<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:20 UTC</creation_date>
  <update_date>2019-11-26 02:57:21 UTC</update_date>
  <accession>FDB002353</accession>
  <name>Ampicillin</name>
  <description>Potential contaminant of cow's milk arising from its veterinary use

Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. It is considered part of the aminopenicillin family and is roughly equivalent to amoxicillin in terms of spectrum and level of activity. Ampicillin is found in milk and milk products and common pea.</description>
  <synonyms>
    <synonym>(2S,5R,6R)-6-[[(2R)-2-amino-2-Phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid</synonym>
    <synonym>(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate</synonym>
    <synonym>(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid</synonym>
    <synonym>(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate</synonym>
    <synonym>(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylIC ACID</synonym>
    <synonym>&amp;alpha;-aminobenzylpenicillin</synonym>
    <synonym>6-(a-Aminophenylacetamido)penicillanic acid</synonym>
    <synonym>6-(D-(2-amino-2-Phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate</synonym>
    <synonym>6-(D-(2-amino-2-Phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid</synonym>
    <synonym>6-(D(-)-alpha-Aminophenylacetamido)penicillanic acid</synonym>
    <synonym>6-[(Aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9CI</synonym>
    <synonym>6-D(-)-&amp;alpha;-Aminophenylacetamido-penicillanic acid</synonym>
    <synonym>6-D(-)-alpha-Aminophenylacetamido-penicillanic acid</synonym>
    <synonym>ABPC</synonym>
    <synonym>Acillin</synonym>
    <synonym>Adobacillin</synonym>
    <synonym>Alpen</synonym>
    <synonym>alpha-Aminobenzylpenicillin</synonym>
    <synonym>Amblosin</synonym>
    <synonym>Amcill</synonym>
    <synonym>Amfipen</synonym>
    <synonym>Amfipen v</synonym>
    <synonym>Aminobenzylpenicillin</synonym>
    <synonym>Amipenix s</synonym>
    <synonym>AMP</synonym>
    <synonym>Ampen</synonym>
    <synonym>AMPI</synonym>
    <synonym>Ampi-bol</synonym>
    <synonym>Ampi-co</synonym>
    <synonym>Ampi-tab</synonym>
    <synonym>Ampichel</synonym>
    <synonym>Ampicil</synonym>
    <synonym>Ampicilina</synonym>
    <synonym>Ampicillin (usan)</synonym>
    <synonym>Ampicillin (usp/inn)</synonym>
    <synonym>Ampicillin [usan:ban:inn:jan]</synonym>
    <synonym>Ampicillin a</synonym>
    <synonym>Ampicillin acid</synonym>
    <synonym>Ampicillin anhydrate</synonym>
    <synonym>Ampicillin anhydrous</synonym>
    <synonym>Ampicillin base</synonym>
    <synonym>Ampicillin sodium</synonym>
    <synonym>Ampicillin trihydrate</synonym>
    <synonym>Ampicillina</synonym>
    <synonym>Ampicilline</synonym>
    <synonym>Ampicillinum</synonym>
    <synonym>Ampifarm</synonym>
    <synonym>Ampikel</synonym>
    <synonym>Ampimed</synonym>
    <synonym>Ampipenin</synonym>
    <synonym>Ampiscel</synonym>
    <synonym>Ampisyn</synonym>
    <synonym>Ampivax</synonym>
    <synonym>Ampivet</synonym>
    <synonym>Amplacilina</synonym>
    <synonym>Amplin</synonym>
    <synonym>Amplipenyl</synonym>
    <synonym>Amplisom</synonym>
    <synonym>Amplital</synonym>
    <synonym>Anhydrous ampicillin</synonym>
    <synonym>Austrapen</synonym>
    <synonym>AY 6108</synonym>
    <synonym>Bayer 5427</synonym>
    <synonym>Binotal</synonym>
    <synonym>Bonapicillin</synonym>
    <synonym>Britacil</synonym>
    <synonym>BRL 1341</synonym>
    <synonym>Campicillin</synonym>
    <synonym>Cimex</synonym>
    <synonym>Copharcilin</synonym>
    <synonym>D-(-)-&amp;alpha;-aminobenzylpenicillin</synonym>
    <synonym>D-(-)-&amp;alpha;-aminopenicillin</synonym>
    <synonym>D-(-)-6-(a-Aminophenylacetamido)penicillanate</synonym>
    <synonym>D-(-)-6-(a-Aminophenylacetamido)penicillanic acid</synonym>
    <synonym>D-(-)-6-(alpha-Aminophenylacetamido)penicillanate</synonym>
    <synonym>D-(-)-6-(alpha-aminophenylacetamido)penicillanic acid</synonym>
    <synonym>D-(-)-6-(α-aminophenylacetamido)penicillanate</synonym>
    <synonym>D-(-)-6-(α-aminophenylacetamido)penicillanic acid</synonym>
    <synonym>D-(-)-alpha-aminobenzylpenicillin</synonym>
    <synonym>D-(-)-alpha-aminopenicillin</synonym>
    <synonym>D-(-)-ampicillin</synonym>
    <synonym>D-a-Aminobenzylpenicillin</synonym>
    <synonym>D-ampicillin</synonym>
    <synonym>D-cillin</synonym>
    <synonym>Delcillin</synonym>
    <synonym>Deripen</synonym>
    <synonym>Divercillin</synonym>
    <synonym>Doktacillin</synonym>
    <synonym>Duphacillin</synonym>
    <synonym>Geocillin</synonym>
    <synonym>Grampenil</synonym>
    <synonym>Guicitrina</synonym>
    <synonym>Guicitrine</synonym>
    <synonym>KS-R1</synonym>
