S-Adenosyl-L-methionine
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S-Adenosyl-L-methionine
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CAS No:
29908-03-0
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Formula:
C15H22N6O5S
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Chemical Name:
S-Adenosyl-L-methionine
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Synonyms:
Adenosine,5′-[[(3S)-3-amino-3-carboxypropyl]methylsulfonio]-5′-deoxy-,inner salt;Adenosine,5′-[(L-3-amino-3-carboxypropyl)methylsulfonio]-5′-deoxy-,hydroxide,inner salt;Adenosine,5′-[(3-amino-3-carboxypropyl)methylsulfonio]-5′-deoxy-,hydroxide,inner salt,(3S)-;Methionine,S-adenosyl-;S-Adenosylmethionine;S-Adenosyl-L-methionine;L-Methionine,S-adenosyl-;L-S-Adenosylmethionine;Ademetionine;SAMe;Adenosyl-L-methionine;Active methionine;S Amet;Donamet;AdoMet;Transmetil;SAM;SAH (S-Adenosylmethionine);S-Adenosyl methionine;2613-02-7;5134-37-2;23095-97-8;28378-99-6;86522-35-2;86866-89-9
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CAS No:
Description
Ademetionine 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.
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 derives from a L-methioninate. It is a conjugate base of a S-adenosyl-L-methionine.|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)
S-Adenosyl-L-methionine Basic Attributes
400.45
398.13723900 g/mol
249-946-8
6EZ5466ZUX|K093C397UL
DTXSID6032019|DTXSID20110014|DTXSID40169160|DTXSID40436187
A - Alimentary tract and metabolism
2934999090
Characteristics
547.02000
-0.26280
247-249ºC
78
-20°C
184.5 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|186.46 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|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)]|185.6 Ų [M+H]+
Safety Information
49-23-34
53-23-36/37/39-45
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P322, P330, P337+P313, P363, and P501|Aggregated GHS information provided by 5 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
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.
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.
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.
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.
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.
Ademetionine
Computed Properties
Molecular Weight:398.4
XLogP3:-2.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:6
Exact Mass:398.13723900
Monoisotopic Mass:398.13723900
Topological Polar Surface Area:187
Heavy Atom Count:27
Complexity:527
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Adenosylmethionine is a physiologically active molecule present in all tissues and body fluids of the human body. It participates in important biochemical reactions in the body as a methyl donor (transmethylation) and a precursor (transsulfuration) of physiological sulfhydryl compounds (such as cysteine, taurine, glutathione and coenzyme A, etc.). In the liver, it regulates the fluidity of liver cell membranes by methylating plasma membrane phospholipids, and promotes the synthesis of sulfide products in the detoxification process through transsulfuration reactions. Supplementation of adenosylmethionine can eliminate metabolic blockage caused by reduced activity of adenosylmethionine synthetase and restore the physiological mechanism of bile excretion.
Registered Holders
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Shandong Ruiyin Biotechnology Co., Ltd.
Active
China
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Shandong Jincheng BIO-PHARMACEUTICAL Co., Ltd.
Active
China
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Zhejiang Apeloa Jiayuan Pharmaceutical Co., Ltd.
Active
China
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