ContaminantDB: Piperacillin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:19:40 UTC

Update Date

2016-11-09 01:17:25 UTC

Accession Number

CHEM022088

Identification

Common Name

Piperacillin

Class

Small Molecule

Description

Semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections. It is also used in combination with other antibiotics.

Contaminant Sources

HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
Piperacillin anhydrous	ChEBI
PIPC	Kegg
Peracin	Kegg
(2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
AB piperacillin	HMDB
Fresenius brand OF piperacillin sodium	HMDB
Pipcil	HMDB
Piperacillin fresenius	HMDB
Piperacillin monosodium salt	HMDB
Piperacillin sodium	HMDB
Piperacillin curasan	HMDB
Sodium, piperacillin	HMDB
Pipera hameln	HMDB
Piperacillin hexal	HMDB
Pipracil	HMDB
Astrapin brand OF piperacillin sodium	HMDB
Hexal brand OF piperacillin sodium	HMDB
Monosodium salt, piperacillin	HMDB
Pipercillin	HMDB
Salt, piperacillin monosodium	HMDB
Wyeth brand OF piperacillin sodium	HMDB
Curasan brand OF piperacillin sodium	HMDB
AB-piperacillin	HMDB
AHP brand OF piperacillin sodium	HMDB
Lederle brand OF pipracillin sodium	HMDB
Pipera-hameln	HMDB
Piperacillin ratiopharm	HMDB
Piperacillin-ratiopharm	HMDB
Pipril	HMDB
Ratiopharm brand OF piperacillin sodium	HMDB
Curasan, piperacillin	HMDB

Chemical Formula

C₂₃H₂₇N₅O₇S

Average Molecular Mass

517.555 g/mol

Monoisotopic Mass

517.163 g/mol

CAS Registry Number

66258-76-2

IUPAC Name

(2S,5R,6R)-6-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

piperacillin

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(CC)C(=O)C1=O)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1

InChI Key

IVBHGBMCVLDMKU-GXNBUGAJSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Penicillin
N-acyl-alpha amino acid or derivatives
N-carbamoyl-alpha-amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Phenylacetamide
Piperazine-1-carboxamide
Dioxopiperazine
Penam
N-alkylpiperazine
Ureide
N-acyl urea
Benzenoid
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Beta-lactam
Dicarboximide
Thiazolidine
Tertiary carboxylic acid amide
Azetidine
Urea
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carbonic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Thioether
Hemithioaminal
Carboxylic acid
Dialkylthioether
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:8232 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	0.67	ALOGPS
logP	-0.26	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.3 m³·mol⁻¹	ChemAxon
Polarizability	51.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1090000000-f466ec6964cefc2de8df	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5491120000-c007c1d461cd55d89ae8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0013090000-813104cd60a9ea3a3859	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0096000000-b0dafe2b22b2f860c497	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0191000000-59dd52b81e08a7665c9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-1590000000-b8040d8994155855d7d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00ec-7940000000-d2ff9e1e0c9df03f7bd7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0094000000-2b4357e65d4f2c23da13	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udl-0890000000-1d19bc9caab1a3f5b623	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000f-0910000000-0c815f0f7a25577e636c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-70932882f6df40d54777	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0900000000-2bb7a0e3a556eadb090d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0900-2944030000-8a9f719c603883b5c9a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08fu-2930000000-e6f8445bc618cee16335	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-5910000000-db843bdc17e32d413fb0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009200000-3986d4bbb9203e5cb14e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-2119400000-a710f78ecf09c22009f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dm-9001000000-cbad9ca9227f864e2d2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0504090000-c0a3d0752174d7f20d46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01sl-1937510000-8c1f827dc2a6ab0481dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-2901100000-aab7f79d6ea92015c63d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-015i-0609140000-503714e67c3f5e51a392	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2904110000-aeb6a7bb580ff398bfb5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9710100000-63cce25700a92a152520	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum