<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2018-07-17 17:20:42 UTC</creation_date>
  <update_date>2020-03-13 17:34:46 UTC</update_date>
  <accession>BMDB0062225</accession>
  <secondary_accessions>
    <accession>BMDB62225</accession>
  </secondary_accessions>
  <name>Arginyl-Cysteine</name>
  <description>Arginyl-cysteine, also known as R-c dipeptide or arg-cys, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Arginyl-cysteine is possibly soluble (in water) and a very strong basic compound (based on its pKa).</description>
  <synonyms>
    <synonym>2-[(2-Amino-5-carbamimidamido-1-hydroxypentylidene)amino]-3-sulfanylpropanoate</synonym>
    <synonym>2-[(2-Amino-5-carbamimidamido-1-hydroxypentylidene)amino]-3-sulphanylpropanoate</synonym>
    <synonym>2-[(2-Amino-5-carbamimidamido-1-hydroxypentylidene)amino]-3-sulphanylpropanoic acid</synonym>
    <synonym>Arg-cys</synonym>
    <synonym>Arginine cysteine dipeptide</synonym>
    <synonym>Arginine-cysteine dipeptide</synonym>
    <synonym>Arginylcysteine</synonym>
    <synonym>L-Arginyl-L-cysteine</synonym>
    <synonym>R-C Dipeptide</synonym>
    <synonym>RC Dipeptide</synonym>
  </synonyms>
  <chemical_formula>C9H19N5O3S</chemical_formula>
  <average_molecular_weight>277.344</average_molecular_weight>
  <monisotopic_moleculate_weight>277.120860189</monisotopic_moleculate_weight>
  <iupac_name>2-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]-3-sulfanylpropanoic acid</iupac_name>
  <traditional_iupac>2-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]-3-sulfanylpropanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>NC(CCCNC(N)=N)C(O)=NC(CS)C(O)=O</smiles>
  <inchi>InChI=1S/C9H19N5O3S/c10-5(2-1-3-13-9(11)12)7(15)14-6(4-18)8(16)17/h5-6,18H,1-4,10H2,(H,14,15)(H,16,17)(H4,11,12,13)</inchi>
  <inchikey>OSASDIVHOSJVII-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Dipeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cysteine and derivatives</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-dipeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic 1,3-dipolar compound</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>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state/>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]-3-sulfanylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>277.344</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>277.120860189</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CCCNC(N)=N)C(O)=NC(CS)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H19N5O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H19N5O3S/c10-5(2-1-3-13-9(11)12)7(15)14-6(4-18)8(16)17/h5-6,18H,1-4,10H2,(H,14,15)(H,16,17)(H4,11,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OSASDIVHOSJVII-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>157.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</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>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>40798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610566</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB098191</foodb_id>
  <chemspider_id>8119125</chemspider_id>
  <pubchem_compound_id>9943513</pubchem_compound_id>
  <chebi_id/>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
