S-adenosyl-L-methionine

HCID 34756CAS 485-80-3

基本情報

標準SMILES: C[S+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
InChIKey: MEFKEPWMEQBLKI-AIRLBKTGSA-O
分子式: C15H23N6O5S+
平均分子量: 399.4 g/mol
単同位体質量: 399.14451526

概要

S-adenosyl-L-methionine is a sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine. It has a role as a Mycoplasma genitalium metabolite, a coenzyme, a cofactor, a micronutrient, a nutraceutical, a Saccharomyces cerevisiae metabolite and a human metabolite. It is a conjugate acid of a S-adenosyl-L-methioninate. It is an enantiomer of a S-adenosyl-D-methionine. It is a tautomer of a S-adenosyl-L-methionine zwitterion.

名称と識別子

優先名称: S-adenosyl-L-methionine
IUPAC: [(3S)-3-amino-3-carboxypropyl]-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-methylsulfanium

名称と別名

S-adenosyl-L-methionine485-80-3SAMeadenosylmethionineCHEMBL224120Methionine, S-adenosyl-S-(5'-Adenosyl)-L-methionineCHEBI:15414(R)-S-adenosyl-L-methionine(S)-S-adenosyl-L-methionine((S)-3-Amino-3-carboxypropyl)(((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)sulfoniumS-(5'-deoxyadenosin-5'-yl)-L-methionine

名称をさらに表示

(R,S)-AdoMet(S,S)-AdoMet2-S-adenosyl-L-methionineSAMNCGC00167546-02ademethionineAdoMeAdenosine, 5'-[[(3S)-3-amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-

データベース識別子

CAS: 485-80-3
PubChem CID: 34756
DTXSID: DTXSID20110014
ChEMBL: CHEMBL224120
ChEBI: CHEBI:15414
Nikkaji: J260.469H

物性

構造計算による物性

XLogP: -3.5
極性表面積: 184 Å²
水素結合供与体数: 5
水素結合受容体数: 10
回転可能結合数: 7
重原子数: 27
形式電荷: 1
複雑度: 533

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

LogP-5.3

Boiling Point78 °C

Physical DescriptionSolid

Collision Cross Section185.6 Å² [M+H]+

安全と法規制

毒性情報

Exposure RoutesS-Adenosylmethionine is absorbed from the small intestine following oral intake. As absorption is affected by food, it is best to take on an empty stomach. Bioavailability is low following oral intake.

Toxicity Summary · 1 件

S-Adenosylmethionine (SAMe) is a natural substance present in the cells of the body. It is a direct metabolite of the essential amino acid L-methionine. SAMe plays a crucial biochemical role in the body by donating a one-carbon methyl group in a process called transmethylation. SAMe, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine and other molecules.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

化学と産業

薬理情報

ATC CodeQA - Alimentary tract and metabolism

Metabolism/Metabolites · 1 件

Significant first-pass metabolism in the liver. Approximately 50% of S-Adenosylmethionine (SAMe) is metabolized in the liver. SAMe is metabolized to S-adenosylhomocysteine, which is then metabolized to homocysteine. Homocysteine can either be metabolized to cystathionine and then cysteine or to methionine. The cofactor in the metabolism of homocysteine to cysteine is vitamin B6. Cofactors for the metabolism of homocysteine to methionine are folic acid, vitamin B12 and betaine.

Tissue LocationsEpidermis

Cellular LocationsEndoplasmic reticulum

Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency

用途と製造

Uses · 1 件

S-Adenosylmethionine (SAMe) is used as a drug in Europe for the treatment of depression, liver disorders, fibromyalgia, and osteoarthritis. It has also been introduced into the United States market as a dietary supplement for the support of bone and joint health, as well as mood and emotional well being.