<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:30:40 UTC</creation_date>
  <update_date>2026-08-19 06:56:14 UTC</update_date>
  <accession/>
  <common_name>Suberoylanilide hydroxamic acid</common_name>
  <class>SmallMolecule</class>
  <description>Suberoylanilide hydroxamic acid belongs to the benzene and substituted derivatives, a class of benzenoids within the organic compounds. It has the chemical formula $\text{C}_{14}\text{H}_{20}\text{N}_2\text{O}_3$ and an average molecular weight of 264.32 g/mol. Biologically, this compound acts as an inhibitor (PMC3145497), a drug (PMC3145497), and a chelator (PMC7052901). It targets nine proteins, serving as an inhibitor of Histone deacetylase 1 (HDAC1), Histone deacetylase 2 (HDAC2), Histone deacetylase 3 (HDAC3), and Protein deacetylase HDAC6, along with five other proteins.

The compound is recorded in 17 sources, including food preservation, antineoplastic agents in healthcare, pharmaceuticals and veterinary products, and household cleaning and consumer products such as perfumes within detergents and soaps, as well as non-electric simulated smoking devices. It is also found in electrical and electronic equipment, including amplifiers, antennas, electric hearing aids, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials. The recorded exposure route is oral.

Regarding health effects, subraylanilide hydroxamic acid is associated with cancer (PMC7824531), as well as an increase in neutropenia (PMC7581128) and thrombocytopenia (PMC7581128). Conversely, it is used as a treatment for cancer (PMC3145497) and has a therapeutic effect on glioblastoma (PMC12466395).</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>Vorinostat</synonym>
  </synonyms>
  <chemical_formula>C14H20N2O3</chemical_formula>
  <average_molecular_weight>264.3202</average_molecular_weight>
  <monisotopic_moleculate_weight>264.147392516</monisotopic_moleculate_weight>
  <iupac_name>N-hydroxy-N'-phenyloctanediamide</iupac_name>
  <traditional_iupac>SAHA</traditional_iupac>
  <cas_registry_number>149647-78-9</cas_registry_number>
  <smiles>ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)</inchi>
  <inchikey>WAEXFXRVDQXREF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class/>
    <direct_parent>Benzene and substituted derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>dicarboxylic acid diamide</descriptor>
      <descriptor>hydroxamic acid</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Vorinostat Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143843</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.16e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-hydroxy-N'-phenyloctanediamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>264.3202</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>264.147392516</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H20N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WAEXFXRVDQXREF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>78.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>73.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f721f741e20&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB02546</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5311</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id/>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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  </targets>
</compound>
