基本情報
- CAS
29908-03-0- 標準SMILES
C[S+](CC[C@H]([NH3+])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
- 399.14506403
概要
S-adenosyl-L-methionine zwitterion is a zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group. It has a role as a cofactor. It is an organic cation and a sulfonium compound. It is a tautomer of a S-adenosyl-L-methionine.
名称と識別子
- 優先名称
- Ademetionine
- IUPAC
- (2S)-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]-2-azaniumylbutanoate
- 現地名
- エスアデノシルメチオニン
- 英語名
- S-adenosylmethionine
- 分子式
- C15H23N6O5S
- 分子量
- 400.45
名称と別名
S-adenosyl-L-methionineAdemetionineadenosylmethionine139517-02-5(R)-S-adenosyl-L-methionine(S)-S-adenosyl-L-methionine(R,S)-AdoMet(S,S)-AdoMet2-S-adenosyl-L-methionine16-DENYPRASTERONEACETATESAM(R,S)-AdoMet zwitterion
名称をさらに表示
5'-[(3-アミノ-3-カルボキシプロピル)メチルスルホニオ]-5'-デオキシアデノシンS-(5'-アデノシル)メチオニン活性メチオニン5'-アデノシル(メチル)(3-アミノ-4-オキソ-4-ヒドロキシブチル)スルホニウムエスアデノシルメチオニン5′-アデノシル(メチル)(3-アミノ-4-オキソ-4-ヒドロキシブチル)スルホニウムS-(5′-アデノシル)メチオニン(3-アミノ-3-カルボキシプロピル)({[(2S,3S,4R,5R)-5-(6-アミノ-9H-プリン-9-イル)-3,4-ジヒドロキシオキソラン-2-イル]メチル})メチルスルファニウム5′-[(3-アミノ-3-カルボキシプロピル)メチルスルホニオ]-5′-デオキシアデノシン13CH3-SAMMethionine,activeS-ADENOSYLMETHIONINEAdenosine Impurity 39S-(5'-Adenosyl)methionineMEFKEPWMEQBLKI-AIRLBKTGSA-OS-adenosylmethionine USP/EP/BPAdemetionine 1,4-Butanedisulfonate Impurity 18 Monomer
物性
構造計算による物性
- XLogP
- -2.8
- 極性表面積
- 188 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 9
- 回転可能結合数
- 6
- 重原子数
- 27
- 形式電荷
- 1
- 複雑度
- 527
実験および物理化学的性質
LogP-5.3
Boiling Point78 °C
Physical DescriptionSolid
物理化学的性質
- InChIKey
- QOWKLNSTGYYNGX-MDHPBGAINA-N
- SMILES
- C(O)(=O)[C@H](CCS(C[C@H]1O[C@@H](N2C3=C(C(=NC=N3)N)N=C2)[C@H](O)[C@@H]1O)C)N |&1:3,8,10,21,23,r|
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302
化学と産業
薬理情報
ATC CodeA - Alimentary tract and metabolism
Pharmacodynamics
S-adenosylmethionine is an intermediate metabolite of methionine. Its involvement in methylation assists in cellular growth and repair, maintains the phospho-bilipid layer in cell membranes. It also helps in the maintenance of the action of several hormones and neurotransmitters that affect mood. Highest concentration are found in the brain and the liver.
Mechanism of Action
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.
Metabolism/Metabolites
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.
Absorption, Distribution and ExcretionS-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.
Tissue LocationsEpidermis
Cellular LocationsEndoplasmic reticulum
Metabolite Pathways
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