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Revision as of 11:57, 15 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit Latest revision as of 17:10, 17 September 2023 edit undoKoIobok (talk | contribs)Extended confirmed users1,350 edits Added Category:Alpha-Amino acids 
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{{DISPLAYTITLE:''S''-Adenosyl-<small>L</small>-homocysteine}} {{DISPLAYTITLE:''S''-Adenosyl-<small>L</small>-homocysteine}}
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 460691502 | verifiedrevid = 460764948
|Name=''S''-Adenosyl-<small>L</small>-homocysteine
|ImageFile=S-Adenosyl-L-homocysteine.svg | Name=''S''-Adenosyl-<small>L</small>-homocysteine
| ImageFile=S-Adenosyl-L-homocystein.svg
|ImageSize= | ImageSize= 300px
|IUPACName= ''S''-(5'-Deoxyadenos-5'-yl)-<small>L</small>-homocysteine
|OtherNames=AdoHcy, 2-''S''-adenosyl-<small>L</small>-homocysteine,<br>5'-''S''-(3-Amino-3-carboxypropyl)-5'-thioadenosine | IUPACName=''S''-(5′-Deoxyadenos-5′-yl)-<small>L</small>-homocysteine
| SystematicName=(2''S'')-2-Amino-4-({methyl}sulfanyl)butanoic acid
| OtherNames=AdoHcy, 2-''S''-adenosyl-<small>L</small>-homocysteine,<br>5′-''S''-(3-Amino-3-carboxypropyl)-5′-thioadenosine
''S''-adenosylhomocysteine, SAH ''S''-adenosylhomocysteine, SAH
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}} | IUPHAR_ligand = 5265
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=979-92-0 | CASNo=979-92-0
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | ChEMBL = 418052
| UNII = 8K31Q2S66S
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 418052
| PubChem = 439155 | PubChem = 439155
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 388301 | ChemSpiderID = 388301
| SMILES = O=C(O)(N)CCSC3O(n2cnc1c(ncnc12)N)(O)3O | SMILES = O=C(O)(N)CCSC3O(n2cnc1c(ncnc12)N)(O)3O
| 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 | 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
| InChIKey = ZJUKTBDSGOFHSH-WFMPWKQPBX | InChIKey = ZJUKTBDSGOFHSH-WFMPWKQPBX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZJUKTBDSGOFHSH-WFMPWKQPSA-N | StdInChIKey = ZJUKTBDSGOFHSH-WFMPWKQPSA-N
| MeSHName=S-Adenosylhomocysteine | MeSHName=S-Adenosylhomocysteine
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI=16680 | ChEBI=16680
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG=C00021 | KEGG=C00021
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=
| Formula=C<sub>14</sub>H<sub>20</sub>N<sub>6</sub>O<sub>5</sub>S
| C=14|H=20|N=6|O=5|S=1 | C=14 | H=20 | N=6 | O=5 | S=1
| Appearance=
| MolarMass=384.412
| Appearance= | Density=
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''''S''-Adenosyl-<small>L</small>-homocysteine''' ('''SAH''') is the ] precursor to ].<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 ] of ].<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> ] converts SAH into homocysteine and ].
'''''S''-Adenosyl-<small>L</small>-homocysteine''' ('''SAH''') is an ] derivative used in several metabolic pathways in most organisms. It is an intermediate in the synthesis of ] and ].


== Biological role ==
SAH is formed by the ] of ] (SAM).
]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 ] products can bind the active site of DNA methyltransferase 3B and prevent the DNA duplex from binding to the ], which inhibits ].<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>


==External links== == References ==
{{Reflist}}

== External links ==
* *


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