ContaminantDB: S-Adenosylmethionine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (12)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:25 UTC

Update Date

2026-05-14 16:24:01 UTC

Accession Number

CHEM003416

Identification

Common Name

S-Adenosylmethionine

Class

Small Molecule

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). S-Adenosylmethionine is only found in individuals that have used or taken this drug. It is a 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-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.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Dietary Supplement
Drug
Ether
Food Toxin
Metabolite
Micronutrient
Natural Compound
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt	ChEBI
[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium	ChEBI
Acylcarnitine	ChEBI
AdoMet	ChEBI
S-(5'-Deoxyadenosin-5'-yl)-L-methionine	ChEBI
SAM	ChEBI
SAMe	ChEBI
(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulphonio]-5'-deoxyadenosine, inner salt	Generator
[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium	Generator
[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium	Generator
[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium	Generator
[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium	Generator
[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium	Generator
(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine	HMDB
2-S-Adenosyl-L-methionine	HMDB
5'-Deoxyadenosine-5'-L-methionine disulfate ditosylate	HMDB
5'-Deoxyadenosine-5'-L-methionine disulphate ditosylate	HMDB
Active methionine	HMDB
Ademetionine	HMDB
Adenosylmethionine	HMDB
Donamet	HMDB
L-S-Adenosylmethionine	HMDB
S-(5'-Adenosyl)-L-methionine	HMDB
S-Adenosyl methionine	HMDB
S-Adenosyl-L-methionine	HMDB
S-Adenosyl-L-methionine disulfate tosylate	HMDB
S-Adenosyl-L-methionine disulphate tosylate	HMDB
S-Adenosyl-methionine	HMDB
ASTA medica brand OF ademetionine tosilate disulfate	HMDB
S Adenosylmethionine sulfate tosylate	HMDB
S-Adenosylmethionine sulfate tosylate	HMDB
Sulfate tosylate, S-adenosylmethionine	HMDB
Ademetionine europharma brand	HMDB
Amet, S	HMDB
Europharma brand OF ademetionine	HMDB
Gumbaral	HMDB
Knoll brand OF brand OF ademetionine tosilate disulfate	HMDB
S Adenosylmethionine	HMDB
S Amet	HMDB
Samyr	HMDB
Tosylate, S-adenosylmethionine sulfate	HMDB
S Adenosyl L methionine	HMDB
SAM-e	HMDB

Chemical Formula

C₁₅H₂₃N₆O₅S

Average Molecular Mass

399.445 g/mol

Monoisotopic Mass

399.145 g/mol

CAS Registry Number

29908-03-0

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

Traditional Name

SAMe

SMILES

C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

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)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1

InChI Key

MEFKEPWMEQBLKI-AIRLBKTGSA-O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

5'-deoxyribonucleosides

Sub Class

5'-deoxy-5'-thionucleosides

Direct Parent

5'-deoxy-5'-thionucleosides

Alternative Parents

Substituents

5'-deoxy-5'-thionucleoside
Methionine or derivatives
N-glycosyl compound
Glycosyl compound
Pentose monosaccharide
6-aminopurine
Alpha-amino acid
L-alpha-amino acid
Alpha-amino acid or derivatives
Imidazopyrimidine
Purine
Aminopyrimidine
Hydroxy fatty acid
Thia fatty acid
N-substituted imidazole
Fatty acyl
Monosaccharide
Imidolactam
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Amino acid or derivatives
1,2-diol
Amino acid
Secondary alcohol
Oxacycle
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Primary aliphatic amine
Amine
Organonitrogen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic cation (CHEBI:59789 )
sulfonium compound (CHEBI:59789 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Endoplasmic reticulum
Membrane
Mitochondria
Nucleus

Biofluid Locations

Not Available

Tissue Locations

Epidermis
Eye Lens
Fibroblasts
Gonads
Intestine
Kidney
Muscle
Myelin
Placenta
Prostate
Skeletal Muscle
Testes

Pathways

Name	SMPDB Link	KEGG Link
Betaine Metabolism	SMP00123	map00260
Carnitine Synthesis	SMP00465	Not Available
Catecholamine Biosynthesis	SMP00012	map00350
Glycine and Serine Metabolism	SMP00004	map00260
Methionine Metabolism	SMP00033	map00270
Spermidine and Spermine Biosynthesis	SMP00445	Not Available
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency	SMP00214	Not Available

