Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 UTC
HMDB IDHMDB0014851
Secondary Accession Numbers
  • HMDB14851
Metabolite Identification
Common NameOxacillin
DescriptionOxacillin is only found in individuals that have used or taken this drug. It is an antibiotic similar to flucloxacillin used in resistant staphylococci infections. [PubChem]By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Oxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Oxacillin interferes with an autolysin inhibitor.
Structure
Data?1582753227
Synonyms
ValueSource
(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 acidChEBI
(5-Methyl-3-phenyl-4-isoxazolyl)penicillinChEBI
5-Methyl-3-phenyl-4-isoxazolyl-penicillinChEBI
6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acidChEBI
OxazocillinChEBI
OxacilinaKegg
(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-carboxylateGenerator
6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanateGenerator
6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acidGenerator
6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanateGenerator
6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanateGenerator
6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acidGenerator
Oxacillin sodiumHMDB
Oxacillin, monosodium salt, anhydrousHMDB
OxazocillineHMDB
Penicillin, methylphenylisoxazolylHMDB
ProstaphlinHMDB
Methylphenylisoxazolyl penicillinHMDB
Oxacillin, sodiumHMDB
Sodium oxacillinHMDB
Oxacillin, monosodium salt, monohydrateHMDB
Sodium, oxacillinHMDB
Chemical FormulaC19H19N3O5S
Average Molecular Weight401.436
Monoisotopic Molecular Weight401.104541423
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 Nameoxacillin
CAS Registry Number66-79-5
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 KeyUWYHMGVUTGAWSP-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.086 g/LNot Available
LogP2.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available189.001http://allccs.zhulab.cn/database/detail?ID=AllCCS00001277
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP2.05ALOGPS
logP1.7ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-0.12ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.74 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.83 m³·mol⁻¹ChemAxon
Polarizability39.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.76331661259
DarkChem[M-H]-179.63931661259
DeepCCS[M-2H]-220.2830932474
DeepCCS[M+Na]+195.70530932474
AllCCS[M+H]+190.532859911
AllCCS[M+H-H2O]+188.032859911
AllCCS[M+NH4]+192.732859911
AllCCS[M+Na]+193.332859911
AllCCS[M-H]-192.832859911
AllCCS[M+Na-2H]-192.832859911
AllCCS[M+HCOO]-192.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Oxacillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O4467.3Standard polar33892256
Oxacillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O2930.1Standard non polar33892256
Oxacillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O3301.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxacillin,1TMS,isomer #1CC1=C(C(=O)N[C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]23)C(C2=CC=CC=C2)=NO13230.8Semi standard non polar33892256
Oxacillin,1TMS,isomer #2CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O)C(C)(C)S[C@H]23)[Si](C)(C)C)C(C2=CC=CC=C2)=NO13219.7Semi standard non polar33892256
Oxacillin,2TMS,isomer #1CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C)C(C2=CC=CC=C2)=NO13167.4Semi standard non polar33892256
Oxacillin,2TMS,isomer #1CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C)C(C2=CC=CC=C2)=NO13045.5Standard non polar33892256
Oxacillin,2TMS,isomer #1CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C)C(C2=CC=CC=C2)=NO13893.2Standard polar33892256
Oxacillin,1TBDMS,isomer #1CC1=C(C(=O)N[C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]23)C(C2=CC=CC=C2)=NO13437.1Semi standard non polar33892256
Oxacillin,1TBDMS,isomer #2CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O)C(C)(C)S[C@H]23)[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)=NO13414.8Semi standard non polar33892256
Oxacillin,2TBDMS,isomer #1CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)=NO13527.6Semi standard non polar33892256
Oxacillin,2TBDMS,isomer #1CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)=NO13469.2Standard non polar33892256
Oxacillin,2TBDMS,isomer #1CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)=NO14054.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxacillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9756000000-f6bf977e3f72e4a53daf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxacillin GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9422200000-f8a5f80c92e02cdcee182017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxacillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOFsplash10-0a4i-0090000000-79c009ac45201875c8092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOFsplash10-0a4i-1290000000-4d46550a2c9c9f77458a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOFsplash10-00di-8890000000-4a47690fda1171ea91912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOFsplash10-00e9-9530000000-81bb9ec609f6a7e8c6dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOFsplash10-00e9-9410000000-b5c01a94c4b4339247222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOFsplash10-00e9-9200000000-4bfc7a848a77bc668c0a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOFsplash10-01b9-9000000000-927fa2d2be3c33adb44c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOFsplash10-014i-9000000000-3661f69f0fee17d6a4992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOFsplash10-014i-9000000000-f568ba02b1720f9fd9512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOFsplash10-03dl-0980000000-62551643a67b5e9a21f82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOFsplash10-03dl-0920000000-69978fc6eeaa10c71f812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOFsplash10-03di-0900000000-92b22bc2f96b5f6127182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOFsplash10-03di-1900000000-4dceea173f6174da433d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOFsplash10-03di-3900000000-3ee73f5cb610870dbdb12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOFsplash10-0ikj-9800000000-fbc9b294222787b35a802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOFsplash10-0k92-9200000000-a405a812cf5f1a2f17e12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOFsplash10-0udj-9100000000-451b59b916ee627de3172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOFsplash10-0udi-9000000000-21eb1aa369a09320f7152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxacillin 45V, Negative-QTOFsplash10-00di-8890000000-be778bbb3e94437c33832021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxacillin 10V, Positive-QTOFsplash10-0ikc-1972400000-1b4711e093e9f42ab8042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxacillin 20V, Positive-QTOFsplash10-03du-1930000000-b12c4b362713b4bb04cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxacillin 40V, Positive-QTOFsplash10-0903-3910000000-8b5cc5bea864dcaf596d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxacillin 10V, Negative-QTOFsplash10-0a4i-0091000000-b65dbdc0c5b20e6296772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxacillin 20V, Negative-QTOFsplash10-0a4i-0692000000-6c32b8616abd8c887bd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxacillin 40V, Negative-QTOFsplash10-0a4i-1910000000-2ad852443371889418402016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00713 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00713 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00713
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5961
KEGG Compound IDC07334
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxacillin
METLIN IDNot Available
PubChem Compound6196
PDB IDNot Available
ChEBI ID7809
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Transporters

General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]