S-Adenosyl-L-homocysteine: Difference between revisions
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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL'). |
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{{DISPLAYTITLE:''S''-Adenosyl-<small>L</small>-homocysteine}} |
{{DISPLAYTITLE:''S''-Adenosyl-<small>L</small>-homocysteine}} |
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{{chembox |
{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 460764948 |
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|Name=''S''-Adenosyl-<small>L</small>-homocysteine |
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| Name=''S''-Adenosyl-<small>L</small>-homocysteine |
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| ImageFile=S-Adenosyl-L-homocystein.svg |
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|ImageSize= |
| ImageSize= 300px |
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|IUPACName= ''S''-(5'-Deoxyadenos-5'-yl)-<small>L</small>-homocysteine |
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| IUPACName=''S''-(5′-Deoxyadenos-5′-yl)-<small>L</small>-homocysteine |
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| SystematicName=(2''S'')-2-Amino-4-({[(2''S'',3''S'',4''R'',5''R'')-5-(6-amino-9''H''-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid |
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| OtherNames=AdoHcy, 2-''S''-adenosyl-<small>L</small>-homocysteine,<br>5′-''S''-(3-Amino-3-carboxypropyl)-5′-thioadenosine |
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''S''-adenosylhomocysteine, SAH |
''S''-adenosylhomocysteine, SAH |
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|Section1= |
|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| IUPHAR_ligand = 5265 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=979-92-0 |
| CASNo=979-92-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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⚫ | |||
| UNII = 8K31Q2S66S |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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⚫ | |||
| PubChem = 439155 |
| PubChem = 439155 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 388301 |
| ChemSpiderID = 388301 |
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| SMILES = O=C(O)[C@@H](N)CCSC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O |
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| InChI = 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/s1 |
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| InChIKey = ZJUKTBDSGOFHSH-WFMPWKQPBX |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZJUKTBDSGOFHSH-WFMPWKQPSA-N |
| StdInChIKey = ZJUKTBDSGOFHSH-WFMPWKQPSA-N |
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| MeSHName=S-Adenosylhomocysteine |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI=16680 |
| ChEBI=16680 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG=C00021 |
| KEGG=C00021 |
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}} |
}} |
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|Section2= |
|Section2={{Chembox Properties |
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| Formula= |
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| Formula=C<sub>14</sub>H<sub>20</sub>N<sub>6</sub>O<sub>5</sub>S |
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| C=14 | H=20 | N=6 | O=5 | S=1 |
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| Appearance= |
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| MolarMass=384.412 |
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| Density= |
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| MeltingPt= |
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| BoilingPt= |
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| Solubility= |
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| Solubility= |
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}} |
}} |
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|Section3= |
|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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| AutoignitionPt = |
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| Autoignition= |
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}} |
}} |
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}} |
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'''''S''-Adenosyl-<small>L</small>-homocysteine''' ('''SAH''') is the [[biosynthetic]] precursor to [[homocysteine]].<ref>{{cite journal | vauthors = Finkelstein JD | title = Pathways and regulation of homocysteine metabolism in mammals | journal = Seminars in Thrombosis and Hemostasis | volume = 26 | issue = 3 | pages = 219–225 | year = 2000 | pmid = 11011839 | doi = 10.1055/s-2000-8466 }}</ref> SAH is formed by the [[demethylation]] of [[S-Adenosyl methionine|''S''-adenosyl-<small>L</small>-methionine]].<ref>{{cite journal | vauthors = Ribbe MW, Hu Y, Hodgson KO, Hedman B | title = Biosynthesis of nitrogenase metalloclusters | journal = Chemical Reviews | volume = 114 | issue = 8 | pages = 4063–4080 | date = April 2014 | pmid = 24328215 | pmc = 3999185 | doi = 10.1021/cr400463x }}</ref><ref>{{cite journal | vauthors = James SJ, Melnyk S, Pogribna M, Pogribny IP, Caudill MA | title = Elevation in S-adenosylhomocysteine and DNA hypomethylation: potential epigenetic mechanism for homocysteine-related pathology | journal = The Journal of Nutrition | volume = 132 | issue = 8 Suppl | pages = 2361S–2366S | date = August 2002 | pmid = 12163693 | doi = 10.1093/jn/132.8.2361S | doi-access = free }}</ref> [[Adenosylhomocysteinase]] converts SAH into homocysteine and [[adenosine]]. |
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'''''S''-Adenosyl-<small>L</small>-homocysteine''' ('''SAH''') is an [[amino acid]] derivative used in several metabolic pathways in most organisms. It is an intermediate in the synthesis of [[cysteine]] and [[adenosine]]. |
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== Biological role == |
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SAH is formed by the [[demethylation]] of [[S-Adenosyl-L-methionine|''S''-adenosyl-<small>L</small>-methionine]] (SAM). |
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[[DNA methyltransferase]]s are inhibited by SAH.<ref>{{cite journal | vauthors = Kumar R, Srivastava R, Singh RK, Surolia A, Rao DN | title = Activation and inhibition of DNA methyltransferases by S-adenosyl-L-homocysteine analogues | journal = Bioorganic & Medicinal Chemistry | volume = 16 | issue = 5 | pages = 2276–2285 | date = March 2008 | pmid = 18083524 | doi = 10.1016/j.bmc.2007.11.075 }}</ref> Two ''S''-adenosyl-<small>L</small>-homocysteine [[Cofactor (biochemistry)|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]].<ref>{{cite journal | vauthors = Lin CC, Chen YP, Yang WZ, Shen JC, Yuan HS | title = Structural insights into CpG-specific DNA methylation by human DNA methyltransferase 3B | journal = Nucleic Acids Research | volume = 48 | issue = 7 | pages = 3949–3961 | date = April 2020 | pmid = 32083663 | pmc = 7144912 | doi = 10.1093/nar/gkaa111 }}</ref> |
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== |
== References == |
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{{Reflist}} |
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== External links == |
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*[http://biocyc.org/ECOLI/NEW-IMAGE?type=COMPOUND&object=ADENOSYL-HOMO-CYS BioCYC E.Coli K-12 Compound: S-adenosyl-L-homocysteine] |
*[http://biocyc.org/ECOLI/NEW-IMAGE?type=COMPOUND&object=ADENOSYL-HOMO-CYS BioCYC E.Coli K-12 Compound: S-adenosyl-L-homocysteine] |
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[[Category:Nucleosides]] |
[[Category:Nucleosides]] |
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[[Category:Purines]] |
[[Category:Purines]] |
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[[Category:Alpha-Amino acids]] |
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[[Category:Amino acid derivatives]] |
[[Category:Amino acid derivatives]] |
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{{biochem-stub}} |
{{biochem-stub}} |
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[[es:S-Adenosil L-homocisteína]] |
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[[fr:S-adénosylhomocystéine]] |
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[[ja:S-アデノシル-L-ホモシステイン]] |
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[[zh:S-腺苷-L-高半胱氨酸]] |