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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 UTC
HMDB IDHMDB0015685
Secondary Accession Numbers
  • HMDB15685
Metabolite Identification
Common NameAzidocillin
DescriptionAzidocillin is only found in individuals that have used or taken this drug. It is a penicillin antibiotic similir to ampicillin.By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Azidocillin 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 Azidocillin interferes with an autolysin inhibitor.
Structure
Data?1582753323
Synonyms
ValueSource
(2S,5R,6R)-6-{[(2R)-2-azido-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
AzidocilinaChEBI
AzidocillineChEBI
AzidocillinumChEBI
D-(-)-(alpha-Azidobenzyl)penicillinChEBI
(2S,5R,6R)-6-{[(2R)-2-azido-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
D-(-)-(a-Azidobenzyl)penicillinGenerator
D-(-)-(Α-azidobenzyl)penicillinGenerator
Azidocillin, monopotassium salt, (2S-(2alpha,5alpha,6beta))-isomerHMDB
Azidocillin, monosodium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomerHMDB
6-(Azido-2-phenylacetamido)penicillanic acidHMDB
Azidocillin, monopotassium salt, (2S-(2alpha,5alpha,6beta(r*)))-isomerHMDB
Azidocillin, 2S-(2alpha,5alpha,6beta)HMDB
AzidobenzylpenicillinHMDB
Azidocillin, monopotassium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomerHMDB
Chemical FormulaC16H17N5O4S
Average Molecular Weight375.402
Monoisotopic Molecular Weight375.100124747
IUPAC Name(2S,5R,6R)-6-[(2R)-2-azido-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameazidocillin
CAS Registry Number17243-38-8
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=[N+]=[N-])C1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1
InChI KeyODFHGIPNGIAMDK-NJBDSQKTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Monocyclic benzene moiety
  • Benzenoid
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Azetidine
  • Secondary carboxylic acid amide
  • Azo compound
  • Azo imide
  • Carboxamide group
  • Dialkylthioether
  • Azacycle
  • Hemithioaminal
  • Thioether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • 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 Solubility0.61 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.61 g/LALOGPS
logP2.32ALOGPS
logP1.19ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area116.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity92.16 m³·mol⁻¹ChemAxon
Polarizability35.87 ųChemAxon
Number of Rings3ChemAxon
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]+183.14931661259
DarkChem[M-H]-177.18931661259
DeepCCS[M-2H]-210.31830932474
DeepCCS[M+Na]+186.6830932474
AllCCS[M+H]+181.632859911
AllCCS[M+H-H2O]+179.132859911
AllCCS[M+NH4]+184.032859911
AllCCS[M+Na]+184.632859911
AllCCS[M-H]-183.032859911
AllCCS[M+Na-2H]-182.932859911
AllCCS[M+HCOO]-182.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Azidocillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=[N+]=[N-])C1=CC=CC=C1)C(O)=O4406.3Standard polar33892256
Azidocillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=[N+]=[N-])C1=CC=CC=C1)C(O)=O2141.2Standard non polar33892256
Azidocillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=[N+]=[N-])C1=CC=CC=C1)C(O)=O3027.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Azidocillin,1TMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2864.0Semi standard non polar33892256
Azidocillin,1TMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2851.2Semi standard non polar33892256
Azidocillin,2TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2798.4Semi standard non polar33892256
Azidocillin,2TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2846.9Standard non polar33892256
Azidocillin,2TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3949.1Standard polar33892256
Azidocillin,1TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3089.0Semi standard non polar33892256
Azidocillin,1TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3054.2Semi standard non polar33892256
Azidocillin,2TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3193.3Semi standard non polar33892256
Azidocillin,2TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3251.1Standard non polar33892256
Azidocillin,2TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C4041.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Azidocillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-39589129d23c7063ed882017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Azidocillin GC-MS (1 TMS) - 70eV, Positivesplash10-001i-2900000000-333a7513f1232f9d54d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Azidocillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Azidocillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azidocillin 10V, Positive-QTOFsplash10-03fr-0906000000-e025b279fdc72aa3eb8f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azidocillin 20V, Positive-QTOFsplash10-03di-0911000000-5adbd4f3a803bd6529242016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azidocillin 40V, Positive-QTOFsplash10-03dl-5900000000-f7b31c1d1b5557339b112016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azidocillin 10V, Negative-QTOFsplash10-00dj-0129000000-3e90a9763793494a051f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azidocillin 20V, Negative-QTOFsplash10-08mi-1915000000-d22ce069665311a4a1e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azidocillin 40V, Negative-QTOFsplash10-00b9-9100000000-b022ba4f897a114e70bf2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08795 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08795 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08795
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16735689
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzidocillin
METLIN IDNot Available
PubChem Compound15574941
PDB IDNot Available
ChEBI ID51758
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 ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]
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. Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [PubMed:8956326 ]
  2. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037 ]
  3. 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 ]
  4. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
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. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
  2. 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 ]