<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:50 UTC</creation_date>
  <update_date>2019-11-26 03:08:47 UTC</update_date>
  <accession>FDB013644</accession>
  <name>Gibberellin A3</name>
  <description>Gibberellic acid is a very potent hormone whose natural occurrence in plants controls their development. Since GA regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect.
Gibberellic acid is a hormone found in plants. Gibberelic acid is a simple gibberellin promoting growth and elongation of cells. Affects decomposition of plants. Helps plants grow if used in small amounts, but eventually plants grow a tolerance for it. Gibberellic acid stimulates the cells of germinating seeds to produce mRNA molecules that code for hydrolytic enzymes. [HMDB]</description>
  <synonyms>
    <synonym>2b-Hydroxygibberellin 1</synonym>
    <synonym>Activol</synonym>
    <synonym>Berelex</synonym>
    <synonym>Brellin</synonym>
    <synonym>GA3</synonym>
    <synonym>Gib-sol</synonym>
    <synonym>Gib-tabs</synonym>
    <synonym>Gibb-tabs</synonym>
    <synonym>Gibberelate</synonym>
    <synonym>Gibberelic acid</synonym>
    <synonym>Gibberelin</synonym>
    <synonym>Gibberellate</synonym>
    <synonym>Gibberellic acid</synonym>
    <synonym>Gibberellic acid, BSI</synonym>
    <synonym>Gibberellin 1</synonym>
    <synonym>Gibberellin X</synonym>
    <synonym>Gibberellins</synonym>
    <synonym>Gibberellinsaeure</synonym>
    <synonym>Gibberillate</synonym>
    <synonym>Gibberillic acid</synonym>
    <synonym>Gibrescol</synonym>
    <synonym>Gibrofit</synonym>
  </synonyms>
  <chemical_formula>C19H22O6</chemical_formula>
  <average_molecular_weight>346.3744</average_molecular_weight>
  <monisotopic_moleculate_weight>346.141638436</monisotopic_moleculate_weight>
  <iupac_name>5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid</iupac_name>
  <traditional_iupac>5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid</traditional_iupac>
  <cas_registry_number>77-06-5</cas_registry_number>
  <smiles>CC12C3C(C(O)=O)C45CC(=C)C(O)(C4)CCC5C3(OC1=O)C=CC2O</smiles>
  <inchi>InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)</inchi>
  <inchikey>IXORZMNAPKEEDV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as c19-gibberellin 6-carboxylic acids. These are c19-gibberellins with a carboxyl group at the 6-position.</description>
    <direct_parent>C19-gibberellin 6-carboxylic acids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Diterpene lactones</alternative_parent>
      <alternative_parent>Gamma butyrolactones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-norgibberellane-6-carboxylic acid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Diterpene lactone</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.95e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.35</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>346.3744</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>346.141638436</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC12C3C(C(O)=O)C45CC(=C)C(O)(C4)CCC5C3(OC1=O)C=CC2O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C19H22O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>IXORZMNAPKEEDV-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>104.06</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>86.42</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>34.86</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</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::CMs</type>
      <spectrum_id>110390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>123350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3436279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3436280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3436281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3436282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3436283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3436284</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB03559</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:0x000055ce31f8ad40&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Apple</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Malus pumila</name_scientific>
      <ncbi_taxonomy_id>283210</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Barley</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hordeum vulgare</name_scientific>
      <ncbi_taxonomy_id>4513</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Black tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Chayote</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sechium edule</name_scientific>
      <ncbi_taxonomy_id>184140</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common grape</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vitis vinifera</name_scientific>
      <ncbi_taxonomy_id>29760</ncbi_taxonomy_id>
    </food>
    <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>Common wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum aestivum</name_scientific>
      <ncbi_taxonomy_id>4565</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cowpea</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vigna unguiculata</name_scientific>
      <ncbi_taxonomy_id>3917</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cucumber</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cucumis sativus</name_scientific>
      <ncbi_taxonomy_id>3659</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Green tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Herbal tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Lettuce</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lactuca sativa</name_scientific>
      <ncbi_taxonomy_id>4236</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Lima bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus lunatus</name_scientific>
      <ncbi_taxonomy_id>3884</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mandarin orange (Clementine, Tangerine)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus reticulata</name_scientific>
      <ncbi_taxonomy_id>85571</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mango</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mangifera indica</name_scientific>
      <ncbi_taxonomy_id>29780</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Muskmelon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cucumis melo</name_scientific>
      <ncbi_taxonomy_id>3656</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Oat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Avena sativa</name_scientific>
      <ncbi_taxonomy_id>4498</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Okra</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Abelmoschus esculentus</name_scientific>
      <ncbi_taxonomy_id>455045</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Papaya</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carica papaya</name_scientific>
      <ncbi_taxonomy_id>3649</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Peach</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus persica</name_scientific>
      <ncbi_taxonomy_id>3760</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pear</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pyrus communis</name_scientific>
      <ncbi_taxonomy_id>23211</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Red tea</name>
      <food_type>Type 1</food_type>
      <category/>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Romaine lettuce</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lactuca sativa L. var. longifolia</name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Rye</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Secale cereale</name_scientific>
      <ncbi_taxonomy_id>4550</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Safflower</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carthamus tinctorius</name_scientific>
      <ncbi_taxonomy_id>4222</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Scarlet bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus coccineus</name_scientific>
      <ncbi_taxonomy_id>3886</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Soft-necked garlic</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Allium sativum L. var. sativum</name_scientific>
      <ncbi_taxonomy_id>4682</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sour cherry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus cerasus</name_scientific>
      <ncbi_taxonomy_id>140311</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Strawberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Fragaria X ananassa</name_scientific>
      <ncbi_taxonomy_id>3747</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Swamp cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ipomoea aquatica</name_scientific>
      <ncbi_taxonomy_id>89636</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Swede</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica napus</name_scientific>
      <ncbi_taxonomy_id>3708</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet cherry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus avium</name_scientific>
      <ncbi_taxonomy_id>42229</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet orange</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus sinensis</name_scientific>
      <ncbi_taxonomy_id>2711</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet potato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ipomoea batatas</name_scientific>
      <ncbi_taxonomy_id>4120</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Tea</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Camellia sinensis</name_scientific>
      <ncbi_taxonomy_id>4442</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turnip</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica rapa var. rapa</name_scientific>
      <ncbi_taxonomy_id>51350</ncbi_taxonomy_id>
    </food>
    <food>
      <name>White lupine</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lupinus albus</name_scientific>
      <ncbi_taxonomy_id>3870</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
