WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 581994
CAS#: 67380-81-8 (sulfate)
Description: S-Adenosyl-3-methylthiopropylamine is a substrate that is involved in the biosynthesis of polyamines including spermidine, spermine, and thermospermine.
MedKoo Cat#: 581994
Name: S-Adenosyl-3-methylthiopropylamine sulfate
CAS#: 67380-81-8 (sulfate)
Chemical Formula: C14H26N6O11S3
Exact Mass:
Molecular Weight: 550.57
Elemental Analysis: C, 30.54; H, 4.76; N, 15.26; O, 31.96; S, 17.47
This product is not in stock, which may be available by custom synthesis.
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Related CAS #: 22365-13-5 (Cation) 67380-81-8 (sulfate)
Synonym: Decarboxylated S-adenosyl methionine Sulfate; S-Adenosyl-3-methylthiopropylamine; S-Adenosyl-L-methionamine; S-Adenosylmethionamine; Decarboxylated S-adenosylmethionine.
IUPAC/Chemical Name: (((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(3-ammoniopropyl)(methyl)sulfonium hydrogen sulfate
InChi Key: NZCXDNATCGDLIE-RGBAOSDGSA-M
InChi Code: InChI=1S/C14H23N6O3S.2H2O4S/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;2*1-5(2,3)4/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18);2*(H2,1,2,3,4)/q+1;;/p-1/t8-,10-,11-,14-,24?;;/m1../s1
SMILES Code: O[C@@H]([C@H]([C@H](N1C=NC2=C(N=CN=C21)N)O3)O)[C@H]3C[S+](CCCN)C.O=S(O)(O)=O.O=S(O)([O-])=O
Appearance: White to off-white solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 550.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Fukui T, Soda K, Takao K, Rikiyama T. Extracellular Spermine Activates DNA Methyltransferase 3A and 3B. Int J Mol Sci. 2019 Mar 12;20(5). pii: E1254. doi: 10.3390/ijms20051254. PubMed PMID: 30871110; PubMed Central PMCID: PMC6429523.
2: Zabala-Letona A, Arruabarrena-Aristorena A, Martín-Martín N, Fernandez-Ruiz S, Sutherland JD, Clasquin M, Tomas-Cortazar J, Jimenez J, Torres I, Quang P, Ximenez-Embun P, Bago R, Ugalde-Olano A, Loizaga-Iriarte A, Lacasa-Viscasillas I, Unda M, Torrano V, Cabrera D, van Liempd SM, Cendon Y, Castro E, Murray S, Revandkar A, Alimonti A, Zhang Y, Barnett A, Lein G, Pirman D, Cortazar AR, Arreal L, Prudkin L, Astobiza I, Valcarcel-Jimenez L, Zuñiga-García P, Fernandez-Dominguez I, Piva M, Caro-Maldonado A, Sánchez-Mosquera P, Castillo-Martín M, Serra V, Beraza N, Gentilella A, Thomas G, Azkargorta M, Elortza F, Farràs R, Olmos D, Efeyan A, Anguita J, Muñoz J, Falcón-Pérez JM, Barrio R, Macarulla T, Mato JM, Martinez-Chantar ML, Cordon-Cardo C, Aransay AM, Marks K, Baselga J, Tabernero J, Nuciforo P, Manning BD, Marjon K, Carracedo A. mTORC1-dependent AMD1 regulation sustains polyamine metabolism in prostate cancer. Nature. 2017 Jul 6;547(7661):109-113. doi: 10.1038/nature22964. Epub 2017 Jun 28. Erratum in: Nature. 2018 Jan 17;:. PubMed PMID: 28658205; PubMed Central PMCID: PMC5505479.
3: Zhang H, Au SWN. Helicobacter pylori does not use spermidine synthase to produce spermidine. Biochem Biophys Res Commun. 2017 Aug 26;490(3):861-867. doi: 10.1016/j.bbrc.2017.06.132. Epub 2017 Jun 22. PubMed PMID: 28648602.
4: Chintapalli VR, Al Bratty M, Korzekwa D, Watson DG, Dow JA. Mapping an atlas of tissue-specific Drosophila melanogaster metabolomes by high resolution mass spectrometry. PLoS One. 2013 Oct 29;8(10):e78066. doi: 10.1371/journal.pone.0078066. eCollection 2013. PubMed PMID: 24205093; PubMed Central PMCID: PMC3812166.
5: Pegg AE, Wang X, Schwartz CE, McCloskey DE. Spermine synthase activity affects the content of decarboxylated S-adenosylmethionine. Biochem J. 2011 Jan 1;433(1):139-44. doi: 10.1042/BJ20101228. PubMed PMID: 20950271.
