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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:15:57 UTC
HMDB IDHMDB0015194
Secondary Accession Numbers
  • HMDB15194
Metabolite Identification
Common NameAzlocillin
DescriptionAzlocillin is only found in individuals that have used or taken this drug. It is a semisynthetic ampicillin-derived acylureido penicillin.By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, azlocillin 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 azlocillin interferes with an autolysin inhibitor.
Structure
Data?1582753269
Synonyms
ValueSource
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
AzlocilinaChEBI
AzlocillineChEBI
AzlocillinumChEBI
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
Azlocillin sodium saltHMDB
Azlocillin, sodiumHMDB
Baye 6905HMDB
Bayer brand OF azlocillinHMDB
SecuropenHMDB
Azlocillin sodiumHMDB
AzlinHMDB
Sodium azlocillinHMDB
Sodium, azlocillinHMDB
Azlocillin bayer brandHMDB
Bay e 6905HMDB
Bay-e 6905HMDB
Chemical FormulaC20H23N5O6S
Average Molecular Weight461.492
Monoisotopic Molecular Weight461.136904183
IUPAC Name(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameazlocillin
CAS Registry Number37091-66-0
SMILES
[H][C@](NC(=O)N1CCNC1=O)(C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@]12[H])C1=CC=CC=C1
InChI Identifier
InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1
InChI KeyJTWOMNBEOCYFNV-NFFDBFGFSA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
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
  • Penam
  • Imidazolidinone
  • Monocyclic benzene moiety
  • Benzenoid
  • Imidazolidine
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Azetidine
  • Urea
  • Carbonic acid derivative
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Hemithioaminal
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Thioether
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 g/LNot Available
LogP0.2Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP0.2ALOGPS
logP-0.33ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area148.15 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.71 m³·mol⁻¹ChemAxon
Polarizability45.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available205.791http://allccs.zhulab.cn/database/detail?ID=AllCCS00001271
DarkChem[M+H]+PredictedNot Available200.02431661259
DarkChem[M-H]-PredictedNot Available191.17531661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Azlocillin,1TMS,#13840.786https://arxiv.org/abs/1905.12712
Azlocillin,1TMS,#23702.19https://arxiv.org/abs/1905.12712
Azlocillin,1TMS,#33580.69https://arxiv.org/abs/1905.12712
Azlocillin,1TMS,#43769.1636https://arxiv.org/abs/1905.12712
Azlocillin,1TBDMS,#14072.0535https://arxiv.org/abs/1905.12712
Azlocillin,1TBDMS,#23941.839https://arxiv.org/abs/1905.12712
Azlocillin,1TBDMS,#33838.5918https://arxiv.org/abs/1905.12712
Azlocillin,1TBDMS,#44012.2505https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9770100000-8492b9b1630f98f790e82017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-2090000000-7ac30823250a688befa12017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9211100000-386db4fc343ba0cb9fe42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9100000000-e2e66b83eab9cb055d8c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-9000000000-227c79047a0dfcc73d8e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1009100000-a664da387030dc08745f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-4119100000-f877d479d0e5f892a5e02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-66f3e846633855262d342016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01061 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01061 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01061
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4980416
KEGG Compound IDC06839
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzlocillin
METLIN IDNot Available
PubChem Compound6479523
PDB IDNot Available
ChEBI ID2956
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [PubMed:10090000 ]