S-Adenosyl-L-homocysteine

S-Adenosyl-L-homocysteine

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^Y
PubChem	439155
ChemSpider	388301^Y
KEGG	C00021^Y
MeSH	S-Adenosylhomocysteine
ChEBI	CHEBI:16680^Y
ChEMBL	CHEMBL418052^Y
Jmol-3D images	Image 1
SMILES O=C(O)[C@@H](N)CCSC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O
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^Y Key: ZJUKTBDSGOFHSH-WFMPWKQPSA-N^Y 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
Properties
Molecular formula	C₁₄H₂₀N₆O₅S
Molar mass	384.41 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

S-Adenosyl-L-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.

SAH is formed by the demethylation of S-adenosyl-L-methionine (SAM).

External links

BioCYC E.Coli K-12 Compound: S-adenosyl-L-homocysteine

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine · Allysine · α-Aminoadipic acid · α-Aminoadipate · Glutaryl-CoA · Glutaconyl-CoA · Crotonyl-CoA · β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid · Isovaleryl-CoA · 3-Methylcrotonyl-CoA · 3-Methylglutaconyl-CoA · HMG-CoA

tryptophan→alanine→	N'-Formylkynurenine · Kynurenine · Anthranilic acid · 3-Hydroxykynurenine · 3-Hydroxyanthranilic acid · 2-Amino-3-carboxymuconic semialdehyde · 2-Aminomuconic semialdehyde · 2-Aminomuconic acid · Glutaryl-CoA

G→pyruvate→citrate

glycine→serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine · Phosphocreatine · Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid · Imidazol-4-one-5-propionic acid · Formiminoglutamic acid · Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Ornithine · Putrescine · Agmatine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid · Isobutyryl-CoA · Methacrylyl-CoA · 3-Hydroxyisobutyryl-CoA · 3-Hydroxyisobutyric acid · 2-Methyl-3-oxopropanoic acid

isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid · 2-Methylbutyryl-CoA · Tiglyl-CoA · 2-Methylacetoacetyl-CoA

methionine→	generation of homocysteine: S-Adenosyl methionine · S-Adenosyl-L-homocysteine · Homocysteine conversion to cysteine: Cystathionine · alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate


phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid · Homogentisic acid · 4-Maleylacetoacetate

G→oxaloacetate

see urea cycle

Other


Cysteine metabolism	Cysteine sulfinic acid

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i