S-adenosyl-L-methionine

HCID 34756CAS 485-80-3

기본 정보

표준 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
분자식: C15H23N6O5S+
평균 분자량: 399.4 g/mol
단동위원소 질량: 399.14451526

개요

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.

이름 및 식별자

우선 이름: 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

이름 및 동의어

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

이름 더 보기

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: -3.5
극성 표면적: 184 Å²
수소 결합 공여자 수: 5
수소 결합 수용자 수: 10
회전 가능 결합 수: 7
무거운 원자 수: 27
형식 전하: 1
복잡도: 533

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15

LogP-5.3

Boiling Point78 °C

Physical DescriptionSolid

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

안전 및 규제

독성 정보

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 · 1건

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).

화학 및 산업

약리 정보

ATC CodeQA - Alimentary tract and metabolism

Metabolism/Metabolites · 1건

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

용도 및 제조

Uses · 1건

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.

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