S-Adenosyl-L-homocysteine

S-Adenosyl-l-homocysteine
Names
	IUPAC name S-(5′-Deoxyadenos-5′-yl)-l-homocysteine
	Other names AdoHcy, 2-S-adenosyl-l-homocysteine,; 5′-S-(3-Amino-3-carboxypropyl)-5′-thioadenosine S-adenosylhomocysteine, SAH
Identifiers
CAS Number	979-92-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16680 ;
ChEMBL	ChEMBL418052 ;
ChemSpider	388301 ;
ECHA InfoCard	100.012.328
IUPHAR/BPS	5265;
KEGG	C00021 ;
MeSH	S-Adenosylhomocysteine
PubChem CID	439155;
UNII	8K31Q2S66S ;
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 Key: ZJUKTBDSGOFHSH-WFMPWKQPSA-N ; 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 Key: ZJUKTBDSGOFHSH-WFMPWKQPBX;
	SMILES O=C(O)[C@@H](N)CCSC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O;
Properties
Chemical formula	C14H20N6O5S
Molar mass	384.412
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

S-Adenosyl-l-homocysteine (SAH) is the biosynthetic precursor to homocysteine.^[1] SAH is formed by the demethylation of S-adenosyl-l-methionine.^[2]^[3] Adenosylhomocysteinase converts SAH into homocysteine and adenosine.

References

^ Finkelstein, J. D. (2000). "Pathways and regulation of homocysteine metabolism in mammals". Semin. Thromb. Hemost. 26 (3): 219–25. doi:10.1055/s-2000-8466. PMID 11011839.
^ Ribbe, M. W.; Hu, Y.; Hodgson, K. O.; Hedman, B. (2014). "Biosynthesis of Nitrogenase Metalloclusters". Chem. Rev. 114 (8): 4063–4080. doi:10.1021/cr400463x. PMC 3999185. PMID 24328215.
^ James, S. Jill; Melnyk, Stepan; Pogribna, Marta; Pogribny, Igor P; Caudill, Marie A (2002). "Elevation in S-Adenosylhomocysteine and DNA Hypomethylation: Potential Epigenetic Mechanism for Homocysteine-Related Pathology". The Journal of Nutrition. 132 (8): 2361S–2366S. doi:10.1093/jn/132.8.2361S. PMID 12163693.

Names

IUPAC name S-(5′-Deoxyadenos-5′-yl)-l-homocysteine
Other names AdoHcy, 2-S-adenosyl-l-homocysteine, 5′-S-(3-Amino-3-carboxypropyl)-5′-thioadenosine S-adenosylhomocysteine, SAH
Identifiers
CAS Number	979-92-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16680
ChEMBL	ChEMBL418052
ChemSpider	388301
ECHA InfoCard	100.012.328
IUPHAR/BPS	5265
KEGG	C00021
MeSH	S-Adenosylhomocysteine
PubChem CID	439155
UNII	8K31Q2S66S
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 Key: ZJUKTBDSGOFHSH-WFMPWKQPSA-N 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 Key: ZJUKTBDSGOFHSH-WFMPWKQPBX
SMILES O=C(O)[C@@H](N)CCSC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O
Properties
Chemical formula	C₁₄H₂₀N₆O₅S
Molar mass	384.412
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).