Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H12N2O3S |
Molecular Weight | 216.257 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N)C(O)=O
InChI
InChIKey=NGHVIOIJCVXTGV-ALEPSDHESA-N
InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
Molecular Formula | C8H12N2O3S |
Molecular Weight | 216.257 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2844714Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/13622762
https://www.ncbi.nlm.nih.gov/pubmed/13742935
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2844714
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/13622762
https://www.ncbi.nlm.nih.gov/pubmed/13742935
6-amino-penicillanic acid is a common parent amine of various penicillins. 6-amino-penicillinic acid possesses definite antibacterial properties but these are much lower order than these of benzylpenicillin. It is destroyed by penicillinase (Beta-lactamase). The first penicillins to appear as derivatives of 6-APA were in fact phenethicillin and propicillin.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14448514 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Some immunochemical properties of penicillenic acid. An antigenic determinant derived from penicillin. | 1960 Dec 1 |
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Hypersensitivity to penicillenic acid derivatives in human beings with penicillin allergy. | 1962 Apr 1 |
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Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy. | 1990 Nov |
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Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity. | 1992 |
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Detection of specific IgE antibodies to major and minor antigenic determinants in sera of penicillin allergic patients. | 2003 Dec |
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Continuous penicillin G hydrolysis in an electro-membrane reactor with immobilized penicillin G acylase. | 2003 Mar |
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Study of nucleophile binding in the penicillin acylase active center. Kinetic analysis. | 2003 Mar |
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Improving the industrial production of 6-APA: enzymatic hydrolysis of penicillin G in the presence of organic solvents. | 2003 Nov-Dec |
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Isolation and characterization of a new strain of Achromobacter sp. with beta-lactam antibiotic acylase activity. | 2003 Oct |
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Kinetics of enzyme acylation and deacylation in the penicillin acylase-catalyzed synthesis of beta-lactam antibiotics. | 2003 Sep |
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Penicillin derivatives induce chemical structure-dependent root development, and application for plant transformation. | 2004 Apr |
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Increasing the synthetic performance of penicillin acylase PAS2 by structure-inspired semi-random mutagenesis. | 2004 Jul |
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[Treatment mostly not in line with current knowledge. New guidelines for sinusitis therapy]. | 2004 Jun 10 |
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Modifying the substrate specificity of penicillin G acylase to cephalosporin acylase by mutating active-site residues. | 2004 Jun 25 |
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Chromophoric spin-labeled beta-lactam antibiotics for ENDOR structural characterization of reaction intermediates of class A and class C beta-lactamases. | 2004 May |
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Evidence for the involvement of arginyl residue at the active site of penicillin G acylase from Kluyvera citrophila. | 2004 Oct |
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UV irradiation and desiccation modulate the three-dimensional extracellular matrix of Nostoc commune (Cyanobacteria). | 2005 Dec 2 |
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[Disseminated actinomycosis]. | 2005 Jun |
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Penicillin acylase catalysis in the presence of ionic liquids. | 2006 Dec |
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Immobilization of permeabilized whole cell penicillin G acylase from Alcaligenes faecalis using pore matrix crosslinked with glutaraldehyde. | 2006 Jul |
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High yield recombinant penicillin G amidase production and export into the growth medium using Bacillus megaterium. | 2006 Nov 28 |
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In vivo transport of the intermediates of the penicillin biosynthetic pathway in tailored strains of Penicillium chrysogenum. | 2007 Aug |
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Application of cross-linked enzyme aggregates of Bacillus badius penicillin G acylase for the production of 6-aminopenicillanic acid. | 2007 Jan |
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The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA). | 2007 Jan |
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Molecularly imprinted polymers as antibody mimics in automated on-line fluorescent competitive assays. | 2007 Jul 1 |
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Enzymatic hydrolysis of penicillin in mixed ionic liquids/water two-phase system. | 2007 Jul-Aug |
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Association of IL-10 level and IL-10 promoter SNPs with specific antibodies in penicillin-allergic patients. | 2007 Mar |
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Molecular cloning and characterization of thermostable beta-lactam acylase with broad substrate specificity from Bacillus badius. | 2007 May |
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Comparative production of 6-aminopenicillanic acid by different E. coli strains and their acridine orange (AO) induced mutants. | 2007 Nov 1 |
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Calixarenes in a membrane environment: a monolayer study on the miscibility of three p-tert-butylcalix[4]arene beta-lactam derivatives with 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine. | 2007 Nov 22 |
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Site-specific protonation microequilibria of penicillin and cephalosporin beta-lactam core molecules. | 2007 Sep |
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6-aminopenicillanic acid production by intact cells of E. coli containing penicillin G acylase (PGA). | 2007 Sep 15 |
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[Etiology of urinary tract infections and antimicrobial susceptibility: a study conducted on a population of children hospitalized in the Department of Pediatrics at Warsaw Bielany Hospital; 2004-2006]. | 2008 Apr-Jun |
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Poststreptococcal dystonia with bilateral striatal enlargement: MR imaging and spectroscopic findings. | 2008 Aug |
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Saturation mutagenesis reveals the importance of residues alphaR145 and alphaF146 of penicillin acylase in the synthesis of beta-lactam antibiotics. | 2008 Jan 1 |
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Development of the semi-synthetic penicillins and cephalosporins. | 2008 Mar |
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Small molecule inhibition of a Group II chaperonin: pinpointing a loop region within the equatorial domain as necessary for protein refolding. | 2009 Jan 1 |
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Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase. | 2009 Jul 15 |
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Hypersensitivity reactions to penicillins: studies in a group of patients with negative benzylpenicillin G skin test. | 2009 Jun |
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Human health risk assessment of penicillin/aminopenicillin resistance in enterococci due to penicillin use in food animals. | 2009 Jun |
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Molecular characterization of a fungal gene paralogue of the penicillin penDE gene of Penicillium chrysogenum. | 2009 May 26 |
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Rhodotorula aurantiaca penicillin V acylase: active site characterization and fluorometric studies. | 2009 Nov 9 |
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Enhanced production of 6-aminopenicillanic acid in aqueous methyl isobutyl ketone system with immobilized penicillin G acylase. | 2010 |
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Improved A. faecalis penicillin amidase mutant retains the thermodynamic and pH stability of the wild type enzyme. | 2010 Apr |
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A process to produce penicillin G acylase by surface-adhesion fermentation using Mucor griseocyanus to obtain 6-aminopenicillanic acid by penicillin G hydrolysis. | 2010 Apr |
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Covalent anchoring of chloroperoxidase and glucose oxidase on the mesoporous molecular sieve SBA-15. | 2010 Feb 24 |
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Heterologous expression of leader-less pga gene in Pichia pastoris: intracellular production of prokaryotic enzyme. | 2010 Feb 3 |
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FT-IR, FT-Raman, ab initio and DFT structural and vibrational frequency analysis of 6-aminopenicillanic acid. | 2010 Jan |
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Immobilized aculeacin A acylase from Actinoplanes utahensis: characterization of a novel biocatalyst. | 2010 Jun |
|
Monitoring bioreactors using principal component analysis: production of penicillin G acylase as a case study. | 2010 Jun |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:23:43 GMT 2023
by
admin
on
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Record UNII |
QR0C4R7XVN
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Record Status |
Validated (UNII)
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Record Version |
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