Applications

nutraceutical

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	78 °C
Solubility	1.19e+00 g/l

Predicted Properties

Property	Value	Source
Water Solubility	1.19 g/L	ALOGPS
logP	-2	ALOGPS
logP	-5.3	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.7	ChemAxon
pKa (Strongest Basic)	9.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.63 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	96.23 m³·mol⁻¹	ChemAxon
Polarizability	40.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5c-5965000000-324e4a3cbf936132bcf1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00ea-7958582000-3dd40cf273f182ee53dd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-0019000000-6dfa0dc65a9863755c2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udj-0293000000-57cc9d4430592060d41d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udr-1940000000-ed4985bea80649d27efe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000b-8920000000-8f05e9898f0d26ddf3f8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000e-9400000000-e5c5617045d9915e8e46	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0udi-0090000000-93017671648813ece8a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0914000000-95030ceaf1c187dcf656	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-c3fae8b7a68475b614a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-44078fd7eaeafcc5bba8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1927000000-02f9d1735282c46e7318	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-aa88bbdd6c68c8e33363	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bti-7900000000-003aba988a5c7e2f6534	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

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.

Mechanism of Toxicity

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

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.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001185

FooDB ID

FDB031152

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

S-Adenosyl_methionine

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Takayasu Tsuchida, Fumihiro Yoshinaga, Shinji Okumura, “Method for producing S-adenosylmethionine or methylthioadenosine by yeast.” U.S. Patent US3962034, issued November, 1971.

MSDS

Link

General References

1. Lin, Jian-Ping; Tian, Jun; You, Jian-Feng; Jin, Zhi-Hua; Xu, Zhi-Nan; Cen, Pei-Lin. An effective strategy for the co-production of S-adenosyl-L-methionine and glutathione by fed-batch fermentation. Biochemical Engineering Journal (2004), 21(1), 19-25.

2. Chamberlin ME, Ubagai T, Mudd SH, Wilson WG, Leonard JV, Chou JY: Demyelination of the brain is associated with methionine adenosyltransferase I/III deficiency. J Clin Invest. 1996 Aug 15;98(4):1021-7.

3. Koeberl DD, Young SP, Gregersen NS, Vockley J, Smith WE, Benjamin DK Jr, An Y, Weavil SD, Chaing SH, Bali D, McDonald MT, Kishnani PS, Chen YT, Millington DS: Rare disorders of metabolism with elevated butyryl- and isobutyryl-carnitine detected by tandem mass spectrometry newborn screening. Pediatr Res. 2003 Aug;54(2):219-23. Epub 2003 May 7.

4. Scalabrino G, Pigatto P, Ferioli ME, Modena D, Puerari M, Caru A: Levels of activity of the polyamine biosynthetic decarboxylases as indicators of degree of malignancy of human cutaneous epitheliomas. J Invest Dermatol. 1980 Mar;74(3):122-4.

5. Struys EA, Jansen EE, de Meer K, Jakobs C: Determination of S-adenosylmethionine and S-adenosylhomocysteine in plasma and cerebrospinal fluid by stable-isotope dilution tandem mass spectrometry. Clin Chem. 2000 Oct;46(10):1650-6.

6. Kaneoka H, Uesugi N, Moriguchi A, Hirose S, Takayanagi M, Yamaguchi S, Shigematsu Y, Yasuno T, Sasatomi Y, Saito T: Carnitine palmitoyltransferase II deficiency due to a novel gene variant in a patient with rhabdomyolysis and ARF. Am J Kidney Dis. 2005 Mar;45(3):596-602.

7. Rosen RT, Hiserodt RD, Fukuda EK, Ruiz RJ, Zhou Z, Lech J, Rosen SL, Hartman TG: The determination of metabolites of garlic preparations in breath and human plasma. Biofactors. 2000;13(1-4):241-9.

8. McFadden PN, Horwitz J, Clarke S: Protein carboxyl methyltransferase from cow eye lens. Biochem Biophys Res Commun. 1983 Jun 15;113(2):418-24.

9. Garibotto G, Sofia A, Valli A, Tarroni A, Di Martino M, Cappelli V, Aloisi F, Procopio V: Causes of hyperhomocysteinemia in patients with chronic kidney diseases. Semin Nephrol. 2006 Jan;26(1):3-7.