKey

• InChI 1.03: OKSUEATVFIVTFV-WBTNSWJXSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (2R,4S)-2-[(R)-carboxy{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• OpenEye OEToolkits 1.7.0: (2R,4S)-2-[(1R)-1-[[(2R)-2-[(4-ethyl-2,3-dioxo-piperazin-1-yl)carbonylamino]-2-phenyl-ethanoyl]amino]-2-hydroxy-2-oxo-ethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

PDB entries

Showing all 3 items

PDB-3q07:
CTX-M-9 S70G in complex with piperacillin

PDB-3q1f:
CTX-M-9 S70G in complex with hydrolyzed piperacillin

PDB-7o4a:
Crystal structure of Penicillin-Binding Protein 1 (PBP1) from Staphylococcus aureus in complex with piperacillin