<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:10:47 UTC</creation_date>
  <update_date>2025-11-19 02:41:13 UTC</update_date>
  <accession>FDB022243</accession>
  <name>Sapropterin</name>
  <description>Sapropterin is converted from 7,8-dihydroneopterin triphosphate by 6-pyruvoyl tetrahydropterin synthase and sepiapterin reductase. It is essential in the formation of neurotransmitters and for nitric oxide synthase (PMID 16946131). [HMDB]</description>
  <synonyms>
    <synonym>(6R)-5,6,7,8-Tetrahydro-L-biopterin</synonym>
    <synonym>(6R)-5,6,7,8-Tetrahydrobiopterin</synonym>
    <synonym>(6R)-L-erythro-5,6,7,8-Tetrahydrobiopterin</synonym>
    <synonym>(6R)-L-erythro-Tetrahydrobiopterin</synonym>
    <synonym>(6R)-Tetrahydrobiopterin</synonym>
    <synonym>[6R-[6R*(1R*,2S*)]]-2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-Pteridinone</synonym>
    <synonym>6b-5,6,7,8-Tetrahydro-L-biopterin</synonym>
    <synonym>6R-BH4</synonym>
    <synonym>6R-Tetrahydro-L-biopterin</synonym>
    <synonym>L-erythro-5,6,7,8-Tetrahydrobiopterin</synonym>
    <synonym>L-erythro-Tetrahydrobiopterin</synonym>
    <synonym>R-THBP</synonym>
    <synonym>Sapropterin</synonym>
  </synonyms>
  <chemical_formula>C9H15N5O3</chemical_formula>
  <average_molecular_weight>241.2471</average_molecular_weight>
  <monisotopic_moleculate_weight>241.117489371</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one</traditional_iupac>
  <cas_registry_number>62989-33-7</cas_registry_number>
  <smiles>C[C@H](O)[C@H](O)C1CNC2=C(N1)C(=O)N=C(N)N2</smiles>
  <inchi>InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4?,6-/m0/s1</inchi>
  <inchikey>FNKQXYHWGSIFBK-BYAPIUGTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1,3-aminoalcohols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1,2-diol</substituent>
      <substituent>1,3-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>5,6,7,8-tetrahydrobiopterin</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.21e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>3.58</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>241.2471</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>241.117489371</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C[C@H](O)[C@H](O)C1CNC2=C(N1)C(=O)N=C(N)N2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H15N5O3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4?,6-/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>FNKQXYHWGSIFBK-BYAPIUGTSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>132</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>68.43</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>23.69</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>6</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>
    <pathway>
      <name>Catecholamine Biosynthesis</name>
      <smpdb_id>SMP00012</smpdb_id>
      <kegg_map_id>map00350</kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365130</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00787</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:0x000055ce31bf27a0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31bf25e8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31bf2430&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Phenylalanine-4-hydroxylase</name>
      <uniprot_id>P00439</uniprot_id>
      <uniprot_name/>
      <gene_name>PAH</gene_name>
    </enzyme>
    <enzyme>
      <name>Sepiapterin reductase</name>
      <uniprot_id>P35270</uniprot_id>
      <uniprot_name/>
      <gene_name>SPR</gene_name>
    </enzyme>
    <enzyme>
      <name>Tryptophan 5-hydroxylase 1</name>
      <uniprot_id>P17752</uniprot_id>
      <uniprot_name/>
      <gene_name>TPH1</gene_name>
    </enzyme>
    <enzyme>
      <name>Tryptophan 5-hydroxylase 2</name>
      <uniprot_id>Q8IWU9</uniprot_id>
      <uniprot_name/>
      <gene_name>TPH2</gene_name>
    </enzyme>
    <enzyme>
      <name>Tyrosine 3-monooxygenase</name>
      <uniprot_id>P07101</uniprot_id>
      <uniprot_name/>
      <gene_name>TH</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