6: Sebastiano R, Knob R, Citterio A, Righetti PG. Analysis of trace degradation products (decarboxylated diastereoisomers) of S-adenosylmethionine by electrophoresis in capillaries with cationic coatings (N-methylpolyvinylpyridinium or divalent barium). Electrophoresis. 2010 Oct;31(21):3592-6. doi: 10.1002/elps.201000292. PubMed PMID: 20925050.
7: Sandmark J, Eliot AC, Famm K, Schneider G, Kirsch JF. Conserved and nonconserved residues in the substrate binding site of 7,8-diaminopelargonic acid synthase from Escherichia coli are essential for catalysis. Biochemistry. 2004 Feb 10;43(5):1213-22. PubMed PMID: 14756557.
8: Wiest L, Pegg AE. Assay of spermidine and spermine synthases. Methods Mol Biol. 1998;79:51-7. PubMed PMID: 9463817.
9: Samejima K. [Methodological approach to regulation of polyamine]. Yakugaku Zasshi. 1997 Nov;117(10-11):690-9. Review. Japanese. PubMed PMID: 9414583.
10: Hamasaki-Katagiri N, Tabor CW, Tabor H. Spermidine biosynthesis in Saccharomyces cerevisae: polyamine requirement of a null mutant of the SPE3 gene (spermidine synthase). Gene. 1997 Mar 10;187(1):35-43. PubMed PMID: 9073064.
11: Frostesjö L, Holm I, Grahn B, Page AW, Bestor TH, Heby O. Interference with DNA methyltransferase activity and genome methylation during F9 teratocarcinoma stem cell differentiation induced by polyamine depletion. J Biol Chem. 1997 Feb 14;272(7):4359-66. PubMed PMID: 9020157.
12: Anderson MM, Ast T, Nicolaou A, Valko K, Gibbons WA. Nitric oxide effects on polyamine pathways in cultured hepatocytes. Biochem Soc Trans. 1994 Aug;22(3):295S. PubMed PMID: 7821554.
13: Smith TK, Lindqvist L, Alakuijala L, Eloranta TO. Effects of dietary polyamine precursors on the metabolism and tissue concentrations of amino acids in the rat. Ann Nutr Metab. 1989;33(3):143-52. PubMed PMID: 2802527.
14: Claverie N, Pasquali JL, Mamont PS, Danzin C, Weil-Bousson M, Siat M. Immunosuppressive effects of (2R,5R)-6-heptyne-2,5-diamine, an inhibitor of polyamine synthesis: II. Beneficial effects on the development of a lupus-like disease in MRL-lpr/lpr mice. Clin Exp Immunol. 1988 May;72(2):293-8. PubMed PMID: 3409547; PubMed Central PMCID: PMC1541544.
15: Haegele KD, Splinter TA, Romijn JC, Schechter PJ, Sjoerdsma A. Decarboxylated-S-adenosylmethionine excretion: a biochemical marker of ornithine decarboxylase inhibition by alpha-difluoromethylornithine. Cancer Res. 1987 Feb 1;47(3):890-5. PubMed PMID: 3100028.
16: Anton DL. A rapid nonchromatographic assay for aminopropyltransferases. Anal Biochem. 1986 Jul;156(1):45-7. PubMed PMID: 3526973.
17: Wagner J, Hirth Y, Claverie N, Danzin C. A sensitive high-performance liquid chromatographic procedure with fluorometric detection for the analysis of decarboxylated S-adenosylmethionine and analogs in urine samples. Anal Biochem. 1986 May 1;154(2):604-17. PubMed PMID: 3728970.
18: McGovern KA, Clark RS, Pegg AE. Effect of 1,3,6-triaminohexane and 1,4,7-triaminoheptane on growth and polyamine metabolism in SV-3T3 cells treated with 2-difluoromethylornithine. J Cell Physiol. 1986 May;127(2):311-6. PubMed PMID: 3009500.
19: Oredsson SM, Kanje M, Mamont PS, Wagner J, Heby O. Polyamine depletion increases cellular ribonucleotide levels. Mol Cell Biochem. 1986 Apr;70(1):89-96. PubMed PMID: 3086709.
20: Wagner J, Hirth Y, Piriou F, Zakett D, Claverie N, Danzin C. N-Acetyl decarboxylated S-adenosylmethionine, a new metabolite of decarboxylated S-adenosylmethionine: isolation and characterization. Biochem Biophys Res Commun. 1985 Dec 17;133(2):546-53. PubMed PMID: 4084287.
