<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:27 UTC</creation_date>
  <update_date>2025-11-18 23:40:26 UTC</update_date>
  <accession>FDB012974</accession>
  <name>Mercenene</name>
  <description>Isolated from the common clam Mercenaria mercenaria and from Mercenaria campechiensis

Carmustine is one of the nitrosoureas indicated as palliative therapy as a single agent or in established combination therapy with other approved chemotherapeutic agents in treatment of brain tumors, multiple myeloma, Hodgkin's disease, and non-Hodgkin's lymphomas. Although it is generally agreed that carmustine alkylates DNA and RNA, it is not cross resistant with other alkylators. As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins. Mercenene is found in mollusks.</description>
  <synonyms>
    <synonym>1,3-Bis(2-Chloroethyl)-1-Nitrosourea</synonym>
    <synonym>1,3-Bis(2-chloroethyl)nitrosourea</synonym>
    <synonym>1,3-Bis(beta-chloroethyl)-1-nitrosourea</synonym>
    <synonym>1,3-BIS(CHLOROETHYL)-1-NITROSOUREA</synonym>
    <synonym>BCNU</synonym>
    <synonym>Bcnu [chloroethyl nitrosoureas]</synonym>
    <synonym>Becenum</synonym>
    <synonym>Bi cnu</synonym>
    <synonym>Bicnu</synonym>
    <synonym>Bicnu (TN)</synonym>
    <synonym>Bis-n,n'-(chloroethyl)nitrosourea</synonym>
    <synonym>Bis(2-chloroethyl)1-nitrosourea</synonym>
    <synonym>Bis(2-chloroethyl)nitrosourea</synonym>
    <synonym>Bis(chloroethyl)nitrosourea</synonym>
    <synonym>Bischlorethylnitrosourea</synonym>
    <synonym>Bischlorethylnitrosurea</synonym>
    <synonym>Bischloroethyl nitrosourea</synonym>
    <synonym>Bischloroethyl nitrosourea [chloroethyl nitrosoureas]</synonym>
    <synonym>Bischloroethylnitrosourea</synonym>
    <synonym>Carmubris</synonym>
    <synonym>Carmustin</synonym>
    <synonym>Carmustina</synonym>
    <synonym>Carmustine</synonym>
    <synonym>Carmustine (usan/inn)</synonym>
    <synonym>Carmustine [usan:inn:ban]</synonym>
    <synonym>Carmustine in ethanol</synonym>
    <synonym>Carmustinum</synonym>
    <synonym>FIVB</synonym>
    <synonym>Gliadel</synonym>
    <synonym>N,N'-Bis(2-Chloroethyl)-N-Nitrosourea</synonym>
    <synonym>Nitrumon</synonym>
    <synonym>Urea, 1,3-bis(2-chloroethyl)-1-nitroso-</synonym>
    <synonym>Urea, N,N'-bis(2-chloroethyl)-N-nitroso-</synonym>
  </synonyms>
  <chemical_formula>C5H9Cl2N3O2</chemical_formula>
  <average_molecular_weight>214.05</average_molecular_weight>
  <monisotopic_moleculate_weight>213.007181961</monisotopic_moleculate_weight>
  <iupac_name>1,3-bis(2-chloroethyl)-3-nitrosourea</iupac_name>
  <traditional_iupac>carmustine</traditional_iupac>
  <cas_registry_number>154-93-8</cas_registry_number>
  <smiles>ClCCNC(=O)N(CCCl)N=O</smiles>
  <inchi>InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)</inchi>
  <inchikey>DLGOEMSEDOSKAD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O.</description>
    <direct_parent>Nitrosoureas</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic carbonic acids and derivatives</class>
    <sub_class>Ureas</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alkyl chlorides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Nitrosamides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Semicarbazides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl chloride</substituent>
      <substituent>Alkyl halide</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Nitrosamide</substituent>
      <substituent>Nitrosourea</substituent>
      <substituent>Organic n-nitroso compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic nitroso compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Semicarbazide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>N-nitrosoureas</external_descriptor>
      <external_descriptor>organochlorine compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.53e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.02</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>11.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-5.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1,3-bis(2-chloroethyl)-3-nitrosourea</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>214.05</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>213.007181961</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>ClCCNC(=O)N(CCCl)N=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C5H9Cl2N3O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>DLGOEMSEDOSKAD-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>61.77</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>46.98</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</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>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>130538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2471178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2471179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2471180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2493905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2493906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2493907</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB14407</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>3423</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Mollusks</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id>6447</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
