<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4510</id>
  <title>T3D4456</title>
  <common-name>S-Adenosylmethionine</common-name>
  <description>Physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed).
S-Adenosylmethionine is only found in individuals that have used or taken this drug. It is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed)S-Adenosylmethionine (SAMe) is a natural substance present in the cells of the body. It is a direct metabolite of the essential amino acid L-methionine. SAMe plays a crucial biochemical role in the body by donating a one-carbon methyl group in a process called transmethylation. SAMe, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine and other molecules.</description>
  <cas>29908-03-0</cas>
  <pubchem-id>34756</pubchem-id>
  <chemical-formula>C15H23N6O5S</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point>78 °C</boiling-point>
  <density nil="true"/>
  <solubility>1.19e+00 g/l</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>S-Adenosylmethionine is absorbed from the small intestine following oral intake. As absorption is affected by food, it is best to take on an empty stomach. Bioavailability is low following oral intake.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>S-Adenosylmethionine (SAMe) is a natural substance present in the cells of the body. It is a direct metabolite of the essential amino acid L-methionine. SAMe plays a crucial biochemical role in the body by donating a one-carbon methyl group in a process called transmethylation. SAMe, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine and other molecules.</mechanism-of-toxicity>
  <metabolism>Significant first-pass metabolism in the liver. Approximately 50% of S-Adenosylmethionine (SAMe) is metabolized in the liver. SAMe is metabolized to S-adenosylhomocysteine, which is then metabolized to homocysteine. Homocysteine can either be metabolized to cystathionine and then cysteine or to methionine. The cofactor in the metabolism of homocysteine to cysteine is vitamin B6. Cofactors for the metabolism of homocysteine to methionine are folic acid, vitamin B12 and betaine.</metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>S-Adenosylmethionine (SAMe) is used as a drug in Europe for the treatment of depression, liver disorders, fibromyalgia, and osteoarthritis. It has also been introduced into the United States market as a dietary supplement for the support of bone and joint health, as well as mood and emotional well being.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects></health-effects>
  <symptoms></symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2014-08-29T06:51:25Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:24:01Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>S-Adenosylmethionine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C00019</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>15414</chebi-id>
  <biocyc-id>S-ADENOSYLMETHIONINE</biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id></stitch-id>
  <drugbank-id>DB00118</drugbank-id>
  <pdb-id>SAM</pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12</moldb-smiles>
  <moldb-formula>C15H23N6O5S</moldb-formula>
  <moldb-inchi>InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1</moldb-inchi>
  <moldb-inchikey>MEFKEPWMEQBLKI-AIRLBKTGSA-O</moldb-inchikey>
  <moldb-average-mass type="decimal">399.445</moldb-average-mass>
  <moldb-mono-mass type="decimal">399.145063566</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp>-5.3</logp>
  <hmdb-id>HMDB01185</hmdb-id>
  <chembl-id>CHEMBL224120</chembl-id>
  <chemspider-id>31983</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Takayasu Tsuchida, Fumihiro Yoshinaga, Shinji Okumura, &amp;#8220;Method for producing S-adenosylmethionine or methylthioadenosine by yeast.&amp;#8221; U.S. Patent US3962034, issued November, 1971.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003416</chemdb-id>
  <dsstox-id>DTXSID6032019</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00014313</susdat-id>
  <iupac>(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(methyl)sulfaniumyl)butanoate</iupac>
  <moldb-polar-surface-area>182.63000000000002</moldb-polar-surface-area>
  <moldb-refractivity>96.2349</moldb-refractivity>
  <moldb-polarizability>40.370553374384066</moldb-polarizability>
  <moldb-rotatable-bond-count>7</moldb-rotatable-bond-count>
  <moldb-acceptor-count>10</moldb-acceptor-count>
  <moldb-donor-count>5</moldb-donor-count>
  <moldb-pka-strongest-acidic>1.7027541004150226</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>9.414366078981788</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>-1.99</moldb-alogps-logp>
  <moldb-alogps-logs>-2.56</moldb-alogps-logs>
  <moldb-alogps-solubility>1.19e+00 g/l</moldb-alogps-solubility>
</compound>
