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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015278
Secondary Accession Numbers
  • HMDB15278
Metabolite Identification
Common NameCloxacillin
DescriptionCloxacillin is only found in individuals that have used or taken this drug. It is a semi-synthetic antibiotic that is a chlorinated derivative of oxacillin. [PubChem]By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, cloxacillin 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 cloxacillin interferes with an autolysin inhibitor.
Structure
Data?1582753278
Synonyms
ValueSource
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
(3-(O-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillinChEBI
6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acidChEBI
CloxacilinaChEBI
CloxacillineChEBI
CloxacillinumChEBI
MCIPCKegg
OrbeninKegg
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanateGenerator
Cloxacillin sodiumHMDB
ChloroxacillinHMDB
TegopenHMDB
Cloxacillin, sodiumHMDB
SyntarpenHMDB
Sodium, cloxacillinHMDB
Sodium cloxacillinHMDB
Chemical FormulaC19H18ClN3O5S
Average Molecular Weight435.881
Monoisotopic Molecular Weight435.065569098
IUPAC Name(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namecloxacillin
CAS Registry Number61-72-3
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O
InChI Identifier
InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
InChI KeyLQOLIRLGBULYKD-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
  • Halobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Beta-lactam
  • Isoxazole
  • Lactam
  • Secondary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organohalogen compound
  • Organochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.053 g/LNot Available
LogP3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP2.61ALOGPS
logP2.3ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.74 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.64 m³·mol⁻¹ChemAxon
Polarizability41.64 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
DeepCCS[M-2H]-224.75630932474
DeepCCS[M+Na]+200.1830932474
AllCCS[M+H]+194.132859911
AllCCS[M+H-H2O]+191.832859911
AllCCS[M+NH4]+196.132859911
AllCCS[M+Na]+196.732859911
AllCCS[M-H]-196.332859911
AllCCS[M+Na-2H]-196.432859911
AllCCS[M+HCOO]-196.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cloxacillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O4615.1Standard polar33892256
Cloxacillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O2947.3Standard non polar33892256
Cloxacillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O3384.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cloxacillin,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=C2Cl)=NO13307.8Semi standard non polar33892256
Cloxacillin,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=C2Cl)=NO13312.3Semi standard non polar33892256
Cloxacillin,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=C2Cl)=NO13279.3Semi standard non polar33892256
Cloxacillin,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=C2Cl)=NO13150.0Standard non polar33892256
Cloxacillin,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=C2Cl)=NO14091.7Standard polar33892256
Cloxacillin,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=C2Cl)=NO13508.2Semi standard non polar33892256
Cloxacillin,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=C2Cl)=NO13484.9Semi standard non polar33892256
Cloxacillin,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=C2Cl)=NO13618.5Semi standard non polar33892256
Cloxacillin,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=C2Cl)=NO13582.7Standard non polar33892256
Cloxacillin,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=C2Cl)=NO14195.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cloxacillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9442300000-e216b172b6089bc0b6282017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cloxacillin GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9201100000-8c62d7bf4821412834e52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cloxacillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cloxacillin 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 - Cloxacillin LC-ESI-qTof , Positive-QTOFsplash10-03fr-0980100000-1acb1c4e617b9afd066c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cloxacillin LC-ESI-qTof , Positive-QTOFsplash10-03fr-0980100000-1acb1c4e617b9afd066c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cloxacillin LC-ESI-qTof , Positive-QTOFsplash10-03fr-0980100000-1acb1c4e617b9afd066c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cloxacillin , positive-QTOFsplash10-0a5a-0560910000-05dcf2cead0bc1f494822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cloxacillin , positive-QTOFsplash10-01q9-1900000000-a2a9637ec3640b22d4392017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 10V, Positive-QTOFsplash10-03g0-1981500000-b5aa89e8243c956612942016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 20V, Positive-QTOFsplash10-03mi-1980000000-5959a8cd3ff0d7b69e862016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 40V, Positive-QTOFsplash10-0900-4940000000-4f39d56cd5b7d76c29f42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 10V, Negative-QTOFsplash10-0006-0092000000-f42335fd75afb22d0d5b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 20V, Negative-QTOFsplash10-0006-0795000000-0f4a7aa6aa6b6709cf762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 40V, Negative-QTOFsplash10-0006-2920000000-e0da457c632e3e5d44da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 10V, Negative-QTOFsplash10-001i-1051900000-02e2b7b8281ef58614902021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 20V, Negative-QTOFsplash10-0006-9250100000-ed86f55f0155aa43591c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 40V, Negative-QTOFsplash10-001m-9632000000-a8ea4618ee5a92c98b3e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 10V, Positive-QTOFsplash10-000i-0110900000-7f26bb1ece4516994fc62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 20V, Positive-QTOFsplash10-022i-0590300000-7f87c7e79e0101a13c0d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cloxacillin 40V, Positive-QTOFsplash10-00dl-1950000000-43f0f287563f32d24bb42021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01147 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01147 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01147
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5873
KEGG Compound IDC06923
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCloxacillin
METLIN IDNot Available
PubChem Compound6098
PDB IDNot Available
ChEBI ID49566
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 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]