<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:44 UTC</creation_date>
  <update_date>2025-11-18 23:45:04 UTC</update_date>
  <accession>FDB013477</accession>
  <name>Savoury taste-enhancing peptide</name>
  <description>Claimed as isolated from beef extract with a taste variously descr. as delicious tasting or umami/sour tasting. More recent workers concluded that the compound was not in fact present in beef extract and furthermore had little or no flavour or flavour enhancing props. Savoury taste-enhancing peptide is found in animal foods.</description>
  <synonyms>
    <synonym>Beefy meaty peptide</synonym>
    <synonym>BMP</synonym>
    <synonym>Delicious peptide</synonym>
    <synonym>Lysylglycylaspartylglutamylglutamylserylleucylalanine</synonym>
    <synonym>STEP</synonym>
  </synonyms>
  <chemical_formula>C48H81N3O36</chemical_formula>
  <average_molecular_weight>1276.161</average_molecular_weight>
  <monisotopic_moleculate_weight>1275.45997594</monisotopic_moleculate_weight>
  <iupac_name>N-[(2R,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4R,5S,6R)-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}oxan-3-yl]oxy}oxan-2-yl]methoxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidic acid</iupac_name>
  <traditional_iupac>N-[(2R,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4R,5S,6R)-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}oxan-3-yl]oxy}oxan-2-yl]methoxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidic acid</traditional_iupac>
  <cas_registry_number>73984-05-1</cas_registry_number>
  <smiles>[H][C@@]1(O)O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O[C@]3([H])O[C@]([H])(CO[C@]4([H])O[C@]([H])(CO)[C@@]([H])(O[C@]5([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]5([H])O)[C@]([H])(O)[C@@]4([H])N=C(C)O)[C@]([H])(O)[C@]([H])(O[C@]4([H])O[C@]([H])(CO)[C@@]([H])(O[C@]5([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]5([H])O)[C@]([H])(O)[C@@]4([H])N=C(C)O)[C@@]3([H])O)[C@]([H])(O)[C@@]2([H])N=C(C)O)[C@@]1([H])O</smiles>
  <inchi>InChI=1S/C48H81N3O36/c1-11(58)49-21-28(65)37(83-46-33(70)31(68)24(61)14(4-52)77-46)17(7-55)79-43(21)75-10-20-27(64)41(87-45-23(51-13(3)60)29(66)38(18(8-56)81-45)84-47-34(71)32(69)25(62)15(5-53)78-47)36(73)48(82-20)85-39-19(9-57)80-44(22(30(39)67)50-12(2)59)86-40-26(63)16(6-54)76-42(74)35(40)72/h14-48,52-57,61-74H,4-10H2,1-3H3,(H,49,58)(H,50,59)(H,51,60)/t14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24+,25+,26+,27+,28-,29-,30-,31+,32+,33-,34-,35-,36-,37-,38-,39-,40+,41+,42-,43-,44+,45+,46+,47+,48+/m1/s1</inchi>
  <inchikey>AMUWCSYEQMOUGI-BLWYTRGFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.</description>
    <direct_parent>Oligosaccharides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>glucosamine oligosaccharide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.99e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 182-184°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>N-[(2R,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4R,5S,6R)-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}oxan-3-yl]oxy}oxan-2-yl]methoxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>1276.161</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>1275.45997594</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@@]1(O)O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O[C@]3([H])O[C@]([H])(CO[C@]4([H])O[C@]([H])(CO)[C@@]([H])(O[C@]5([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]5([H])O)[C@]([H])(O)[C@@]4([H])N=C(C)O)[C@]([H])(O)[C@]([H])(O[C@]4([H])O[C@]([H])(CO)[C@@]([H])(O[C@]5([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]5([H])O)[C@]([H])(O)[C@@]4([H])N=C(C)O)[C@@]3([H])O)[C@]([H])(O)[C@@]2([H])N=C(C)O)[C@@]1([H])O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C48H81N3O36</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C48H81N3O36/c1-11(58)49-21-28(65)37(83-46-33(70)31(68)24(61)14(4-52)77-46)17(7-55)79-43(21)75-10-20-27(64)41(87-45-23(51-13(3)60)29(66)38(18(8-56)81-45)84-47-34(71)32(69)25(62)15(5-53)78-47)36(73)48(82-20)85-39-19(9-57)80-44(22(30(39)67)50-12(2)59)86-40-26(63)16(6-54)76-42(74)35(40)72/h14-48,52-57,61-74H,4-10H2,1-3H3,(H,49,58)(H,50,59)(H,51,60)/t14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24+,25+,26+,27+,28-,29-,30-,31+,32+,33-,34-,35-,36-,37-,38-,39-,40+,41+,42-,43-,44+,45+,46+,47+,48+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AMUWCSYEQMOUGI-BLWYTRGFSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>622.36</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>265.27</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>122.06</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>39</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>23</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::MsMs</type>
      <spectrum_id>108903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605520</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
