Basic information
- CAS
29908-03-0- Standard 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- Molecular formula
- C15H23N6O5S+
- Average molar mass
- 399.4 g/mol
- Monoisotopic mass
- 399.14506403
Overview
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.
Names & identifiers
- Preferred name
- Ademetionine
- IUPAC
- (2S)-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]-2-azaniumylbutanoate
- English name
- S-adenosylmethionine
- Molecular formula
- C15H23N6O5S
- Molecular weight
- 400.45
Names & synonyms
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
Show more names
13CH3-SAMMethionine,activeS-ADENOSYLMETHIONINEAdenosine Impurity 39S-(5'-Adenosyl)methionineMEFKEPWMEQBLKI-AIRLBKTGSA-OS-adenosylmethionine USP/EP/BPAdemetionine 1,4-Butanedisulfonate Impurity 18 MonomerGalactose Impurity 1 (Galactose EP Impurity A)(Lactose)S-Adenosyl-L-methionine sulfate p-toluene sulfonate salt
(S,S)-AdoMet zwitterionCHEBI:59789CHEBI:142093CHEBI:142094S-adenosyl-L-methionine zwitterion(R)-S-adenosyl-L-methionine zwitterion(S)-S-adenosyl-L-methionine zwitterion(R,S)-S-adenosyl-L-methionine zwitterion
Database identifiers
- CAS
29908-03-0、485-80-3- PubChem CID
- 24762165
- ChEMBL
CHEMBL1088977- ChEBI
CHEBI:59789
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 188 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 6
- Heavy atoms
- 27
- Formal charge
- 1
- Complexity
- 527
Experimental & physicochemical properties
LogP-5.3
Boiling Point78 °C
Physical DescriptionSolid
Physicochemical properties
- 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|
- NCI Drug Dictionary
- S-adenosylmethionine
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
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.
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 Pathways3-Phosphoglycerate dehydrogenase deficiency
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >100
Applications
UsesS-Adenosyl-methionine labelled-15N5 is a useful research chemical. CAS# 485-80-3 is used in ReFlexIn, flexible receptor protein-ligand docking scheme evaluated on HIV-1 protease.
Suppliers24 total
Shaanxi LonierHerb Bio Technology Co Ltd+86-86-+86-86-029-87551862 15002946897 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
济南洣林医药技术有限公司0531-68659554 +8613031714605 · [email protected]
广东元丰化学试剂有限公司0751-2829979 13318593351 · [email protected]
广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]
广东方信生物科技有限公司0751-2838688 13376594225 · [email protected]
上海梅凯科技有限公司021-68689288 15300790979 · [email protected]
天成化工(江苏)有限公司0512-66387919 18662433356 · [email protected]
南通嘉星泰生物科技有限公司18795782766 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
北京秦岭医药科技有限公司010-61241352 18901327973 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
武汉华翔科洁生物技术有限公司
Additional notes
DefinitionChEBI: S-adenosyl-L-methionine is a sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine. It has a role as a coenzyme, a nutraceutical, a micronutrient, a human metabolite, a Saccharomyces cerevisiae metabolite, a Mycoplasma genitalium metabolite and a cofactor. It is a conjugate acid of a S-adenosyl-L-methioninate. It is an enantiomer of a S-adenosyl-D-methionine. It is a tautomer of a S-adenosyl-L-methionine zwitterion.
Related reactions
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Compound notes
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