CAS 29908-03-0|AdoMet|SAMe Rx-Mood|(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(methyl)sulfaniumyl)butanoate|S-Adenosyl-L-methionine|S-Adenosylmethionine|Sa...

General Information

Structure

Molecular Formula

C₁₅H₂₂N₆O₅S

Molecular Mass

398.43738

Exact Mass

398.13723883

Charge

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

Canonic Smiles

C[S+](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)[O-])N

Isomeric 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

Calculated Properties

JChem

Acid pKa

1.6665175

H Acceptors

H Donor

LogD (pH = 5.5)

-5.312802

LogD (pH = 7.4)

-5.3263273

Log P

-5.3237367

Molar Refractivity

107.072

Polarizability

38.454018

Polar Surface Area

185.46

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

-1.99

LOG S

-2.56

Solubility (Water)

1.19e+00 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

AdoMetS-Adenosyl-L-methionineS-AdenosylmethionineSAMSAM-e

Brand Name

SAMe Rx-MoodSam-Sulfate

IUPAC Traditional name

(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(methyl)sulfaniumyl)butanoate

IUPAC name

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

Names and Identifiers

Registration numbers

PubChem CID

3475534756

PubChem SID

16096346846505280

CAS Number

29908-03-0

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00118

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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• Synonyms

• Brand Name

• IUPAC Traditional name

• IUPAC name

Registration numbers

• PubChem CID

• PubChem SID

• CAS Number

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Synonyms

AdoMetS-Adenosyl-L-methionineS-AdenosylmethionineSAMSAM-e

Brand Name

SAMe Rx-MoodSam-Sulfate

IUPAC Traditional name

(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(methyl)sulfaniumyl)butanoate

IUPAC name

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

PubChem CID

3475534756

PubChem SID

16096346846505280

CAS Number

29908-03-0

From Data Sources

• 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

• 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

DrugBank

DB00118

Drug Groups

approved; nutraceutical

Description

Indication

Pharmacology

Toxicity

Irritating to mucus membranes and upper respiratory tract. Can cause CNS depression.

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

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]

Molecule

ID:5