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S-Adenosyl-L-homocysteine
S-Adenosyl-L-homocysteine (SAH) is the biosynthetic precursor to homocysteine. SAH is formed by the demethylation of S-adenosyl-L-methionine. Adenosylhomocysteinase converts SAH into homocysteine and adenosine.
| Column 1 | Column 2 |
|---|---|
| IUPAC name | |
| S-(5′-Deoxyadenos-5′-yl)-L-homocysteine | |
| Systematic IUPAC name | |
| (2S)-2-Amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid | |
| Other names | |
| AdoHcy, 2-S-adenosyl-L-homocysteine,5′-S-(3-Amino-3-carboxypropyl)-5′-thioadenosine | |
| S-adenosylhomocysteine, SAH | |
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}979-92-0 Y |
| 3D model (JSmol) | Interactive image |
| ChEBI | CHEBI:16680 Y |
| ChEMBL | ChEMBL418052 Y |
| ChemSpider | 388301 Y |
| ECHA InfoCard | 100.012.328 |
| IUPHAR/BPS | 5265 |
| KEGG | C00021 Y |
| MeSH | S-Adenosylhomocysteine |
| PubChem CID | 439155 |
| UNII | 8K31Q2S66S Y |
| CompTox Dashboard (EPA) | DTXSID30895860 |
| InChI | |
| InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1 YKey: ZJUKTBDSGOFHSH-WFMPWKQPSA-N YInChI=1/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1Key: ZJUKTBDSGOFHSH-WFMPWKQPBX | |
| SMILES | |
| O=C(O)C@@HCCSC[C@H]3OC@@HC@H[C@@H]3O | |
| Chemical formula | C14H20N6O5S |
| Molar mass | 384.41 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Y verify (what is YN ?) |
Infobox references | |
S-Adenosyl-L-homocysteine (SAH) is the biosynthetic precursor to homocysteine. SAH is formed by the demethylation of S-adenosyl-L-methionine. Adenosylhomocysteinase converts SAH into homocysteine and adenosine.
DNA methyltransferases are inhibited by SAH. Two S-adenosyl-L-homocysteine cofactor products can bind the active site of DNA methyltransferase 3B and prevent the DNA duplex from binding to the active site, which inhibits DNA methylation.
- BioCYC E.Coli K-12 Compound: S-adenosyl-L-homocysteine
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