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Record Information
Version	2.0
Creation Date	2012-05-31 14:39:22 -0600
Update Date	2015-06-03 17:19:47 -0600
Secondary Accession Numbers	ECMDB20325
Identification
Name:	Decarboxy-SAM
Description	dcSAM is a member of the chemical class known as Purine Nucleosides and Analogues. These are compounds comprising a purine base attached to a sugar. [2-(Amino-oxy)ethyl](5'-deoxyadenosin-5'-yl)(methyl)sulphonium+ ++, the amino-oxy analogue of decarboxylated S-adenosylmethionine, is a potent irreversible inhibitor of Escherichia coli S-adenosylmethionine decarboxylase [Khomutov, Zavalova, Syrku, Artamonova & Khomutov (1983) Bioorg. (PMID 1872800)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae35b3a4> 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:	C14H24N6O3S
Weight:	Average: 356.444 Monoisotopic: 356.163059354
InChI Key:	ZUNBITIXDCPNSD-LSRJEVITSA-O
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/p+1/t8-,10-,11-,14-,24?/m1/s1
CAS number:	Not Available
IUPAC Name:	{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-azaniumylpropyl)methylsulfanium
Traditional IUPAC Name:	S-adenosylmethioninaminium
SMILES:	[H][C@]1(C[S+](C)CCC[NH3+])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])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	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	ammonium ion (CHEBI:57443 ) sulfonium compound (CHEBI:57443 )
Physical Properties
State:	Not Available
Charge:	2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.47 g/L ALOGPS logP -1.7 ALOGPS logP -2.8 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 12.45 ChemAxon pKa (Strongest Basic) 10.09 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 146.95 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 101.7 m³·mol⁻¹ ChemAxon Polarizability 37.34 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-adenosyl-L-methionine + Hydrogen ion > Decarboxy-SAM + Carbon dioxide Cadaverine + Decarboxy-SAM > Aminopropylcadaverine + 5'-Methylthioadenosine + Hydrogen ion Decarboxy-SAM + Putrescine > 5'-Methylthioadenosine + Spermidine + Hydrogen ion
SMPDB Pathways:	Spermidine Biosynthesis I PW002040 aminopropylcadaverine biosynthesis PW002039
KEGG Pathways:	Not Available
EcoCyc Pathways:	aminopropylcadaverine biosynthesis PWY0-1303 spermidine biosynthesis I BSUBPOLYAMSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key 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 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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 Weitkamp, E. L., Dixon, H. B., Khomutov, A. R., Khomutov, R. M. (1991). "Effect of magnesium ions on the inhibition of S-adenosylmethionine decarboxylase from Escherichia coli by [2-(amino-oxy)ethyl](5'-deoxyadenosin-5'-yl)(methyl)sulphonium ." Biochem J 277 ( Pt 3):643-645. Pubmed: 1872800
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 57443 HMDB ID HMDB0304476 Pubchem Compound ID 25203490 Kegg ID Not Available ChemSpider ID 26330790 Wikipedia ID Not Available BioCyc ID S-ADENOSYLMETHIONINAMINE EcoCyc ID S-ADENOSYLMETHIONINAMINE

Enzymes