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29908-03-0 分子结构
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(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(methyl)sulfaniumyl)butanoate

ChemBase编号:5
分子式:C15H22N6O5S
平均质量:398.43738
单一同位素质量:398.13723883
SMILES和InChIs

SMILES:
[S+](C[C@H]1O[C@@H](n2c3ncnc(N)c3nc2)[C@H](O)[C@@H]1O)(CC[C@H](N)C(=O)[O-])C
Canonical SMILES:
C[S+](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)[O-])N
InChI:
InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/t7-,8+,10+,11+,14+,27?/m0/s1
InChIKey:
MEFKEPWMEQBLKI-AIRLBKTGSA-N

引用这个纪录

CBID:5 http://www.chembase.cn/molecule-5.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(methyl)sulfaniumyl)butanoate
IUPAC传统名
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(methyl)sulfaniumyl)butanoate
商标名
Sam-Sulfate
SAMe Rx-Mood
别名
SAM-e
S-Adenosyl-L-methionine
SAM
AdoMet
S-Adenosylmethionine
CAS号
29908-03-0
PubChem SID
160963468
46505280
PubChem CID
34755
34756

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00118 external link
PubChem 34755 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 1.6665175  质子受体 10 
质子供体 LogD (pH = 5.5) -5.312802 
LogD (pH = 7.4) -5.3263273  Log P -5.3237367 
摩尔折射率 107.072 cm3 极化性 38.454018 Å3
极化表面积 185.46 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -1.99  LOG S -2.56 
溶解度 1.19e+00 g/l 

分子性质

分子性质

生物活性(PubChem)

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00118 external link
Item Information
Drug Groups approved; nutraceutical
Description Physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed)
Indication 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.
Pharmacology 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.
Toxicity Irritating to mucus membranes and upper respiratory tract. Can cause CNS depression.
Affected Organisms
Humans and other mammals
Biotransformation 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 S-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.
References
Finkelstein JD, Martin JJ: Homocysteine. Int J Biochem Cell Biol. 2000 Apr;32(4):385-9. [Pubmed]
Fodinger M, Horl WH, Sunder-Plassmann G: Molecular biology of 5,10-methylenetetrahydrofolate reductase. J Nephrol. 2000 Jan-Feb;13(1):20-33. [Pubmed]
Roje S: S-Adenosyl-L-methionine: beyond the universal methyl group donor. Phytochemistry. 2006 Aug;67(15):1686-98. [Pubmed]
Loenen WA: S-adenosylmethionine: jack of all trades and master of everything? Biochem Soc Trans. 2006 Apr;34(Pt 2):330-3. [Pubmed]
Chiang PK, Gordon RK, Tal J, Zeng GC, Doctor BP, Pardhasaradhi K, McCann PP: S-Adenosylmethionine and methylation. FASEB J. 1996 Mar;10(4):471-80. [Pubmed]
External Links
Wikipedia
PDRhealth
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Finkelstein JD, Martin JJ: Homocysteine. Int J Biochem Cell Biol. 2000 Apr;32(4):385-9. Pubmed
  • Fodinger M, Horl WH, Sunder-Plassmann G: Molecular biology of 5,10-methylenetetrahydrofolate reductase. J Nephrol. 2000 Jan-Feb;13(1):20-33. Pubmed
  • Roje S: S-Adenosyl-L-methionine: beyond the universal methyl group donor. Phytochemistry. 2006 Aug;67(15):1686-98. Pubmed
  • Loenen WA: S-adenosylmethionine: jack of all trades and master of everything? Biochem Soc Trans. 2006 Apr;34(Pt 2):330-3. Pubmed
  • Chiang PK, Gordon RK, Tal J, Zeng GC, Doctor BP, Pardhasaradhi K, McCann PP: S-Adenosylmethionine and methylation. FASEB J. 1996 Mar;10(4):471-80. Pubmed
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专利

专利

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