ContaminantDB: Oxacillin

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

Record Information

Version

1.0

Creation Date

2016-05-25 18:22:28 UTC

Update Date

2016-11-09 01:17:26 UTC

Accession Number

CHEM022166

Identification

Common Name

Oxacillin

Class

Small Molecule

Description

An antibiotic similar to [flucloxacillin] used in resistant staphylococci infections.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,5R,6R)-3,3-Dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
(5-Methyl-3-phenyl-4-isoxazolyl)penicillin	ChEBI
5-Methyl-3-phenyl-4-isoxazolyl-penicillin	ChEBI
6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acid	ChEBI
Oxazocillin	ChEBI
Oxacilina	Kegg
(2S,5R,6R)-3,3-Dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanate	Generator
6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acid	Generator
6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanate	Generator
6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanate	Generator
6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid	Generator
Oxacillin sodium	HMDB
Oxacillin, monosodium salt, anhydrous	HMDB
Oxazocilline	HMDB
Penicillin, methylphenylisoxazolyl	HMDB
Prostaphlin	HMDB
Methylphenylisoxazolyl penicillin	HMDB
Oxacillin, sodium	HMDB
Sodium oxacillin	HMDB
Oxacillin, monosodium salt, monohydrate	HMDB
Sodium, oxacillin	HMDB

Chemical Formula

C₁₉H₁₉N₃O₅S

Average Molecular Mass

401.436 g/mol

Monoisotopic Mass

401.105 g/mol

CAS Registry Number

66-79-5

IUPAC Name

(2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

oxacillin

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1

InChI Key

UWYHMGVUTGAWSP-JKIFEVAISA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Penam
Benzenoid
Monocyclic benzene moiety
Isoxazole
Tertiary carboxylic acid amide
Azole
Thiazolidine
Heteroaromatic compound
Beta-lactam
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azetidine
Oxacycle
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Dialkylthioether
Hemithioaminal
Thioether
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:7809 )

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	0.086 g/L	ALOGPS
logP	2.05	ALOGPS
logP	1.7	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-0.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	112.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.83 m³·mol⁻¹	ChemAxon
Polarizability	39.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9756000000-f6bf977e3f72e4a53daf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9422200000-f8a5f80c92e02cdcee18	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-0090000000-79c009ac45201875c809	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-1290000000-4d46550a2c9c9f77458a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-8890000000-4a47690fda1171ea9191	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00e9-9530000000-81bb9ec609f6a7e8c6dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00e9-9410000000-b5c01a94c4b433924722	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00e9-9200000000-4bfc7a848a77bc668c0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-01b9-9000000000-927fa2d2be3c33adb44c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014i-9000000000-3661f69f0fee17d6a499	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014i-9000000000-f568ba02b1720f9fd951	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03dl-0980000000-62551643a67b5e9a21f8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03dl-0920000000-69978fc6eeaa10c71f81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-92b22bc2f96b5f612718	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-1900000000-4dceea173f6174da433d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-3900000000-3ee73f5cb610870dbdb1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0ikj-9800000000-fbc9b294222787b35a80	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0k92-9200000000-a405a812cf5f1a2f17e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udj-9100000000-451b59b916ee627de317	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-9000000000-21eb1aa369a09320f715	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00di-8890000000-be778bbb3e94437c3383	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ikc-1972400000-1b4711e093e9f42ab804	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03du-1930000000-b12c4b362713b4bb04cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0903-3910000000-8b5cc5bea864dcaf596d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0091000000-b65dbdc0c5b20e629677	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0692000000-6c32b8616abd8c887bd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1910000000-2ad85244337188941840	Spectrum