    <synonym>Lifeampil</synonym>
    <synonym>Magnapen</synonym>
    <synonym>Marcillin</synonym>
    <synonym>Morepen</synonym>
    <synonym>Norobrittin</synonym>
    <synonym>Novo-ampicillin</synonym>
    <synonym>NSC 528986</synonym>
    <synonym>Nuvapen</synonym>
    <synonym>Olin kid</synonym>
    <synonym>Omnipen</synonym>
    <synonym>Orbicilina</synonym>
    <synonym>Pen a</synonym>
    <synonym>Pen ampil</synonym>
    <synonym>Penbristol</synonym>
    <synonym>Penbritin</synonym>
    <synonym>Penbrock</synonym>
    <synonym>Penicline</synonym>
    <synonym>Penimic</synonym>
    <synonym>Pensyn</synonym>
    <synonym>Pentrex</synonym>
    <synonym>Pentrexl</synonym>
    <synonym>Pentrexyl</synonym>
    <synonym>Pentritin</synonym>
    <synonym>Pfizerpen a</synonym>
    <synonym>Polycillin</synonym>
    <synonym>Ponecil</synonym>
    <synonym>Princillin</synonym>
    <synonym>Principen</synonym>
    <synonym>Qidamp</synonym>
    <synonym>Racenacillin</synonym>
    <synonym>Ro-ampen</synonym>
    <synonym>Rosampline</synonym>
    <synonym>Roscillin</synonym>
    <synonym>Semicillin</synonym>
    <synonym>Servicillin</synonym>
    <synonym>SK-ampicillin</synonym>
    <synonym>Sumipanto</synonym>
    <synonym>Supen</synonym>
    <synonym>Synpenin</synonym>
    <synonym>Texcillin</synonym>
    <synonym>Tokiocillin</synonym>
    <synonym>Tolomol</synonym>
    <synonym>Totacillin</synonym>
    <synonym>Totalciclina</synonym>
    <synonym>Totapen</synonym>
    <synonym>Trifacilina</synonym>
    <synonym>Ukapen</synonym>
    <synonym>Ultrabion</synonym>
    <synonym>Ultrabron</synonym>
    <synonym>Vampen</synonym>
    <synonym>Viccillin</synonym>
    <synonym>Vidocillin</synonym>
    <synonym>Vidopen</synonym>
    <synonym>Wypicil</synonym>
  </synonyms>
  <chemical_formula>C16H19N3O4S</chemical_formula>
  <average_molecular_weight>349.405</average_molecular_weight>
  <monisotopic_moleculate_weight>349.109626801</monisotopic_moleculate_weight>
  <iupac_name>6-[(2-amino-1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid</iupac_name>
  <traditional_iupac>6-[(2-amino-1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>69-53-4</cas_registry_number>
  <smiles>CC1(C)SC2C(NC(=O)C(N)C3=CC=CC=C3)C(=O)N2C1C(O)=O</smiles>
  <inchi>InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)</inchi>
  <inchikey>AVKUERGKIZMTKX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.</description>
    <direct_parent>N-acyl-alpha amino acids and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Azetidines</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Penams</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
      <alternative_parent>Thiazolidines</alternative_parent>
      <alternative_parent>Thiohemiaminal derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azetidine</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Beta-lactam</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Hemithioaminal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Penam</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
      <substituent>Thiazolidine</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.25e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 199-202° dec.</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>2.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>8.42</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>6-[(2-amino-1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>349.405</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>349.109626801</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1(C)SC2C(NC(=O)C(N)C3=CC=CC=C3)C(=O)N2C1C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H19N3O4S</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AVKUERGKIZMTKX-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>116.22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>88.05</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>35.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <hmdb_id>HMDB14559</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>28971</chebi_id>
  <biocyc_id/>
  <het_id>AIC</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce3248f188&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3248efd0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3248ee18&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3248ec60&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3248eaa8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Common pea</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pisum sativum</name_scientific>
      <ncbi_taxonomy_id>3888</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Milk and milk products</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
