Clavulanic Acid
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Clavulanic Acid(F05681) |
| 2D Structure | |
| FRCD ID | F05681 |
| CAS Number | 58001-44-8 |
| PubChem CID | 5280980 |
| Formula | C8H9NO5 |
| IUPAC Name | (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| InChI Key | HZZVJAQRINQKSD-PBFISZAISA-N |
| InChI | InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1 |
| Canonical SMILES | C1C2N(C1=O)C(C(=CCO)O2)C(=O)O |
| Isomeric SMILES | C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O |
| Synonyms |
Antibiotic MM 14151
CLAVULANIC ACID
Clavulanate
Acido clavulanico
Acide clavulanique
acidum clavulanicum
58001-44-8
Clavulansaeure
MM 14151
Sodium Clavulanate
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives |
| Direct Parent | Alpha amino acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Alpha-amino acid or derivatives - Clavam - Para-oxazepine - Beta-lactam - Tertiary carboxylic acid amide - Oxazolidine - Azetidine - Carboxamide group - Lactam - Oxacycle - Azacycle - Organoheterocyclic compound - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Primary alcohol - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organopnictogen compound - Organic oxygen compound - Alcohol - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 199.162 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Complexity | 324 |
| Monoisotopic Mass | 199.048 |
| Exact Mass | 199.048 |
| XLogP | -1.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.6848 |
| Human Intestinal Absorption | HIA+ | 0.7450 |
| Caco-2 Permeability | Caco2- | 0.6054 |
| P-glycoprotein Substrate | Non-substrate | 0.7667 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9483 |
| Non-inhibitor | 0.9902 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8446 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5321 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8719 |
| CYP450 2D6 Substrate | Non-substrate | 0.8279 |
| CYP450 3A4 Substrate | Non-substrate | 0.5362 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8694 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8957 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9295 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8915 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9798 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9926 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9875 |
| Non-inhibitor | 0.9753 | |
| AMES Toxicity | Non AMES toxic | 0.7146 |
| Carcinogens | Non-carcinogens | 0.8718 |
| Fish Toxicity | Low FHMT | 0.9260 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.7075 |
| Honey Bee Toxicity | Low HBT | 0.5673 |
| Biodegradation | Ready biodegradable | 0.8501 |
| Acute Oral Toxicity | IV | 0.6106 |
| Carcinogenicity (Three-class) | Non-required | 0.5265 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.2363 | LogS |
| Caco-2 Permeability | 0.3385 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.4312 | LD50, mol/kg |
| Fish Toxicity | 1.4014 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1007 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Milk | Japan | 0.1ppm | |||
| Pig,Edible Offal | Japan | 0.2ppm | |||
| Cattle,Edible Offal | Japan | 0.01ppm | |||
| Pig,Kidney | Japan | 0.4ppm | |||
| Cattle,Kidney | Japan | 0.2ppm | |||
| Pig,Liver | Japan | 0.2ppm | |||
| Cattle,Liver | Japan | 0.1ppm | |||
| Pig,Fat | Japan | 0.1ppm | |||
| Cattle,Fat | Japan | 0.1ppm | |||
| Pig,Muscle | Japan | 0.1ppm | |||
| Cattle,Muscle | Japan | 0.06ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Prevalence, bioserotyping and antibiotic resistance of pathogenic Yersiniaenterocolitica detected in pigs at slaughter in Sardinia. | Int J Food Microbiol | 2018 Oct 20 | 29929063 |
| Comparative Study on Antibiotic Resistance and DNA Profiles of Salmonellaenterica Serovar Typhimurium Isolated from Humans, Retail Foods, and theEnvironment in Shanghai, China. | Foodborne Pathog Dis | 2018 May 9 | 29741928 |
| Interventions for necrotizing soft tissue infections in adults. | Cochrane Database Syst Rev | 2018 May 31 | 29851032 |
| Antibiotic resistance phenotypes and virulence-associated genes in Escherichiacoli isolated from animals and animal food products in Tunisia. | FEMS Microbiol Lett | 2018 May 1 | 29635468 |
| The prevalence of Clostridium difficile in cattle and sheep carcasses and the antibiotic susceptibility of isolates. | Meat Sci | 2018 May | 29413671 |
| Antibiotic susceptibilities of livestock isolates of leptospira. | Int J Antimicrob Agents | 2018 May | 29305960 |
| Salmonella, including antibiotic-resistant Salmonella, from flies captured fromcattle farms in Georgia, U.S.A. | Sci Total Environ | 2018 Mar | 29107782 |
| Azithromycin and Sensorineural Hearing Loss in Adults: A Retrospective CohortStudy. | Otol Neurotol | 2018 Jun 29 | 29965935 |
| In Vitro Antistaphylococcal Synergistic Effect of Isoflavone MetaboliteDemethyltexasin with Amoxicillin and Oxacillin. | Microb Drug Resist | 2018 Jan/Feb | 28570834 |
| Prevalence, Virulence Genes and Antimicrobial Resistance Profiles of SalmonellaSerovars from Retail Beef in Selangor, Malaysia. | Front Microbiol | 2018 Jan 11 | 29379488 |
| Carbapenemases and Extended-Spectrum β-Lactamase-Producing Multidrug-ResistantEscherichia coli Isolated from Retail Chicken in Peshawar: First Report fromPakistan. | J Food Prot | 2018 Aug | 30019956 |
| Characterization of Toxin Genes and Antimicrobial Susceptibility of Staphylococcus aureus from Retail Raw Chicken Meat. | J Food Prot | 2018 Apr | 29513103 |
| Simultaneous determination of clavulanic acid and tazobactam in bovine milk byHPLC. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2017Apr | 28156210 |
| Antimicrobial resistance in clinical Escherichia coli isolates from poultry andlivestock, China. | PLoS One | 2017 Sep 21 | 28934348 |
| Effect of Enterococcus Faecium Strain SF68 on Gastrointestinal Signs and FecalMicrobiome in Cats Administered Amoxicillin-Clavulanate. | Top Companion Anim Med | 2017 Sep | 29291771 |
| Prevalence of antimicrobial resistance in fecal Escherichia coli and Salmonellaenterica in Canadian commercial meat, companion, laboratory, and shelter rabbits (Oryctolagus cuniculus) and its association with routine antimicrobial use incommercial meat rabbits. | Prev Vet Med | 2017 Nov 1 | 29254727 |
| Third-Generation Cephalosporin-Resistant Non-Typhoidal Salmonella Isolated fromHuman Feces in Japan. | Jpn J Infect Dis | 2017 May 24 | 27580578 |
| Prevalence and clonal relationship of ESBL-producing Salmonella strains fromhumans and poultry in northeastern Algeria. | BMC Vet Res | 2017 May 15 | 28506272 |
| Antibiotic and Desiccation Resistance of Cronobacter sakazakii and C. malonaticusIsolates from Powdered Infant Formula and Processing Environments. | Front Microbiol | 2017 Mar 2 | 28303125 |
| Prevalence and antibiotic resistance of coagulase-negative Staphylococci isolatedfrom poultry farms in three regions of Ghana. | Infect Drug Resist | 2017 Jun 13 | 28652785 |