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^Y
ChEBI	CHEBI:16680^Y
ChEMBL	ChEMBL418052^Y
ChemSpider	388301^Y
IUPHAR/BPS	5265
Jmol interactive 3D	Image
KEGG	C00021^Y
MeSH	S-Adenosylhomocysteine
PubChem	439155
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
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).
Y verify (what is ^YN ?)
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-Ketoadipate 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→	Agmatine Ornithine Cadaverine Putrescine

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-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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