<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:55 UTC</creation_date>
  <update_date>2019-11-26 03:09:04 UTC</update_date>
  <accession>FDB013798</accession>
  <name>beta-Boswellic acid</name>
  <description>Constituent of frankincense (Boswellia subspecies) and olibanum oil

Boswellic acid (BA) is an active component of Boswellia serrata (also known as Salai guggul). Extensive research in the past 30 years identified the active component of this resin as BA (a pentacyclic triterpenic acid) and its derivatives (acetyl-beta-boswellic acid, 11-keto-beta-boswellic acid and acetyl-11-keto-beta-boswellic acid). In animal models of inflammation, BA has been shown to be an effective adjuvant mitigating bovine serum albumin-induced arthritis and osteoarthritis. The anti-arthritic potential of BA is a result of its anti-inflammatory activity, mediated through inhibition of NF-kB, COX-2 and 5-LOX. ((PMID: 17475558, 3429205). beta-Boswellic acid is found in herbs and spices.</description>
  <synonyms>
    <synonym>(3alpha,4beta)-3-Hydroxy-urs-12-en-23-Oate</synonym>
    <synonym>(3alpha,4beta)-3-Hydroxy-urs-12-en-23-Oic acid</synonym>
    <synonym>3-Hydroxy-12-ursen-24-oic acid</synonym>
    <synonym>b-Boswellate</synonym>
    <synonym>b-Boswellic acid</synonym>
    <synonym>beta-Boswellate</synonym>
    <synonym>beta-Boswellic acid</synonym>
    <synonym>Boswellate</synonym>
    <synonym>Boswellic acid</synonym>
    <synonym>β-boswellate</synonym>
    <synonym>β-boswellic acid</synonym>
  </synonyms>
  <chemical_formula>C30H48O3</chemical_formula>
  <average_molecular_weight>456.7003</average_molecular_weight>
  <monisotopic_moleculate_weight>456.360345402</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid</iupac_name>
  <traditional_iupac>3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4-carboxylic acid</traditional_iupac>
  <cas_registry_number>631-69-6</cas_registry_number>
  <smiles>CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C5CCC34C)C(O)=O)C2C1C</smiles>
  <inchi>InChI=1S/C30H48O3/c1-18-10-13-26(3)16-17-28(5)20(24(26)19(18)2)8-9-21-27(4)14-12-23(31)30(7,25(32)33)22(27)11-15-29(21,28)6/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)</inchi>
  <inchikey>NBGQZFQREPIKMG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <direct_parent>Triterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxysteroids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>15-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.94e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 238-240° (228-232°)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>6.58</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.57</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>456.7003</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>456.360345402</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C5CCC34C)C(O)=O)C2C1C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C30H48O3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C30H48O3/c1-18-10-13-26(3)16-17-28(5)20(24(26)19(18)2)8-9-21-27(4)14-12-23(31)30(7,25(32)33)22(27)11-15-29(21,28)6/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>NBGQZFQREPIKMG-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>57.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>133.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>55.17</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>107932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>120400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>122636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>123444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>129935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>851805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>851806</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB02388</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31845670&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31845440&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Herbs and Spices</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>
