P. aeruginosa Metabolome Database: S-Adenosylmethionine (PAMDB000289)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000289

Identification

Name:

S-Adenosylmethionine

Description:

S-Adenosylmethionine is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase (EC 2.5.1.6). Transmethylation, transsulfuration, and aminopropylation are the metabolic pathways that use S-Adenosylmethionine. In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. (Wikipedia)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(3S)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine
(3S)-5'-[(3-amino-3-carboxypropyl)methylsulphonio]-5'-deoxyadenosine
2-S-adenosyl-L-methionine
2-S-Adenosyl-L-methionine
5'-Deoxyadenosine-5'-L-methionine disulfate ditosylate
5'-Deoxyadenosine-5'-L-methionine disulfuric acid ditosylic acid
5'-Deoxyadenosine-5'-L-methionine disulphate ditosylate
5'-Deoxyadenosine-5'-L-methionine disulphuric acid ditosylic acid
S-adenosyl-methionine
S-adenosylmethionine
Active methionine
Ademetionine
Adenosylmethionine
AdoMet
Donamet
L-S-Adenosylmethionine
S-(5'-Adenosyl)-L-methionine
S-(5'-Deoxyadenosin-5'-yl)-L-methionine
S-Adenosyl methionine
S-Adenosyl-L-methionine
S-Adenosyl-L-Methionine Disulfate Tosylate
S-Adenosyl-L-methionine disulfuric acid tosylic acid
S-Adenosyl-L-methionine disulphate tosylate
S-Adenosyl-L-methionine disulphuric acid tosylic acid
S-Adenosyl-methionine
S-Adenosylmethionine
SAM

Chemical Formula:

C₁₅H₂₃N₆O₅S

Average Molecular Weight:

399.445

Monoisotopic Molecular Weight:

399.145063566

InChI Key:

MEFKEPWMEQBLKI-AIRLBKTGSA-O

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

CAS number:

29908-03-0

IUPAC Name:

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

Traditional IUPAC Name:

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

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Glycosyl compounds

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
D-alpha-amino acid
Methionine or derivatives
Alpha-amino acid or derivatives
Alpha-amino acid
6-aminopurine
Purine
Imidazopyrimidine
Thia fatty acid
Aminopyrimidine
Amino fatty acid
Fatty acyl
Imidolactam
Pyrimidine
Primary aromatic amine
N-substituted imidazole
Monosaccharide
Heteroaromatic compound
Oxolane
Imidazole
Azole
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	1.19 mg/mL	ALOGPS
logP	-2	ALOGPS
logP	-5.3	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.71	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	39.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

More...

Pathways:

Arginine and proline metabolism pae00330
Biotin metabolism pae00780
Cysteine and methionine metabolism pae00270
Lipoic acid metabolism pae00785
Metabolic pathways pae01100
Mismatch repair pae03430
Porphyrin and chlorophyll metabolism pae00860
Selenoamino acid metabolism pae00450
Sulfur relay system pae04122
Thiamine metabolism pae00730
Two-component system pae02020
Ubiquinone and other terpenoid-quinone biosynthesis pae00130

Spectra

Spectra:

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	15414
HMDB ID	HMDB01185
Pubchem Compound ID	1079
Kegg ID	C00019
ChemSpider ID	21169292
Wikipedia	S-Adenosylmethionine
BioCyc ID	S-ADENOSYLMETHIONINE
EcoCyc ID	S-ADENOSYLMETHIONINE

S-Adenosylmethionine (PAMDB000289)

Structure for S-Adenosylmethionine (PAMDB000289)