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Record Information
Version	2.0
Creation Date	2012-05-31 13:02:56 -0600
Update Date	2015-06-03 15:53:38 -0600
Secondary Accession Numbers	ECMDB00988
Identification
Name:	S-Adenosylmethioninamine
Description	S-Adenosylmethioninamine is a biological sulfonium compound known as the major biological methyl donor. It is also a donor of methylene groups, amino groups, ribosyl groups and aminopropyl groups (PMID 15130560). S-Adenosylmethioninamine is a prodcut of enzyme adenosylmethionine decarboxylase [EC 4.1.1.50] in methionine metabolism pathway (KEGG).
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb00271e0> Close
Synonyms:	(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulphonium salt 3-amino-propyl-S-adenosine 3-Amino-propyl-S-adenosine S-adenosylmethioninamine S-methyl-S-adenosyl homocysteamine DAdoMet DcSAM Decarboxylated AdoMet Decarboxylated S-adenosylmethionine Decarboxylated SAM S-Adenosyl-(5')-3-methylthiopropylamine S-Adenosyl-L-methioninamine S-Adenosylmethioninamine S-Methyl-S-adenosyl homocysteamine
Chemical Formula:	C14H23N6O3S
Weight:	Average: 355.436 Monoisotopic: 355.155234322
InChI Key:	ZUNBITIXDCPNSD-LSRJEVITSA-N
InChI:	InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1
CAS number:	22365-13-5
IUPAC Name:	{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium
Traditional IUPAC Name:	decarboxylated sam
SMILES:	C[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
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	Glycosylamines Pentoses 6-aminopurines Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols 1,2-diols Oxacyclic compounds Azacyclic compounds Organosulfur compounds Hydrocarbon derivatives Monoalkylamines Organopnictogen compounds Organic cations
Substituents	5'-deoxy-5'-thionucleoside Glycosyl compound N-glycosyl compound 6-aminopurine Pentose monosaccharide Purine Imidazopyrimidine Aminopyrimidine Imidolactam Pyrimidine Monosaccharide N-substituted imidazole Heteroaromatic compound Tetrahydrofuran Azole Imidazole Secondary alcohol 1,2-diol Oxacycle Azacycle Organoheterocyclic compound Organopnictogen compound Hydrocarbon derivative Organonitrogen compound Primary aliphatic amine Organooxygen compound Organosulfur compound Organic oxygen compound Organic nitrogen compound Primary amine Amine Alcohol Organic cation Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	sulfonium compound (CHEBI:15625 ) adenosines (CHEBI:15625 ) Biogenic amines (C01137 )
Physical Properties
State:	Solid
Charge:	2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 1.27 g/L ALOGPS logP 0.28 ALOGPS logP -2.8 ChemAxon logS -2.5 ALOGPS pKa (Strongest Acidic) 12.45 ChemAxon pKa (Strongest Basic) 10.09 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 145.33 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 90.4 m³·mol⁻¹ ChemAxon Polarizability 36.97 ų 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:	S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide S-Adenosylmethioninamine + Putrescine + Ethylenediamine <> 5'-Methylthioadenosine + Hydrogen ion + Spermidine Cadaverine + S-Adenosylmethioninamine > 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine S-Adenosylmethioninamine + Putrescine <> 5'-Methylthioadenosine + Spermidine S-Adenosylmethioninamine + Spermidine <> 5'-Methylthioadenosine + Spermine S-Adenosylmethioninamine + Cadaverine <> 5'-Methylthioadenosine + Aminopropylcadaverine Hydrogen ion + S-Adenosylmethionine > Carbon dioxide + S-Adenosylmethioninamine Putrescine + S-Adenosylmethioninamine > Hydrogen ion + Spermidine + 5'-Methylthioadenosine S-Adenosylmethioninamine + Putrescine > 5'-Methylthioadenosine + Spermidine S-adenosyl-L-methionine + Hydrogen ion > Carbon dioxide + S-Adenosylmethioninamine Putrescine + S-Adenosylmethioninamine > Spermidine + Hydrogen ion + 5'-S-methyl-5'-thioadenosine S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine Cadaverine + S-Adenosylmethioninamine >5 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine
SMPDB Pathways:	Glutathione metabolism PW000833 S-adenosyl-L-methionine biosynthesis PW000837 Spermidine biosynthesis and metabolism PW002085 beta-Alanine metabolism PW000896
KEGG Pathways:	Arginine and proline metabolism ec00330 Cysteine and methionine metabolism ec00270 Glutathione metabolism ec00480 Metabolic pathways eco01100 beta-Alanine metabolism ec00410
EcoCyc Pathways:	aminopropylcadaverine biosynthesis PWY0-1303 spermidine biosynthesis I BSUBPOLYAMSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-06wi-7923000000-45e056b479c0e2cba364 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00ai-8291700000-8e1b09746b1c704e209f View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0904000000-5a1b6a3a878c0630e6ea View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-1900000000-70103a635ebc7c51a985 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-3900000000-65b9306b33b0ffc5e9fc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-052r-0916000000-8fc88153f214f58b3dc2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0900000000-8c8ee467ecf1a037a37b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05mx-7900000000-b79675da812011642f0b View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	Fontecave, M., Atta, M., Mulliez, E. (2004). "S-adenosylmethionine: nothing goes to waste." Trends Biochem Sci 29:243-249. Pubmed: 15130560 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:	Pegg, Anthony E. Assay of aminopropyltransferases. Methods in Enzymology (1983), 94(Polyamines), 260-5.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15625 HMDB ID HMDB00988 Pubchem Compound ID 1078 Kegg ID C01137 ChemSpider ID 388529 Wikipedia ID S-Adenosylmethioninamine BioCyc ID S-ADENOSYLMETHIONINAMINE EcoCyc ID S-ADENOSYLMETHIONINAMINE

Enzymes