基本情報
- CAS
29908-03-0- 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-N- 分子式
- C15H22N6O5S
- 平均分子量
- 398.4 g/mol
- 単同位体質量
- 398.137239
概要
S-adenosyl-L-methioninate is a sulfonium betaine that is a conjugate base of S-adenosyl-L-methionine obtained by the deprotonation of the carboxy group. It has a role as a human metabolite. It is functionally related to a L-methioninate. It is a conjugate base of a S-adenosyl-L-methionine.
名称と識別子
- 優先名称
- S-Adenosylmethionine
- IUPAC
- (2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]butanoate
- 現地名
- アデノシルメチオニン
- 英語名
- Ademetionine
- 分子式
- C15H22N6O5S
- 分子量
- 398.44
名称と別名
S-adenosylmethionineActive methionineS Adenosyl L MethionineS-adenosyl methionineDTXSID6032019S Adenosylmethionine Sulfate TosylateAdenosine, 5'-((3-amino-3-carboxypropyl)methylsulfonio)-5'-deoxy-, inner salt, (3S)-FO 1561S-adenosyl-methionineS AdenosylmethionineRefChem:53996((3R)-3-amino-3-carboxypropyl)((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methyl))methylsulfanium
名称をさらに表示
S-アデノシル-L-メチオニンメチオニルアデニラート活性メチオニンS-アデノシルメチオニンアデノシルメチオニンメチオニルアデノシンアデメチオニン(5'-アデノシル)[(S)-3-アミノ-3-カルボキシラトプロピル](メチル)スルホニウム5'-[[(S)-3-アミノ-3-カルボキシラトプロピル]メチルスルホニオ]-5'-デオキシアデノシン(S)-2-アミノ-4-(メチル(5′-アデノシル)スルホニオ)酪酸アニオン(2S)-2-アミノ-4-({[(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)スルファニウミル)ブタノアート5′-[[(S)-3-アミノ-3-カルボキシラトプロピル]メチルスルホニオ]-5′-デオキシアデノシン(5′-アデノシル)[(S)-3-アミノ-3-カルボキシラトプロピル](メチル)スルホニウム
物性
構造計算による物性
- XLogP
- -2.8
- 極性表面積
- 186 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 10
- 回転可能結合数
- 6
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 527
実験および物理化学的性質
Human DrugsBreast Feeding; Lactation; Milk, Human; Complementary Therapies
Collision Cross Section
184.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
184 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine]
185.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
186.46 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
物理化学的性質
- 貯蔵温度
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- 溶解性
- DMSO (Slightly, Sonicated), Water (Slightly)
- 外見
- Solid
- 色
- White to Yellow
- 安定性
- Very Hygroscopic
- InChIKey
- MEFKEPWMEQBLKI-WGIZDKKNNA-N
- SMILES
- O[C@@H]1[C@@H]([C@@H](C[S+](C)CC[C@H](N)C(=O)[O-])O[C@H]1N1C=NC2C(=NC=NC1=2)N)O |&1:1,2,3,9,15,r|
- CAS データベース
- 29908 · 29908-03-0(CAS DataBase Reference)
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。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 80% (4 of 5) of all reports.
Warning
H302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
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
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).
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- hs_code
- 29349990
- risk_code
- 49-23-34
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.
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.
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