S-Adenosylmethionine
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Basic information
- CAS
29908-03-0- Standard 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- Molecular formula
- C15H22N6O5S
- Average molar mass
- 398.4 g/mol
- Monoisotopic mass
- 398.137239
Overview
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.
Names & identifiers
- Preferred name
- S-Adenosylmethionine
- IUPAC
- (2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]butanoate
- English name
- Ademetionine
- Molecular formula
- C15H22N6O5S
- Molecular weight
- 398.44
Names & synonyms
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
Show more names
SAMSAM-EadenosylmethionineSAM-Bp-Toluenesulfonate saltAdemetioninS-adenosyl-L-methioninate
((3S)-3-amino-3-carboxypropyl)((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methyl))methylsulfaniumDTXCID4012019FO15615'-((3-Amino-3-carboxypropyl)methylsulfonio)-5'-deoxyadenosine Hydroxide, Inner SaltS-adenosyl-L-methionine29908-03-0AdemetionineSAMe
Properties
Computed structural propertiesFilling in
- XLogP
- -2.8
- Topological polar surface area
- 186 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 6
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 527
Experimental & physicochemical properties
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]
Physicochemical properties
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- DMSO (Slightly, Sonicated), Water (Slightly)
- form
- Solid
- color
- White to Yellow
- Stability
- 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|
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Toxicology
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
Safety data
Chemistry & industry
Pharmacology
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.
Related reactions
0 records
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Compound notes
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